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Studies On The Chemical Constituents And Anti-tumor Promoting Activity Of Dioscorea Bulbifera L. And Chaenomeles Sinensis (Thouin) Koehne

Posted on:2003-07-01Degree:DoctorType:Dissertation
Country:ChinaCandidate:H Y GaoFull Text:PDF
GTID:1104360092492308Subject:Medicinal chemistry
Abstract/Summary:PDF Full Text Request
In order to take an advantage of the edible plants and find most promising chemopreventers from the natural sources, by means of the assay- anti the promotion of JB-6 tumorigenic cell lines Cl 22, Cl 41 induced by TPA (Ing/ml, as a promoter) in vitro, the inhibitory effects of more than 100 kinds of plants were evaluated. Among them, 75% ethanol extract of the rhizomes of Dioscorea bulbifera L. (DB75-E) and methanol extract (CSM) from twigs of Chaenomeles sinensis (Thouin) Koehne showed potent the inhibitory effects on the tumor promotion. Further investigation on the chemical constituents of two kinds of plants were carried out, at same time, the activity of some typical compounds were examined, and relationship between the activity and structures were discussed.DB75-E and CSM showed the potent activity on anti tumor promotion. The average of inhibitory rate were 76.5% and 96.8% respectively. The rhizome of Dioscorea bulbifera L.(Dioscoreaceae), as a traditional medicine was usually used to treat sore throat and struma in ancient times of China. Chaenomeles sinensis (Thouin) Koehne (Rosaceae) is a special woody plant of eastern Asia, and distributes widely in China and Japan. The fruit, called "Mu Gua" is a traditional medicine showed the activity against the pneumonia, pulmonary tuberculosis, cholera and so on.DB75-E was suspended in water and partitioned successively with CHC13(DB-C), EtOAc(DB-A), BuOH(DB-B). The activity of every layer including the residues of aqueous (DB-W)was evaluated by the same method, and the average of inhibitory rates were 38.6%, 100%, 92.6%, 66.4% respectively at their maximal concentration. The fact was shown that the activity of DB-A was the most potent. Further investigation on the chemical constituents of the extract of Dioscorea bulbifera L. by the chromatographs and HPLC techniques, 28 compounds were isolated and the structures of 26 compounds were identified by the physical-chemical properties and spectral methods. They were elucidated as diosbulbin-B (1), daucosterol(2), P -sitosterol(3), palmatic acid(4), succinic acid(5), shikimic acid(6) 3,5-dimethoxykaempferol(7), 3,5,3 ' -trimethoxyquercetin(8), caryatin(9), (+)catechin(10), myricetin(11), myricetin-3-O- β -D-galactopyranoside(12), myricetin-3-O-β -D-glucopyranoside(13), hyperoside(14), kaempferol-3-O-β -D-galactopyranoside(15), protocatechuic acid (16), vanillic acid(17), isovanillic acid(18), (+)epicatechin(19), methyl-O- a - D-fructofuranoside (20), butyl-O- a - D-fructofuranoside, (21), ethyl-O- a -D-fructopyranoside(22), butyl-O- a -D-fructopyranoside(23), benzyl-O-β -D-glucopyranoside(24), 2-(4-methoxyphenyl)ethyl-O-β -D-glucopyranoside(25), 3-phenyl-2-propenol-3-O-β -D-glucopyranoside(26). Among them compounds 7, 8, 9, 11, 12, 13, 14,15,16, 20, 21, 22, 23, 25, 26 were obtained from Dioscorea genus for the first time, and 5,6,17,18,24 were isolated from this plant for the first time.One part of the extract of twigs of Chaenomeles sinensis (Thouin) Koehne was suspended in water and partitioned successively with EtOAc(CSMA),n-BuOH(CSMB). The bioactivity of each layer was tested by the same way. The EtOAc soluble fraction exhibited the most potent inhibitory effects on the tumorigenic cells' promotion. By the chromatographs and HPLC techniques, 27 compounds were isolated and the structures of 23 were elucidiated by the physical-chemical properties and spectral methods. Compounds 27(chaenomone), 34(lup-20(29)-en-3 P , 24, 28-triol), 48(genistein-5-O- β -D-galactopyranoside) and 49(genistein-7-O- β -D-galactopyranoside) were four novel constituents, while the other known components were identified as β -sitosterol(28), erythodiol(29), maslinic acid (30),betulinic acid(31), 2 a -hydroxybetulinic acid(32), betulin(33), 3-(E)-p-coumaroylbetulin(35), 3-(Z)-p-coumaroylbetulin(36), 3-(E)-feruloylbetulin(37), 3- (E)-caffeoylbetulin(38), 2 a -hydroxyursolic acid (39), euscaphic acid(40), tormentic acid(41), lyoniresinol -9 ' -O- β -D- glucopyranoside(42), lyoni...
Keywords/Search Tags:Constituents
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