1.Chemical constituents of diterpenoids from Boswellia carterii.
Rong-Ye WANG ; Hui XIA ; Yong-Xiang WANG ; Hao HUANG ; Bo-Kai WANG ; Meng DU ; Yue-Lin SONG ; Yun-Fang ZHAO ; Jiao ZHENG ; Hui-Xia HUO ; Jun LI
China Journal of Chinese Materia Medica 2023;48(9):2464-2470
This paper explored the chemical constituents of Boswellia carterii by column chromatography on silica gel, Sephadex LH-20, ODS column chromatography, and semi-preparative HPLC. The structures of the compounds were identified by physicochemical properties and spectroscopic data such as infrared radiation(IR), ultra violet(UV), mass spectrometry(MS), and nuclear magnetic resonance(NMR). Seven diterpenoids were isolated and purified from n-hexane of B. carterii. The isolates were identified as(1S,3E,7E,11R,12R)-11-hydroxy-1-isopropyl-4,8,12-trimethyl-15-oxabicyclo[10.2.1]pentadeca-3,7-dien-5-one(1),(1R,3S,4R,7E,11E)-4,8,12,15,15-pentamethyl-14-oxabicyclo[11.2.1]hexadeca-7,11-dien-4-ol(2), incensole(3),(-)-(R)-nephthenol(4), euphraticanoid F(5), dilospirane B(6), and dictyotin C(7). Among them, compounds 1 and 2 were new and their absolute configurations were determined by comparison of the calculated and experimental electronic circular dichroisms(ECDs). Compounds 6 and 7 were obtained from B. carterii for the first time.
Molecular Structure
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Boswellia/chemistry*
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Diterpenes/chemistry*
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Mass Spectrometry
2.Determination of five boswellic acids in Boswellia serrata.
Chun WANG ; Lei XIA ; Zhiqian SONG ; Qing LI ; Chao WANG ; Linyan ZENG ; Zhenli LIU
China Journal of Chinese Materia Medica 2011;36(10):1330-1333
OBJECTIVETo develop an HPLC method for determinating the contents of five boswellic acids in Boswellia serrata.
METHODAnalysis was performed on a zorbax SB C18 column eluted with acetonitrile-0.1% phosphoric acid in water as mobile phases in gradient elution and the detection wavelengths were 210 nm and 250 nm.
RESULTThe five ingredients were separated well. The content ranges of alpha-boswellic acid, beta-boswellic acid, 3-acetyl-beta-boswellic acid, 11-keto-beta-boswellic acid and 11-keto-beta-acetyl- boswellic acid were 8.68-16.1, 53.5-246.9, 38.4-192.9, 4.48-5.81, 32.7-44.2 mg x g(-1), respectively.
CONCLUSIONThe contents of five individual boswellic acids were different in 12 batches of B. serrata samples.
Boswellia ; chemistry ; Chromatography, High Pressure Liquid ; Plant Extracts ; analysis ; isolation & purification ; Triterpenes ; analysis ; isolation & purification
3.Determination of alpha-pinene and octyl acetate contents in Boswellia serrata.
Zhiqian SONG ; Lei XIA ; Zheng WEI ; Yuna CAO ; Linlin ZHANG ; Zhenli LIU
China Journal of Chinese Materia Medica 2012;37(10):1431-1433
OBJECTIVETo 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.
METHODApplication 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.
RESULTSample 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).
CONCLUSIONThe method is a stable and reliable for determining the contents of alpha-pinene and octyl acetate in B. serrata.
Acetates ; analysis ; Boswellia ; chemistry ; Gas Chromatography-Mass Spectrometry ; methods ; Monoterpenes ; analysis
4.Herbalism, botany and components analysis study on original plants of frankincense.
Lei SUN ; Jimin XU ; Hongyu JIN ; Jingai TIAN ; Ruichao LIN
China Journal of Chinese Materia Medica 2011;36(2):112-116
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.
