| 1. |
Advances and Challenges in the Analysis of Boswellic Acids by Separation Methods.
Kosolapov D, Jáč P, Riasová P, Poušková J, Polášek M, Nováková L
resin is an exudate from the cut bark of trees. The main constituents of pharmacological interest are boswellic acids (pentacyclic triterpenoids), namely α-boswellic acid, β-boswellic acid, 3--acetyl-α-boswellic acid, 3-acetyl-β-boswellic acid, 11-keto-β-boswellic acid, and 3--acetyl-11-keto-β-boswellic acid. Nowadays, dietary supplements with extract are used in the treatment of inflammatory joint diseases. Additionally, the constituents of resin have shown potential for the treatment of other chronic inflammatory diseases and various types of cancer. Separation methods including ultra/high-performance liquid chromatography, gas chromatography, thin layer chromatography, supercritical fluid chromatography, and capillary electrochromatography coupled with UV or MS detection have been used for the determination of boswellic acids in various matrices (mostly plant material and biological samples). This review aims to provide a comprehensive summary of these separation methods, offering a critical discussion of their strengths and limitations in the analysis of boswellic acids. The knowledge of various separation methods plays a pivotal role in the quality control of herbal dietary supplements and the monitoring of the metabolism and pharmacokinetics of their constituents. The approaches based on metabolomics and network pharmacology represent new ways of fingerprinting secondary metabolites in resin increasing the comprehensiveness of the output of these methods resulting in safer dietary supplements.
Crit Rev Anal Chem. 2024 Mar;():1-27.
PMID: 38462842 [PubMed - as supplied by publisher]
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| 2. |
Rapid Detection of Adulteration in Extracts with Citric Acid by UPLC-HRMS and H NMR.
Püski P, Körmöczi T, Berkecz R, Barta A, Bajtel Á, Kiss T
ole-gum-resin extracts (BSEs) are commonly used as food supplements, especially in osteoarthritis management. The quality standard is established by determining 11-keto-β-boswellic acid (KBA) and acetyl-11-keto-boswellic acid (AKBA) content using high-performance liquid chromatography (HPLC) or assessing the total boswellic acid (TBA) content by titrimetry. The limited geographical distribution of species and increasing industrial demand could increase the risk of adulteration in -containing products. In this study, 14 BSEs from commercial sources, used in food supplements, were analyzed in comparison with a USP Reference Standard extract. The KBA and AKBA content was determined by HPLC, whereas the TBA content was determined by titration. Targeted UHPLC-high-resolution mass spectrometry (HRMS) was applied to identify the carboxylic acid content in the samples. The H NMR spectra of extracts were also analyzed. Only two products met the criteria for KBA and AKBA content. Although, the TBA content complied with the expected amount, 10 extracts contained citric acid levels of 6-11% even though citric acid is not a cha-racteristic component of BSEs. Our results suggest undeclared addition of citric acid to comply with declared contents of TBA when using titration methods. Incorporation of citric acid to industrial samples - in order to alter the outcomes of the titration analysis - was demonstrated for the first time.
J Diet Suppl. 2024 Jan;():1-16.
PMID: 38165273 [PubMed - as supplied by publisher]
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| 3. |
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]
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| 4. |
A Simple HPTLC Approach of Quantification of Serratol and Tirucallic Acid with Boswellic Acids in Boswellia serrata by Validated Densitometric Method with MS/MS Characterization.
Mukadam S, Ghule C, Girme A, Shinde VM, Hingorani L, Mahadik KR
This study was planned to develop a simple high-performance thin-layer chromatography method for qualitative and quantitative estimation of 3-acetyl-11-keto-β-boswellic acid (AKBBA), β-boswellic acid (BBA), 3-oxo-tirucallic acid (TCA) and serratol (SRT) with HPTLC-ESI-MS/MS for characterization in Boswellia serrata Roxb. oleo gum resin extract. The method was developed with hexane-ethyl acetate-toluene-chloroform-formic acid as mobile phase. RF values observed for AKBBA, BBA, TCA and SRT were 0.42, 0.39, 0.53 and 0.72, respectively. The method was validated according to International Council for Harmonisation guidelines. The concentration range for linearity was 100-500 ng/band for AKBBA and 200-700 ng/band for the other three markers with r2 > 0.99. The method resulted in good recoveries as 101.56, 100.68, 98.64 and 103.26%. The limit of detection was noticed as 25 , 37, 54 and 38 ng/band, with a limit of quantification as 76, 114, 116 and 115 ng/band, for AKBBA, BBA, TCA and SRT, respectively. The four markers were identified and confirmed in B. serrata extract using TLC-MS by indirect profiling by LC-ESI-MS/MS and were identified as terpenoids, TCA and cembranoids: AKBBA (mass/charge (m/z) = 513.00), BBA (m/z = 455.40), 3-oxo-tirucallic acid (m/z = 455.70) and SRT (m/z = 291.25), respectively.
J Chromatogr Sci. 2023 Dec;61(10):953-962.
PMID: 36892162 [PubMed - indexed for MEDLINE]
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| 5. |
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]
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| 6. |
Retention index based approach for simulation of results and application for validation of compound identification in comprehensive two-dimensional gas chromatography.
Kakanopas P, Janta P, Vimolmangkang S, Hermatasia F, Kulsing C
In this work, first and second dimensional retention index (I and I) based calculation approach is established to simulate peak retention times (t and t) of samples for the given sets of volatile compounds in comprehensive two-dimensional gas chromatography-mass spectrometry (GC×GC-MS). For the result without t and t data of alkane references (t and t), the following steps were applied: (1) curve fitting based on van den Dool and Kratz relationship in order to simulate t using a training set of volatile compounds in a sample with their experimental t data, and (2) simulation of t at different t to construct their isovolatility curves based on a nonlinear equation with p-p parameters and a constant (within the ranges of -0.0052 to 0.0049, -0.6181 to -0.0230, -26.4775 to -0.2698, 0.0050 to 9.6259, -7.2976 to -3.9524 and 0.9157 to 4.0779, respectively). These parameters were obtained by performing curve fitting according to the experimental t data of the same training set with the least square values ranging from 4.58×10 to 32.55. Simulation of t and t of target analytes (t and t) with known I and I were performed using t and the simulated isovolatility curves. All the calculations and curve fittings were carried out by using Solver in Microsoft Excel. The approach was applied to simulate results for 542 compounds in several samples including analysis of saffron (Crocus sativas L.), Boswellia papyrifera, acacia honey and incense powder/smoke, perfume and cannabis either reported from literature or from the experiments in this work using different experimental approaches. These were compared with the experimental data showing correlation with the R ranges of 0.98-1.00 and 0.80-0.97 for t and t, respectively. This approach was then applied to propose 6 compounds which may be incorrectly identified based on the differences of >2 times of the standard deviations between t and the experimental t in both residue and leave-one-out analyses.
J Chromatogr A. 2022 Aug;1679():463394.
PMID: 35970049 [PubMed - indexed for MEDLINE]
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| 7. |
Analysis of boswellic acids in dietary supplements containing Indian frankincense (Boswellia serrata) by Supercritical Fluid Chromatography.
