1.Systematic identification of chemical forms of key terpene synthase in Cinnamomum camphora.
Qing MA ; Rui MA ; Ping SU ; Ye SHEN ; Mei-Lan CHEN ; Bao-Long JIN ; Shao-Lin OUYANG ; Juan GUO ; Guang-Hong CUI ; Lu-Qi HUANG
China Journal of Chinese Materia Medica 2023;48(9):2307-2315
Cinnamomum camphora is an important economic tree species in China. According to the type and content of main components in the volatile oil of leaf, C. camphora were divided into five chemotypes, including borneol-type, camphor-type, linalool-type, cineole-type, and nerolidol-type. Terpene synthase(TPS) is the key enzyme for the formation of these compounds. Although several key enzyme genes have been identified, the biosynthetic pathway of(+)-borneol, which has the most economic value, has not been reported. In this study, nine terpenoid synthase genes CcTPS1-CcTPS9 were cloned through transcriptome analysis of four chemical-type leaves. After the recombinant protein was induced by Escherichia coli, geranyl pyrophosphate(GPP) and farnesyl pyrophosphate(FPP) were used as substrates for enzymatic reaction, respectively. Both CcTPS1 and CcTPS9 could catalyze GPP to produce bornyl pyrophosphate, which could be hydrolyzed by phosphohydrolase to obtain(+)-borneol, and the product of(+)-borneol accounted for 0.4% and 89.3%, respectively. Both CcTPS3 and CcTPS6 could catalyze GPP to generate a single product linalool, and CcTPS6 could also react with FPP to generate nerolidol. CcTPS8 reacted with GPP to produce 1,8-cineol(30.71%). Nine terpene synthases produced 9 monoterpene and 6 sesquiterpenes. The study has identified the key enzyme genes responsible for borneol biosynthesis in C. camphora for the first time, laying a foundation for further elucidating the molecular mechanism of chemical type formation and cultivating new varieties of borneol with high yield by using bioengineering technology.
Cinnamomum camphora/enzymology*
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Alkyl and Aryl Transferases/chemistry*
2.Chromatographic fingerprint peak matching of Semen Cassiae by asymptotic window orthoganality projection analytical method.
Chuncai ZOU ; Haiyan YAN ; Hongzhuang FANG
China Journal of Chinese Materia Medica 2009;34(22):2876-2879
OBJECTIVETo investigate the principle and basis about the chromatographic fingerprint peak matching of Semen Cassiae by the asymptotic window orthogonal projection analytical method.
METHODThe samples of Semen Cassiae were hydrolyzed in the 1.5 mol x L(-1) hydrochloride acid and then reflux extracted with chloroform. The chromatographic condition was that the HPLC was run on Agilent 1100 column, Zorbax Eclipse XDB-C18 (4.6 mm x 250 mm, 5 microm). The protected column was Scienhome C18 column (3.0 mm x 20 mm, 5 microm) with acetonitrile-water (0.1% phosphoric acid) as mobile phase in gradient elution at a flow rate of 1.0 mL x min(-1). The detection wavelength and reference wavelength were 278 nm and 550 nm, respectively.
RESULTThe characteristic fingerprint collection of illustrative plates of Semen Cassiae were obtained with different HPLC instruments and chromatographic columns. And the asymptotic window orthogonal projection analytical method was used to decide the chromatographic fingerprint peak matching of Semen Cassiae, promptly and prapidly.
CONCLUSIONThe asymptotic window orthogonal projection analytical method can progress the matching of different fingerprint collection of illustrative plates peak matching well and truly.
Chromatography ; methods ; Cinnamomum aromaticum ; chemistry ; Drugs, Chinese Herbal ; chemistry
3.Research progress of trans-cinnamaldehyde pharmacological effects.
Li-qing ZHANG ; Zhan-gang ZHANG ; Yan FU ; Ying XU
China Journal of Chinese Materia Medica 2015;40(23):4568-4572
Trans-cinnamaldehyde, the main component of volatile oil from cassia twig or Cinnamomum cassia, which is a traditional Chinese herbal medicine. Trans-cinnamaldehyde is a kind olefine aldehyde of organic compounds and has many pharmacological properties, such as anti-inflammatory, anti-tumor, anti-bacterial, antidiabetic, anti-obesity, and neuroprotection etc. The compound has preventive and therapeutic effects on the nervous system, cardiovascular, cancer, diabetes and other diseases. Trans-cinnamaldehyde, as a preventive care of nature medicine, has great clinical and market potential. This paper gives a review about the pharmacological effects and mechanism of trans-cinnamaldehyde researched in the latest five years. We hope to provide some basic information for further research on trans-cinnamaldehyde.
Acrolein
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analogs & derivatives
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chemistry
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pharmacology
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Animals
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Cinnamomum aromaticum
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chemistry
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Drugs, Chinese Herbal
;
chemistry
;
pharmacology
;
Humans
4.Variation and regularity of volatile oil constituents in fruits of national medicine Cinnamomum migao.
