3.2 Inhaltsstoffe

Zusammensetzung des Harzes

Mehr als 200 verschiedene Substanzen wurden bisher in den Harzen von verschiedenen Boswelliaspezies identifiziert. Hauptkomponenten sind flüchtiges Öl, das reine Harz sowie Schleim. Der Gehalt dieser Stoffe variiert von Spezies zu Spezies und ist abhängig von Erntezeitpunkt und Standort. Eine ungefähre Zusammensetzung einiger Harze zeigt die untenstehende Tabelle. Die reinen Harze der Boswelliaspezies enthalten pentazyklische und tetrazyklische Triterpene. Unter den pentazyklischen Triterpenen sind besonders einige Boswelliasäuren für viele der pharmakologischen Wirkungen verantwortlich. Weitere Verbindungen sind tetrazyklische Triterpensäuren. Zu ihnen gehören auch die Tirukalsäuren, bei denen ebenfalls beobachtet wurde, dass sie biologische aktiv sind.

Zusammensetzung des Harzes von zwei verschiedenen Boswelliaspezies (aus Kreck und Saller, 1998):

Bosw. carteri Birdw. Bosw. serrata Roxb.
Flüchtige Öle: 5-9% 7,5-9% bis zu 15%
Reines Harz: ca. 66% 55-57%
Schleim: 12-20% ca. 23%

Boswellic Acids from Acid Fraction of Boswellia-Species

  • 11-keto-β-boswellic acid (KBA)
  • 3-acetyl-11-keto-β-boswellic acid (AKBA)
  • 3-acetyl-11-hydroxy-β-boswellic acid
  • β-boswellic acid
  • α-boswellic acid
  • 3-acetyl-β-boswellic acid
  • 3-acetyl-α-boswellic acid



Unraveling the terpene synthase family and characterization of BsTPS2 contributing to (S)-( +)-linalool biosynthesis in Boswellia.
Bhargav P, Chaurasia S, Kumar A, Srivastava G, Pant Y, Chanotiya CS, Ghosh S

Boswellia tree bark exudes oleo-gum resin in response to wounding, which is rich in terpene volatiles. But, the molecular and biochemical basis of wound-induced formation of resin volatiles remains poorly understood. Here, we combined RNA-sequencing (RNA-seq) and metabolite analysis to unravel the terpene synthase (TPS) family contributing to wound-induced biosynthesis of resin volatiles in B. serrata, an economically-important Boswellia species. The analysis of large-scale RNA-seq data of bark and leaf samples representing more than 600 million sequencing reads led to the identification of 32 TPSs, which were classified based on phylogenetic relationship into various TPSs families found in angiosperm species such as TPS-a, b, c, e/f, and g. Moreover, RNA-seq analysis of bark samples collected at 0-24 h post-wounding shortlisted 14 BsTPSs that showed wound-induced transcriptional upregulation in bark, suggesting their important role in wound-induced biosynthesis of resin volatiles. Biochemical characterization of a bark preferentially-expressed and wound-inducible TPS (BsTPS2) in vitro and in planta assays revealed its involvement in resin terpene biosynthesis. Bacterially-expressed recombinant BsTPS2 catalyzed the conversion of GPP and FPP into (S)-( +)-linalool and (E)-(-)-nerolidol, respectively, in vitro assays. However, BsTPS2 expression in Nicotiana benthamiana found that BsTPS2 is a plastidial linalool synthase. In contrast, cytosolic expression of BsTPS2 did not form any product. Overall, the present work unraveled a suite of TPSs that potentially contributed to the biosynthesis of resin volatiles in Boswellia and biochemically characterized BsTPS2, which is involved in wound-induced biosynthesis of (S)-( +)-linalool, a monoterpene resin volatile with a known role in plant defense.

Plant Mol Biol. 2023 Nov;113(4-5):219-236.
PMID: 37898975 [PubMed - indexed for MEDLINE]


Guided discovery of hepatoprotective polyhydroxy cembrane-type diterpenoids from the gum resin of Boswellia carterii by MS/MS molecular networking.
Yu J, Zhao L, Wang Z, Yue T, Wang X

Seven previously undescribed polyhydroxy cembrane-type diterpenoids, olibanols A-G (1-7) were obtained from the gum resin of Boswellia carterii by means of MS/MS molecular networking. Compound 2 possessed four hydroxy groups, 1, 3, 4, 5, and 6 had three hydroxy groups, 7 with one hydroxy group, among which 1 and 4 were a pair of epimers with double bond at C-3 and hydroxy at C-8. Structures of these previously undescribed compounds were determined by NMR analysis and ECD calculations. All the polyhydroxy cembrane-type diterpenoids obtained were assayed for their hepatoprotective effects against the anti-tuberculosis drug-induced hepatic damage to the HRZ-induced HepG2 cells. As results indicated, compounds 3, 4, and 6 showed significant hepatoprotective effects against the hepatic damage via the Nrf2 signal pathway, which could be developed as potential hepatoprotective agents against the anti-tuberculosis drug-induced hepatic damage.

Phytochemistry. 2023 Dec;216():113897.
PMID: 37866446 [PubMed - indexed for MEDLINE]


Antimicrobial Activity of Frankincense () Oil and Smoke against Pathogenic and Airborne Microbes.
Al-Kharousi ZS, Mothershaw AS, Nzeako B

As they continuously evolve, plants will remain a renewable source for antimicrobial compounds. Omani frankincense is produced by trees and is graded into Hojari, Nejdi, Shazri or Sha'bi. Air can be a source for pathogenic or food spoilage microbes; thus, inactivating airborne microbes is necessary in environments such as food and animal production areas. This study investigated the antimicrobial activity and the chemistry of steam-distilled oils of Hojari and Sha'bi grades. It also analyzed the antimicrobial activity of frankincense smoke and the size of its solid particles. Chemical analysis was performed using gas chromatography mass spectrometry (GC-MS). The antimicrobial activity of the oils against (NCTC 6571), spp., (NCTC 10418), (NCTC 10662), , , , , , , and was determined using well diffusion and micro-well dilution methods. A microscopic technique was used to determine the size of frankincense smoke solid particles. Microbes were exposed to frankincense smoke to test their susceptibility to the smoke. Hojari and Sha'bi oils were similar in composition and contained monoterpenes and sesquiterpenes. The Hojari and the Sha'bi oils possessed broad spectrum antimicrobial activity. The largest growth inhibition zones were obtained with and . An MIC of 1.56% (/) was found with , and . Frankincense smoke contained fine irregular solid particles with a diameter range of 0.8-2287.4 µm, and thus may pose a health risk to susceptible individuals. The smoke had potent antimicrobial activity against , , and airborne bacteria, yeast and mold, with a maximum inhibition of 100%. It was concluded that Hojari and Sha'bi frankincense oils and smoke had significant antimicrobial activity that can be exploited in controlling human, animal and plant pathogenic microbes.

Foods. 2023 Sep;12(18):.
PMID: 37761150 [PubMed - as supplied by publisher]


Evaluating the Potential of to Provide Sustainable Livelihood Benefits in Eastern Ethiopia.
DeCarlo A, Johnson S, Abdikadir A, Satyal P, Poudel A, Setzer WN

Frankincense is an oleo-gum-resin collected from wild spp. trees, and widely used in perfumery, cosmetics, aromatherapy, incense, and other industries. , growing in Ethiopia, Somalia, and Kenya, is one source of frankincense, but is little-commercialized compared to species such as , , and . In this study, we examine the resin essential oil chemistry and harvesting systems of in order to evaluate its potential for increased trade and potential positive livelihood benefits. produces an essential oil rich in α-thujene (0.1-12.4%), α-pinene (5.5-56.4%), β-pinene (0.3-13.0%), δ-3-carene (0.1-31.5%), -cymene (1.4-31.2%), limonene (1.8-37.3%), β-phellandrene (tr-5.6%), -pinocarveol (0.1-5.0%), -verbenol (0.1-11.2%), and -β-elemene (0-5.7%), similar to major commercial species, although it is difficult to detect mixing of and resins from chemistry alone. The trees are not actively tapped, so resin collection has a neutral impact on the health of the trees, and resin production is unaffected by drought. Consequently, collecting resins acts as a key income supplementing livestock herding, as well as a safety net protecting pastoral communities from the severe negative effects of climate change-exacerbated drought on livestock. Therefore, is well positioned chemically, ecologically, and socially to support expanded trade.

Plants (Basel). 2023 May;12(10):.
PMID: 37653941 [PubMed - as supplied by publisher]


Simultaneous identification and quantification of pentacyclic triterpenoids and phenolic compounds from the leaves of Boswellia serrata using LC-MS/MS tandem mass spectrometry.
Trivedi MK, Branton A, Trivedi D, Sharma T, Mondal S, Jana S

Boswellia serrata (B. serrata) is an important medicinal plant widely used as dietary supplements to provide a support for osteoarthritic and inflammatory diseases. The occurrence of triterpenes in leaves of B. serrata is very little or none. Therefore, the qualitative and quantitative determination of phytoconstituents (triterpenes and phenolics) present in the leaves of B. serrata is very much needed. The aim of this study was to develop an easy, rapid, efficient and simultaneous liquid chromatography-mass spectrometry (LC-MS/MS) method for the identification and quantification of the compounds present in the leaves extract of B. serrata. The purification of ethyl acetate extracts of B. serrata was performed by solid phase extraction method, followed by HPLC-ESI-MS/MS analysis. Chromatographic parameters of the analytical method included negative electrospray ionization (ESI) with a flow of 0.5 mL/min in gradient mode consisting of acetonitrile (A) and water (B) containing 0.1% formic acid, at 20 °C. Total 19 compounds (13 triterpenes and 6 phenolic compounds) were separated, and simultaneously quantified using a validated LC-MS/MS method with high accuracy and sensitivity. Good linearity was obtained with r > 0.973 in the calibration range. The overall recoveries were in a range between 95.78 and 100.2% with relative standard deviations (RSD) below 5% for the entire procedure of matrix spiking experiments. Overall, there was no ion suppression from the matrix. The quantification data showed that the total amount of triterpenes and phenolic compounds in the leaves of B. serrata ethyl acetate extract samples ranged from 14.54 to 102.14 mg/g and 2.14 to 93.12 mg/g of dry extract, respectively. This work provides, for the first time, a chromatographic fingerprinting analysis on the leaves of B. serrata. A rapid, efficient, and simultaneous liquid chromatography-mass spectrometry (LC-MS/MS) method was developed and used for the both identification and quantification of triterpenes and phenolic compounds in the leaves extracts of B. serrata. The method established in this work can be used as quality-control method for other market formulations or dietary supplements containing leaf extract of B. serrata.

Anal Sci. 2023 Oct;39(10):1741-1756.
PMID: 37386278 [PubMed - indexed for MEDLINE]


Phytochemical study of Boswellia dalzielii oleo-gum resin and evaluation of its biological properties.
Massei K, Michel T, Obersat GI, Al-Harrasi A, Baldovini N

Boswellia dalzielii is a resin-producing tree endemic to West and Central Africa, used by local populations for various medicinal purposes. In this study, B. dalzielii gum resin was analyzed by GC-MS and UHPLC-MS to identify and quantify volatile and non-volatile compounds. Its main volatile constituents were α-pinene (54.9%), followed by α-thujene (4.4%) and α-phellandren-8-ol (4.0%). Pentacyclic triterpenoids such as β-boswellic acids and their derivatives were quantified by UHPLC-MS and their content was shown to reach around 22% of the gum resin. Since some of the volatile and non-volatile compounds identified in this work are known to possess biological effects, the bioactivities of B. dalzielii ethanolic extract, essential oil, as well as fractions of the oil and extract were evaluated. Some of these samples exhibited interesting anti-inflammatory properties, and their antioxidant, anti-ageing and skin-bleaching activities were also tested.

Phytochemistry. 2023 Sep;213():113751.
PMID: 37307887 [PubMed - indexed for MEDLINE]


[Chemical constituents of diterpenoids from Boswellia carterii].
Wang RY, Xia H, Wang YX, Huang H, Wang BK, DU M, Song YL, Zhao YF, Zheng J, Huo HX, Li J

This paper explored the chemical constituents of Boswellia carterii by column chromatography on silica gel, Sephadex LH-20, ODS column chromatography, and semi-preparative HPLC. The structures of the compounds were identified by physicochemical properties and spectroscopic data such as infrared radiation(IR), ultra violet(UV), mass spectrometry(MS), and nuclear magnetic resonance(NMR). Seven diterpenoids were isolated and purified from n-hexane of B. carterii. The isolates were identified as(1S,3E,7E,11R,12R)-11-hydroxy-1-isopropyl-4,8,12-trimethyl-15-oxabicyclo[10.2.1]pentadeca-3,7-dien-5-one(1),(1R,3S,4R,7E,11E)-4,8,12,15,15-pentamethyl-14-oxabicyclo[11.2.1]hexadeca-7,11-dien-4-ol(2), incensole(3),(-)-(R)-nephthenol(4), euphraticanoid F(5), dilospirane B(6), and dictyotin C(7). Among them, compounds 1 and 2 were new and their absolute configurations were determined by comparison of the calculated and experimental electronic circular dichroisms(ECDs). Compounds 6 and 7 were obtained from B. carterii for the first time.

Zhongguo Zhong Yao Za Zhi. 2023 May;48(9):2464-2470.
PMID: 37282875 [PubMed - indexed for MEDLINE]


New verticillane-diterpenoid as potent NF-κB inhibitor isolated from the gum resin of Boswellia sacra.
Yuan Z, Liu D, Zhang B, Cao S, Yao T, Zhao Q, Qiu F, Zhao F

Two new verticillane-diterpenoids (1 and 2) were isolated from the gum resin Boswellia sacra. Their structures were elucidated by physiochemical and spectroscopic analysis, as well as ECD calculation. In addition, the in vitro anti-inflammatory activities of the isolated compounds were evaluated by determining the inhibitory effects on lipopolysaccharide (LPS)-induced NO production in RAW 264.7 mouse monocyte-macrophages. The results showed that compound 1 exhibited significant inhibitory effect on NO generation with an IC value of 23.3 ± 1.7 μM suggesting that it might be a candidate for an anti-inflammatory agent. Furthermore, 1 potently inhibited the release of inflammatory cytokines IL-6 and TNF-α induced by LPS in a dose-dependent manner. Using Western blot and Immunofluorescence methods, compound 1 was found to inhibit inflammation mainly by restraining the activation of NF-κB pathway. And in the MAPK signaling pathway, it was found to have inhibitory effects on the phosphorylation of JNK and ERK proteins and have no effect on the phosphorylation of p38 protein.