Zwerger M, Ganzera M
Boswellic acids, a class of triterpenes, are the bioactive constituents in Indian frankincense, an herbal drug with pronounced anti-inflammatory activity. In this study their separation and quantification in B. serrata extracts is reported for the first time by using Supercritical Fluid Chromatography. Under optimized conditions, i.e. a Viridis HSS C18 SB column and carbon dioxide, methanol, acetonitrile and ammonium hydroxide as mobile phase, six boswellic acids could be separated in under 6 min. The assay fulfilled all validation criteria with coefficients of determination higher than 0.999, a wide linear range (30-1000 μg/mL), recovery rates from 97.1-103.0 %, excellent precision, and detection limits typical for SFC with UV-detection (≤ 5.5 μg/mL). The method could easily be hyphenated to mass spectrometry, which was helpful to tentatively assign further compounds (mainly derivatives of tirucallic acid) and to increase the assay's sensitivity. Its practical applicability was confirmed by analyzing several commercial products, which mainly contained β-boswellic acid as dominant triterpene, yet in extremely variable amounts ranging from 0.9 to 16.9 %.
J Pharm Biomed Anal. 2021 Jul;201():114106.
PMID: 33962180 [PubMed - indexed for MEDLINE]
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| 8. |
Rapid Identification of Commercial Frankincense Products by MALDITOF Mass Spectrometry.
Lai SC, You RI, Chen TT, Chang Y, Liu CZ, Chen HP, Wu C
BACKGROUND: Frankincense is a resin secreted by the Boswellia tree. It is used in perfumery, aromatherapy, skincare, and traditional Chinese medicine. However, all Boswellia species are under threat owing to habitat loss and overexploitation. As a result, the market is getting flooded with counterfeit frankincense products.
OBJECTIVE: This study aims to establish a high-throughput method to screen and identify the authenticity of commercial frankincense products. We report, for the first time, a matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS)-based method for rapid and high-throughput screening of frankincense samples.
METHODS: MALDI-TOF MS, HPLC, thin-layer chromatography (TLC), and in vitro antiinflammatory activity assay were used to examine the frankincense samples.
RESULTS: Well-resolved peaks of frankincense triterpenoids in the spectra were observed in the crude extract of commercial samples, including α-boswellic acids (αBAs), β-boswellic acids (βBAs), 11-keto-β-boswellic acids (KBAs), acetyl-11-keto-β-boswellic acids (AKBAs), and their esters. These compounds can be used as indicators for determining the authenticity of frankincense.
CONCLUSION: Unlike LC-MS, which is a time-consuming and expensive method, and TLC, which requires a reference sample, our inexpensive, rapid high-throughput identification method based on MALDI-TOF MS is ideal for large-scale screening of frankincense samples sold in the market.
Comb Chem High Throughput Screen. 2022;25(5):895-905.
PMID: 33645476 [PubMed - indexed for MEDLINE]
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| 9. |
Development and validation of a sensitive UHPLC-MS/MS method for the measurement of β-elemonic acid in rat plasma and tissues and its application to pharmacokinetics and tissue distribution study.
Zhang Y, Huo XX, Cheng LY, Chen MY, Song L, Yu YL, Zhou K
β-Elemonic acid is one of the main active ingredients isolated from Boswellia carterii Birdw. which has been reported to exhibit potential anti-inflammatory and anti-cancer activities. There is few information about pharmacokinetics and tissue distribution of β-elemonic acid by now. In this study, an ultra-high-performance liquid chromatography coupled with triple quadrupole mass spectrometry (UHPLC-MS/MS) method has been developed and validated to determine β-elemonic acid in rat plasma and various tissues after intragastric administration. Oleanolic acid was chosen as an internal standard (IS) and the plasma/tissue samples were pretreated with one-step liquid-liquid extraction. Chromatographic separation was accomplished on Eclipse Plus C18 analytical column (2.1 × 50 mm, 1.8 μm) utilizing a gradient mobile phase system consisting of water (with 0.1% ammonia-solution) and acetonitrile. β-Elemonic acid and IS were detected and quantified using negative electrospray ionization in multiple reaction monitoring (MRM) mode with transitions of m/z 453.3 → 423.5 for β-elemonic acid and m/z 455.3 → 407.6 for IS. β-Elemonic acid showed good linearity over the investigated concentration range (r > 0.9934) in rat plasma and tissue sample. The method was successfully applied for determination of β-elemonic acid in bio-samples. A bimodal phenomenon appeared in the plasma concentration-time curve of the β-elemonic acid. The highest tissue concentrations were found in the intestine including jejunum, ileum and colon.
J Chromatogr B Analyt Technol Biomed Life Sci. 2021 Mar;1167():122566.
PMID: 33578281 [PubMed - indexed for MEDLINE]
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| 10. |
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]
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| 11. |
A Validated LC-MS/MS Method for Simultaneous Determination of 3-O-Acetyl-11-Keto-β-Boswellic Acid (AKBA) and its Active Metabolite Acetyl-11-Hydroxy-β-Boswellic Acid (Ac-11-OH-BA) in Rat Plasma: Application to a Pharmacokinetic Study.
Sharma T, Jana S
The aim of this study was to develop and validate a new, rapid, sensitive, selective and reliable liquid chromatography-tandem mass spectrometry method for simultaneous determination of 3-O-Acetyl-11-keto-β-boswellic acid (AKBA) and its active metabolite 3-O-Acetyl-11-hydroxy-β-boswellic acid (Ac-11-hydroxy-BA) in rat plasma. Both analytes (AKBA and Ac-11-hydroxy-BA) and the internal standard (IS, ursolic acid) were extracted from 100 μL of rat plasma by protein precipitation. Chromatographic separation was achieved on PRP-H1 RP-C18 column (75 mm × 2 mm, 1.6 μm) using acetonitrile-water (95.5 v/v) as the mobile phase. Mass detection was conducted by electrospray ionization in positive ion multiple reaction monitoring (MRM) mode. A linear dynamic range of 1-1,000 ng/mL for both AKBA and Ac-11-hydroxy-BA was established with mean correlation coefficient (r (1)) of 0.999. Intra- and inter-day precision (% CV) of analysis were found in the range of 1.9-7.4%. The accuracy determined for these analytes ranged from 92.4 to 107.2%. The extraction recoveries for both analytes ranged from 92.6 to 97.3% for spiked plasma samples and were consistent. The % change in stability samples compared to nominal concentration ranged from 0.4 to 4.2%. This method was successfully tested to a pharmacokinetic (PK) study for estimation of AKBA and acetyl-11-hydroxy-BA in rat plasma following oral administration of AKBA. This method has been validated with the advantage of shorter run time that can be used for high-throughput analysis and has been successfully applied to the pharmacokinetic study of AKBA in rats.
J Chromatogr Sci. 2020 Jun;58(6):485-493.
PMID: 32134105 [PubMed - indexed for MEDLINE]
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| 12. |
Exploiting the versatility of vacuum-assisted headspace solid-phase microextraction in combination with the selectivity of ionic liquid-based GC stationary phases to discriminate Boswellia spp. resins through their volatile and semivolatile fractions.
Capetti F, Rubiolo P, Bicchi C, Marengo A, Sgorbini B, Cagliero C
The frankincense resins, secreted from Boswellia species, are an uncommon example of a natural raw material where every class of terpenoids is present in similar proportions. Diterpenoids (serratol, incensole, and incensole acetate) are used to discriminate samples from different species and origins. Headspace solid-phase microextraction has been used for frankincense analysis, although it requires long sampling time for medium- to low-volatility markers; headspace solid-phase microextraction under vacuum can overcome this limit. Gas chromatography is used for analysis but the separation of incensole and serratol needs polar stationary phases. In this study, we develop a method to discriminate frankincenses based on vacuum-assisted headspace solid-phase microextraction combined with fast gas chromatography-mass spectrometry with ionic liquid-based stationary phases. The optimized conditions for solid samples were: air evacuation below 0°C, 15 min of incubation time, and 15 min of extraction time. Losses of volatiles due to vial air-evacuation in the presence of the sample were minimized by sample amount above 100 mg and low sample temperature. Fast gas chromatography provides the baseline separation of all markers in 20 min. By applying vacuum sampling and fast gas chromatography, the total analysis was reduced to 50 min compared to 120 min (60 min sampling plus 60 min analysis) as previously reported. The method was successfully applied to commercial frankincense samples.
