1.Anti-inflammatory constituents from Inula japonica.
Hong ZHU ; Sheng-An TANG ; Nan QIN ; Hong-Quan DUAN ; Mei-Hua JIN
China Journal of Chinese Materia Medica 2014;39(1):83-88
Chemical constituents of Inula japonica were isolated and purified by repeated column chromatographies, over silica gel, and Toyopearl HW-40, and preparative HPLC. On the basis of spectral data analysis, including NMR and MS data, the structures of the isolates were elucidated and their anti-inflammatory activities were assayed. Fifteen compounds were isolated from the ethyl acetate extract of I. japonica, and their structures were elucidated as dihydrosyringenin (1), (3S, 5R, 6S, 7E)-5,6-epoxy-3-hydroxy-7-megastigmen-9-one (2), (6R, 7E) -9-hydroxy-4,7-megastigmadien-3-one (3), arnidiol (4), taraxasterol acetate (5), 8,9,10-trihydroxythymol (6), taxifolin (7), luteolin (8), napetin (9), eupatin (10), spinacetin (11), quercetin (12), p-hydroxycinnamic acid (13), caffeic acid (14), and caffeoyl acetate (15). Compounds 1, 2, 7, 13 and 15 were isolated from the genus Inula for the first time, and compounds 3, 4, 9-11 and 14 were isolated from this plant for the first time. The anti-inflammatory activity result showed that compounds 3, 6-12 and 14 exhibited inhibition effect against leukotriene C4 (LTC4) synthesis and degranulation definitely in c-Kit Ligand (KL) induced mast cells, and compound 8 and 12 also had the suppression effect against lipopolysacharide(LPS) induced nitric oxide (NO) activity in RAW264.7 macrophages. It is firstly reported that compounds 7 and 9-11 possessed potent inhibition activities against LTC4 generation and degranulation in mast cells.
Animals
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Anti-Inflammatory Agents
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chemistry
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pharmacology
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Cell Line
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Inula
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chemistry
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Macrophages
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drug effects
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Mast Cells
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drug effects
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Mice
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Mice, Inbred BALB C
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Plant Extracts
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chemistry
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pharmacology
2.Chemical constituents from herb of Alternanthera philoxeroides.
Jin-bo FANG ; Hong-quan DUAN ; Yan-wen ZHANG ; Takaishi YOSHIHISA
China Journal of Chinese Materia Medica 2006;31(13):1072-1075
OBJECTIVETo study the active constituents from Alternanthera philoxeroides.
METHODThe constituents were isolated with silica gel and Toyopearl HW-40C gel column chromatography and purified by HPLC. Their structures were elucidated by spectroscopy.
RESULTNine compounds were isolated and identified as phaeophytin a (1), pheophytin a' (2), oleanoic acid (3), beta-sitosterol (4), 3beta-hydroxystigmast-5-en-7-one (5), alpha-spinasterol (6), 24-methylenecycloartanol (7), cycloeucalenol (8), phytol (9).
CONCLUSIONCompounds 1,2,5,7-9 were isolated from this plant for the first time.
Amaranthaceae ; chemistry ; Chlorophyll ; chemistry ; isolation & purification ; Phytol ; chemistry ; isolation & purification ; Phytosterols ; chemistry ; isolation & purification ; Plant Leaves ; chemistry ; Plant Stems ; chemistry ; Plants, Medicinal ; chemistry
3.Studies on chemical constituents in herb of Centella asiatica.
Quan-lin YU ; Wen-yuan GAO ; Yan-wen ZHANG ; Jie TENG ; Hong-quan DUAN
China Journal of Chinese Materia Medica 2007;32(12):1182-1184
OBJECTIVETo study the chemical constituents from Centella asiatica.
METHODChemical constituents were isolated by repeated column chromatography (Toyopearl HW-40C and HPLC) and their structures were elucidated on the basis of spectroscopic method.
RESULTFive compounds were identified as: docosyl ferulates (1), bayogenin (2), 3beta-6beta-23-trihydroxyolean-12-en-28-oic acid (3), 3beta-6beta-23-trihydroxyurs-12-en-28-oic acid (4), D-gulonic acid (5).
CONCLUSIONAll of the Compounds were isolated for the first time from C. asiatica.