Fitoterapia. 2023 Apr;166():105460.
PMID: 36801349 [PubMed - indexed for MEDLINE]


Synthesis and antidepressant-like effects of new 5-epi-incensole and 5-epi- incensole acetate in chronic unpredictable mild stress model of depression; behavioural and biochemical correlates.
Avula SK, Khan A, Halim SA, Rehman NU, Karim N, Khan I, Csuk R, Das B, Al-Harrasi A

In the current investigation, 5-epi-incensole (3) and 5-epi-incensole acetate (5) were synthesized from the most potent anti-depressant constituents incensole (1) and incensole acetate (2) of Boswellia papyrifera Hochst. The resulting compounds were evaluated for their ability to ameliorate depressive symptoms in forced swim test (FST) and tail suspension test (TST) in chronic unpredictable mild stress (CUMS) induced depression paradigm. The results demonstrated that compounds 3 and 5 at the doses of 1 and 3 mg/kg administered for 28 days, significantly reduced the immobility time in FST and TST and were devoid of any effect on locomotor activity in the open field test (OFT). Both compounds 3 and 5 also reversed CUMS-induced reduction in the weight of animals and aversion in sucrose preference. The tested compounds also inhibited Monoamine oxidase-A (MAO) enzyme and increased the levels of brain noradrenaline (NA) and 5-Hydroxytryptamine (5-HT), decreased plasma corticosterone and pro-inflammatory cytokines including TNF-α, IL-6 in hippocampal homogenates. Compounds 3 and 5 also significantly reduced the increased lipid peroxidation and nitrite levels; decreased glutathione levels, and catalase activities in mice undergoing CUMS protocol. The binding mode of compounds 3 and 5 was predicted at the monoamine oxidase substrate binding site by molecular docking having docking scores of > -6 kcal/mol. Taken together these data revealed that compounds 3 and 5 exerted antidepressant-like effects in chronic unpredictable mild stress-induced depression paradigm and are likely mediated via modulating the central oxidative stress, MAO-A activity with a consequent increase in brain NA and 5-HT levels in inflammatory pathways.

Biomed Pharmacother. 2022 Dec;156():113960.
PMID: 36411640 [PubMed - indexed for MEDLINE]


Comparison of Volatile Constituents Present in Commercial and Lab-Distilled Frankincense () Essential Oils for Authentication.
Ojha PK, Poudel DK, Rokaya A, Satyal R, Setzer WN, Satyal P

A comparative analysis of the chemical constituents present in twenty-one commercial and two lab-distilled frankincense () essential oils was carried out using gas chromatography-mass spectrometry (GC-MS) and chiral gas chromatography-mass spectrometry (CGC-MS) for authentication. Out of the twenty-one commercial samples, six were adulterated with synthetic limonene, three were contaminated with synthetic octyl acetate, three were adulterated with castor oil, and two samples each were contaminated with frankincense resin and species, respectively, and one was contaminated with the species. Additionally, one sample was contaminated with phthalates as well as a cheap essential oil with similar compositions. Furthermore, one sample was adulterated with copaiba resin and frankincense resin in combination with synthetic octyl acetate. Additionally, one was contaminated with species, which was further adulterated with castor oil and frankincense resin. To the best of our knowledge, this is the first report to compare the enantiomeric distribution of chiral terpenoids present in commercial frankincense essential oil with lab-distilled frankincense oil for authentication. The CGC-MS analysis showed the presence of a total of eight chiral terpenoids in lab-distilled frankincense essential oils, which can be used as chemical fingerprints for the authentication of frankincense essential oil.

Plants (Basel). 2022 Aug;11(16):.
PMID: 36015437 [PubMed - as supplied by publisher]


Tracing analgesic constituents from crude and vinegar-processed resin of Boswellia carterii by integrating ultra-performance liquid chromatography tandem mass spectrometry-based determination, analgesic evaluation in mice, and gray relationship analysis.
Xie X, Liu Q, Zhu F, Zhang T, Xu X, Tao Y

The analgesic effect of the resin of Boswellia carterii (BC) is well known; however, the constituents that contribute to the analgesic effect remain elusive. The current study integrates ultrasonic-assisted extraction, quantitative determination, analgesic evaluation in rats, and gray relationship analysis for tracing analgesic constituents from the resin of BC. First, a robust and precise ultra-performance liquid chromatography tandem mass spectrometry approach with multiple reaction monitoring mode was developed for the simultaneous quantification of seven major constituents in crude and vinegar-processed resin of BC. Glycyrrhetinic acid was chosen as the internal standard. The approach showed good linearity. The intra- and inter-day precisions of each constituent were within 3.0%. The recoveries of each constituent were in the range of 96.4-102.7%. The approach was then applied to determine the seven constituents in 10 batches of crude and vinegar-processed resin of BC. Second, the analgesic effects of crude and vinegar-processed resin of BC were assessed in mice. Third, chemometrics methods, gray relationship analysis, and partial least squares regression were employed for determining the relationship between the contents of seven constituents and their analgesic effects. 11-Keto-β-boswellic acid, 3-acetyl-β-boswellic acid, 3-acetyl-α-boswellic acid, 3-acetyl-11-keto-β-boswellic acid, and β-sitosterol were identified as the key analgesic constituents of BC.

Biomed Chromatogr. 2022 Sep;36(9):e5430.
PMID: 35727297 [PubMed - indexed for MEDLINE]


Pilot Study of Trace Elements in the Infusion of Medicinal Plants Used for Diabetes Treatment.
Brima EI, Siddeeg SM

The purpose of this study was to evaluate trace element contents in different medicinal plants used for diabetes treatments by residents in Asir region. Five medicinal plants-Tut leaves (), olive leaves (), clove (), Luban Dhakar (), and Karela or bitter melon ()-were collected from two cities, Khamis Mushait and Abha, in the Asir region, Saudi Arabia. Infusions (hot water extracts) were obtained from each plant, and elemental analysis was conducted using inductively coupled plasma mass spectrometry (ICP-MS). Fourteen elements (Al, Cr, Mn, Fe, Co, Ni, Cu, Zn, As, Se, Sr, Cd, Ba, and Pb) were measured in all plants. The results revealed that the fourteen elements were present at different levels (µg/g) in all plants. exhibited high levels of essential (Mn (251.4), Co (1.18), Cu (54.64), and Se (2.18)) and toxic elements (Al (39.20), As (0.57), Cd (0.33), and Pb (4.48)), followed by (Mn (736.36)) and (Pb (0.93)), which exceeded the PMTDI in traditional doses used for diabetes treatments. However, and did not exceed the daily guideline values for all elements. Based on our findings, we cautiously recommend the latter two plants for the traditional treatment of diabetes, because they are not considered as source of harm based on their levels of elements. Their use should be restricted by comprehensive compound analysis to guarantee their safe use.

Int J Anal Chem. 2022;2022():3021396.
PMID: 35478694 [PubMed - as supplied by publisher]


Synergistic combination of PMBA and 5-fluorouracil (5-FU) in targeting mutant KRAS in 2D and 3D colorectal cancer cells.
Qayum A, Magotra A, Shah SM, Nandi U, Sharma PR, Shah BA, Singh SK

β-Boswellic acid (β-BA), a potent NF-kB signaling pathway inhibitor, has shown synergistic anti-cancerous activity (NCT03149081, NCT00243022 and NCT02977936) in various clinical trials as complementary therapies. The study has been conducted to investigate the effect and efficacy of 2-pyridin-4-yl methylene β-boswellic acid (PMBA) and 5-Flourouracil (5-FU) in combination therapy for the treatment of KRAS mutant colon cancer. Analysis of isobologram showed synergistic combination index (CI > 1) of PMBA and 5-FU against the HCT-116 and SW-620 cell lines. The growth-inhibiting PMBA also caused apoptosis mediating effects with dose-dependent increase in caspase-3 activity, while inhibiting the formation of colonies in combination with 5-FU. As evident, PMBA affected colorectal 3D CSC properties including the ability to self-renew along with the expression of multi-drug resistance genes, ., ABCB1, ABCC1 and ALDH1A1, ALDH1A2, ALDH1A3, ALDH3A1, and CSC markers like CD44, CD166, EPCAM, OCT-4, SOX-2, and NANOG compared with those in 2D model explaining the expression pattern of oncogenic KRAS mutation. When examined for plasma level of PMBA (20 mg) and PMBA+5-FU (20 + 40 mg), a time-dependent increase in the level of the drug (5-FU) was detected, indicating its absorption and bioavailability with excellent half-life of the PMBA for both routes of administration (IV and Oral), thereby indicating a new adjuvant therapy for KRAS mutant colon cancer.

Heliyon. 2022 Apr;8(4):e09103.
PMID: 35445157 [PubMed - as supplied by publisher]


Frankincense diterpenes as a bio-source for drug discovery.
Hussain H, Rashan L, Hassan U, Abbas M, Hakkim FL, Green IR

INTRODUCTION: Frankincense ( sp.) gum resins have been employed as an incense in cultural and religious ceremonies for many years. Frankincense resin has over the years been employed to treat depression, inflammation, and cancer in traditional medicines.

AREAS COVERED: This inclusive review focuses on the significance of frankincense diterpenoids, and in particular, incensole derivatives for establishment future treatments of depression, neurological disorders, and cancer. The authors survey the available literature and furnish an overview of future perspectives of these intriguing molecules.

EXPERT OPINION: Numerous diterpenoids including cembrane, prenylaromadendrane, and the verticillane-type have been isolated from various resins. Cembrane-type diterpenoids occupy a crucial position in pharmaceutical chemistry and related industries because of their intriguing biological and encouraging pharmacological potentials. Several cembranes have been reported to possess anti-Alzheimer, anti-inflammatory, hepatoprotective, and antimalarial effects along with a good possibility to treat anxiety and depression. Although some slight drawbacks of these compounds have been noted, including the selectivity of these diterpenoids, there is a great need to address these in future research endeavors. Moreover, it is vitally important for medicinal chemists to prepare libraries of incensole-heterocyclic analogs as well as hybrid compounds between incensole or its acetate and anti-depressant or anti-inflammatory drugs.

Expert Opin Drug Discov. 2022 May;17(5):513-529.
PMID: 35243948 [PubMed - indexed for MEDLINE]


Taxonomical Investigation, Chemical Composition, Traditional Use in Medicine, and Pharmacological Activities of Flueck.
Miran M, Amirshahrokhi K, Ajanii Y, Zadali R, Rutter MW, Enayati A, Movahedzadeh F

Aromatic oleo-gum-resin secreted from , reputed as frankincense, is widely used in traditional medicine to treat Alzheimer's disease, gastric disorders, hepatic disorders, etc. Frankincense is also used in the cosmetic, perfume, and beverage and food industries. Frankincense is a rich resource for bioactive compounds, especially boswellic acids and derivatives. Although several reports have described frankincense's constituents and pharmacological activities, there is no comprehensive study that covers the valuable information on this species. Therefore, the current review will focus on the phytochemistry, traditional uses, and pharmacological activities of .

Evid Based Complement Alternat Med. 2022;2022():8779676.
PMID: 35222678 [PubMed - as supplied by publisher]


Chemical composition and antimicrobial activity of oleo-gum-resin essential oil extracted by superheated steam.
Ayub MA, Hanif MA, Blanchfield J, Zubair M, Abid MA, Saleh MT

Oleo-gum-resin is a complex mixture of essential oils, polysaccharides, and resin acids. The objectives of the present study were to evaluate the variation in chemical components and antimicrobial activity of essential oils extracted by superheated steam at various temperatures. The optimum essential oil yield was obtained at the highest superheated steam temperature (210 °C). In total, twenty-one compounds were quantified by GC-MS with α-pinene as the major compound, followed by α-thujene, -verbenol, β-thujone, -cymene, -cymene, and sabinene. Antimicrobial activity was performed by disc diffusion, resazurin microtitre-plate and micro-dilution broth susceptibility assays in which essential oil extracted at 150 °C and 180 °C revealed the highest antibacterial and antifungal activity, respectively. It is concluded that superheated steam is an effective method for the isolation of essential oil from oleo-gum-resin that improves the recovery of essential oil as well as antimicrobial activity.

Nat Prod Res. 2023 Jul;37(14):2451-2456.
PMID: 35200079 [PubMed - indexed for MEDLINE]


Five terpenoids from the gum resin of Boswellia carterii and their cytotoxicity.
Feng Y, Zhang Q, Sun L

One undescribed tetracyclic triterpene (boswellicarin A), four undescribed pentacyclic triterpenes (boswellicarterins A-C) and one undescribed prenylaromadendrane-type diterpene (boscarterin A) were isolated from the gum resin of Boswellia carterii Birdw. (Burseraceae). Their structures were elucidated from NMR and HRESIMS spectroscopic data and ECD spectra. Boswellicarterins A-C and boscarterin A displayed weak and selective cytotoxicity against three human cancer cells (HepG2, A549 and MCF-7) by MTT assay.

Fitoterapia. 2021 Oct;154():105017.
PMID: 34418492 [PubMed - indexed for MEDLINE]


Analysis of Boswellic Acid Contents and Related Pharmacological Activities of Frankincense-Based Remedies That Modulate Inflammation.
Börner F, Werner M, Ertelt J, Meins J, Abdel-Tawab M, Werz O

Extracts of frankincense, the gum resin of species, have been extensively used in traditional folk medicine since ancient times and are still of great interest as promising anti-inflammatory remedies in Western countries. Despite their common therapeutic use and the intensive pharmacological research including studies on active ingredients, modes of action, bioavailability, pharmacokinetics, and clinical efficacy, frankincense preparations are available as nutraceuticals but have not yet approved as a drug on the market. A major issue of commercially available frankincense nutraceuticals is the striking differences in their composition and quality, especially related to the content of boswellic acids (BAs) as active ingredients, mainly due to the use of material from divergent species but also because of different work-up and extraction procedures. Here, we assessed three frequently used frankincense-based preparations for their BA content and the interference with prominent pro-inflammatory actions and targets that have been proposed, that is, 5-lipoxygenase and leukotriene formation in human neutrophils, microsomal prostaglandin E synthase-1, and inflammatory cytokine secretion in human blood monocytes. Our data reveal striking differences in the pharmacological efficiencies of these preparations in inflammation-related bioassays which obviously correlate with the amounts of BAs they contain. In summary, high-quality frankincense extracts display powerful anti-inflammatory effectiveness against multiple targets which can be traced back to BAs as bioactive ingredients.

Pharmaceuticals (Basel). 2021 Jul;14(7):.
PMID: 34358086 [PubMed - as supplied by publisher]


Chemical Composition, Antibacterial Activity, and Antibiotic Potentiation of Flueck. Oleoresin Extracts from the Dhofar Region of Oman.
Rashan L, White A, Haulet M, Favelin N, Das P, Cock IE

The emergence of MDR bacterial pathogens has directed antibiotic discovery research towards alternative therapies and traditional medicines. oleoresin (frankincense) was used to treat bacterial infections in traditional Arabian and Asian healing systems for at least 1000 years. Despite this, extracts have not been rigorously tested for inhibitory activity against gastrointestinal pathogens or bacterial triggers of autoimmune diseases. Solvent extracts were prepared from oleoresins obtained from three regions near Salalah, Oman. MIC values were quantified against gastrointestinal pathogens and bacterial triggers of selected autoimmune diseases by disc diffusion and broth dilution methods. The antibacterial activity was also evaluated in combination with conventional antibiotics, and the class of interaction was determined by ΣFIC analysis. Isobolograms were used to determine the optimal ratios for synergistic combinations. Toxicity was evaluated by ALA and HDF cell viability bioassays. The phytochemical composition of the volatile components of all extracts was identified by nontargeted GC-MS headspace analysis. All methanolic extracts inhibited the growth of all of the bacteria tested, although the extracts prepared using Najdi oleoresin were generally more potent than the Sahli and Houjari extracts. Combinations of the methanolic extracts and conventional antibiotics were significantly more effective in inhibiting the growth of several bacterial pathogens. In total, there were 38 synergistic and 166 additive combinations. Approximately half of the synergistic combinations contained tetracycline. All extracts were nontoxic in the ALA and HDF cell viability assays. Nonbiased GC-MS headspace analysis of the methanolic extracts putatively identified a high diversity of monoterpenoids, with particularly high abundances of -pinene. The antibacterial activity and lack of toxicity of the extracts indicate their potential in the treatment and prevention of gastrointestinal and autoimmune diseases. Furthermore, the extracts potentiated the activity of several conventional antibiotics, indicating that they may contain resistance-modifying compounds.