J Sep Sci. 2020 May;43(9-10):1879-1889.
PMID: 32072762 [PubMed - indexed for MEDLINE]
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| 13. |
Estimation of boswellic acids in herbal formulations containing extract and comprehensive characterization of secondary metabolites using UPLC-Q-Tof-MS.
Katragunta K, Siva B, Kondepudi N, Vadaparthi PRR, Rama Rao N, Tiwari AK, Suresh Babu K
is a widely used herb in Indian systems of medicine and is well known for its potential medicinal properties. A chromatographic method was developed for the analysis and quantification of six boswellic acid marker compounds, i.e., keto boswellic acid (), 3-O-Acetyl 11-keto β-boswellic acid (), ɑ-Boswellic acid (), β-Boswellic acid (), 3-O-Acetyl-ɑ-boswellic acid () and 3-O-Acetyl-β-boswellic acid () in commercial herbal products containing as an ingredient. Combining UPLC with Q-Tof-MS/MS makes the better identification of secondary metabolites and adulterants in the herbal formulations containing in rapid time using fragmentation approach than the traditional approaches. In this study quantification of boswellic acids with UPLC-PDA method was performed as per the pharmacopeia guidelines. Furthermore, minor phytochemical constituents were identified and characterized with the help of LC-Q-Tof-MS/MS fragmentation data and various isoforms of boswellic acids and tirucallic acids in oleo-gum-resin extract were identified.
J Pharm Anal. 2019 Dec;9(6):414-422.
PMID: 31890341 [PubMed - as supplied by publisher]
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| 14. |
Biophysical properties and finger print of Sp. .
Alotaibi SH
For the first time a finger print analysis via high-performance thin layer chromatography (HPTLC) of Sp. was accomplished. A preliminary investigation of the Sp. displayed the presence of chemical constituents that could be involved in the production of innovative pharmaceuticals for an array of antiviral, anticancer, and antibacterial uses. Moreover, the finger print analysis would deem useful for establishing HPTLC standardization for natural and herbal photochemical constituents.
Saudi J Biol Sci. 2019 Nov;26(7):1450-1457.
PMID: 31762608 [PubMed - as supplied by publisher]
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| 15. |
Corrigendum to "Analytical investigations on Boswellia occulta essential oils" [Phytochemistry 164 (2019) 78-85].
Ayubova M, Brevard H, Baldovini N
Phytochemistry. 2019 Sep;165():112053.
PMID: 31253423 [PubMed - as supplied by publisher]
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| 16. |
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]
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| 17. |
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]
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| 18. |
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]
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| 19. |
Comprehensive 2D gas chromatography-time-of-flight mass spectrometry with 2D retention indices for analysis of volatile compounds in frankincense (Boswellia papyrifera).
Jiang M, Kulsing C, Marriott PJ
Frankincense gum resin secreted from Boswellia papyrifera was analysed by comprehensive 2D gas chromatography hyphenated with accurate mass time-of-flight mass spectrometry (GC×GC-accTOFMS). Direct multiple injection experiments with stepwise isothermal temperature programming were then performed to construct isovolatility curves for reference alkane series in GC×GC. This provides access to calculation of second dimensional retention indices (I). More than 500 peaks were detected and 220 compounds mainly comprising monoterpenes, sesquiterpenes, diterpenes and oxygenated forms of these compounds were identified according to their I, I and accurate mass data. The study demonstrates the capability of GC×GC-accTOFMS with retention data on two separate column phases, as an approach for improved component identification. A greater number of identified and/or tentatively identified terpenoids in this traditional Chinese medicine allow for a more comprehensive coverage of the volatile composition of frankincense.
Anal Bioanal Chem. 2018 May;410(13):3185-3196.
PMID: 29582122 [PubMed - indexed for MEDLINE]
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| 20. |
Quantification of AKBA in Boswellia sacra Using NIRS Coupled with PLSR as an Alternative Method and Cross-Validation by HPLC.
Rehman NU, Ali L, Al-Harrasi A, Mabood F, Al-Broumi M, Khan AL, Hussain H, Hussain J, Csuk R
INTRODUCTION: 3-O-Acetyl-11-keto-β-boswellic acid (AKBA), one of the pentacyclic triterpenoids, is the main biologically active constituent in the resin of Boswellia sacra and has received significant pharmacological interest in recent years.
OBJECTIVE: It was aimed to develop a robust method to quantify the AKBA content in methanolic extracts of different parts of B. sacra plants and in various fractions of its resin exudates through near-infrared spectroscopy (NIRS) coupled with partial least squares regression (PLSR).
MATERIAL AND METHODS: The near-infrared (NIR) spectra were used to measure the AKBA standards and B. sacra samples at a wavelength range between 700 and 2500 nm in absorption mode. A PLSR model was built from the obtained spectral data using 70% of the AKBA working standard solutions (training set), ranging from 0.1 ppm to 100 ppm. The final PLSR showed a R value of 99% with a root mean square error of cross-validation (RMSECV) value of 0.39% and a R value of 99%.
RESULTS: The results showed that a 50% CHCl /n-hexane sub-fraction has the highest concentration of AKBA (14.8%), followed by 55% CHCl /n-hexane (13.6%), and 40% CHCl /n-hexane (6.1%).
CONCLUSION: As the results achieved with the proposed NIRS methodology are in close agreement to the results of AKBA analysis using HPLC, we suggest that our proposed NIRS method is a fast alternative and non-destructive method for the analysis of AKBA in different samples of B. sacra. Copyright © 2017 John Wiley & Sons, Ltd.
Phytochem Anal. 2018 Mar;29(2):137-143.
PMID: 28881407 [PubMed - indexed for MEDLINE]
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| 21. |
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]
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| 22. |
Application of NIRS coupled with PLS regression as a rapid, non-destructive alternative method for quantification of KBA in Boswellia sacra.
Al-Harrasi A, Rehman NU, Mabood F, Albroumi M, Ali L, Hussain J, Hussain H, Csuk R, Khan AL, Alam T, Alameri S
In the present study, for the first time, NIR spectroscopy coupled with PLS regression as a rapid and alternative method was developed to quantify the amount of Keto-β-Boswellic Acid (KBA) in different plant parts of Boswellia sacra and the resin exudates of the trunk. NIR spectroscopy was used for the measurement of KBA standards and B. sacra samples in absorption mode in the wavelength range from 700-2500nm. PLS regression model was built from the obtained spectral data using 70% of KBA standards (training set) in the range from 0.1ppm to 100ppm. The PLS regression model obtained was having R-square value of 98% with 0.99 corelationship value and having good prediction with RMSEP value 3.2 and correlation of 0.99. It was then used to quantify the amount of KBA in the samples of B. sacra. The results indicated that the MeOH extract of resin has the highest concentration of KBA (0.6%) followed by essential oil (0.1%). However, no KBA was found in the aqueous extract. The MeOH extract of the resin was subjected to column chromatography to get various sub-fractions at different polarity of organic solvents. The sub-fraction at 4% MeOH/CHCl (4.1% of KBA) was found to contain the highest percentage of KBA followed by another sub-fraction at 2% MeOH/CHCl (2.2% of KBA). The present results also indicated that KBA is only present in the gum-resin of the trunk and not in all parts of the plant. These results were further confirmed through HPLC analysis and therefore it is concluded that NIRS coupled with PLS regression is a rapid and alternate method for quantification of KBA in Boswellia sacra. It is non-destructive, rapid, sensitive and uses simple methods of sample preparation.