Boswellia
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chemistry
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classification
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Chromatography, High Pressure Liquid
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Herbal Medicine
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Plant Extracts
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analysis
5.GC-MS analysis of volatile oil of olibanum.
Jinfeng ZHAO ; Chunlan ZHOU ; Fengqin ZHOU ; Taiming WEI
China Journal of Chinese Materia Medica 2011;36(8):1050-1053
OBJECTIVETo analyze the volatile oil of olibanum and apply scientific evidences for its applications.
METHODThe volatile oil was analyzed by GC-MS.
RESULTOne 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.
CONCLUSIONThe components of olibanum volatile oil were complicated; the connatural transdermal absorption enhancers make it possible to use in external preparation.
Acetates ; isolation & purification ; Boswellia ; chemistry ; Gas Chromatography-Mass Spectrometry ; methods ; Oils, Volatile ; isolation & purification ; Sesquiterpenes ; isolation & purification
6.Cembrane diterpenes in olibanum.
Feng WANG ; Zhanlin LI ; Tao LIU ; Huiming HUA
China Journal of Chinese Materia Medica 2009;34(19):2477-2480
OBJECTIVETo study the constituents in the chloroform extract of olibanum and their antitumor activities.
METHODThe compounds were isolated by chromatographic methods and their structures were identified on the basis of spectroscopic methods and X-ray diffraction. The antiproliferative effect of the compounds in human leukemia HL-60 cells was tested by viable cell counting.
RESULTFour cembrane diterpenes were isolated and identified as incensole-oxide (1), acetyl incensole-oxide (2), incensole (3), and acetyl incensole (4).
CONCLUSIONCompounds 2 and 4 were isolated from the genus Boswellia for the first time. Compound 4 showed growth inhibitory effect against human leukemia HL-60 cell lines with IG50 value of (16.3 +/- 3.4) micromol x L(-1).
Antineoplastic Agents, Phytogenic ; chemistry ; isolation & purification ; pharmacology ; Boswellia ; chemistry ; Cell Line, Tumor ; Cell Proliferation ; drug effects ; Diterpenes ; chemistry ; isolation & purification ; pharmacology ; Humans ; Plant Extracts ; chemistry ; isolation & purification ; pharmacology
7.Chemical components of Boswellia carterii.
Acta Pharmaceutica Sinica 2002;37(8):633-635
AIMTo investigate the chemical components of Boswellia carterii.
METHODSChromatographic technologies were used for separation and purification, while spectral analysis was used for structure elucidation.
RESULTSSix compounds were isolated and their structures were identified as acetyl-alpha-boswellic acid (1), acetyl-beta-boswellic acid (2), lup-20(29)-ene-3 alpha-acetoxy-24-oic acid (3), alpha-boswellic acid (4), beta-boswellic acid (5) and acetyl-11-keto-beta-boswellic acid (6).
CONCLUSIONCompound 3 is a new constituent.
Antineoplastic Agents, Phytogenic ; isolation & purification ; pharmacology ; Boswellia ; chemistry ; Cell Division ; drug effects ; HL-60 Cells ; Humans ; Molecular Structure ; Plants, Medicinal ; chemistry ; Triterpenes ; chemistry ; isolation & purification ; pharmacology
8.Study on the detecting methods of the imported materia medica--olibanum.
Shang-mei SHI ; Jin-gai TIAN ; Bao-qin WANG
China Journal of Chinese Materia Medica 2002;27(3):170-173
OBJECTIVETo 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.
METHODTwo 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.
RESULT40 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%.
CONCLUSIONThis study can be used for the setting up of the specification of Olibanum.
Acetates ; analysis ; Boswellia ; chemistry ; Materia Medica ; standards ; Monoterpenes ; analysis ; Oils, Volatile ; chemistry ; isolation & purification ; Plants, Medicinal ; chemistry ; Quality Control ; Species Specificity
9.Cardioprotective and antioxidant effects of oleogum resin "Olibanum" from Bos Boswellia carteri Birdw. (Bursearceae).