Evid Based Complement Alternat Med. 2021;2021():9918935.
PMID: 34122610 [PubMed - as supplied by publisher]


Prenylaromadendrane-type diterpenoids from the gum resin of flueck and their cytotoxic effects.
Wang JJ, Suo XY, Sun HR, Wang X, Lin MB, Wang JH, Jiang JD, Ji TF

Two new prenylaromadendrane-type diterpenoids, and three known analogues, were isolated from the ethanol extract of the gum resin of Flueck. The structures of the new compounds were elucidated using 1 D and 2 D NMR spectroscopic analyses, mass spectrometric data, circular dichroism spectra, and comparison with the other compounds in the literature. One diterpenoid represents the first example of an acetoxyl-substituted prenylaromadendranoid in frankincense. All compounds exhibited notable cytotoxicity against human malignant glioma (U87-MG) cell line, with inhibitory rates exceeding that of the positive control 5-fluorouracil. However, nitric oxide inhibition induced by lipopolysaccarides was not observed in primary mouse peritoneal macrophages.

Nat Prod Res. 2022 Nov;36(21):5400-5406.
PMID: 34121549 [PubMed - indexed for MEDLINE]


[One new cembranoid diterpene from gum resin of Boswellia carterii].
Xia H, Wang CC, Wang RY, Liang NY, Wang XY, Song YL, Zhao YF, Huo HX, Li J

This study aims to study the chemical components from the gum resin of Boswellia carterii. Five cembranoid diterpenes were isolated from the gum resin of B. carterii by various of column chromatographies including silica gel, Sephadex LH-20, and semi-preparative HPLC. Their structures were identified on the basis of physicochemical properties, mass spectrometry(MS), nuclear magnetic resonance(NMR), Ultraviolet(UV) and infrared(IR) spectroscopic data. These compounds were identified as(1S,2E,4R,5S,7E,11E)-4-methoxy-5-hydroxycembrane(1),(1R~*,4R~*,5E,8E,12E,15E)-4-hydroxycembra-5,8,12,15-tetraene(2), cembrene A(3),(3S,4S,7R)-4-hydroxycembrane(4), and pavidolide D(5). Compound 1 was a new compound. Compounds 2, 4, and 5 were obtained from the gum resin of B. carterii for the first time. Compound 2 showed weak inhibition on the human liver cancer cell line HepG2.

Zhongguo Zhong Yao Za Zhi. 2021 May;46(9):2215-2219.
PMID: 34047123 [PubMed - indexed for MEDLINE]


Nano-Magnetic NiFeO and Its Photocatalytic Oxidation of Vanillyl Alcohol-Synthesis, Characterization, and Application in the Valorization of Lignin.
Al-Hunaiti A, Ghazzy A, Sweidan N, Mohaidat Q, Bsoul I, Mahmood S, Hussein T

Here, we report on a phyto-mediated bimetallic (NiFeO) preparation using a extract, which was characterized by XRD, FT-IR, TGA, electron microscopy, magnetic spectroscopy, and Mössbauer spectroscopy measurements. The prepared nano-catalysts were tested for oxidation of lignin monomer molecules-vanillyl alcohol and cinnamyl alcohol. In comparison with previously reported methods, the nano NiFeO catalysts showed high photocatalytic activity and selectivity, under visible light irradiation with a nitroxy radical initiator (2,2,6,6-tetramethylpiperidinyloxy or 2,2,6,6-tetramethylpiperidine 1-oxyl; TEMPO) at room temperature and aerobic conditions. The multifold advantages of the catalyst both in terms of reduced catalyst loading and ambient temperature conditions were manifested by higher conversion of the starting material.

Nanomaterials (Basel). 2021 Apr;11(4):.
PMID: 33920911 [PubMed - as supplied by publisher]


Sacraoxides A-G, Bioactive Cembranoids from Gum Resin of .
Zhang B, Liu D, Ji W, Otsuki K, Higai K, Zhao F, Li W, Koike K, Qiu F

Seven undescribed cembranoids, sacraoxides A-G (-) were isolated from the gum resin of . Their structures were elucidated by extensive physicochemical and spectroscopic analysis, as well as ECD calculation, modified Mosher's method and X-ray diffraction crystallography. Compounds and exhibited inhibitory activities on nitric oxide (NO) production induced by lipopolysaccharide in RAW264.7 cells with IC values of 24.9 ± 1.7 and 36.4 ± 2.9 M.

Front Chem. 2021;9():649287.
PMID: 33869144 [PubMed - as supplied by publisher]


Roles of ethylene, jasmonic acid, and salicylic acid and their interactions in frankincense resin production in Boswellia sacra Flueck. trees.
Yamamoto F, Iwanaga F, Al-Busaidi A, Yamanaka N

The roles of ethylene, jasmonic acid, and salicylic acid and their interactions in frankincense resin production in Boswellia sacra trees growing in the drylands of Oman were studied. On March 18 (Experiment 1) and September 17 (Experiment 2), 2018, 32-year-old B. sacra trees with multiple trunks were selected at the Agricultural Experiment Station, Sultan Qaboos University, Oman. Various lanolin pastes containing Ethrel, an ethylene-releasing compound; methyl jasmonate; sodium salicylate; and combinations of these compounds were applied to debarked wounds 15 mm in diameter on the trunks. After a certain period, the frankincense resin secreted from each wound was harvested and weighed. The anatomical characteristics of the resin ducts were also studied in the bark tissue near the upper end of each wound. The combination of Ethrel and methyl jasmonate greatly enhanced frankincense resin production within 7 days in both seasons. The application of methyl jasmonate alone, sodium salicylate alone or a combination of both did not affect resin production. These findings suggest a high possibility of artificial enhancement of frankincense resin production by the combined application of Ethrel and methyl jasmonate to B. sacra trees.

Sci Rep. 2020 Oct;10(1):16760.
PMID: 33028915 [PubMed - indexed for MEDLINE]


Extraction of 11-Keto-β -Boswellic Acid from Indian Olibanum by Contemporary Extraction Modes: Optimization and Validation of HPTLC.
Abidin L, Singla P, Kausar H, Mujeeb M, Rahman A, Aqil M, Najmi AK

BACKGROUND: Boswellic acids are the main constituents of Boswellia serrata gum. These comprise of four pentacyclic triterpenes, 11-keto-β-boswellic acid (KBA) being one of them.

OBJECTIVES: Comparing the extraction efficiency of KBA through microwave-assisted extraction (MAE) and ultrasound-assisted extraction (UAE) followed by optimizing the extraction process using response surface methodology (RSM) and validation of HPTLC.

METHODS: UAE and MAE of KBA were carried out employing methanol as an extracting solvent. To figure out the better mode of extraction, single factorial experiments were conducted for further optimization. Design expert software was used for optimization purposes where solvent to drug ratio, extraction temperature and extraction time were taken as input variables. Quantification of KBA in each extract was done through High-Performance Thin Layer Chromatography (HPTLC), and the method was validated as per International Council for Harmonization (ICH) guidelines.

RESULTS: UAE stood out to be a better mode of extraction for KBA. Solvent to drug ratio of 20.42 mL/gram, extraction temperature of 44.01°C and extraction time of 11.54 minutes were established as optimum conditions, which yielded 8.44%w/w of KBA. Regarding HPTLC, the Rf value of KBA was measured, and the correlation coefficient was calculated from the standard curve. Accuracy, precision and recovery were found within limits.

CONCLUSION: From this study, it was concluded that a non-thermal method is a better choice of extraction for KBA. All the input variables significantly affected KBA content, which was confirmed by model fitting. Moreover, the HPTLC method was developed for the quantification of KBA, which was found to be accurate, reliable and highly sensitive.

Comb Chem High Throughput Screen. 2021;24(8):1309-1321.
PMID: 32928084 [PubMed - indexed for MEDLINE]


Bioactive cembrane diterpenoids from the gum resin of Boswellia carterii.
Yu J, Zhao L, Sun X, Geng Y, Wang X

Eight new cembrane-type diterpenoids, boscartins AP-AW (1-8) were obtained from the gum resin of Boswellia carterii. Among which, six ones (2-7) were isomers, with one hydroxy group and two double bonds migrating along the carbocycle. The structures were elucidated by spectroscopic examination. All isolates were evaluated for anti-inflammatory activity and hepatoprotective activity by cell models of LPS-induced RAW 264.7 mouse peritoneal macrophages and APAP-induced HepG2 cells, respectively. As for anti-inflammatory activity assay, compound 1 exhibited potent activity against NO production (IC of 13.1 μM), with the other ones exhibiting weak anti-inflammatory activity (IC > 50 μM). As for hepatoprotective activity assay, compound 1 exhibited more significant activity (inhibition rate of 30.7%) than that of the positive control (bicyclol, inhibition rate of 27.2%), and compounds 4, and 6 showed nearly the same activities as the control (inhibition rates of 26.7% and 25.9%, respectively), with the other ones exhibiting weak hepatoprotective activity.

Fitoterapia. 2020 Oct;146():104699.
PMID: 32763364 [PubMed - indexed for MEDLINE]


Bioguided chemical study of Hutch. (Burseraceae) for antibacterial agents and a new glucopyranoxylmethoxybenzyle.
Tegasne C, Kapche GDWF, Mawabo IK, Talla RM, Jouda JB, Happi GM, Lenta BN, Frese M, Abegaz BM, Sewald N

Stem barks of are used traditionally for the treatment of various bacterial infections. A bioassay guided fractionation of the MeOH-CHCl (1/1, v/v) stem barks extract led to the isolation of fourteen compounds , identified based on spectroscopic data. Dalzienoside ( is reported here for the first time. The broth microdilution method was used to evaluate the antibacterial activity of the crude extract, fractions and compounds against six bacterial strains. The crude extract exhibited moderate antibacterial activity with MIC of 250 μL/ml; two fractions showed significant activities with MICs ranging from 7.8 to 125 μg/ml, while -boswellic acid (), -boswellic acid (), acetyl-11-keto--boswellic acid () from these fractions exhibited strong activities with MIC value of 3.125 µg/mL against and . This study gives insight into the antibacterial constituents of the stem bark of and justifies its use in ethnomedicine.

Nat Prod Res. 2021 Dec;35(23):5199-5208.
PMID: 32729328 [PubMed - indexed for MEDLINE]


Ten undescribed cembrane-type diterpenoids from the gum resin of Boswellia sacra and their biological activities.
Wang JJ, Sun HR, Suo XY, Xue Wang , Sun H, Wang XL, Jiang JD, Ji TF

Ten undescribed cembrane-type diterpenes boscartins AL-AU, as well as five known analogues were isolated from Boswellia sacra Flueck. The relative configurations of these boscartins were established by extensive spectroscopic analysis of NMR spectra, IR and MS. The absolute configurations of boscartin AL, boscartin AN and isoincensole oxide were unequivocally assigned by single crystal X-ray diffraction. Meanwhile, the absolute configurations of boscartin AM, boscartin AP and boscartin AQ were determined by an empirical in situ formed Rh-complex ECD method. Biological evaluations showed that four compounds exhibited obvious hepatoprotective activities against paracetamol-induced HepG2 cell damage at 10 μM. Regarding neuroprotective activity, some isolates displayed moderate to evident protective effects against glutamate-induced toxicity in primary cultured fetal rat cortical neurons or oxygen-glucose deprivation toxicity in SK-N-SH Cells at 10 μM.

Phytochemistry. 2020 Sep;177():112425.
PMID: 32535347 [PubMed - indexed for MEDLINE]


[Chemical and pharmacological progress on a Tibetan folk medicine formula Bawei Chenxiang Powder].
Wang JM, Cao JR, Gao XL, Kang LL, Yang ZZ, Sha-Na W, Li JJ, Tu PF, Chai XY

Bawei Chenxiang Powder is a traditional Tibetan folk medicine formula, consisting of resinous wood of Aquilaria sinensis, kernel of Myristica fragrans, fruit of Choerospondias axillaris, travertine, resin of Boswellia carterii or B. bhaw-dajiana, stem of Aucklandia lappa, fruit of Terminalia chebula(roasted), and flower of Gossampinus malabarica. It has the function of clearing heart heat, nourishing heart, tranquilizing mind, and inducing resuscitation, which has been used for the treatment of coronary heart disease and angina pectoris. Modern research shows that the medicine materials of this formula mainly contain terpenoids like sesquiterpenes and triterpenes and polyphenols like flavonoids, lignans, and tannins, displaying some pharmacological activities such as anti-myocardial ischemia, anti-cerebral ischemia, and spatial learning and memory promotion. This review summaries the traditional uses, chemical constituents, and pharmacological activities research progress, hopefully to provide a reference for clarification of its pharmacological active ingredients.

Zhongguo Zhong Yao Za Zhi. 2020 May;45(9):2063-2072.
PMID: 32495555 [PubMed - indexed for MEDLINE]


Triterpenic Acids as Non-Competitive α-Glucosidase Inhibitors from with Structure-Activity Relationship: In Vitro and In Silico Studies.
Ur Rehman N, Halim SA, Al-Azri M, Khan M, Khan A, Rafiq K, Al-Rawahi A, Csuk R, Al-Harrasi A

Fourteen triterpene acids, viz., three tirucallane-type (-), eight ursane-type (-), two oleanane-type (, ) and one lupane type (), along with boswellic aldehyde (), α-amyrine (), epi-amyrine (), straight chain acid (), sesquiterpene () and two cembrane-type diterpenes (, ) were isolated, first time, from the methanol extract of resin. Compound () was isolated for first time as a natural product, while the remaining compounds (‒) were reported for first time from The structures of all compounds were confirmed by advanced spectroscopic techniques including mass spectrometry and also by comparison with the reported literature. Eight compounds (- and ) were further screened for in vitro α-glucosidase inhibitory activity. Compounds - and showed significant activity against α-glucosidase with IC values ranging from 9.9-56.8 μM. Compound (IC = 9.9 ± 0.48 μM) demonstrated higher inhibition followed by (IC = 14.9 ± 1.31 μM), (IC = 20.9 ± 0.05 μM) and (IC = 56.8 ± 1.30 μM), indicating that carboxylic acid play a key role in α-glucosidase inhibition. Kinetics studies on the active compounds - and were carried out to investigate their mechanism (mode of inhibition and dissociation constants ). All compounds were found to be non-competitive inhibitors with values in the range of 7.05 ± 0.17-51.15 ± 0.25 µM. Moreover, in silico docking was performed to search the allosteric hotspot for ligand binding which is targeted by our active compounds investigates the binding mode of active compounds and it was identified that compounds preferentially bind in the allosteric binding sites of α-glucosidase. The results obtained from docking study suggested that the carboxylic group is responsible for their biologic activities. Furthermore, the α-glucosidase inhibitory potential of the active compounds is reported here for the first time.