Spectrochim Acta A Mol Biomol Spectrosc. 2017 Sep;184():277-285.
PMID: 28525862 [PubMed - indexed for MEDLINE]
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| 23. |
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]
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| 24. |
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]
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| 25. |
Development of a gas chromatography-mass spectrometry method to monitor in a single run, mono- to triterpenoid compounds distribution in resinous plant materials.
Jemmali Z, Chartier A, Elfakir C
A new procedure based on gas chromatography coupled to mass spectrometry (GC-MS) was developed for the simultaneous determination of mono- to triterpenoid compounds in resinous materials. Given the difference of volatility and polarity of the studied compounds some critical steps in this methodology had to be identified and investigated. The recovery of volatile compounds after sample extraction was studied. A recovery range from 30% to 100% from the more volatile monoterpene to the least one was observed. Then the mandatory derivatization step for the analysis of pentacyclic triterpenes bearing hydroxyl and carboxyl groups was optimized. Results showed that derivatization using N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA) and trimethylchlorosilane (TMCS) in pyridine (22:13:65 v/v/v) for 2h at 30 °C was the most efficient method of derivatizing all the hydroxyl and carboxylic acid groups contained in the triterpene structures. After choosing the best injection parameters for these compounds, the selectivity of the GC column towards the separation of these terpenoids was investigated using statistical tools (principal component analysis and desirability functions). A separation with a good resolution was achieved on an HP-5ms column using a programmed temperature vaporizing injector (PTV). The method was pre-validated in terms of detection limits (LOD from 100 μg L(-1) to 200 μg L(-1) depending on the compound), linearity and repeatability using seven compounds representative of mono- and triterpenoid classes. An exhaustive characterization of various types of resins (di-, triterpenic and oleo-gum resins) was achieved.
J Chromatogr A. 2016 Apr;1443():241-53.
PMID: 27018190 [PubMed - indexed for MEDLINE]
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| 26. |
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]
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| 27. |
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]
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| 28. |
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]
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| 29. |
Combination of quantitative analysis and chemometric analysis for the quality evaluation of three different frankincenses by ultra high performance liquid chromatography and quadrupole time of flight mass spectrometry.
Zhang C, Sun L, Tian RT, Jin HY, Ma SC, Gu BR
Frankincense has gained increasing attention in the pharmaceutical industry because of its pharmacologically active components such as boswellic acids. However, the identity and overall quality evaluation of three different frankincense species in different Pharmacopeias and the literature have less been reported. In this paper, quantitative analysis and chemometric evaluation were established and applied for the quality control of frankincense. Meanwhile, quantitative and chemometric analysis could be conducted under the same analytical conditions. In total 55 samples from four habitats (three species) of frankincense were collected and six boswellic acids were chosen for quantitative analysis. Chemometric analyses such as similarity analysis, hierarchical cluster analysis, and principal component analysis were used to identify frankincense of three species to reveal the correlation between its components and species. In addition, 12 chromatographic peaks have been tentatively identified explored by reference substances and quadrupole time-of-flight mass spectrometry. The results indicated that the total boswellic acid profiles of three species of frankincense are similar and their fingerprints can be used to differentiate between them.
J Sep Sci. 2015 Oct;38(19):3324-30.
PMID: 26228790 [PubMed - indexed for MEDLINE]
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| 30. |
Identification of odorants in frankincense (Boswellia sacra Flueck.) by aroma extract dilution analysis and two-dimensional gas chromatography-mass spectrometry/olfactometry.
Niebler J, Buettner A
Frankincense has been known, traded and used throughout the ages for its exceptional aroma properties, and is still commonly used in both secular and religious settings to convey a pleasant odor. Surprisingly, the odoriferous principle(s) underlying its unique odor profile have never been published. In this study, resin samples of Boswellia sacra Flueck. from both Somalia and Oman were investigated by aroma extract dilution analysis. In a comprehensive, odor-activity guided approach both chemo-analytical and human-sensory parameters were used to identify odor active constituents of the volatile fraction of B. sacra. Among the key odorants found were α-pinene, β-myrcene, linalool, p-cresol and two unidentified sesquiterpenoids. Overall, a total of 23 odorants were detected and analyzed by gas chromatography-olfactometry and heart-cut two-dimensional gas chromatography-mass spectrometry/olfactometry. The majority of the identified odorant compounds were oxygenated monoterpenes, along with some relevant mono- and sesquiterpenes and only one diterpenoid substance. Several of these compounds were reported here for the first time as odorous constituents in B. sacra. Identifying bioactive compounds might support a better understanding with regard to the potential benefits of frankincense, for example in aromatherapy or ecclesial settings.
Phytochemistry. 2015 Jan;109():66-75.
PMID: 25468535 [PubMed - indexed for MEDLINE]
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| 31. |
Comprehensive identification of active triterpenoid metabolites in frankincense using a coupling strategy.
Liu Y, Liu Z, Lu C, Li J, Ning Z, Song Z, Wang C, Du Z, Lu X, Zhao S, Lu A
Frankincense resins are extensively used as natural remedies in regions ranging from North Africa to China. Triterpenoid metabolites from frankincense exhibit notable anti-inflammatory and anti-tumor properties. In the present paper, without the use of an isolation process, the fragmentation rules and NMR spectral characteristics of triterpenoid metabolites in frankincense are summarized through a coupling method using high performance liquid chromatography-diode array detection/electrospray ionization tandem mass spectrometry (HPLC-DAD/ESI-MS(n)) combined with HPLC-nuclear magnetic resonance (NMR) experiments. Based on this groundwork, a coupling strategy for the comprehensive metabolic profiling of active triterpenoid metabolites from enriched fractions of frankincense was developed. The proposed strategy may serve as a method for the holistic screening of bioactive metabolites in complex TCM samples.
J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Jul;963():90-8.
PMID: 24946158 [PubMed - indexed for MEDLINE]
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| 32. |
Parameters optimization of supercritical fluid-CO2 extracts of frankincense using response surface methodology and its pharmacodynamics effects.
Zhou J, Ma XM, Qiu BH, Chen JX, Bian L, Pan LM
The volatile oil parts of frankincense (Boswellia carterii Birdw.) were extracted with supercritical carbon dioxide under constant pressure (15, 20, or 25 MPa) and fixed temperature (40, 50, or 60°C), given time (60, 90, or 120 min) aiming at the acquisition of enriched fractions containing octyl acetate, compounds of pharmaceutical interest. A mathematical model was created by Box-Behnken design, a popular template for response surface methodology, for the extraction process. The response value was characterized by synthetical score, which comprised yields accounting for 20% and content of octyl acetate for 80%. The content of octyl acetate was determined by GC. The supercritical fluid extraction showed higher selectivity than conventional steam distillation. Supercritical fluid-CO(2) for extracting frankincense under optimum condition was of great validity, which was also successfully verified by the pharmacological experiments.
J Sep Sci. 2013 Jan;36(2):383-90.
PMID: 23255314 [PubMed - indexed for MEDLINE]
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| 33. |
Classification of natural resins by liquid chromatography-mass spectrometry and gas chromatography-mass spectrometry using chemometric analysis.