Centella ; chemistry ; Chromatography, High Pressure Liquid ; methods ; Coumaric Acids ; chemistry ; isolation & purification ; Molecular Structure ; Plants, Medicinal ; chemistry ; Triterpenes ; chemistry ; isolation & purification
4.Determination of aisaticoside in Centella asiatica extract by HPLC-ELSD.
Quan-Lin YU ; Wen-Yuan GAO ; Hai-Xia CHEN ; Hong-Quan DUAN
China Journal of Chinese Materia Medica 2007;32(6):503-505
OBJECTIVEA HPLC-ELSD method was established for the simultaneous quantitative determination of asiaticoside in Centella asiatica extract.
METHODThe column was packed with 5 m HIQ C18 stationary phase. The mobile phase consisted of acetonitrile-water, eluted in gradient mode. The temperature of drift tube was 105 degrees C and the nebulizer nitrogen flow rate was 2.9 L min(-1).
RESULTThe linear ranges of the asiaticoside were 0.35-7.0 microg. The recovery of the asiaticoside in C. asiatica extract was 94.9% (RSD 1.7%).
CONCLUSIONThe method is reliable, simple, precise and could be used for the quality control of C. asiatica extract.
Centella ; chemistry ; Chromatography, High Pressure Liquid ; methods ; Drugs, Chinese Herbal ; analysis ; chemistry ; standards ; Light ; Molecular Structure ; Plants, Medicinal ; chemistry ; Quality Control ; Reproducibility of Results ; Scattering, Radiation ; Triterpenes ; analysis ; chemistry
5.Studies on chemical constituents from rhizome of Anemone flaccida.
Lan-tian ZHANG ; Yoshihisa TAKAISHI ; Yan-wen ZHANG ; Hong-quan DUAN
China Journal of Chinese Materia Medica 2008;33(14):1696-1699
OBJECTIVETo study the chemical constituents from Anemone flaccida.
METHODChemical constituents were isolated by repeated column chromatography (silica gel, Toyopearl HW-40C and preparative HPLC). The structures were elucidated on the basis of spectral data analysis.
RESULTTwelve triterpenes were isolated and their structures were identified as follow: oleanolic acid (1), oleanolic acid 3-O-beta-D-glccopyranosyl-(1-->2)-beta-D-xylopyranoside (2), eleutheroside K (3), oleanolic acid 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranoside (4), oleanolic acid 3-O-beta-D-glccopyranosyl-(1-->2)-alpha-L-arabinofurnoside (5), oleanolic acid 3-O-beta-D-glccuronopyranose (6), oleanolic acid 3-O-beta-D-glccuronopyranose methyl ester (7), oleanolic acid 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glccopyranosyl (1-->6)-beta-D-glccopyranosyl (8), oleanolic acid 3-O-beta-D-glccuronopyranose 28-O-alpha-L-rhamnopyranosyl (1-->4)-beta-D-glccopyranosyl (1-->6)-beta-D-glccopyranoside (9), oleanolic acid 3-O-beta-D-glccopyranosyl methyl ester 28-O-alpha-L-rhamnopyranosyl (1-->4)-beta-D-glccopyranosyl (1-->6)-beta-D-glccopyranoside (10), oleanolic acid 3-O-beta-D-glccopyranosyl-(1-->2)-beta-D-xylopyranosyl-28-O-alpha-L-rhamnopyranosyl (1-->4)-beta-D-glccopyranosyl (1-->6)-beta-D-glccopyranoside (11), oleanolic acid 3-O-alpha-L-rh-amnopyranosyl-(1-->2)-alpha-L-arabinopyrnosyl-28-O-alpha-L-rhamnopyranosyl (1-->4)-beta-D-glccopyranosyl (1-->6)-beta-D-glccopyranoside (12).
CONCLUSIONcompounds 5-8, 10, 12 were isolated from this plant for the first time. Compounds 2, 5 and 11 showed positive anti-tumor activities.
Anemone ; chemistry ; Antineoplastic Agents ; chemistry ; pharmacology ; Cell Proliferation ; drug effects ; Drugs, Chinese Herbal ; chemistry ; pharmacology ; Eleutherococcus ; chemistry ; Glycosides ; chemistry ; pharmacology ; HeLa Cells ; Humans ; Magnetic Resonance Spectroscopy ; Oleanolic Acid ; chemistry ; pharmacology ; Plant Extracts ; chemistry ; pharmacology ; Rhizome ; chemistry ; Spectrometry, Mass, Electrospray Ionization
6.A new cycloartane triterpene saponin from rhizome of Actaea asiatica.