Biomolecules. 2020 May;10(5):.
PMID: 32408614 [PubMed - indexed for MEDLINE]


Structural and mechanistic insights into 5-lipoxygenase inhibition by natural products.
Gilbert NC, Gerstmeier J, Schexnaydre EE, Börner F, Garscha U, Neau DB, Werz O, Newcomer ME

Leukotrienes (LT) are lipid mediators of the inflammatory response that are linked to asthma and atherosclerosis. LT biosynthesis is initiated by 5-lipoxygenase (5-LOX) with the assistance of the substrate-binding 5-LOX-activating protein at the nuclear membrane. Here, we contrast the structural and functional consequences of the binding of two natural product inhibitors of 5-LOX. The redox-type inhibitor nordihydroguaiaretic acid (NDGA) is lodged in the 5-LOX active site, now fully exposed by disordering of the helix that caps it in the apo-enzyme. In contrast, the allosteric inhibitor 3-acetyl-11-keto-beta-boswellic acid (AKBA) from frankincense wedges between the membrane-binding and catalytic domains of 5-LOX, some 30 Å from the catalytic iron. While enzyme inhibition by NDGA is robust, AKBA promotes a shift in the regiospecificity, evident in human embryonic kidney 293 cells and in primary immune cells expressing 5-LOX. Our results suggest a new approach to isoform-specific 5-LOX inhibitor development through exploitation of an allosteric site in 5-LOX.

Nat Chem Biol. 2020 Jul;16(7):783-790.
PMID: 32393899 [PubMed - indexed for MEDLINE]


Cembrane-type diterpenoids from the gum resin of and their biological activities.
Sun X, Geng Y, Wang X, Qin D, Yu J

Eight new cembrane-type diterpenoids, boscartins AH-AK (1-8), along with two known ones (9-10), were isolated from the gum resin of . Compounds 1-3 were characteristic of high oxidation assignable to three epoxy groups, while compounds 4-8 were characteristic of two epoxy groups. Spectroscopic examination was used to elucidate their structures. All isolates were evaluated for antiproliferative activity against HCT-116 human colon cancer cells, anti-inflammatory activity against nitric oxide (NO) production, and hepatoprotective activity . All of them showed weak antiproliferative activity (IC > 100 μM), 8 exhibited potent inhibitory effects on NO production (IC of 14.8 μM), with the others showing weak anti-inflammatory activity (IC > 30 μM), and 1 exhibited more potent hepatoprotective activity than the positive control, bicyclol, at 10 μM against the damage induced by paracetamol in HepG2 cells.

RSC Adv. 2020 Jan;10(2):746-755.
PMID: 35494443 [PubMed - as supplied by publisher]


Chemical Composition and in Vitro Cytotoxic Screening of Sixteen Commercial Essential Oils on Five Cancer Cell Lines.
Najar B, Shortrede JE, Pistelli L, Buhagiar J

The in vitro cytotoxic activity on human cancer cell lines of sixteen commercial EOs such as Aloysia citriodora, Boswellia sacra, Boswellia serrata, Cinnamomum zeylanicum, Cistus ladanifer, Citrus × aurantium, Citrus limon, Citrus sinensis, Cymbopogon citratus, Foeniculum vulgare, Illicium verum, Litsea cubeba, Satureja montana, Syzygium aromaticum, Thymus capitatus and Thymus vulgaris was performed using the MTT reduction assay. The screening was carried out on human cancer cells of breast adenocarcinoma (MCF7, T47D and MDA-MB-231), chronic myelogenous erythroleukemia (K562) and neuroblastoma cell lines (SH-SY5Y). C. zeylanicum and L. cubeba EOs were the most active on almost all the cell lines studied and thus could be promising as an anticancer agent. These two species showed a difference in their composition even though they belong to the Lauraceae family. Almost 57 % of the true cinnamon composition was made of (E)-cinnamaldehyde, while L. cubeba showed citral as the major compound (68.9 %). The K562 cells were the most sensitive to these oils with an IC ranging from 5.2 parts-per million (ppm) (C. zeylanicum) to 11.1 ppm (L. cubeba). The latter oil also showed an important cytotoxicity on MDA-MB-231 (13.4 ppm).

Chem Biodivers. 2020 Jan;17(1):e1900478.
PMID: 31713998 [PubMed - indexed for MEDLINE]


Chemical Composition of the Oleogum Resin Essential Oils of from Burkina Faso.
DeCarlo A, Johnson S, Ouédraogo A, Dosoky NS, Setzer WN

Frankincense, the oleogum resin from members of , has been used as medicine and incense for thousands of years, and essential oils derived from frankincense are important articles of commerce today. A new source of frankincense resin, from West Africa has been presented as a new, alternative source of frankincense. In this work, the oleogum resins from 20 different trees growing in Burkina Faso, West Africa were collected. Hydrodistillation of the resins gave essential oils that were analyzed by GC-MS and GC-FID. The essential oils were dominated by α-pinene (21.0%-56.0%), followed by carvone (2.1%-5.4%) and α-copaene (1.8%-5.0%). Interestingly, there was one individual tree that, although rich in α-pinene (21.0%), also had a substantial concentration of myrcene (19.2%) and α-thujene (9.8%). In conclusion, the oleogum resin essential oil compositions of , rich in α-pinene, are comparable in composition to other frankincense essential oils, including , , and . Additionally, the differences in composition between samples from Burkina Faso and those from Nigeria are very slight. There is, however, a rare chemotype of that is dominated by myrcene, found both in Burkina Faso as well as Nigeria.

Plants (Basel). 2019 Jul;8(7):.
PMID: 31337133 [PubMed - as supplied by publisher]


Bioactive cembrane-type diterpenoids from the gum-resin of Boswellia carterii.
Wang YG, Ren J, Ma J, Yang JB, Ji T, Wang AG

Chemical examination of the gum-resin of Boswellia carterii resulted in the isolation and characterization of eighteen new cembrane-type diterpenoids, named as Boscartins P-AG (1-18) and eight known ones. Their structures were established on the basis of extensive spectroscopic (2D NMR, IR, CD, MS and X-ray) analysis in combination with modified Mosher's method. All compounds featured unusual 1,12-oxygenated tetrahydrofuran functionalities, and were evaluated for hepatoprotective activity against D-galactosamine-induced HL-7702 cell damage and cytotoxic activity against MCF-7 human breast cancer cell in vitro. Compounds 1, 6-10, 12-13, 16-17 and 21-25 (10 μM) showed some hepatoprotective activity against D-galactosamine-induced HL-7702 cell damage.

Fitoterapia. 2019 Sep;137():104263.
PMID: 31295512 [PubMed - indexed for MEDLINE]


Comparative Analysis of Pentacyclic Triterpenic Acid Compositions in Oleogum Resins of Different Species and Their In Vitro Cytotoxicity against Treatment-Resistant Human Breast Cancer Cells.
Schmiech M, Lang SJ, Werner K, Rashan LJ, Syrovets T, Simmet T

Pentacyclic triterpenic acids from oleogum resins of species are of considerable therapeutic interest. Yet, their pharmaceutical development is hampered by uncertainties regarding botanical identification and the complexity of triterpenic acid mixtures. Here, a highly sensitive, selective, and accurate method for the simultaneous quantification of eight boswellic and lupeolic acids by high-performance liquid chromatography with tandem mass spectrometry detection (HPLC-MS/MS) was developed. The method was applied to the comparative analysis of 41 oleogum resins of the species , , , , , , , , and . Multivariate statistical analysis of the data revealed differences in the triterpenic acid composition that could be assigned to distinct species and to their geographic growth location. Extracts of the oleogum resins exhibited cytotoxicity against the human, treatment-resistant, metastatic breast cancer cell line MDA-MB-231. Extracts from were the most potent ones with an average IC of 8.3 ± 0.6 µg/mL. The oleogum resin of the was further fractionated to enrich different groups of substances. The cytotoxic efficacy against the cancer cells correlates positively with the contents of pentacyclic triterpenic acids in extracts.

Molecules. 2019 Jun;24(11):.
PMID: 31181656 [PubMed - indexed for MEDLINE]


Analytical investigations on Boswellia occulta essential oils.
Ayubova M, Guelleh ZO, Guelleh MO, Brévard H, Baldovini N

Three samples of Boswellia occulta gum resin (Grades I, II and III) were analyzed by GC-MS and GC-FID. Fifty constituents could be identified, and several of them were isolated by flash chromatography and characterized by NMR. The combinatorial synthesis of homologous series of reference constituents permitted the unambiguous identification of five 1-methoxyalkanes and one 1-methoxyalkene. In addition, we measured the C content of one sample of essential oil and of a methoxyalkanes rich fraction and demonstrated that the origin of these materials is totally natural.

Phytochemistry. 2019 Aug;164():78-85.
PMID: 31102998 [PubMed - indexed for MEDLINE]


Compositional analysis of the essential oil of Boswellia dalzielii frankincense from West Africa reveals two major chemotypes.
DeCarlo A, Johnson S, Okeke-Agulu KI, Dosoky NS, Wax SJ, Owolabi MS, Setzer WN

Frankincense, an oleoresin produced by Boswellia species, has historical medicinal and religious significance, and is today used extensively for its essential oil. Boswellia dalzielii, a species found in West Africa, is one of the few frankincense species for which there is no information on the oleoresin essential oil. In order to correct this deficiency, the chemical compositions of the essential oil hydrodistilled from 21 samples of oleoresin taken directly from B. dalzielii trees in northern Nigeria, were analyzed by gas chromatography - mass spectrometry as well as chiral gas chromatography. In addition, a hierarchical cluster analysis was performed on the essential oil compositions from the 21 oleoresin samples from northern Nigeria as well as two samples from Ghana. The essential oil fractions obtained by hydrodistillation of B. dalzielii oleoresins were dominated by α-pinene (21.7-76.6%), followed by α-thujene (2.0-17.6%), myrcene (up to 35.2%), p-cymene (0.3-15.6%), and limonene (1.1-32.9%). The levorotatory enantiomers predominated for the monoterpenes with 98.1 ± 1.5% (-)-α-thujene, 99.2 ± 0.5% (-)-α-pinene, and 96.8 ± 1.4% (-)-β-pinene. Limonene showed the largest variation in enantiomeric distribution [67.3 ± 12.1% (-)-limonene]. The cluster analysis revealed two major chemotypes, one dominated by α-pinene and one much rarer chemotype rich in myrcene.

Phytochemistry. 2019 Aug;164():24-32.
PMID: 31071599 [PubMed - indexed for MEDLINE]


Boscartins L-O: Cembrane-type diterpenoids from the gum resin of Boswellia sacra Flueck.
Wang J, Zhen B, Hu J, Shi M, Wei C, Wang X, Sun H, Ji T

Four undescribed cembrane-type diterpenoids, boscartins L-O, as well as five known compounds (1S, 3R, 11S, 12R, 7E)-1,12-epoxy-4-methylenecembr-7- ene- 3,11-diol, isoincensole oxide, incensole oxide, incensole acetate and incensole oxide acetate were isolated from the gum resin of Boswellia sacra Flueck. (Burseraceae). The structures of these compounds were elucidated by extensive 1D and 2D NMR spectroscopic and mass spectrometric analysis, as well as comparisons with known compounds. The absolute configurations of the known compound (1S, 3R, 7E, 11S, 12R)-1,12-epoxy-4-methylenecembr-7-ene-3,11-diol was unequivocally confirmed by single-crystal X-ray diffraction analysis with Cu Kα radiation. Incensole acetate exhibited significant hepatoprotective activity at 10 μM against paracetamol-induced HepG2 cell damage.

Phytochemistry. 2019 Jul;163():126-131.
PMID: 31059964 [PubMed - indexed for MEDLINE]


Isolation, structure elucidation, and immunostimulatory activity of polysaccharide fractions from Boswellia carterii frankincense resin.
Hosain NA, Ghosh R, Bryant DL, Arivett BA, Farone AL, Kline PC

Frankincense has a long history in religious, cultural, and medicinal use. In this study polysaccharides were extracted from frankincense from Boswellia carterii. The polysaccharides were purified by anion exchange chromatography on a DEAE-Sepharose Fast Flow 16/10 FPLC column. Six fractions were obtained and the three most active immunomodulatory fractions were further purified by size exclusion chromatography on a Superdex-200 column. The composition showed the monosaccharides present were predominantly galactose, arabinose, and glucuronic acid along with small amounts of rhamnose and glucose. The monosaccharide composition and glycosyl linkage analysis revealed the polysaccharides belong to the type II arabinogalactans. Fourier-transform infrared spectroscopy and bicinchoninic acid assay showed that the amount of protein in the samples was <1 wt%. One-dimensional H NMR were consistent with high molecular weight compounds. The monosaccharides were primarily in the β conformation. The three fractions exhibited an immunostimulatory effect on RAW 264.7 murine macrophage cells. The most active immunostimulatory fraction FA2, stimulated a range of pro-inflammatory mediators including iNOS, NO, TNF-α, and IL-6 in RAW 264.7 cells. The fractions were effective in proliferating primary murine splenocytes. The results indicate that the polysaccharides isolated from frankincense have the potential to be used as an immunological stimulant or nutraceutical.

Int J Biol Macromol. 2019 Jul;133():76-85.
PMID: 30981779 [PubMed - indexed for MEDLINE]


Endogenous phytohormones of frankincense producing Boswellia sacra tree populations.
Khan AL, Mabood F, Akber F, Ali A, Shahzad R, Al-Harrasi A, Al-Rawahi A, Shinwari ZK, Lee IJ

Boswellia sacra, an endemic tree to Oman, is exposed to man-made incisions for commercial level frankincense production, whereas unsustainable harvesting may lead to population decline. In this case, assessment of endogenous phytohormones (gibberellic acid (GA), indole-acetic acid (IAA), salicylic acid (SA) and kinetin) can help to understand population health and growth dynamics. Hence, it was aimed to devise a robust method using Near-Infrared spectroscopy (NIRS) coupled with multivariate methods for phytohormone analysis of thirteen different populations of B. sacra. NIRS data was recorded in absorption mode (10000-4000 cm-1) to build partial least squares regression model (calibration set 70%). Model was externally cross validated (30%) as a test set to check their prediction ability before the application to quantify the unknown amount of phytohormones in thirteen different populations of B. sacra. The results showed that phytohormonal contents varied significantly, showing a trend of SA>GA/IAA>kinetin across different populations. SA and GA contents were significantly higher in Pop13 (Hasik), followed by Pop2 (Dowkah)-an extreme end of B. sacra tree cover in Dhofar region. A similar trend in the concentration of phytohormones was found when the samples from 13 populations were subjected to advance liquid chromatography mass spectrophotometer and gas chromatograph with selected ion monitor analysis. The current analysis provides alternative tool to assess plant health, which could be important to in situ propagation of tree population as well as monitoring tree population growth dynamics.

PLoS One. 2018;13(12):e0207910.
PMID: 30566477 [PubMed - indexed for MEDLINE]


Optimal Processing Conditions of Birdw. Using Response Surface Methodology.
Yoon JH, Kim JH, Ham SS, Gang BY, Lee SH, Choi G, Kim YS, Lee G, Ju YS

BACKGROUND: Bridw. is being widely used for its anti-inflammatory properties, as well as for wound healing, antimicrobial, and immunomodulatory properties, and boswellic acids (BAs) are considered to be the main active constituents.