Rhourrhi-Frih B, West C, Pasquier L, André P, Chaimbault P, Lafosse M
Twenty-six resins from six botanical sources belonging to the class Magnoliopsida were compared based on gas chromatography-mass spectrometry and liquid chromatography-mass spectrometry data. The extracts were analysed by GC after silylation and by reversed phase LC combined with atmospheric pressure photoionisation (APPI) mass spectrometry. The chromatograms were re-organized in data matrices, where each sample was represented by a single column comprising 2755 observations (intensity, time, m/z) in GC-MS and 360 observations in LC-MS. A simple comparison of resin fingerprints was attempted by organizing data according to a three dimensional bubble chart (retention time against m/z where each point was a bubble which size represented the ion intensity) where it is possible to easily superimpose the fingerprints. Thus the common and different species can be easily observed enabling to classify the resins. Hierarchical cluster analysis based on characteristics of GC-MS and LC-MS profiles affords a complete description of the classes of the resins and shows that 26 resins are divided into five main clusters Commiphora mukul, Daniella oliveri, Gardenia gummifera, Canarium madagascariensis, Boswellia dalzielii and Boswellia serrata, respectively. In conclusion, the proposed method has been applied to three other resinous samples from the Burseraceae family to evaluate their alteration state.
J Chromatogr A. 2012 Sep;1256():177-90.
PMID: 22885042 [PubMed - indexed for MEDLINE]
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| 34. |
[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]
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| 35. |
Chemical differentiation of Boswellia sacra and Boswellia carterii essential oils by gas chromatography and chiral gas chromatography-mass spectrometry.
Woolley CL, Suhail MM, Smith BL, Boren KE, Taylor LC, Schreuder MF, Chai JK, Casabianca H, Haq S, Lin HK, Al-Shahri AA, Al-Hatmi S, Young DG
Major botanical and scientific references currently identify two species of frankincense, Boswellia carterii and Boswellia sacra, as being synonymous. We evaluated the Somalian (B. carterii) and Omani/Yemeni (B. sacra) species by chemical analyses to determine if there were any minor or major differences between the two species of frankincense. Components identified with their average percent for B. sacra are α-thujene (0.6%), α-pinene (68.2%), camphene (2.1%), sabinene (2.9%), β-pinene (2.0%), myrcene (0.7%), limonene+β-phellandrene (6.2%). Components identified with their average percent for B. carterii are α-thujene (7.9%), α-pinene (37.3%), camphene (0.8%), sabinene (4.9%), β-pinene (1.8%), myrcene (7.3%), limonene+β-phellandrene (14.4%). Initially, GC-MS analysis did not reveal major statistical differences. However, optical rotation values, B. Sacra (+30.1°) and B. carterii (-13.3°), demonstrated a greater significant difference. Enantiomeric ratio (+)/(-) values of α-pinene for B. sacra and B. carterii are 8.24 and 0.68, respectively, were also calculated aiding our conclusion that B. sacra and B. carterii are not synonymous but rather two distinct and individual frankincense species.
J Chromatogr A. 2012 Oct;1261():158-63.
PMID: 22835693 [PubMed - indexed for MEDLINE]
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| 36. |
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]
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| 37. |
A thin-layer chromatography method for the identification of three different olibanum resins (Boswellia serrata, Boswellia papyrifera and Boswellia carterii, respectively, Boswellia sacra).
Paul M, Brüning G, Bergmann J, Jauch J
INTRODUCTION: Resins of the genus Boswellia are currently an interesting topic for pharmaceutical research since several pharmacological activities (e.g. anti-inflammatory, anti-microbial, anti-tumour) are reported for extracts and compounds isolated from them. Unambiguous identification of these resins, by simple and convenient analytical methods, has so far not clearly been verified.
OBJECTIVE: For differentiation and identification of three important Boswellia species (Boswellia serrata Roxb., Boswellia papyrifera Hochst. and Boswellia carterii Birdw., respectively Boswellia sacra Flueck.), possible even for minimally equipped laboratories, a thin-layer chromatography (TLC) method was developed, allowing unambiguous identification of the three species.
METHODOLOGY: Crude resin samples (commercial samples and a voucher specimen) were extracted with methanol or diethyl ether and subjected to TLC analysis (normal phase). A pentane and diethyl ether (2:1) with 1% acetic acid eluent was used. Chromatograms were analysed by UV detection (254 nm) and dyeing with anisaldehyde dyeing reagent. Significant spots were isolated and structures were assigned (mass spectrometry; nuclear magnetic resonance spectroscopy).
RESULTS: Incensole and incensole acetate are specific biomarkers for Boswellia papyrifera. Boswellia carterii/Boswellia sacra reveal ß-caryophyllene oxide as a significant marker compound. Boswellia serrata shows neither incensole acetate nor ß-caryophyllene oxide spots, but can be identified by a strong serratol and a sharp 3-oxo-8,24-dien-tirucallic acid spot.
CONCLUSION: The TLC method developed allows unambiguous identification of three different olibanum samples (Boswellia papyrifera, Boswellia serrata, Boswellia carterii/Boswellia sacra). Evidence on the specific biosynthesis routes of these Boswellia species is reported.
Phytochem Anal. 2012;23(2):184-9.
PMID: 21858880 [PubMed - indexed for MEDLINE]
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| 38. |
[GC-MS analysis of volatile oil of olibanum].
Zhao J, Zhou C, Zhou F, Wei T
OBJECTIVE: To analyze the volatile oil of olibanum and apply scientific evidences for its applications.
METHOD: The volatile oil was analyzed by GC-MS.
RESULT: One hundred components were identified,accounting for 91.26% of the total volatile oil, and the main components were octyl acetate, beta-elemene. It contains some transdermal absorption enhancers.
CONCLUSION: The components of olibanum volatile oil were complicated; the connatural transdermal absorption enhancers make it possible to use in external preparation.
Zhongguo Zhong Yao Za Zhi. 2011 Apr;36(8):1050-3.
PMID: 21809584 [PubMed - indexed for MEDLINE]
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| 39. |
[Herbalism, botany and components analysis study on original plants of frankincense].
Sun L, Xu J, Jin H, Tian J, Lin R
In order to clarify original plants of traditional Chinese medicine (TCM) frankincense, a GC method for determination essential oils and a HPLC method for determination boswellic acids were carried out together with analysis of herbalism, botany, components and pharmacology papers of frankincense. It was concluded that original plants of TCM frankincense include at least Boswellia sacra, B. papyrifera and B. serrata.
Zhongguo Zhong Yao Za Zhi. 2011 Jan;36(2):112-6.
PMID: 21506404 [PubMed - indexed for MEDLINE]
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| 40. |
Comparative study of the chemical composition and antioxidant activity of six essential oils and their components.
Yang SA, Jeon SK, Lee EJ, Shim CH, Lee IS
The antioxidant activities and the determined major components of six popular and commercially available herb essential oils, including lavender (Lavendular angustifolia), peppermint (Mentha piperita), rosemary (Rosmarius officinalis), lemon (Citrus limon), grapefruit (Citrus paradise), and frankincense (Boswellia carteri), were compared. The essential oils were analysed by GC-MS and their antioxidant activities were determined by testing free radical-scavenging capacity and lipid peroxidation in the linoleic acid system. The major components of the essential oils of lavender, peppermint, rosemary, lemon, grapefruit, and frankincense were linalyl acetate (28.2%), menthol (33.4%), 1,8-cineole (46.1%), limonene (64.5 and 94.2%), and p-menth-2-en-ol (34.5%), respectively. The highest DPPH radical-scavenging activity was obtained by the lavender essential oil and limonene, with RC50 values of 2.1 +/- 0.23% and 2.1 +/- 0.04%, respectively. Radical-scavenging activity against the ABTS radical was highest in peppermint essential oil (1.6 +/- 0.09). Lavender oil was most effective for inhibiting linoleic acid peroxidation after 10 days.
