1.Diterpenes from Tripterygium wilfordii and their anti-cancer activities
Zhi YAO ; Wenyuan GAO ; Yoshihisa TAKAISHI ; Hongquan DUAN
Chinese Traditional and Herbal Drugs 1994;0(11):-
Objective To study the anti-cancer constituents from Tripterygium wilfordii. Methods Chemical constituents were isolated by repeated column chromatography (silica gel, Toyopearl HW-40 C and preparative HPLC), their structures were elucidated on the basis of spectroscopic methods, and the anti-cancer activity was screened by MTT method. Results Five diterpenes, 3-epi-triptobenzene B (Ⅰ), 3?, 14-dihydroxy-abieta-8, 11, 13-triene (triptobenzene B,Ⅱ), wilforol E (Ⅲ), triptohairic acid (Ⅳ), and 11-hydroxy-14-methoxy-18(4→3)-abeo-abietan-3, 8, 11, 13-tetraen-18-oic-acid (hypoglic acid, Ⅴ) were isolated from T. wilfordii. Conclusion Compound Ⅰ is a new compound named as triptobenzene L, compound Ⅳ is isolated for the first time. The compounds Ⅰ-Ⅴ show the positive anti-cancer effects on HeLa and L929 cell lines.
2.Search for the substances causing allergic contact dermatitis by chrysanthemums on the growers.
Tetsuro FUJITA ; Kazunori KATO ; Yoshio TAKEDA ; Yoshihisa TAKAISHI ; Teruyoshi ICHIHARA ; Akiyoshi BANDO ; Tsuyoshi IMURA
Journal of the Japanese Association of Rural Medicine 1986;35(1):27-33
Since 1976, allergic contact dermatitis caused by Chrysanthemum morifolium Ramalk (commercial name: Kinriki) occured on the grower in Tokushima Prefecture. Consequently, a systematic study aimed at the isolation of the allergen of the chrysanthemum was udertaken.
The allergens were contained in the fresh juice of the leaves of chrysanthemum and they were of two types: one was water-soluble and the other was fat-soluble, judging from the results of application test of the skin reaction for sensitized guinea pigs.
The fresh juice of the chrysanthemums was fractionated with ammonioum sulfate saturation method and the active precipitates were chromatographed on Sephacryl S-300 and DEAE-cellulose column, successively. The most active fractions contained sugar and protein, suggesting that the water-soluble principles are high molecular glyco-protein. The other hand fat-soluble fraction was obtained from ethyl acetate extract of the supernatant of 65% ammonium sulfate saturation. The extract was chromatographed on silica gel column and on the thin layer to yield 5, 7-dihydroxychromone (I) and sesquiterpens (II-VI). Unfortunately, at that time the sensitization of ginea pigs was unsuccessfuly. Therefore their compounds could not be tested for the allergenic reaction.
When the precipitates of ammonium sulfate were extrcted with ethyl acetate, the allergenic activeity of the precipitates decreased. However, re-addition of the ethyl acetate extracts to the extracted precipitates recovered the activity. Cross reaction between the juice of leaves and sesquiterpene lactone, alantolactone, failed on skin reaction of sensitized ginea pigs.
3.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
4.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
5.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
6.Allergic contact dermatitis caused by chrysanthemum and lettuce and dermatitis due to TPN (tetrachloroisophalonitrile) (Daconil).
Akiyoshi BANDO ; Tsuyoshi IMURA ; Hajime MATSUURA ; Nobuko KISHIMOTO ; Harumi SUMITOMO ; Reiko HAMADA ; Keiko HAYASHI ; Iwao OHKUBO ; Tetsuro FUJITA ; Kazunori KATOH ; Yoshio TAKEDA ; Yoshihisa TAKAISHI ; Teruyoshi ICHIHARA
Journal of the Japanese Association of Rural Medicine 1986;35(1):34-38
We have reported that many chrysanthemum- and lettuce-growers have dermatitis caused by juice of the leaves of these plants and that this dermatitis is caused by an allergic mechanism. In arecent questionnaire on the cause of this dermatitis, half the farmers answerd that it was due to agricultural chemicals. Therefore, we tested the farmers by skin patch tests with several widely used chemicals. In the tests, daconil gave the strongest reaction, results being positive in 60% of the farmers. Daconil was very irritative and phototoxic, the percentage of positive reactions in the patch test with 800 times diluted daconil solution of the concentration commonly used being about 30% after 48 hours and about 60% at 48 hours after peeling off the patch.
The parcentage of positive reactions in the skin patch test with several fractions of chrysanthemums on chrysanthemum-growers were significantly higher than non-farm-workers. Similary, tests with allergen extracted from lettuce showed a significantly higher percentage incidence in lettuce -growers than in other subjects. The patch test with 4000 times diluted daconil solution showed ahigher incidence in farmers than in other subjects. Therefore, 4000 times diluted daconil solution seems to cause allergic contact dermatitis in farmers, and as farmers reported, dermatitis seems to be caused by allergy to farm products, and the irritability, phototoxicity and allergenicity of TPN (Daconil).
7.Chemical constituents from rhizome of Phlomis umbrosa.
Pu LIU ; Jie TENG ; Yan-wen ZHANG ; Yoshihisa TAKAISHI ; Hong-quan DUAN
Acta Pharmaceutica Sinica 2007;42(4):401-404
Phlomis umbrosa is a traditional medicinal plant, distributed in the north of China. In the west of Hubei province, its roots were used in the treatment of the rheumatic diseases in Tujia nationality. To study the chemical constituents from the rhizome of Phlomis umbrosa chemical constituents were isolated from the plant by using repeated silica gel, toyopearl HW-40 and preparative HPLC chromatography. The structures of the compounds were elucidated on the basis of one and two dimensional NMR spectroscopic techniques and HRESI-MS. Ten compounds, 6"-syringyl-sesamoside (1), decaffeoylverbascoside (2), calcelarioside B (3), verbascoside (4), isoverbascoside (5), alyssonoside (6), sesamoside (7), shanzhiside methyl ester (8), 8-acetyl-shanzhiside methyl ester (9), 7-epiphlomiol (10) were isolated from P. umbrosa. Compound 1 is a new compound. Compounds 2-6 are isolated from this plant for the first time.
Chromatography, High Pressure Liquid
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Glucosides
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chemistry
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isolation & purification
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Glycosides
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chemistry
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isolation & purification
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Magnetic Resonance Spectroscopy
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Molecular Conformation
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Molecular Structure
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Phenols
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chemistry
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isolation & purification
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Phlomis
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chemistry
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Plants, Medicinal
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chemistry
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Rhizome
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chemistry
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Spectrophotometry, Infrared
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Spectrophotometry, Ultraviolet