OBJECTIVES: To investigate optimal conditions of stir-baking process for the resin of with vinegar of using response surface methodology (RSM).

MATERIALS AND METHODS: The concentration of acetic acid, heating temperature, and heating time were set as influential factors, and the yields of chemical compounds were the response values which were optimally designed by a Box-Behnken design. The amounts of 11-keto-β-boswellic acid (KBA) and α-boswellic acid (αBA) in resin were quantified using high-performance liquid chromatography analysis.

RESULTS: Maximum amounts of KBA and αBA in resin were obtained using 6% acetic acid for 10 min at 90°C in preliminary test. Two factor interactions, such as acetic acid concentration-heating temperature and heating temperature-heating time, were significantly observed by multiple regression analysis. Optimal processing conditions from RSM were 5.83% for acetic acid concentration, 9.56 min for heating time, and 89.87°C for heating temperature. Under the modified conditions, the experimental value of the response was 11.25 mg/g, which was similar to the predicted value.

CONCLUSIONS: The results suggest that the optimal conditions for the stir-baking process of resin were determined by RSM, which was reliable and applicable to practical processing of herbal medicine.

SUMMARY: The resin of was macerated in aqueous acetic acid and heated using an oven for stir baking processThe interaction between heating temperature and heating time was the most significantOptimal conditions for processing resin were determined as 5.83% acetic acid, 9.56 min for heating time, and 89.87°C for heating temperature. BAs: Boswellic acids; KBA: 11 keto β boswellic acid; αBA: α boswellic acid; BBD: Box-Behnken design; RSM: Response surface method; HPLC: High performance liquid chromatography; LOD: Limits of determination; LOQ: Limits of quantification; RSD: Relative standard deviation; ANOVA: Analysis of variance.

Pharmacogn Mag. 2018;14(54):235-241.
PMID: 29720838 [PubMed - as supplied by publisher]


New α-Glucosidase inhibitors from the resins of Boswellia species with structure-glucosidase activity and molecular docking studies.
Ur Rehman N, Khan A, Al-Harrasi A, Hussain H, Wadood A, Riaz M, Al-Abri Z

Phytochemical investigation of the oleo-gum resins from Boswellia papyrifera afforded one new triterpene, named 3α-hydroxyurs-5:19-diene (1) together with twelve known compounds including eight triterpenoids (2-9), two diterpenoids (10 and 11) and two straight chain alkanes (12 and 13). Similarly ten more known compounds were isolated from the resin of Boswellia sacra including one triterpene (20) and nine boswellic acids (14-19 and 21-23). Herein the compound 2 was first time reporting from natural source along with complete NMR assignment, while compounds 3-11 are known, but reported for the first time from the resin of B. papyrifera. The structure elucidation was done by advance spectroscopic D and D NMR techniques viz., H, C, DEPT, HSQC, HMBC, and COSY, and NEOSY, ESI-MS and compared with the reported literature. All compounds were evaluated for their α-glucosidase inhibitory activity and as result eight of them 1, 3, 10, 11, 15, and 17-19 were found significantly active against α-glucosidase with an IC value ranging from 15.0 ± 0.84 to 80.3 ± 2.33 µM, while 21 exhibited moderate activity with IC of 799.9 ± 4.98 µM. Furthermore, two compounds 24 and 25 were synthesised from 16 and 17 to see the effect of carboxyl group in structural-activity relationship (SAR) study. Compounds 24 and 25 retained good α-glucosidase inhibition as compared to 16 and 17, indicating that carboxylic group play a key role in SAR. In addition, the aforementioned activity of all the active compounds was first time reported for their α-glucosidase inhibition potential. The molecular docking studies showed that all the active compounds well accommodate in the active site of the enzyme. Moreover pharmacokinetic properties of the compounds were predicted in silico, suggesting that the compounds possess drug like properties and excellent ADMET profile.

Bioorg Chem. 2018 Sep;79():27-33.
PMID: 29715636 [PubMed - indexed for MEDLINE]


Chemical Variation in Essential Oils from the Oleo-gum Resin of Boswellia carteri: A Preliminary Investigation.
DeCarlo A, Johnson S, Poudel A, Satyal P, Bangerter L, Setzer WN

Frankincense, the oleo-gum resin of Boswellia species, has been an important element of traditional medicine for thousands of years. Frankincense is still used for oral hygiene, to treat wounds, and for its calming effects. Different Boswellia species show different chemical profiles, and B. carteri, in particular, has shown wide variation in essential oil composition. In order to provide insight into the chemical variability in authentic B. carteri oleoresin samples, a hierarchical cluster analysis of 42 chemical compositions of B. carteri oleo-gum resin essential oils has revealed at least three different chemotypes, i) an α-pinene-rich chemotype, ii) an α-thujene-rich chemotype, and iii) a methoxydecane-rich chemotype.

Chem Biodivers. 2018 Jun;15(6):e1800047.
PMID: 29696822 [PubMed - indexed for MEDLINE]


The amino analogue of β-boswellic acid efficiently attenuates the release of pro-inflammatory mediators than its parent compound through the suppression of NF-κB/IκBα signalling axis.
Gupta S, Ahsan AU, Wani A, Khajuria V, Nazir LA, Sharma S, Bhagat A, Raj Sharma P, Bhardwaj S, Peerzada KJ, Ali Shah B, Ahmed Z

Natural product derivatives have proven to be cutting edge window for drug discovery and development. BA-25 (3-α-o-acetoxy-4β-amino-11-oxo-24-norurs-12-ene) an amino analogue of β-boswellic acid exhibited inhibition of TNF-α and IL-6 in THP-1 cells as demonstrated previously, however, the effect on principal inflammatory mediators such as cyclooxygenase-2 (COX-2), inducible nitric oxide synthase (iNOS) and the pathways that mediate this function remains unknown. This study was designed to examine the comparative anti-inflammatory activity of BA-25 with its parent compound, β boswellic acid both in vitro and in vivo. The effect of BA and BA-25 on suppression of NO, PGE LTB, COX-2 in LPS-stimulated RAW 264.7 cells was determined by ELISA, RT-PCR and ROS by flow cytometry. Phosphorylation of NF-kBp65, IKB degradation was determined by western blotting and also the nuclear localization of NF-kBp65 was assessed by immunofluorescence. Furthermore, this study was extended on Carrageenan induced paw oedema modelled BALB/c mice. A novel derivative BA-25, reported first time notably decreased the LPS (1 μg/mL) induced upregulation in the transcription of TNF-α, IL-6, iNOS and COX-2. Also the protein expression of iNOS and COX-2 as well as their downstream products NO and PGE2 respectively, were also decreased efficiently at a concentration of 10 μM than BA. Moreover, LPS upregulated NF-kB p65 expression and IκB degradation was significantly decreased after BA-25 treatment. In addition, the treatment of BA-25 also restored the paw oedema and decreased the magnitude of histopathological alterations. Our data together suggested that BA-25 might be regarded as prospective therapeutic anti-inflammatory alternative and demands further investigation in pharmacological studies.

Cytokine. 2018 Jul;107():93-104.
PMID: 29229421 [PubMed - indexed for MEDLINE]


A novel boswellic acids delivery form (Casperome®) in the management of musculoskeletal disorders: a review.
Riva A, Allegrini P, Franceschi F, Togni S, Giacomelli L, Eggenhoffner R

Standard pharmacological treatment of musculoskeletal conditions is often associated with relevant side effects. Botanical preparations endowed with a good tolerability profile, therefore, could have a role in the management of these disorders. Among different natural products, Boswellia serrata extracts have long been used for the treatment of musculoskeletal disorders, given their marked anti-inflammatory activity and their ability to promote tissue regeneration. However, standard preparations of Boswellia serrata show overall modest pharmacokinetic properties, a limitation which may ultimately lead to reduced efficacy. In an effort to improve the pharmacokinetic properties, Casperome®, a lecithin-based formulation of Boswellia serrata extract representing the whole natural bouquet, has been developed. This formulation was effective in the treatment of Achilles tendonitis, epicondylitis, radiculopathies, ankle sprains and sport injuries as shown in several clinical studies, the majority of which with a randomized design and all evaluating a number of well-recognized parameters of efficacy for the therapy of musculoskeletal disorder. All studies were consistent in showing a prompt decrease of pain and improvement of functionality of the affected area after supplementation with Casperome®, without any relevant adverse effect. Remarkably, these symptomatic improvements were paralleled by reduced plasmatic levels of inflammatory markers and by a diminished need for rescue analgesics. On these bases, Casperome® may have a role in the treatment of musculoskeletal disorders. Clinical studies in other similar conditions (e.g., osteoarthritis) appear warranted to further investigate the efficacy of this botanical product in more specific settings.

Eur Rev Med Pharmacol Sci. 2017 Nov;21(22):5258-5263.
PMID: 29228442 [PubMed - indexed for MEDLINE]


Chemical Composition and Monoterpenoid Enantiomeric Distribution of the Essential Oils from Apharsemon (Commiphora gileadensis).
Dudai N, Shachter A, Satyal P, Setzer WN

(Hebrew: apharsemon) has been used since Biblical times to treat various ailments, and is used today in the traditional medicine of some Middle Eastern cultures. The essential oils from the stem bark, leaves, and fruits of -collected at the Ein Gedi Botanical Garden, Israel-were obtained by hydrodistillation and analyzed by gas chromatography-mass spectrometry. In addition, the enantiomeric distributions of the monoterpenoids in the essential oils have been determined by chiral gas chromatography. The essential oils were dominated by monoterpene hydrocarbons, followed by oxygenated monoterpenoids. The major components in oils were the monoterpenes α-pinene (11.1-18.4%), sabinene (15.8-35.9%), β-pinene (5.8-18.0%), -cymene (4.8-8.4%), limonene (1.3-6.2%), γ-terpinene (0.7-8.1%), and terpinen-4-ol (5.3-18.5%). The (-)-enantiomers predominated for α-pinene, sabinene, β-pinene, limonene, and terpinen-4-ol. The chemical compositions of the essential oils from Israel are markedly different from previously reported samples, which were rich in sesquiterpenoids. Likewise, the enantiomeric distribution of monoterpenoids is very different from spp. essential oils.

Medicines (Basel). 2017 Sep;4(3):.
PMID: 28930280 [PubMed - as supplied by publisher]


Extraction and purification of five terpenoids from olibanum by ultrahigh pressure technique and high-speed countercurrent chromatography.
Yu J, Zhao H, Wang D, Song X, Zhao L, Wang X

Five terpenoids, including two new ones, 3,7-dioxo-tirucalla-8,24-dien-21-oic acid (2) and 3α-acetoxyl-7-oxo-tirucalla-8,24-dien-21-oic acid (3), and three known ones, boscartol A (1), 11-keto-β-boswellic acid (4), and acetyl-11-keto-boswellic acid (5), have been extracted by the ultrapressure extraction and purified by pH-zone-refining countercurrent chromatography and high-speed countercurrent chromatography from olibanum. For ultrapressure extraction, the optimal condition including 200 MPa of extraction pressure, ethyl acetate of extraction solvent, 1:20 (g/mL) of solid/liquid ratio, and 2 min of extraction time were obtained. For the separation, from 1.5 g of the terpenoid extract, 220.1 mg of 4, 255.5 mg of 5, and 212.3 mg of the mixture of 1, 2, and 3 were obtained by pH-zone-refining countercurrent chromatography under the solvent system of chloroform/ethyl acetate/methanol/water (3:1:3:2, v/v/v/v) with aqueous ammonia and trifluoroacetic acid as retention and eluter agents. The enriched mixture (210 mg) was further separated by conventional high-speed countercurrent chromatography with petroleum ether/ethyl acetate/methanol/water (1:0.8:1.1:0.6, v/v/v/v), yielding 30.1 mg of 1, 35.5 mg of 2, 12.3 mg of 3. The structures of these five terpenoids were elucidated by extensive spectroscopic methods.

J Sep Sci. 2017 Jul;40(13):2732-2740.
PMID: 28544633 [PubMed - indexed for MEDLINE]


Quantitative Determination of 3-O-Acetyl-11-Keto-βBoswellic Acid (AKBA) and Other Boswellic Acids in Boswellia sacra Flueck (syn. B. carteri Birdw) and Boswellia serrata Roxb.
Mannino G, Occhipinti A, Maffei ME

Boswellia serrata and Boswellia sacra (syn. B. carteri) are important medicinal plants widely used for their content of bioactive lipophilic triterpenes. The qualitative and quantitative determination of boswellic acids (BAs) is important for their use in dietary supplements aimed to provide a support for osteoarthritic and inflammatory diseases. We used High Performance Liquid Chromatography (HPLC)-Diode Array Detector (DAD) coupled to ElectroSpray Ionization and tandem Mass Spectrometry (ESI-MS/MS) for the qualitative and quantitative determination of BAs extracted from the gum resins of B. sacra and B. serrata. Limit of detection (LOD), limit of quantification (LOQ), and Matrix Effect were assessed in order to validate quantitative data. Here we show that the BAs quantitative determination was 491.20 g·kg-1 d. wt (49%) in B. sacra and 295.25 g·kg-1 d. wt (30%) in B. serrata. Lower percentages of BAs content were obtained when BAs were expressed on the gum resin weight (29% and 16% for B. sacra and B. serrata, respectively). The content of Acetyl-11-Keto-β-Boswellic Acid (AKBA) was higher in B. sacra (70.81 g·kg-1 d. wt; 7%) than in B. serrata (7.35 g·kg-1 d. wt; 0.7%). Our results show that any claim of BAs content in either B. sacra or B. serrata gum resins equal to or higher than 70% or AKBA contents of 30% are simply unrealistic or based on a wrong quantitative determination.

Molecules. 2016 Oct;21(10):.
PMID: 27782055 [PubMed - indexed for MEDLINE]


Chemical composition and biological activities of extracts and essential oil of Boswellia dalzielii leaves.
Kohoude MJ, Gbaguidi F, Agbani P, Ayedoun MA, Cazaux S, Bouajila J

CONTEXT: Boswellia dalzielii Hutch. (Burseraceae) is an aromatic plant. The leaves are used for beverage flavouring.

OBJECTIVE: This study investigates the chemical composition and biological activities of various extracts.

MATERIALS AND METHODS: The essential oil was prepared via hydrodistillation. Identification and quantification were realized via GC-MS and GC-FID. Consecutive extractions (cyclohexane, dichloromethane, ethyl acetate and methanol) were carried out and various chemical groups (phenolics, flavonoids, tannins, antocyanins and sugar) were quantified. The volatile compounds of organic extracts were identified before and after derivatization. Antioxidant, antihyperuricemia, anti-Alzheimer, anti-inflammatory and anticancer activities were evaluated.

RESULTS: In the essential oil, 50 compounds were identified, including 3-carene (27.72%) and α-pinene (15.18%). 2,5-Dihydroxy acetophenone and β-d-xylopyranose were identified in the methanol extract. Higher phenolic (315.97 g GAE/kg dry mass) and flavonoid (37.19 g QE/kg dry mass) contents were observed in the methanol extract. The methanol extract has presented remarkable IC=6.10 mg/L for antiDPPH, 35.10 mg/L for antixanthine oxidase and 28.01 mg/L for anti-5-lipoxygenase. For acetylcholinesterase inhibition, the best IC (76.20 and 67.10 mg/L) were observed, respectively, with an ethyl acetate extract and the essential oil. At 50 mg/L, the dichloromethane extract inhibited OVCAR-3 cell lines by 65.10%, while cyclohexane extract inhibited IGROV-1 cell lines by 92.60%.