Nat Prod Res. 2010;24(2):140-51.
PMID: 20077307 [PubMed - indexed for MEDLINE]
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| 41. |
Phytochemical analysis of the essential oil from botanically certified oleogum resin of Boswellia sacra (Omani Luban).
Al-Harrasi A, Al-Saidi S
The yield of hydrodistillation of a botanically certified Oleogum Resin of Boswellia sacra essential oil (5.5%); and its chemical constituents were determined. The GC/MS technique was used for the analysis of the oil. Several oil components were identified based upon comparison of their mass spectral data with those of reference compounds published in literature or stored in a computer library. The oil was characterized by the high content of the monoterpenes (34) which constituted 97.3% in which E-beta-ocimene and limonene were the major constituents. The remaining 2.7% was accounted for the sesquiterpenes (16) in which the E-caryophyllene was the major constituent. The analysis proved the complete absence of the diterpenes.
Molecules. 2008 Sep;13(9):2181-9.
PMID: 18830149 [PubMed - indexed for MEDLINE]
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| 42. |
A simple high-performance liquid chromatographic method for the estimation of boswellic acids from the market formulations containing Boswellia serrata extract.
Shah SA, Rathod IS, Suhagia BN, Pandya SS, Parmar VK
A simple, rapid, and reproducible reverse-phase high-performance liquid chromatographic method is developed for the estimation of boswellic acids, the active constituents in Boswellia serrata oleo-gum resin. The chromatographic separation is performed using a mobile phase consisting of acetonitrile-water (90:10, % v/v) adjusted to pH 4 with glacial acetic acid on a Kromasil 100 C18 analytical column with flow rate of 2.0 mL/min and detection at 260 nm. The elution times are 4.30 and 7.11 min for 11-keto beta-boswellic acid (11-KBA) and 3-acetyl 11-keto beta-boswellic acid (A-11-KBA), respectively. The calibration curve is linear in the 11.66-58.30 microg/mL and 6.50-32.50 microg/mL range for 11-KBA and A-11-KBA, respectively. The limits of detection are 2.33 microg/mL and 1.30 microg/mL for 11-KBA and A-11-KBA, respectively. The mean recoveries are 98.24% to 104.17% and 94.12% to 105.92% for 11-KBA and A-11-KBA, respectively. The inter- and intra-day variation coefficients are less than 5%. The present method is successfully applied for the estimation of boswellic acids from the market formulations containing Boswellia serrata extract.
J Chromatogr Sci. 2008 Sep;46(8):735-8.
PMID: 18796232 [PubMed - indexed for MEDLINE]
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| 43. |
Estimation of boswellic acids from market formulations of Boswellia serrata extract and 11-keto beta-boswellic acid in human plasma by high-performance thin-layer chromatography.
Shah SA, Rathod IS, Suhagia BN, Patel DA, Parmar VK, Shah BK, Vaishnavi VM
A rapid and sensitive high-performance thin-layer chromatographic (HPTLC) method was developed and validated for the quantitative estimation of boswellic acids in formulation containing Boswellia serrata extract (BSE) and 11-keto beta-boswellic acid in human plasma. Simple extraction method was used for isolation of boswellic acid from formulation sample and acidified plasma sample. The isolated samples were chromatographed on silica gel 60F(254)-TLC plates, developed using ternary-solvent system (hexane-chloroform-methanol, 5:5:0.5, v/v) and scanned at 260 nm. The linearity range for 11-KBA spiked in 1 ml of plasma was 29.15-145.75 ng with average recovery of 91.66%. The limit of detection and limit of quantification for 11-KBA in human plasma were found to be 8.75 ng/ml and 29.15 ng/ml. The developed method was successfully applied for the assay of market formulations containing BSE and to determine plasma level of 11-keto beta-boswellic acid in a clinical pilot study.
J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Apr;848(2):232-8.
PMID: 17101304 [PubMed - indexed for MEDLINE]
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| 44. |
Separation and quantification of terpenoids of Boswellia serrata Roxb. extract by planar chromatography techniques (TLC and AMD).
Pozharitskaya ON, Ivanova SA, Shikov AN, Makarov VG
An high-performance TLC (HPTLC) method for the separation of boswellic acids, the active constituents in Boswellia serrata extract, has been developed and TLC of these compounds on silica by automated multiple development (AMD) using solvent gradients was performed. Enhancement of the separation of boswellic acids on HPTLC plates was carried out by AMD chromatography. Densitometric analysis of the developed plate was carried out to quantify the four boswellic acids. 11-Keto-beta-boswellic acid (KBA) and acetyl-11-keto-beta-boswellic acid (AKBA) were quantified by densitometric scanning of the developed plate at 254 nm. beta-Boswellic acid (BA) and acetyl-beta-boswellic acid (ABA) were quantified after derivatization with anisaldehyde sulfuric acid reagent at 560 nm. The AMD system provided a clean separation according to polarity for each of the four groups studied and good results were obtained. The proposed HPTLC method for the simultaneous quantification of the major boswellic acids BA, ABA, KBA, and AKBA was found to be simple, precise, specific, sensitive, and accurate and can be used for routine quality control and for the quantification of these compounds in plant materials. The study of market products revealed significant variations in the content of these pharmacologically active compounds in commercial samples.
J Sep Sci. 2006 Sep;29(14):2245-50.
PMID: 17069256 [PubMed - indexed for MEDLINE]
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| 45. |
Chemical study of triterpenoid resinous materials in archaeological findings by means of direct exposure electron ionisation mass spectrometry and gas chromatography/mass spectrometry.
Modugno F, Ribechini E, Colombini MP
A systematic study of standard triterpenes (alpha-amyrine, oleanolic acid, betulin, lupeol, betulinic acid and lupenone) and of raw resinous materials (frankincense resin, mastic resin and birch bark pitch) was performed using direct exposure electron ionisation mass spectrometry (DE-MS) and gas chromatography/mass spectrometry (GC/MS). DE-MS provides a mass spectral fingerprint of organic materials in a few minutes which highlights the compounds that are the main components in the sample. The application of principal component analysis (PCA) on DE-MS data in the mass ranges m/z 181-260 and m/z 331-500, corresponding to the fragmentation of triterpenoid molecules, enabled us to distinguish between different triterpenoid materials such as mastic resin, frankincense resin and birch bark pitch, and to graphically plot the resinous substances in three separate clusters, retaining 89% of the total variance. GC/MS analysis of the same materials has permitted us to elucidate in detail the molecular composition and to identify minor components and species that act as markers of the degradation undergone by the materials. The paper also reports the results for the organic residues contained in an Egyptian censer (5th-7th century AD) which was recovered in the excavation of the Necropolis of Antinoe (Egypt), and for the hafting material found on a Palaeolithic tool recovered at the site of Campitello (Arezzo, Tuscany), dating back to the Mid-Pleistocene period. Although DE-MS was found to be a fast analytical tool, it failed to give any information on the presence of less abundant compounds when applied to mixtures of different materials: only mastic resin was found in the residues from the Roman censer, whereas GC/MS analysis identified the presence of a vegetable oil from Brassicaceae seeds and Pinaceae resin. Birch bark pitch as a pure material was identified in the sample from the Palaeolithic flint flake using both procedures.
Rapid Commun Mass Spectrom. 2006;20(11):1787-800.
PMID: 16676320 [PubMed - indexed for MEDLINE]
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| 46. |
Analysis of frankincense from various Boswellia species with inhibitory activity on human drug metabolising cytochrome P450 enzymes using liquid chromatography mass spectrometry after automated on-line extraction.