Tao ZHOU ; Zhannan YANG ; Weike JIANG ; Qiang AI ; Peiguo GUO
China Journal of Chinese Materia Medica 2010;35(7):852-856
OBJECTIVETo compare the constituents of the volatile oil in Cinnamomum migao from different regions of southwest in China in order to evaluate the quality of C. migao.
METHODGC-MS was employed to analyze the constituents of the volatile oil in C. migao.
RESULTThe volatile oil compositions of C. migao collected from 27 of cultivation regions were obviously different. Based on the chemical differences of the volatile oil compositions, C. migao was divided into four chemotype, they were eucalyptol, eucalyptol -cyclohexene, eucalyptol -alpha-terpineol, and eucalyptol -sabinene. The eucalyptol-type was cultivated in Luodian, guizhou province and Funing regions, Yunan province. The eucalyptol-cyclohexene-type was cultivated in Zhengfeng and Wangmo regions, Guizhou province. The type of eucalyptol, eucalyptol -sabinene and eucalyptol -alpha-terpineol were cultivated in Ceheng and Libo regions, Guizhou province.
CONCLUSIONCombined with the geographical distribution, It is indicated that the volatile oil compositions in fruit of C. migao may have some relations to the specie itself characteristics and different elevations environment.
Cinnamomum ; chemistry ; Drugs, Chinese Herbal ; chemistry ; Fruit ; chemistry ; Oils, Volatile ; analysis
5.AMWFA method applied to research on changes of essential components and extractive ratioes of herbal pair Cinnamomum cassia and Poria cocos.
Zheng XIANG ; Xian-Qin WANG ; Xiao-Min YU ; Tao WEI ; Yan-Xia LI
China Journal of Chinese Materia Medica 2008;33(18):2056-2060
Gas chromatography/mass spectrometry, chemometric resolution method-Alternative movingwindow factor analysis that were proposed recently and the Kovats retention index were used to analyze the essential components of herbal pair Cinnamomum cassia Presl and Poria cocos (CCP-PC) and compare them with those of single herbal Cinnamomum cassia Presl (CCP). 46 and 42 essential components in essential oil of CCP and CCP-PC have been identified individually. Results shows that the number of essential components of CCP and CCP-PC were almost the same, but extractive ratioes of them have changed significantly, some of them were increased obviously, most of them were declined notably instead and even several ingredients of CCP-PC were disappeared due to CCP PC's interaction probably. The main pharmacodynamic ingredients of CCP-PC, 3-phenyl-2-propenal and Cinnamaldehyde were obviously higher contents than that of single CCP. It suggested that there exist certain interactions of the chemical ingredients in compound medicine rather than their sum effect of single medicines. There is a litter difference in quality and quantity between single medicines and pair medicines, so the application of pair medicines can expand single medicine's adaptive disease and has a good clinical referenced valuation.
Cinnamomum aromaticum
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chemistry
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Drugs, Chinese Herbal
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chemistry
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Gas Chromatography-Mass Spectrometry
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Poria
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chemistry
6.Study on fingerprints of chemical constituents of cinnamomi ramulus and cinnamomi cortex.
Peng-fei YUAN ; Ming-ying SHANG ; Shao-qing CAI
China Journal of Chinese Materia Medica 2012;37(19):2917-2921
OBJECTIVETo compare the difference of chemical constituents of Cinnamomi Ramulus and Cinnamomi Cortex,and study the characteristics of their chemical constituents, in order to provide basis for clinical application and quality control.
METHODHPLC fingerprint method was used to analyze chemical constituents of Cinnamomi Ramulus and Cinnamomi Cortex compare the difference between.
RESULTCinnamomi Ramulus and Cinnamomi Cortex had similar HPLC fingerprint profiles, but with difference in peak areas of their chemical constituents. Specifically, the average peak areas of cinnamyl alcohol, cinnamic acid and 2-methoxy cinnamic acid were higher than that of Cinnamomi Cortex, whereas the average peak areas of 2-hydroxyl cinnamaldehyde, coumarin, cinnamaldehyde and 2-methoxy cinnamaldehyde in Cinnamomi Cortex were higher than that of Cinnamomi Ramulus.
CONCLUSIONThis method can be used for evaluating quality of Cinnamomi Ramulus and Cinnamomi Cortex. The ratio between the peak areas of cinnamaldehyd and cinnamic acid can be used to discriminate most Cinnamomi Ramulus samples (<23) and Cinnamomi Cortex samples (>23). Cinnamomi Ramulus and Cinnamomi Cortex have the similar types of chemical constituents but with difference in content. This study provides reference for the pharmacodynamic difference of Cinnamomi Ramulus and Cinnamomi Cortex.
Chromatography, High Pressure Liquid ; Cinnamomum ; chemistry ; Cluster Analysis ; Drugs, Chinese Herbal ; chemistry ; standards
7.Determination of d-borneol in the different parts of Cinnamomum camphora by GC-MS.
Tasi LIU ; Limin GONG ; Ying GUO ; Shouli REN ; Li YANG ; Bingmei XIAO ; Qingping PAN
China Journal of Chinese Materia Medica 2009;34(13):1692-1694
OBJECTIVETo measure and compare the content of d-borneol in the different parts of Cinnamomum camphora by GC-MS.