DISCUSSION AND CONCLUSION: Biological activities were fully correlated with the chemical groups of the extracts. The ethyl acetate and methanol extracts could be considered as potential alternatives for use in dietary supplements for the prevention or treatment of diseases because of these extracts natural antioxidant, antihyperuricemic and anti-inflammatory activities.

Pharm Biol. 2017 Dec;55(1):33-42.
PMID: 27650786 [PubMed - indexed for MEDLINE]


Chemical composition, antiproliferative, antioxidant and antibacterial activities of essential oils from aromatic plants growing in Sudan.
Yagi S, Babiker R, Tzanova T, Schohn H

OBJECTIVE: To explore the potential of essential oil, as therapeutic molecule source, from olibanum of Boswellia papyrifera (Burseraceae), leafy stems of Cymbopogon schoenanthus (Poaceae) and Croton zambesicus (Euphorbiaceae) and rhizome of Cyperus rotundus (Cyperaceae) found in Sudan. Respective essential oil was evaluated for anti-proliferative, antibacterial and antioxidant activity.

METHODS: Essential oils were extracted by hydrodistillation and then analysed by gas chromatography coupled to mass spectrometry (GC-MS). Anti-proliferative activity was determined against human cell lines (MCF7 and MDA-MB231, HT29 and HCT116) by the thiazolyl blue tetrazolium bromide (MTT) procedure. Antioxidant activity was evaluated by diphenyl 2 pycril hydrazil (DPPH) assay. Antibacterial activity was determined against two Gram-positive and two Gram-negative bacteria by microdilution method.

RESULTS: The essential oil from olibanum of Boswellia papyrifera contained mainly alcohol and ester derivatives (46.82%) while monoterpenes (69.84%) dominated in Corton zambesicus oil. Sesquiterpenes were the most highly represented classes of terpene derivatives in Cyperus schoenanthus (71.59%) and Cyperus rotundus (44.26%). Oil of Cymbopogon schoenanthus revealed the best anti-proliferative activity against HCT116 cell line with IC50 value at (19.1 ± 2.0) μg/mL. Oil of Croton zambesicus showed the best antioxidant activity [EC50 (4.20 ± 0.19) mg/mL]. All oils showed good antibacterial activity against Escherichia coli, Bacillus subtilis and Staphylococcus aureus with minimum inhibitory concentration (MIC) value ranged from 16 to 250 μg/mL.

CONCLUSIONS: The results suggest that the essential oils of these plants could be used as a source of natural anti-proliferative, antioxidant and antibacterial agents.

Asian Pac J Trop Med. 2016 Aug;9(8):763-70.
PMID: 27569885 [PubMed - as supplied by publisher]


Simultaneous quantification of triterpenoic acids by high performance liquid chromatography method in the extracts of gum resin of Boswellia serrata obtained by different extraction techniques.
Sharma N, Bhardwaj V, Singh S, Ali SA, Gupta DK, Paul S, Satti NK, Chandra S, Verma MK

BACKGROUND: Boswellia serrata, also known as Indian frankincense is a commercially important medicinal plant which has been used for hundreds of years as an Ayurvedic medicine for the attempted treatment of arthritis. It contains naturally occurring triterpenoic acids, called as boswellic acids (BA's).

RESULTS: A highly reproducible High performance liquid chromatography-ultraviolet diode array detection (HPLC-UV-DAD) method was developed for the simultaneous determination and quantitative analysis of eight major triterpenoic acids in Boswellia serrata gum resin obtained by different extraction techniques. All the calibration curves exhibited good linear regression (R(2) > 0.997) within the test ranges. The established method showed good precision and overall recoveries of the boswellic acids.

CONCLUSIONS: The eight triterpenoic acids coded as BS-1 (11-keto-beta-boswellic acid), BS-2 (3-O-acetyl-11-keto-beta-boswellic acid), BS-3 (3-keto tirucallic acid), BS-4 (3-O-acetyl-alpha-tirucallic acid), BS-5 (3-O-acetyl-beta-tirucallic acid), BS-6 (alpha-boswellic acid), BS-7 (beta-boswellic acid) and BS-8 (3-O-acetyl-beta-boswellic acid) were isolated from the processed gum resin of Boswellia serrata by column chromatography. The proposed HPLC method is simple, reliable and has been very useful for the qualitative as well as quantitative analysis of boswellic acids in the gum resin of Boswellia serrata. The proposed method allows to quantify boswellic acids in appreciable amounts by HPLC-UV (DAD) method in the extracts and the available marketed formulations.Graphical abstractIsolation & separation of eight Triterpenoic acids from Boswellia serrata.

Chem Cent J. 2016;10():49.
PMID: 27493682 [PubMed - as supplied by publisher]


Endophytic Fungi from Frankincense Tree Improves Host Growth and Produces Extracellular Enzymes and Indole Acetic Acid.
Khan AL, Al-Harrasi A, Al-Rawahi A, Al-Farsi Z, Al-Mamari A, Waqas M, Asaf S, Elyassi A, Mabood F, Shin JH, Lee IJ

Boswellia sacra, an economically important frankincense-producing tree found in the desert woodlands of Oman, is least known for its endophytic fungal diversity and the potential of these fungi to produce extracellular enzymes and auxins. We isolated various fungal endophytes belonging to Eurotiales (11.8%), Chaetomiaceae (17.6%), Incertae sadis (29.5%), Aureobasidiaceae (17.6%), Nectriaceae (5.9%) and Sporomiaceae (17.6%) from the phylloplane (leaf) and caulosphere (stem) of the tree. Endophytes were identified using genomic DNA extraction, PCR amplification and sequencing the internal transcribed spacer regions, whereas a detailed phylogenetic analysis of the same gene fragment was made with homologous sequences. The endophytic colonization rate was significantly higher in the leaf (5.33%) than the stem (0.262%). The Shannon-Weiner diversity index was H' 0.8729, while Simpson index was higher in the leaf (0.583) than in the stem (0.416). Regarding the endophytic fungi's potential for extracellular enzyme production, fluorogenic 4-methylumbelliferone standards and substrates were used to determine the presence of cellulases, phosphatases and glucosidases in the pure culture. Among fungal strains, Penicillum citrinum BSL17 showed significantly higher amounts of glucosidases (62.15±1.8 μM-1min-1mL) and cellulases (62.11±1.6 μM-1min-1mL), whereas Preussia sp. BSL10 showed significantly higher secretion of glucosidases (69.4±0.79 μM-1min-1mL) and phosphatases (3.46±0.31μM-1min-1mL) compared to other strains. Aureobasidium sp. BSS6 and Preussia sp. BSL10 showed significantly higher potential for indole acetic acid production (tryptophan-dependent and independent pathways). Preussia sp. BSL10 was applied to the host B. sacra tree saplings, which exhibited significant improvements in plant growth parameters and accumulation of photosynthetic pigments. The current study concluded that endophytic microbial resources producing extracellular enzymes and auxin could establish a unique niche for ecological adaptation during symbiosis with the host Frankincense tree.

PLoS One. 2016;11(6):e0158207.
PMID: 27359330 [PubMed - indexed for MEDLINE]


Sensitivity of clinical isolates of Candida to essential oils from Burseraceae family.
Nikolic M, Smiljkovic M, Markovic T, Cirica A, Glamoclija J, Markovic D, Sokovic M

The aim of this study was to investigate the chemical composition and antifungal activity of four commercial essential oils from the Burseraceae family - two Boswellia carterii Flueck oils, Canarium luzonicum (Blume) A. Gray oil, and Commiphora myrrha (Nees) Engl oil, against most common Candida spp. recovered from the human oral cavity. The essential oil samples were analyzed by GC-FID and GC/MS. The analysis showed that major essential oils' components were α-pinene (23.04 % and 31.84 %), limonene (45.62 %) and curzerene (34.65 %), respectively. Minimum inhibitory (MIC) and minimum fungicidal (MFC) concentrations were determined using a microdilution standardized technique. All tested Candida spp. clinical isolates and ATCC strains showed susceptibility to tested essential oils in a dose dependent manner. The strongest antifungal activity was shown by essential oil of B. carterii, sample 2; the average MIC values ranged from 1.25 to 1.34 mg/ml, and MFC values ranged from 2.50 to 3.75 mg/ml, depending on the fungus. This study supports the possible use of essential oils from the Bursecaceae family in reduction and elimination of Candida spp. populations in patients with oral cavity fungal infections.

EXCLI J. 2016;15():280-9.
PMID: 27330531 [PubMed - as supplied by publisher]


Ursane and tirucallane-type triterpenes of Boswellia rivae oleo-gum resin.
Manguro LO, Wagai SO

Two new ursane-type triterpenes characterized as 3-oxo-24-acetoxy-11α-hydroxy-urs-12-ene (1) and methyl 3α-acetoxy-11α-methoxy-urs-12-en-24-oate (2), together with known compounds 3-11, were isolated from Boswellia rivae oleo-gum resin exudate. Their structural elucidation was accomplished using physical, chemical, and spectroscopic methods. The compounds exhibited weak to moderate antibacterial activities against some Gram-positive and Gram-negative bacteria.

J Asian Nat Prod Res. 2016 Sep;18(9):854-64.
PMID: 27049028 [PubMed - indexed for MEDLINE]


Frankincense Revisited, Part II: Volatiles in Rare Boswellia Species and Hybrids.
Niebler J, Eslamieh J, Buettner A

In this second part of the investigation of volatiles and semivolatiles in Boswellia gum resins, an additional five less common species were analyzed by (SPME-)GC/MS, namely B. ameero, B. elongata, B. neglecta, B. popoviana, and B. rivae. Moreover, the results of hybridization experiments are reported in combination with the volatile composition of their gum resins. Our study shows that B. sacra benefits from an intraspecific cross-pollination, as the resulting hybrid B. sacra var. supersacra has a far higher seed germination rate and viability.

Chem Biodivers. 2016 May;13(5):630-43.
PMID: 27012302 [PubMed - indexed for MEDLINE]


Frankincense Revisited, Part I: Comparative Analysis of Volatiles in Commercially Relevant Boswellia Species.
Niebler J, Buettner A

The genus Boswellia comprises many species which are famous for their production of frankincense, a fragrant gum resin. In the published literature, manifold studies on the volatiles and semivolatiles in individual samples of these gum resins exist, yet very few studies have investigated multiple samples. Contradictory results with regard to the volatile composition exist in literature. In this first part of the study, a large sample set (n = 46) of mostly commercially obtained gum resins and essential oils was investigated by solid-phase microextraction gas chromatography/mass spectrometry. A total of 216 compounds were identified or tentatively identified from the four commercially relevant species, namely B. sacra, B. serrata, B. papyrifera, and B. frereana, and the statistical evaluation of the resulting chemical profiles allowed a clear distinction between the species by their volatile profile. With only few exceptions, the designated species was found to be in accordance with the composition reported in reliable literature sources and detected in botanically identified samples. Chemotaxonomic marker substances were suggested to facilitate the differentiation of commercial gum resins or essential oils based on their volatile profile.

Chem Biodivers. 2016 May;13(5):613-29.
PMID: 27012219 [PubMed - indexed for MEDLINE]


Fragrant Sesquiterpene Ketones as Trace Constituents in Frankincense Volatile Oil of Boswellia sacra.
Niebler J, Zhuravlova K, Minceva M, Buettner A

In a previous study, two highly potent yet unidentified odorants were detected that were present at trace levels in the volatile fraction of Boswellia sacra gum resin. These two compounds were isolated semipreparatively from the volatile oil by a sensory-guided fractionation process involving microscale bulb-to-bulb distillation, countercurrent chromatography, and preparative gas chromatography. In this manner, the two oxygenated sesquiterpenes could be identified as rotundone (1) and mustakone (2). Compound 2 is described for the first time as a potent odorant with a very low odor threshold.

J Nat Prod. 2016 Apr;79(4):1160-4.
PMID: 27010489 [PubMed - indexed for MEDLINE]


Extraction and Characterization of Boswellia Serrata Gum as Pharmaceutical Excipient.
Panta S, Malviya R, Sharma P

BACKGROUND: This manuscript deals with the purification and characterization of Boswellia serrata gum as a suspending agent. The Boswellia serrata gum was purchased as crude material, purified and further characterized in terms of organoleptic properties and further micromeritic studies were carried out to characterize the polymer as a pharmaceutical excipient. The suspending properties of the polymer were also evaluated. The results showed that the extracted gum possesses optimum organoleptic as well as micromeritic and suspending properties.

OBJECTIVES: To characterize Boswellia serrata gum as a natural excipient.

MATERIAL AND METHODS: Boswellia serrata gum, paracetamol, distilled water.

RESULTS: The results showed that the extracted gum possesses optimum organoleptic as well as micromeritic and suspending properties.

CONCLUSIONS: It is concluded from the research work that the gum extracted from Boswellia serrata shows the presence of carbohydrates after chemical tests. All the organoleptic properties evaluated were found to be acceptable. The pH was found to be slightly acidic. Swelling Index reveals that the gum swells well in water. Total ash value was within the limits. The values of angle of repose and Carr's Index of powdered gum powder showed that the flow property was good. IR spectra confirmed the presence of alcohol, amines, ketones, anhydrides and aromatic rings. The suspending properties of Boswellia serrata gum were found to be higher as compared to gum acacia while the flow rate of Boswellia serrata gum (1% suspension) was less than gum acacia (1% suspension). The viscosity measurement of both Boswellia serrata gum suspension and gum acacia suspension showed approximately similar results.