Frank A, Unger M
In our search for herbal remedies with inhibitory activity on cytochrome P450 (CYP) enzymes, we identified extracts of the gum-resin of Boswellia carteri, Boswellia frereana, Boswellia sacra and Boswellia serrata as equally potent, non-selective inhibitors of the major drug metabolising CYP enzymes 1A2/2C8/2C9/2C19/2D6 and 3A4. LC/LC/ESI-MS fingerprint analyses of the boswellic acids 11-keto-beta-boswellic acid, alpha-boswellic acid, beta-boswellic acid and their 3-O-acylated derivatives were used for the authentication of the commercially obtained frankincense samples. Although the boswellic acids could be identified as moderate to potent inhibitors of the applied CYP enzymes, they are not the major CYP inhibitory principle of frankincense.
J Chromatogr A. 2006 Apr;1112(1-2):255-62.
PMID: 16364338 [PubMed - indexed for MEDLINE]
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| 47. |
High-performance liquid chromatographic determination of acetyl-11-keto-alpha-boswellic acid, a novel pentacyclic triterpenoid, in plasma using a fluorinated stationary phase and photodiode array detection: application in pharmacokinetic studies.
Büchele B, Zugmaier W, Genze F, Simmet T
A rapid, sensitive and selective HPLC separation with photodiode array detection was developed for the analysis of the novel pentacyclic triterpenoid acetyl-11-keto-alpha-boswellic acid. Complete baseline separation of acetyl-11-keto-alpha-boswellic acid from the corresponding isomer acetyl-11-keto-beta-boswellic acid was achieved on a fluorinated stationary phase. The standard curve was linear from 0.98 nmol/l to 196 nmol/l acetyl-11-keto-alpha-boswellic acid. The compound was isolated from chick embryonic plasma using extraction on diatomaceous earth with an overall average extraction yield of 82%. This method was applied in a kinetic study on the chick chorioallantoic membrane model (CAM) and showed unequivocal separation between acetyl-11-keto-alpha-boswellic acid and acetyl-11-keto-beta-boswellic acid unachievable so far.
J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Dec;829(1-2):144-8.
PMID: 16266833 [PubMed - indexed for MEDLINE]
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| 48. |
Determination of boswellic acids in brain and plasma by high-performance liquid chromatography/tandem mass spectrometry.
Reising K, Meins J, Bastian B, Eckert G, Mueller WE, Schubert-Zsilavecz M, Abdel-Tawab M
Peritumoral edema, one of the major causes for neurological disorders in brain tumor patients, is mainly treated with steroids, which unfortunately have significant side effects and interfere with the efficacy of chemotherapy. Boswellic acids, the main active ingredients of Boswellia serrata, are antiinflammatory agents, inhibiting 5-lipoxygenase, the key enzyme of leukotriene biosynthesis and one of the pathophysiological mechanisms of peritumoral edema. Based on positive results in clinical trials and animal studies, B. serrata resin dry extract was designated an orphan drug by the European Commission for the treatment of peritumoral edema resulting from brain tumors. Thus boswellic acids may be alternative drugs to corticosteroids. However, the question of the availability of boswellic acids in brain has not been addressed until now. Accordingly, a highly sensitive LC/MS method has been developed for the simultaneous determination of KBA and AKBA, the most potent boswellic acids, in plasma and brain. This method involves matrix-assisted liquid-liquid extraction on Extrelut NT followed by separation on reversed-phase high-performance liquid chromatography and tandem mass spectrometry detection using atmospheric pressure chemical ionization. Excellent linearity was obtained for the entire calibration range from 5 to 1500 ng/mL KBA and AKBA in plasma and 5 to 1000 ng/mL KBA and AKBA in brain. Validation assays of the lower limit of quantification as well as for the intra- and interday precision and accuracy met the international acceptance criteria for bioanalytical method validation. Moreover, the interchangeability of calibration curves generated in pork and rat brain homogenates could be demonstrated. Using the developed analytical method, KBA and AKBA could be detected for the first time in brain up to a concentration of 99 and 95 ng/g of brain, respectively, 3 h after the single oral administration of 240 mg/kg of dry B. serrata resin extract to Wistar rats. The developed method represents an appropriate tool to further study the time-dependent distribution of KBA and AKBA in plasma and brain as well as the absolute brain concentration after multiple doses and contributes thus to the optimization of the dosage regimen and to a better understanding of the therapeutic effects of B. serrata.
Anal Chem. 2005 Oct;77(20):6640-5.
PMID: 16223251 [PubMed - indexed for MEDLINE]
|
| 49. |
A chemical investigation by headspace SPME and GC-MS of volatile and semi-volatile terpenes in various olibanum samples.
Hamm S, Bleton J, Connan J, Tchapla A
Six different olibanum samples with certified botanical origin were analyzed by headspace SPME-GC/MS in order to define their mono-, sesqui- and diterpenic composition, as pertinent criteria of identification. Boswellia carteri and Boswellia sacra olibanum have quite similar chemical composition, with isoincensole acetate as the main diterpenic biomarker. Although Boswellia serrata olibanum also exhibits this biomarker, the presence of methylchavicol, methyleugenol and an unidentified oxygenated sesquiterpene distinguishes B. serrata olibanum from the two other species. The characteristic chemical compounds of Boswellia papyrifera are the diterpenic biomarkers incensole and its oxide and acetate derivatives, n-octanol and n-octyl acetate. Boswellia frereana olibanum is devoid of diterpenes of the incensole family but contains a high amount of many dimers of alpha-phellandrene. The chemical composition of olibanum, which is demonstrated to be different for each Boswellia species allowed the determination of the taxonomic origin of frankincense samples purchased on various markets in East Africa, in the Near East and in Yemen. Moreover, terpenic fingerprints allowed the botanical origin of olibanum used in traditional incense mixtures to be identified. Furthermore, this study gave us the opportunity to assign a botanical origin to an archaeological frankincense sample.
Phytochemistry. 2005 Jun;66(12):1499-514.
PMID: 15922374 [PubMed - indexed for MEDLINE]
|
| 50. |
Characterization of archaeological frankincense by gas chromatography-mass spectrometry.
Mathe C, Culioli G, Archier P, Vieillescazes C
A simple gas chromatography-mass spectrometry (GC-MS) method has been developed for the characterization of frankincense in archaeological samples. After trimethylsilylation of the methanolic extract, 15 triterpenoids have been found among the chemical constituents of commercial olibanum (alpha-boswellic acid, 3-O-acetyl-alpha-boswellic acid, beta-boswellic acid, 3-O-acetyl-beta-boswellic acid, alpha-amyrin, beta-amyrin, lupeol, 3-epi-beta-amyrin, 3-epi-beta-amyrin, 3-epi-lupeol, alpha-amyrenone, beta-amyrenone, lupenone, 3alpha-hydroxy-lup-20(29)-en-24-oic acid and 3-O-acetyl-hydroxy-lup-20(29)-en-24-oic acid). These compounds have been unequivocally identified by retention time and mass spectral comparison with pure standards previously isolated, for the most part, in our laboratory. Within these triterpenes, acid ones, the corresponding O-acetates, and their products of degradation were found to be characteristic of frankincense (Boswellia resin). The presence of these unusual triterpenic compounds in an archaeological resinous sample, recovered during excavations from Dahshour site (Egypt, XIIth Dynasty), enabled us to identify unambiguously frankincense resin among several other materials. Additional chromatographic peaks of this sample were assigned to broad chemical classes using retention time and mass spectra features.
J Chromatogr A. 2004 Jan;1023(2):277-85.
PMID: 14753694 [PubMed - indexed for MEDLINE]
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| 51. |
Optimization of headspace solid phase microextraction for gas chromatography/mass spectrometry analysis of widely different volatility and polarity terpenoids in olibanum.