Ahmed A ZAKI ; Nadia E HASHISH ; Mohamed A AMER ; Mohamed-Farid LAHLOUB
Chinese Journal of Natural Medicines (English Ed.) 2014;12(5):345-350
One of the leading causes of death worldwide is cardiovascular disease, hence searching for a cure is an important endeavor. The totally safe, edible, and inexpensive Boswellia plant exudate, known as olibanum or frankincense, is considered to possess diverse medicinal values in traditional medicine and from recent biological studies. Investigating the cardioprotective and antioxidant activities of olibanum from a Boswellia species, family Bursearaceae, namely Boswellia carteri Birdw. was the aim of this study. Cardioprotective activity was evaluated using a model of myocardial infarction induced by isoprenaline (ISO), while antioxidant activity was tested adopting nitric oxide scavenging (NOS) and azino-bis-3-ethyl benzthiazoline-6-sulfonic acid (ABTS) assays. The results revealed a mild cardioprotective effect and weak antioxidant activity.
Animals
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Antioxidants
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administration & dosage
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analysis
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Boswellia
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chemistry
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Frankincense
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administration & dosage
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analysis
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Humans
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Male
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Myocardial Infarction
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drug therapy
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pathology
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Myocardium
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pathology
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Rats
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Rats, Wistar
10.Change in dissolution of chemical components of frankincense-myrrh before and after their compatibility and effect on no release of LPS-induced macrophage cells.
Ting CHEN ; Shu-Lan SU ; Jin-Ao DUAN ; Er-Xin SHANG ; Da-Wei QIAN ; Yu-Ping TANG
China Journal of Chinese Materia Medica 2013;38(2):179-185
OBJECTIVETo analyze the difference of chemical compounds of frankincense-myrrh before and after their compatibility, and evaluate the effect of differentiated compounds on NO generated by LPS-induced peritoneal macrophage cells in rats, in order to discuss synergetic material basis of frankincense-myrrh compatibility from the prospective of change in chemical constituents.
METHODUPLC-Q-TOF-MS/MS combined technology was used to analyze the chemical components of frankincense-myrrh before and after their compatibility. MarkerLynx 4. 1 statistical software was used to analyze differentiated compounds before and after their compatibility.
RESULTThe results of PCA showed that there were significant differences in the combined extracts of frankincense-myrrh and the chromatogram of their combined liquid, suggesting significant differences in their chemical compounds before and after their compatibility; after their compatibility, the dissolution of pentacyclic triterpenoid (alpha-boswellic acid, beta-boswellic acid) and tetracyclic triterpenoid (elemonic acid, 3-acetoxy-16-hydroxy-dammar-24-ene, 3-hydroxytirucalla-8,24-dien-21-oic acid or 3-hydroxytirucalla-7,24-dien-21-oic acid) increased notably, while the dissolution of both yclic sesquiterpenes and macrocyclic diterpenoids decreased. According to the evaluation on in vitro activity, 2-methoxy-8, 12-epoxy-germa-1 (10), 7, 11-triene-6-ketone, 2-methoxy-5-acetoxyl-furan-germa-1 (10)-alkene-6-ketone and 3-carbonyl Euphorbia kansui-8, 24-diene-21-carboxylic acid notably inhibited NO generated by LPS-induced peritoneal macrophage cells in rats.
CONCLUSIONThese findings provide scientific basis and reference for studies on anti-inflammatory material basis of frankincense-myrrh compatibility.
Animals ; Anti-Inflammatory Agents, Non-Steroidal ; chemistry ; isolation & purification ; Boswellia ; chemistry ; Chromatography, Liquid ; Commiphora ; chemistry ; Drug Synergism ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Lipopolysaccharides ; pharmacology ; Macrophages, Peritoneal ; drug effects ; Male ; Mice ; Mice, Inbred BALB C ; Molecular Structure ; Nitric Oxide ; metabolism ; Tandem Mass Spectrometry ; Terpenes ; chemistry ; isolation & purification ; Triterpenes ; chemistry ; isolation & purification