METHODWith water-steam distillation and GC-MS method, d-borneol was extracted and determined.
RESULTThe linear range of d-borneol was 0.4-2.8 microg (r = 0.999 9). The average recovery was 95.40%, and RSD was 0.56%.
CONCLUSIONThe method is simple and accurate with good separation. The content of d-borneol in the dried leaves 63.97% in the crude exfract. It can provide the proof of the exploitation of C. camphora.
Bornanes ; analysis ; Cinnamomum camphora ; chemistry ; Gas Chromatography-Mass Spectrometry ; methods ; Plant Extracts ; analysis ; Plant Structures ; chemistry
8.Chemical constituents from Cinnamomum cassia.
Shan HE ; Yong JIANG ; Peng-fei TU
China Journal of Chinese Materia Medica 2015;40(18):3598-3602
Various column chromatography, such as silica gel, Sephadex LH-20, ODS, and semi-preparative HPLC was used to isolate and purify the chemical constituents from Cinnamomum cassia. The structures were determined on the basis of NMR and MS spectral data analysis, together with the comparison with literature data. Fifteen compounds were isolated from the 85% aqueous ethanol extract of C. cassia, and their structures were identified as (2R, 3R)-5,7,3',4'-tetramethoxyflavan-3-ol( 1), (2R, 3R)-5,7-dimethoxy-3',4'-methylenedioxyflavan-3-ol (2), coumarin (3), cinnamic acid (4), (E)-2-hydroxy-phenylpropionic acid cinnamoyl ester (5), 3, 3', 4, 4'-tetrahydroxy biphenyl (6), methylstictic acid (7), epi-boscialin (8), (1R,2S,3S,4S)-2,3-epoxy-1, 4-dihydroxy-5-methyl-5-cyelohexene (9), 4,5-dihydroxy-3-methyl cyclohex-2-enone (10), cis-4-hydroxymellein (11), and 2-hydroxy-4-methoxyl-cinnamaldehyde (12). Compounds 5-11 were obtained from this genus plants for the first time.
Cinnamomum aromaticum
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chemistry
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Drugs, Chinese Herbal
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chemistry
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isolation & purification
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Mass Spectrometry
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Molecular Structure
9.Determination of aurantio-obtusin and chrysophanol in cassiae semen by HPLC.
Xiaoping HUANG ; Guoyue ZHONG ; Xuemei ZHANG ; Yi ZHANG
China Journal of Chinese Materia Medica 2010;35(16):2065-2067
OBJECTIVETo improve the determination method of Cassiae Semen in China Pharmacopeia edition 2005. MMETHOD: Aurantio-obtusin and chrysophanol were separated on an Inertsil ODS-3 column with acetonitrile-0.1% phosphoric acid solutiona as mobile phase in gradient elution.
RESULTThe linear ranges of aurantio-obtusin and chrysophanol were 2.3-230, 2.87-286 mg x L(-1), respectively. The average recover were 100.3% (RSD 3.1%), and 99.5% (RSD 2.5%) respectively.
CONCLUSIONThis method is specific, accurate and reproducible, and can be used for the assay of Cassiae Semen in the new edition of Chinese pharmacopoeia.
Anthraquinones ; analysis ; Chromatography, High Pressure Liquid ; Cinnamomum aromaticum ; chemistry ; Drugs, Chinese Herbal ; analysis ; chemistry ; Reproducibility of Results
10.Comparision study pharmacokinetics of different source cinnamon acid.
Wen-Lan LI ; Xiao-Dong WHANG ; Yu-Bin JI ; Zheng-Ting HU ; Xiao-Lei REN ; Jia WHANG
China Journal of Chinese Materia Medica 2008;33(10):1192-1195
OBJECTIVETo study relatively pharmacological activities of cinnamon acid in blood serum of rabbit administered cinnamon acid, cinnamon and Jingui Shenqi pills.
METHODRP-HPLC determine and analysis blood serum sample from rabbits administered cinnamon acid, cinnamon and Jingui Shenqi pills. Condition of colour spectrum was Symmetry C18 (3.9 mm x 150 mm, 5 microm) chromato bar, mobile phase was methanol-1% glacial acetic acid water-solution (45:55), flow rate was 0.8 mL x min(-1), temperature of bar was 35 degrees C, detection wave length was 285 nm. The serum pharmacokinetic parameters were calculated with 3p87.
RESULTLinear range of cinnamon acid is from 0.06-15 microg x mL(-1) (r = 0.9997), the lowest detectability is 0.054 microg x mL(-1). Pharmacokinetic process of cinnamon acid in rabbit could be all fitted to two-compartment model.
CONCLUSIONSensitive and exclusive HPLC that adopt can exactly detect serum concentration in rabbits administerd cinnamon acid. Pharmacokinetic parameters of three conditions can reveal pharmacokinetics regularity of cinnamon acid in rabbit.
Animals ; Cinnamomum zeylanicum ; chemistry ; Drugs, Chinese Herbal ; administration & dosage ; pharmacokinetics ; Male ; Rabbits ; Serum ; chemistry ; drug effects