Hamm S, Lesellier E, Bleton J, Tchapla A
The aim of this study was the optimization of headspace SPME conditions for trapping diterpenes present in frankincense (olibanum). Diterpenes like cembrenes or incensole and its derivatives are characteristic of olibanum. So in order to detect by SPME the occurrence of olibanum in archeological objects, it appears essential to have the best extraction conditions for these diterpenes that will be in very small quantities. Both sampling time and extraction temperature were studied and five fiber coatings were tested: polydimethylsiloxane (PDMS), polydimethylsiloxane/divinylbenzene (PDMS/DVB), carboxen/polydimethylsiloxane (CAR/PDMS), divinylbenzene/carboxen/polydimethylsiloxane (DVB/CAR/PDMS) and carbowax/divinylbenzene (CW/DVB). The PDMS/DVB fiber was found to be the most efficient for trapping olibanum characteristic diterpenes, with a sampling time of 1 h and a sampling temperature of 80 degrees C.
J Chromatogr A. 2003 Nov;1018(1):73-83.
PMID: 14582628 [PubMed - indexed for MEDLINE]
|
| 52. |
Analysis of 12 different pentacyclic triterpenic acids from frankincense in human plasma by high-performance liquid chromatography and photodiode array detection.
Büchele B, Simmet T
For the determination of pentacyclic triterpenes of the boswellic acid family in human plasma a novel sensitive method was developed combining serial extraction on diatomaceous earth and graphitized carbon black followed by reversed phase high-performance liquid chromatography (HPLC) and photodiode array detection. The overall average extraction yield of 12 different pentacyclic triterpenic acids was approximately 66%. The calibration graphs were linear with coefficients of correlation for all compounds greater than 0.999. The overall within-day and between-day coefficients of variation (CV) for the 12 pentacyclic triterpenic acids were 5.6 and 6.8%, respectively. This HPLC procedure delivers the analytical sensitivity, precision and accuracy required for clinical pharmacokinetic and therapeutic studies.
J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Oct;795(2):355-62.
PMID: 14522040 [PubMed - indexed for MEDLINE]
|
| 53. |
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]
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| 54. |
[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]
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| 55. |
Fourier Transform-Raman spectroscopic study of natural resins of archaeological interest.
Brody RH, Edwards HG, Pollard AM
Resins from several different genera are studied using Fourier transform (FT)-Raman spectroscopy. Tree resins can be broadly divided into those that contain diterpenoid components and those that contain triterpenoid components. The diterpenoid resins analyzed are from the genera Pinus, Cedrus, and Agathis (kauri resin) and the triterpenoid resins examined are samples from Pistacia, Boswellia (frankincense), and Commiphora (myrrh) genera. A protocol is developed to nondestructively distinguish diterpenoid and triterpenoid resins and to differentiate the genera within the two types. The effects of oxidation on the discrimination of the FT-Raman spectra are considered.
Biopolymers. 2002;67(2):129-41.
PMID: 12073935 [PubMed - indexed for MEDLINE]
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| 56. |
Determination of 11-keto-boswellic acid in human plasma.
Kaunzinger A, Baumeister A, Cuda K, Häring N, Schug B, Blume HH, Raddatz K, Fischer G, Schubert-Zsilavecz M
A sensitive, specific, accurate, fast and reproducible GC/MS-method for the quantitative determination of 11-keto-boswellic acid in human plasma using 18alpha-glycyrrhetinic acid as the internal standard was developed and validated. 11-Keto-boswellic acid and the internal standard were separated from acidified plasma by liquid/liquid extraction. The extracted samples were methylated and analyzed by GC/MS in the negative ion chemical ionization mode (NICI) and selected ion monitoring (SIM). The total run time was 8 min between injections. The assay described in this paper demonstrates a validated lower limit of quantification of 0.0100 microg/ml using 1 ml of plasma. The calibration curves are linear in the measured range between 10.0 and 2000 ng/ml plasma. The overall precision (expressed as CV) and accuracy (expressed as bias) for all concentrations of quality controls and standards is better than 15%. No indications were found for possible instabilities of 11-keto-boswellic acid in plasma, in whole blood, in the extraction solvent or after repeated thawing/freezing cycles. The recovery of the extraction method is calculated as 84%. The assay was applied successfully to determine the plasma level of 11-keto-boswellic acid in a clinical pilot study.
J Pharm Biomed Anal. 2002 May;28(3-4):729-39.
PMID: 12008153 [PubMed - indexed for MEDLINE]
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| 57. |
High-performance thin layer chromatographic analysis of anti-inflammatory triterpenoids from Boswellia serrata Roxb.
Krohn K, Rao MS, Raman NV, Khalilullah M
A rapid and simple high-performance thin layer chromatographic (HPTLC) method was developed for the simultaneous quantitative estimation of the biologically active triterpenoids beta-boswellic acid, 3-O-acetyl-beta-boswellic acid, 11-keto-beta-boswellic acid and 3-O-acetyl-11-keto-beta-boswellic acid from the gum resin of Boswellia serrata. The assay combines the isolation and separation of boswellic acid derivatives on silica gel 60F254-HPTLC plates with spot visualisation and scanning at 250 nm. Methanol was found to be the most appropriate solvent for the exhaustive extraction of boswellic acid derivatives.
Phytochem Anal. 2001;12(6):374-6.
PMID: 11793815 [PubMed - indexed for MEDLINE]
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| 58. |
A reversed phase high performance liquid chromatography method for the analysis of boswellic acids in Boswellia serrata.
Ganzera M, Khan IA
An HPLC method for the separation of boswellic acids, the active constituents in Boswellia serrata resin has been developed. The first accurate determination of 6 individual acids was possible in the resin as well as in multi-component preparations. By using an acidic mobile phase, raised temperature and a 4 microm Synergi MAX-RP 80 A column the acids could be detected at levels as low as 0.9 microg/ml. The study of market products revealed significant variations in the content of these pharmacologically active compounds in commercial samples.
Planta Med. 2001 Nov;67(8):778-80.
PMID: 11731931 [PubMed - indexed for MEDLINE]
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| 59. |
Development of a high-performance liquid chromatographic method for the determination of 11-keto-beta-boswellic acid in human plasma.
Tawab MA, Kaunzinger A, Bahr U, Karas M, Wurglics M, Schubert-Zsilavecz M
A validated HPLC method for the determination of 11-keto-beta-boswellic acid (KBA) in human plasma was developed. The method involves the solid-phase extraction of KBA from plasma followed by a separation with reversed-phase HPLC. Calibration was based on external standardisation and ranged between 0.1 and 2.0 microg KBA per ml plasma. Linearity was established over the entire calibration range and in each case the coefficient of correlation (r2) was above 0.99. The recovery of KBA from plasma was 85.7%. It was further demonstrated that the method can be applied successfully to monitor the level of KBA in plasma.
J Chromatogr B Biomed Sci Appl. 2001 Sep;761(2):221-7.
PMID: 11587352 [PubMed - indexed for MEDLINE]
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| 60. |
CHEMICAL STANDARDIZATION OF 'KUNDUR' (Oleo-Gum-Resin of Boswellia serrata Roxb).
Siddiqui MM, Afaq SH, Asif M
A comparative study of the original and market samples of the KUNDUR (Oleo-Gum-Resin of Boswellia serrata Roxb.) with special reference to its chemical standardization and the qualitative and quantitative studies have been discussed here.
Anc Sci Life. 1984 Jul;4(1):48-50.
PMID: 22557448 [PubMed - as supplied by publisher]
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