Bin LU ; Yun-Shuang FAN ; Hong-Quan DUAN
China Journal of Chinese Materia Medica 2008;33(13):1558-1561
OBJECTIVETo isolate and elucidate the chemical constituents with the cytotoxicity activity from the rhizome of Actaea asiatica.
METHODThe chemical constituents were isolated by repeated column chromatography (Toyopearl HW40C and preparative HPLC) and the structure of compound 1 was elucidated by spectral data analysis.
RESULTA cycloartane triterpene saponin com- pound was isolated and identified to be (23R)-16beta, 23: 23alpha, 26: 24alpha: 25-triepoxy-9, 19-cyclolanost-7-en-3beta-O-beta-D-xylopyranoside.
CONCLUSIONCompound 1 was a new compound and named (23R)-26-deoxycimicifugoside. The IC50 values of compound 1 for cell growth inhibition of Hela and L929 cell lines were 72.24 and 55.97 mg x L(-1), respectively.
Actaea ; chemistry ; Animals ; Cell Line, Tumor ; Cell Proliferation ; drug effects ; Humans ; Mice ; Plant Structures ; chemistry ; Saponins ; isolation & purification ; pharmacology
7.Studies on diterpenes in needles of Pinus sylvestris.
Rong ZHANG ; Hong-quan DUAN ; Zhi YAO ; Qin PAN ; Fu-geng ZHANG
China Journal of Chinese Materia Medica 2006;31(23):1956-1959
OBJECTIVETo research the constituents in needles of Pinus sylvestris.
METHODRepeated column chromatography and preparation HPLC are used for compound isolation, and their structures were elucidated on the basis of spectral data analysis.
RESULTSix compounds, pinifolic acid (1), 15-oxo-8 (17) -labden-18-oic acid (2) , 15-acetoxy-labd-8 ( 17)-en-18-oic acid (3), dehydroabietic acid (4), 7alpha-hydroxydehydroabietic acid (5), 7beta-hydroxydehydroabietic acid (6) were isolated from the needles of P. sylvestris.
CONCLUSIONCompound 3-6 were isolated from the needles of P. sylvestris for the first time, and compound 3 is a new natural product. The petroleum ether and EtOAc extracts showed significant cytotoxic effects to Hela and A549. Compounds 2, 4-6 revealed a positive distinction compared to the control group.
Antineoplastic Agents, Phytogenic ; chemistry ; isolation & purification ; pharmacology ; Cell Line, Tumor ; Cell Survival ; drug effects ; Chromatography, High Pressure Liquid ; Diterpenes ; chemistry ; isolation & purification ; pharmacology ; Diterpenes, Abietane ; chemistry ; isolation & purification ; pharmacology ; HeLa Cells ; Humans ; Molecular Structure ; Pinus sylvestris ; chemistry ; Plant Leaves ; chemistry ; Plants, Medicinal ; chemistry ; Structure-Activity Relationship
8.Triterpenes from herb of Potentilla chinesis.
Pu LIU ; Hong-quan DUAN ; Qin PAN ; Yan-wen ZHANG ; Zhi YAO
China Journal of Chinese Materia Medica 2006;31(22):1875-1879
OBJECTIVETo study the chemical constituents of Potentilla chinesis and their anticancer activities.
METHODChemical constituents were isolated by repeated column chromatography (Toyopearl HW-40C and preparative HPLC). The structures were elucidated on the basis of spectral data analysis. The isolated compounds were screened with two anticancer models.
RESULTFifteen triterpenes, alpha-amyrin (1) , beta-amyrin (2) , ursolic acid (3) , corosolic acid (4), euscaphic acid (5) , pomolic acid (6) , tormentic acid (7), 2alpha, 3alpha-dihydroxyurs-12-en-28-oic acid (8), 2beta, 3beta, 19alpha-trihydroxyurs-12-en-28-oic acid (9), asiatic acid (10) , 24-hydroxy tormentic acid (11) , myrianthic acid (12), oleanolic acid (13), maslinic acid (14) and 2alpha, 3alpha-dihydroxyolean-12-en-28-oic acid (15) , were isolated from P. chinesis.