Polim Med. 2015;45(1):25-30.
PMID: 26630726 [PubMed - indexed for MEDLINE]


Phytochemical Analysis and Anti-cancer Investigation of Boswellia serrata Bioactive Constituents In Vitro.
Ahmed HH, Abd-Rabou AA, Hassan AZ, Kotob SE

Cancer is a major health obstacle around the world, with hepatocellular carcinoma (HCC) and colorectal cancer (CRC) as major causes of morbidity and mortality. Nowadays, there isgrowing interest in the therapeutic use of natural products for HCC and CRC, owing to the anticancer activity of their bioactive constituents. Boswellia serrata oleo gum resin has long been used in Ayurvedic and traditional Chinese medicine to alleviate a variety of health problems such as inflammatory and arthritic diseases. The current study aimed to identify and explore the in vitro anticancer effect of B. Serrata bioactive constituents on HepG2 and HCT 116 cell lines. Phytochemical analysis of volatile oils of B. Serrata oleo gum resin was carried out using gas chromatography- mass spectrometry (GC/MS). Oleo-gum-resin of B. Serrata was then successively extracted with petroleum ether (extract 1) and methanol (extract 2). Gas-liquid chromatography (GLC) analysis of the lipoidal matter was also performed. In addition, a methanol extract of B. Serrata oleo gum resin was phytochemically studied using column chromatography (CC) and thin layer chromatography (TLC) to obtain four fractions (I, II, III and IV). Sephadex columns were used to isolate β-boswellic acid and identification of the pure compound was done using UV, mass spectra, 1H NMR and 13C NMR analysis. Total extracts, fractions and volatile oils of B. Serrata oleo-gum resin were subsequently applied to HCC cells (HepG2 cell line) and CRC cells (HCT 116 cell line) to assess their cytotoxic effects. GLC analysis of the lipoidal matter resulted in identification of tricosane (75.32%) as a major compound with the presence of cholesterol, stigmasterol and β-sitosterol. Twenty two fatty acids were identified of which saturated fatty acids represented 25.6% and unsaturated fatty acids 74.4% of the total saponifiable fraction. GC/MS analysis of three chromatographic fractions (I,II and III) of B. Serrata oleo gum resin revealed the presence of pent-2-ene-1,4-dione, 2-methyl- levulinic acid methyl ester, 3,5- dimethyl- 1- hexane, methyl-1-methylpentadecanoate, 1,1- dimethoxy cyclohexane, 1-methoxy-4-(1-propenyl)benzene and 17a-hydroxy-17a-cyano, preg-4-en-3-one. GC/MS analysis of volatile oils of B. Serrata oleo gum resin revealed the presence of sabinene (19.11%), terpinen-4-ol (14.64%) and terpinyl acetate (13.01%) as major constituents. The anti-cancer effect of two extracts (1 and 2) and four fractions (I, II, III and IV) as well as volatile oils of B. Serrata oleo gum resin on HepG2 and HCT 116 cell lines was investigated using SRB assay. Regarding HepG2 cell line, extracts 1 and 2 elicited the most pronounced cytotoxic activity with IC50 values equal 1.58 and 5.82 μg/mL at 48 h, respectively which were comparable to doxorubicin with an IC50 equal 4.68 μg/mL at 48 h. With respect to HCT 116 cells, extracts 1 and 2 exhibited the most obvious cytotoxic effect; with IC50 values equal 0.12 and 6.59 μg/mL at 48 h, respectively which were comparable to 5-fluorouracil with an IC50 equal 3.43 μg/ mL at 48 h. In conclusion, total extracts, fractions and volatile oils of B. Serrata oleo gum resin proved their usefulness as cytotoxic mediators against HepG2 and HCT 116 cell lines with different potentiality (extracts > fractions > volatile oil). In the two studied cell lines the cytotoxic acivity of each of extract 1 and 2 was comparable to doxorubicin and 5-fluorouracil, respectively. Extensive in vivo research is warranted to explore the precise molecular mechanisms of these bioactive natural products in cytotoxicity against HCC and CRC cells.

Asian Pac J Cancer Prev. 2015;16(16):7179-88.
PMID: 26514509 [PubMed - indexed for MEDLINE]


Cembranoids from the Gum Resin of Boswellia carterii as Potential Antiulcerative Colitis Agents.
Ren J, Wang YG, Wang AG, Wu LQ, Zhang HJ, Wang WJ, Su YL, Qin HL

Eight new cembranoids, boscartins A-H (1, 2, and 4-9), and the known incensole oxide were isolated from the gum resin of Boswellia carterii. The absolute configurations of 1, 2, 4, and incensole oxide were unequivocally resolved using single-crystal X-ray diffraction analysis with Cu Kα radiation, and the absolute configuration of 5 was resolved via electronic circular dichroism data. The antiulcerative colitis activities of the compounds were evaluated in an in vitro x-box-binding protein 1 (XBP 1) transcriptional activity assay using dual luciferase reporter detection. At 10 μM, compounds 1, 5, 6, and 7 significantly activated XBP 1 transcription with EC50 values of 0.34, 1.14, 0.88, and 0.42 μM, respectively, compared with the pGL3-basic vector control.

J Nat Prod. 2015 Oct;78(10):2322-31.
PMID: 26457560 [PubMed - indexed for MEDLINE]


Identification of dehydroabietc acid from Boswellia thurifera resin as a positive GABAA receptor modulator.
Rueda DC, Raith M, De Mieri M, Schöffmann A, Hering S, Hamburger M

In a two-microelectrode voltage clamp assay with Xenopus laevis oocytes, a petroleum ether extract (100 μg/mL) of the resin of Boswellia thurifera (Burseraceae) potentiated GABA-induced chloride currents (IGABA) through receptors of the subtype α₁β₂γ₂s by 319.8% ± 79.8%. With the aid of HPLC-based activity profiling, three known terpenoids, dehydroabietic acid (1), incensole (2), and AKBA (3), were identified in the active fractions of the extract. Structure elucidation was achieved by means of HR-MS and microprobe 1D/2D NMR spectroscopy. Compound 1 induced significant receptor modulation in the oocyte assay, with a maximal potentiation of IGABA of 397.5% ± 34.0%, and EC₅₀ of 8.7 μM ± 1.3 μM. This is the first report of dehydroabietic acid as a positive GABAA receptor modulator.

Fitoterapia. 2014 Dec;99():28-34.
PMID: 25200370 [PubMed - indexed for MEDLINE]


Micropropagation and non-steroidal anti-inflammatory and anti-arthritic agent boswellic acid production in callus cultures of Boswellia serrata Roxb.
Nikam TD, Ghorpade RP, Nitnaware KM, Ahire ML, Lokhande VH, Chopra A

Micropropagation through cotyledonary and leaf node and boswellic acid production in stem callus of a woody medicinal endangered tree species Boswellia serrata Roxb. is reported. The response for shoots, roots and callus formation were varied in cotyledonary and leafy nodal explants from in vitro germinated seeds, if inoculated on Murshige and Skoog's (MS) medium fortified with cytokinins and auxins alone or together. A maximum of 8.0 ± 0.1 shoots/cotyledonary node explant and 6.9 ± 0.1 shoots/leafy node explants were produced in 91 and 88 % cultures respectively on medium with 2.5 μM 6-benzyladenine (BA) and 200 mg l(-1) polyvinylpyrrolidone (PVP). Shoots treated with 2.5 μM IBA showed the highest average root number (4.5) and the highest percentage of rooting (89 %). Well rooted plantlets were acclimatized and 76.5 % of the plantlets showed survival upon transfer to field conditions. Randomly amplified polymorphic DNA (RAPD) analysis of the micropropagated plants compared with mother plant revealed true-to-type nature. The four major boswellic acid components in calluses raised from root, stem, cotyledon and leaf explants were analyzed using HPLC. The total content of four boswellic acid components was higher in stem callus obtained on MS with 15.0 μM IAA, 5.0 μM BA and 200 mg l(-1) PVP. The protocol reported can be used for conservation and exploitation of in vitro production of medicinally important non-steroidal anti-inflammatory metabolites of B. serrata.

Physiol Mol Biol Plants. 2013 Jan;19(1):105-16.
PMID: 24381442 [PubMed - as supplied by publisher]


11α-Ethoxy-β-boswellic acid and nizwanone, a new boswellic acid derivative and a new triterpene, respectively, from Boswellia sacra.
Al-Harrasi A, Ali L, Ur Rehman N, Hussain J, Hussain H, Al-Rawahi A, Shamim Rizvi T

A new boswellic acid derivative, 11α-ethoxy-β-boswellic acid (EBA; 1) and a new ursane-type triterpene, named nizwanone (2), were isolated from Omani frankincense Boswellia sacra Flueck. together with two known compounds papyriogenin B and rigidenol. The structures of 1 and 2 were elucidated by detailed spectroscopic analysis using (1) H- and (13) C-NMR, (1) H,(1) H-COSY, HMQC, HMBC, and HR-EI-MS techniques. The relative configurations of 1 and 2 were assigned by comparative analysis of the NMR spectral data with those of known analogs together with NOESY experiments. Structures of known compounds were identified by comparison with the reported data.

Chem Biodivers. 2013 Aug;10(8):1501-6.
PMID: 23939798 [PubMed - indexed for MEDLINE]


Chemistry and biology of essential oils of genus boswellia.
Hussain H, Al-Harrasi A, Al-Rawahi A, Hussain J

The properties of Boswellia plants have been exploited for millennia in the traditional medicines of Africa, China, and especially in the Indian Ayurveda. In Western countries, the advent of synthetic drugs has obscured the pharmaceutical use of Boswellia, until it was reported that an ethanolic extract exerts anti-inflammatory and antiarthritic effects. Frankincense was commonly used for medicinal purposes. This paper aims to provide an overview of current knowledge of the volatile constituents of frankincense, with explicit consideration concerning the diverse Boswellia species. Altogether, more than 340 volatiles in Boswellia have been reported in the literature. In particular, a broad diversity has been found in the qualitative and quantitative composition of the volatiles with respect to different varieties of Boswellia. A detailed discussion of the various biological activities of Boswellia frankincense is also presented.

Evid Based Complement Alternat Med. 2013;2013():140509.
PMID: 23533463 [PubMed - as supplied by publisher]


[Determination of alpha-pinene and octyl acetate contents in Boswellia serrata].
Song Z, Xia L, Wei Z, Cao Y, Zhang L, Liu Z

OBJECTIVE: To establish method for determining the contents of alpha-pinene and octyl acetate in Boswellia serrata, in order to provide preference for making quality standards for B. serrata and processed B. serrata.

METHOD: Application of orthogonal design was employed to optimize the solvent, solvent quantity and extraction time. The GC-MS analysis was performed on a Rxi-5ms silica capillary column, running in the electron impact (EI) mode, with ion trap and injector temperature of 200 degrees C and 250 degrees C, respectively. The column oven was initially 50 degrees C and was held for 1 min after injection, followed by temperature ramping at 5 degrees C x min(-1) up to 130 degrees C, holding for 1 min. 1 microL of samples solution were injected in the split mode (1:60). Helium was the carrier gas. The mass spectrometer was set to scan m/z 45450 with an ionizing voltage at 70 eV.

RESULT: Sample solutions were prepared for 50-fold dose by ultrasonic extraction with hexane for 30 min. The content of alpha-pinene and octyl acetate in 10 batches of B. serrata were 0.021 3-0.149 5, 2.519 6-9.098 0 mg x g(-1), respectively. And, those of alpha-pinene and octyl acetate in processed B. serrata were 0.015 9-0.065 9, 0.801 0-12.812 2 mg x g(-1).

CONCLUSION: The method is a stable and reliable for determining the contents of alpha-pinene and octyl acetate in B. serrata.

Zhongguo Zhong Yao Za Zhi. 2012 May;37(10):1431-3.
PMID: 22860456 [PubMed - indexed for MEDLINE]


[Does a positive finding of tetrahydrocannabinol in the blood result from ingestion of Indian frankincense (Boswellia serrata)?].
Skopp G, Schmitt G

The exculpatory statement that a positive THC finding in the blood is due to the consumption of hemp products or passive exposure to cannabis smoke has been disproved by the monitoring of hemp products and recent passive inhalation studies conducted in social settings, which showed that these conditions are unlikely to produce a positive result in the blood. The defense that the ingestion of Indian olibanum may result in a positive THC concentration in the blood is unusual; it is based on older publications where authors had speculated on a possible association of the synthetic pathways of THC from terpenoid precursors also being present in olibanum and the biogenesis of THC in hemp. It had further been speculated whether chemical or plant-derived pathways may also occur in humans. A thorough understanding of the different pathways and recently published results have outdated these speculations.

Arch Kriminol. 2012;229(5-6):154-62.
PMID: 22834359 [PubMed - indexed for MEDLINE]


Proteoglycans from Boswellia serrata Roxb. and B. carteri Birdw. and identification of a proteolytic plant basic secretory protein.
Herrmann A, König S, Lechtenberg M, Sehlbach M, Vakhrushev SY, Peter-Katalinic J, Hensel A

Water-soluble high molecular weight compounds were isolated in yields of 21-22% from the oleogum of Boswellia serrata and B. carteri. Using anion exchange chromatography and gel permeation chromatography, different proteoglycans were purified and characterized, leading to four principally different groups: (i) Hyp-/Ser-rich extensins with O-glycosidic attached arabinan side chains; (ii) Modified extensins, with arabinogalactosylated side chains containing GlA and 4-O-Me-GlcA; (iii) Glycoproteins with N-glycosidic side chains containing higher amounts of Fuc, Man and GluNH(2,) featuring a 200 kD metalloproteinase that has been de novo sequenced and is described for the first time; (iv) Type II arabinogalactans-proteins. Significant differences between the gums from the two species were observed in the protein content (6% vs 22%), offering the possibility of a quick differentiation of gums from both species for analytical quality control. The data also offer an insight into the plant response towards wound-closing by the formation of extensin and AGP-containing gum.

Glycobiology. 2012 Nov;22(11):1424-39.
PMID: 22773449 [PubMed - indexed for MEDLINE]


Efficient preparation of incensole and incensole acetate, and quantification of these bioactive diterpenes in Boswellia papyrifera by a RP-DAD-HPLC method.
Paul M, Jauch J

Incensole and incensole acetate, found in incense, are encouraging potent bioactive diterpenic cembrenoids, inhibiting Nuclear Factor-kappaB activation. Furthermore, incensole acetate elicits psycho-activity in mice by activating the TRPV3 channels in the brain. Starting from crude extracts of the incense species Boswellia papyrifera Hochst., a convenient procedure for the efficient large-scale synthesis of incensole and its acetate is presented. Additionally, a reversed-phase, diode-array-detection, high-performance liquid chromatography (RP-DAD-HPLC) method for the quantification of incensole and incensole acetate is reported, indicating that these two compounds are typical biomarkers for B. papyrifera.

Nat Prod Commun. 2012 Mar;7(3):283-8.
PMID: 22545396 [PubMed - indexed for MEDLINE]


Composition and antibacterial activity of the essential oils of four commercial grades of Omani luban, the oleo-gum resin of Boswellia sacra FLUECK.
Al-Saidi S, Rameshkumar KB, Hisham A, Sivakumar N, Al-Kindy S

The essential oil compositions of four botanically certified and commercially available samples of Omani lubans (oleo-gum resins of Boswellia sacra Flueck.), locally known as Hoojri, Najdi, Shathari, and Shaabi in Jibali Arabic, obtained from plants growing in four different geographic locations of the Dhofar region of Oman, were analyzed by GC-FID, GC/MS, and (13) C-NMR spectroscopy. The market price of these four grades of lubans differed considerably, according to their color, clump size, and texture. However, this study revealed that Hoojri, the first grade luban, and Shaabi, the fourth grade luban, which greatly differed in their price, closely resembled each other in their essential oil composition, yield, and physicochemical characteristics, except the color and texture. The composition, yield, and specific rotation of the oils of Najdi and Shathari, the second and the third grade lubans, respectively, were different from those of Hoojri and Shaabi, but they both had high limonene contents. Najdi oil was different from the other three oils in terms of its high myrcene content. α-Pinene was the principal component in all the oils and can be considered as a chemotaxonomical marker that confirms the botanical and geographical source of the resins. All the oils showed pronounced activity against a panel of bacteria, and the trend in their bioactivity and their mode of action are discussed.

Chem Biodivers. 2012 Mar;9(3):615-24.
PMID: 22422529 [PubMed - indexed for MEDLINE]


[Determination of five boswellic acids in Boswellia serrata].
Wang C, Xia L, Song Z, Li Q, Wang C, Zeng L, Liu Z

OBJECTIVE: To develop an HPLC method for determinating the contents of five boswellic acids in Boswellia serrata.

METHOD: Analysis was performed on a zorbax SB C18 column eluted with acetonitrile-0.1% phosphoric acid in water as mobile phases in gradient elution and the detection wavelengths were 210 nm and 250 nm.