CONCLUSIONCompounds 1, 2, 4 -15 were isolated from the plant for the first time. Compounds 4, 8 - 10, 12, 14 and 15 show anticancer activities. Compounds 4, 9 show strong activities.
Animals ; Antineoplastic Agents, Phytogenic ; chemistry ; isolation & purification ; pharmacology ; Cell Line ; Cell Survival ; drug effects ; Chromatography, High Pressure Liquid ; Fibroblasts ; cytology ; drug effects ; HeLa Cells ; Humans ; Mice ; Molecular Structure ; Plants, Medicinal ; chemistry ; Potentilla ; chemistry ; Triterpenes ; chemistry ; isolation & purification ; pharmacology
9.Anti-tumor metastatic constituents from Rhodiola wallichiana.
Ya-qing CHAI ; Guo-hua ZHAO ; Ren-jiu WANG ; Ming-guang CAO ; Hai-bo WU ; Sheng-an TANG ; Hong-quan DUAN
China Journal of Chinese Materia Medica 2015;40(2):258-263
To study the anti-tumor metastatic constituents in Rhodiola wallichiana (HK) S H Fu var Cholaensis (Praeg) S H Fu, chemical constituents were isolated and purified by repeated column chromatography (silica gel, Toyopearl HW-40C and preparative HPLC). Their structures were elucidated on the basis of spectral data analysis. The anti-tumor metastasis assay was applied to evaluate the activities of the isolated compounds. Ten compounds (1-10) were isolated and their structures were identified by comparison of their spectral data with literature as follows: syringic acid (1), salidroside (2), tyrosol (3), scaphopetalone (4), berchemol (5), 2,6-dimethoxyacetophenone (6), rhobupcyanoside A (7), miyaginin (8), chavicol-4-O-β-D-apiofuranosyl-(1 --> 6)-O-β-D-glucopyranoside (9), eugenyol-O-β-D-apiofuranosyl-(1 --> 6)-O-β-D-glucopyranoside (10). Compounds 4-6 and 8-10, were isolated from this genus for the first time, while compound 7 was isolated from this plant for the first time. Compounds 2, 6-8 showed positive anti-tumor metastatic activities, and compounds 2 and 8 showed significant anti-tumor metastatic activities.
Antineoplastic Agents, Phytogenic
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isolation & purification
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pharmacology
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Cell Line, Tumor
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Humans
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Neoplasm Metastasis
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prevention & control
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Rhodiola
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chemistry
10.Study on chromatographic fingerprint of extractive from Tripterygium wilfordii with supercritical carbon dioxide.
Wen ZHOU ; Hong-ru LI ; Shu-fen LI ; Yoshihisa TAKAISHI ; Hong-quan DUAN
China Journal of Chinese Materia Medica 2007;32(8):706-709
OBJECTIVETo establish the chromatographic fingerprint of supercritical carbon dioxide extract of Tripterygium wilfordii.
METHODHPLC method was applied for quality assessment of T. Wilfordii, HPLC analysis was performed on Kromasil C18 (4. 6 mm x 250 mm, 5 microm) with the mixture of acetonitrile-1% per thousand H3PO4, as mobile phase in gradient mode. The samples were detected at UV of 267 nm with column temperature of 35 degrees C, analytic time was 80 min; Flow-rate was 1.0 mL x min(-1). The chromatographic fingerprint of ten batches of samples was determined, for establishing the chromatographic fingerprint of T. Wilfordii.
RESULTIndicating 27 peaks in common, identified 21 peaks with chemical reference and HPLC-MS, and the HPLC fingerprint was established.
CONCLUSIONThe method is steady and accurate with a good repeatability and can be used as a quality control method for T. Wilfordii.
Carbon Dioxide ; chemistry ; Chromatography, High Pressure Liquid ; methods ; Chromatography, Supercritical Fluid ; methods ; Plant Extracts ; analysis ; chemistry ; isolation & purification ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry ; Reproducibility of Results ; Spectrometry, Mass, Electrospray Ionization ; methods ; Tripterygium ; chemistry