RESULT: The five ingredients were separated well. The content ranges of alpha-boswellic acid, beta-boswellic acid, 3-acetyl-beta-boswellic acid, 11-keto-beta-boswellic acid and 11-keto-beta-acetyl- boswellic acid were 8.68-16.1, 53.5-246.9, 38.4-192.9, 4.48-5.81, 32.7-44.2 mg x g(-1), respectively.

CONCLUSION: The contents of five individual boswellic acids were different in 12 batches of B. serrata samples.

Zhongguo Zhong Yao Za Zhi. 2011 May;36(10):1330-3.
PMID: 21837977 [PubMed - indexed for MEDLINE]


Two new triterpenoids from the resin of Boswellia carterii.
Wang F, Li ZL, Cui HH, Hua HM, Jing YK, Liang SW

Two new triterpenoids, 3-oxotirucalla-7,9(11),24-trien-21-oic acid (1) and 18Hα,3β,20β-ursanediol (2), along with 15 known triterpenes, α-amyrin, α-boswellic acid, β-boswellic acid, acetyl α-boswellic acid, acetyl β-boswellic acid, 9,11-dehydro-β-boswellic acid, 9,11-dehydro-α-boswellic acid, acetyl 11α-methoxy-β-boswellic acid, 11-keto-β-boswellic acid, acetyl 11-keto-β-boswellic acid, acetyl α-elemolic acid, 3β-hydroxytirucalla-8,24-dien-21-oic acid, elemonic acid, 3α-hydroxytirucalla-7,24-dien-21-oic acid, and 3α-hydroxytirucall-24-en-21-oic acid, were isolated from the resin of Boswellia carterii Birdw.

J Asian Nat Prod Res. 2011 Mar;13(3):193-7.
PMID: 21409679 [PubMed - indexed for MEDLINE]


Four new ursane-type triterpenes, olibanumols K, L, M, and N, from traditional egyptian medicine olibanum, the gum-resin of Boswellia carterii.
Morikawa T, Oominami H, Matsuda H, Yoshikawa M

Four new ursane-type triterpenes, olibanumols K (1), L (2), M (3), and N (4), were isolated from traditional Egyptian medicine olibanum, the exuded gum-resin from Boswellia carterii BIRDW. Their structures were elucidated on the basis of chemical and physicochemical evidence.

Chem Pharm Bull (Tokyo). 2010 Nov;58(11):1541-4.
PMID: 21048352 [PubMed - indexed for MEDLINE]


New terpenoids, olibanumols D-G, from traditional Egyptian medicine olibanum, the gum-resin of Boswellia carterii.
Morikawa T, Oominami H, Matsuda H, Yoshikawa M

A new prenylaromadendrane-type diterpene, olibanumol D (1), and three new oleanane- and lupane-type triterpenes, olibanumols E (2), F (3), and G (4), were isolated from the traditional Egyptian medicine olibanum, the exuded gum-resin from Boswellia carterii Birdw. Their structures were established mainly on the basis of 1D and 2D NMR spectral data. Compounds 1 and 2 exhibited nitric oxide production inhibitory activity in lipopolysaccharide-activated mouse peritoneal macrophages.

J Nat Med. 2011 Jan;65(1):129-34.
PMID: 20953724 [PubMed - indexed for MEDLINE]


Chemical composition and antimicrobial activity of some oleogum resin essential oils from Boswellia spp. (Burseraceae).
Camarda L, Dayton T, Di Stefano V, Pitonzo R, Schillaci D

The chemical composition of Boswellia carteri (Somalia), B. papyrifera (Ethiopia), B. serrata (India) and B. rivae (Ethiopia) oleogum resin essential oils was investigated using GC-MS to identify chemotaxonomy marker components. Total ion current peak areas gave good approximations to relative concentrations based on GC-MS peak areas. B. carteri and B. serrata oleogum resin oils showed similar chemical profiles, with isoincensole and isoincensole acetate as the main diterpenic components. Both n-octanol and n-octyl acetate, along with the diterpenic components incensole and incensole acetate, were the characteristic compounds of B. papyrifera oleogum resin oil. Hydrocarbon and oxygenated monoterpenes were the most abundant classes of compounds identified in the B. rivae oleogum resin oil. The antimicrobial activities of the essential oils were individually evaluated against different microorganisms including fungi, Gram-positive and Gram-negative bacteria strains. The essential oils with the best activity against fungal strains were those obtained from B. carteri and B. papyrifera with MIC values as low as 6.20 microg/ml. The essential oil of B. rivae resin showed the best activity against C. albicans with a MIC value of 2.65 microg/ml.

Ann Chim. 2007 Sep;97(9):837-44.
PMID: 17970299 [PubMed - indexed for MEDLINE]


Cytotoxic and apoptotic activities of novel amino analogues of boswellic acids.
Shah BA, Kumar A, Gupta P, Sharma M, Sethi VK, Saxena AK, Singh J, Qazi GN, Taneja SC

4-Amino analogues prepared from beta-boswellic acid and 11-keto-beta-boswellic acid, wherein the carboxyl group in ursane nucleus was replaced by an amino function via Curtius reaction, displayed improved cytotoxicity than the parent molecules. The same molecules also exhibited apoptotic activity by inducing DNA fragmentation.

Bioorg Med Chem Lett. 2007 Dec;17(23):6411-6.
PMID: 17950603 [PubMed - indexed for MEDLINE]


Incensole acetate, a novel anti-inflammatory compound isolated from Boswellia resin, inhibits nuclear factor-kappa B activation.
Moussaieff A, Shohami E, Kashman Y, Fride E, Schmitz ML, Renner F, Fiebich BL, Munoz E, Ben-Neriah Y, Mechoulam R

Boswellia resin is a major anti-inflammatory agent in herbal medical tradition, as well as a common food supplement. Its anti-inflammatory activity has been attributed to boswellic acid and its derivatives. Here, we re-examined the anti-inflammatory effect of the resin, using inhibitor of nuclear factor-kappaB alpha (IkappaB alpha) degradation in tumor necrosis factor (TNF) alpha-stimulated HeLa cells for a bioassay-guided fractionation. We thus isolated two novel nuclear factor-kappaB (NF-kappaB) inhibitors from the resin, their structures elucidated as incensole acetate (IA) and its nonacetylated form, incensole (IN). IA inhibited TAK/TAB-mediated IkappaB kinase (IKK) activation loop phosphorylation, resulting in the inhibition of cytokine and lipopolysaccharide-mediated NF-kappaB activation. It had no effect on IKK activity in vitro, and it did not suppress IkappaB alpha phosphorylation in costimulated T-cells, indicating that the kinase inhibition is neither direct nor does it affect all NF-kappaB activation pathways. The inhibitory effect seems specific; IA did not interfere with TNFalpha-induced activation of c-Jun N-terminal kinase (JNK) and p38 mitogen-activated protein kinase. IA treatment had a robust anti-inflammatory effect in a mouse inflamed paw model. Cembrenoid diterpenoids, specifically IA and its derivatives, may thus constitute a potential novel group of NF-kappaB inhibitors, originating from an ancient anti-inflammatory herbal remedy.

Mol Pharmacol. 2007 Dec;72(6):1657-64.
PMID: 17895408 [PubMed - indexed for MEDLINE]


Bioactive constituents from Boswellia papyrifera.
Atta-ur-Rahman , Naz H, Fadimatou , Makhmoor T, Yasin A, Fatima N, Ngounou FN, Kimbu SF, Sondengam BL, Choudhary MI

Phytochemical investigation of the stem bark extract of Boswellia papyrifera afforded two new stilbene glycosides, trans-4',5-dihydroxy-3-methoxystilbene-5-O-{alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-glucopyranoside (1), trans-4',5-dihydroxy-3-methoxystilbene-5-O-[alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-glucopyranoside (2), and a new triterpene, 3alpha-acetoxy-27-hydroxylup-20(29)-en-24-oic acid (3), along with five known compounds, 11-keto-beta-boswellic acid (4), beta-elemonic acid (7), 3alpha-acetoxy-11-keto-beta-boswellic acid (8), beta-boswellic acid (9), and beta-sitosterol (10). The stilbene glycosides exhibited significant inhibition of phosphodiesterase I and xanthine oxidase. The triterpenes (3-9) exhibited prolyl endopeptidase inhibitory activities.

J Nat Prod. 2005 Feb;68(2):189-93.
PMID: 15730241 [PubMed - indexed for MEDLINE]


Aromatic components of the leaves of the New Zealand lemonwood tree Pittosporum eugenioides.
Weston RJ

The major aromatic components of the essential leaf oil of the New Zealand lemonwood tree Pittosporum eugenioides are octyl acetate (33%), terpinen-4-ol (13%), decanol (6%) and (Z)-hex-3-enol (5%). These products are responsible for the characteristic Citrus-like aroma which is detected when the leaves are crushed, a phenomenon which provided the species with its common name. The major component of the oil, octyl acetate is also an abundant component of the essential oils of Heracleum and Boswellia species.

Z Naturforsch C J Biosci. 2004;59(1-2):32-4.
PMID: 15018048 [PubMed - indexed for MEDLINE]


Two new macrocyclic diaryl ether heptanoids from Boswellia ovalifoliolata.
Lakshmi Niranjan Reddy V, Ravinder K, Srinivasulu M, Venkateshwar Goud T, Malla Reddy S, Srujankumar D, Prabhakar Rao T, Suryanarayana Murty U, Venkateswarlu Y

The stems of Boswellia ovalifoliolata BAL. & HENRY (Burseraceae) afforded two new macrocyclic diaryl ether heptanoids, ovalifoliolatin A (1) and B (2) together with three known compounds; acerogenin C (3), 3 alpha-hydroxyurs-12-ene (4), and sitost-4-en-3-one (5). The structures were established by means of spectroscopic analysis and compounds 1, 3-5 were evaluated for their antibacterial activity.

Chem Pharm Bull (Tokyo). 2003 Sep;51(9):1081-4.
PMID: 12951452 [PubMed - indexed for MEDLINE]


Immunomodulatory triterpenoids from the oleogum resin of Boswellia carterii Birdwood.
Badria FA, Mikhaeil BR, Maatooq GT, Amer MM

The immunomodulatory bioassay-guided fractionation of the oleogum resin of frankincense (Boswellia carterii Birdwood) resulted in the isolation and identification of 9 compounds; palmitic acid and eight triterpenoids belonging to lupane, ursane, oleanane, and tirucallane skeleta were isolated form the resin. These triterpenoids are lupeol, beta-boswellic acid, 11-keto-beta-boswellic acid, acetyl beta-boswellic acid, acetyl 11-keto-beta-boswellic acid, acetyl-alpha-boswellic acid, 3-oxo-tirucallic acid, and 3-hydroxy-tirucallic acid. The structures of the isolated compounds were deduced based on spectroscopic evidences. The lymphocyte transformation assay of the isolated compounds proved that the total extract retained more activity than that of any of the purified compounds.

Z Naturforsch C J Biosci. 2003;58(7-8):505-16.
PMID: 12939036 [PubMed - indexed for MEDLINE]


Analysis of pentacyclic triterpenic acids from frankincense gum resins and related phytopharmaceuticals by high-performance liquid chromatography. Identification of lupeolic acid, a novel pentacyclic triterpene.
Büchele B, Zugmaier W, Simmet T

An HPLC gradient method with photodiode array detection was developed for the simultaneous analysis of 12 different pentacyclic triterpenic acids in Indian and African frankincense gum resins as well as in related phytopharmaceuticals. The triterpenic acids were obtained by an exhaustive extraction procedure. Identification of the compounds was based on retention times, UV-spectra and add on technique with standards isolated from African frankincense. The method allows differentiation of frankincense of different origin and standardization of frankincense-based phytopharmaceuticals. Further, this is the first report identifying a novel pentacyclic triterpene, lupeolic acid, as a constituent of frankincense gum resins.

J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul;791(1-2):21-30.
PMID: 12798161 [PubMed - indexed for MEDLINE]


[Study on the detecting methods of the imported materia medica--olibanum].
Shi SM, Tian JG, Wang BQ

OBJECTIVE: To analyse the chemical components of the essential oil of Gum olibanum somalilnds and Gum olibanum Ethiopia, and to set up determination methods of their main components.

METHOD: Two kinds of essential oil are identified by GC-MS, and assayed by Gas chromatography, using SE-54 as the packing material (column 2.1 m x 3.2 mm), with column temperature starting from 80 degrees C, holding for 1 min, and then rising at the rate of 15 degrees C per minute to 170 degrees C.

RESULT: 40 kinds of chemical compounds in the essential oil of Gum olibanum somalilnds and 22 kinds of those of Gum olibanum Ethiopia were identified by GC-MS, the main component in the essential oil of Gum olibanum somalilnds being alpha-pinene, and the main one of Gum olibanum Ethiopia being Octyl acetate 17 batches of samples were determined with the linear range of alpha-pinene being 0-10.80 micrograms, the correlation coefficient being 0.9995, the recovery being 98.16%, RSD being 1.83%; the linear range of Octyl acetate being 0-10.32 micrograms, the correlation coefficient being 0.9996, the recovery being 99.56%, and RSD being 1.36%.

CONCLUSION: This study can be used for the setting up of the specification of Olibanum.

Zhongguo Zhong Yao Za Zhi. 2002 Mar;27(3):170-3.
PMID: 12774394 [PubMed - indexed for MEDLINE]


[Chemical components of Boswellia carterii].
Zhou JY, Cui R

AIM: To investigate the chemical components of Boswellia carterii.

METHODS: Chromatographic technologies were used for separation and purification, while spectral analysis was used for structure elucidation.

RESULTS: Six compounds were isolated and their structures were identified as acetyl-alpha-boswellic acid (1), acetyl-beta-boswellic acid (2), lup-20(29)-ene-3 alpha-acetoxy-24-oic acid (3), alpha-boswellic acid (4), beta-boswellic acid (5) and acetyl-11-keto-beta-boswellic acid (6).

CONCLUSION: Compound 3 is a new constituent.

Yao Xue Xue Bao. 2002 Aug;37(8):633-5.
PMID: 12567779 [PubMed - indexed for MEDLINE]


A lupane triterpene from frankincense (Boswellia sp., Burseraceae).
Culioli G, Mathe C, Archier P, Vieillescazes C

A new lupane-type triterpene, 3alpha-hydroxy-lup-20(29)-en-24-oic acid, was isolated from the methanolic extract of "Erytrean-type" resin of commercial frankincense together with the known 3alpha-hydroxy-olean-12-en-24-oic acid (alpha-boswellic acid) and 3alpha-hydroxy-urs-12-en-24-oic acid (beta-boswellic acid). Their structures were characterized on the basis of chemical and spectral evidence including two dimensional NMR experiments and mass spectrometric techniques.

Phytochemistry. 2003 Feb;62(4):537-41.
PMID: 12560022 [PubMed - indexed for MEDLINE]


Isolation and structure of a 4-O-methyl-glucuronoarabinogalactan from Boswellia serrata.
Sen AK, Das AK, Banerji N, Vignon MR

Carbohydr Res. 1992 Jan;223():321-7.
PMID: 1596930 [PubMed - indexed for MEDLINE]


Triterpenes of Boswellia frereana.
Proietti G, Strapaghetti G, Corsano S

Planta Med. 1981 Apr;41(4):417.
PMID: 17401871 [PubMed - as supplied by publisher]