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Studies On The Bioacive Constituents Of Ardisia Crenat Sims And Bulbophyllum Ororatissimum Lindl.

Posted on:2005-07-07Degree:DoctorType:Dissertation
Country:ChinaCandidate:D L LiuFull Text:PDF
GTID:1104360122490679Subject:Medicinal chemistry
Abstract/Summary:PDF Full Text Request
In this dissertation, the Pyricularia oryzae bioassay was used to search anticancer compounds, 24 compounds were obtained from Ardisia crenata Sims and 29 compounds were obtained from Bulbophyllum odoratissimum Lindl.. Their structures were elucidated on the basis of chemical evidences and spectral analysis.The 24 compounds from A. crenata Suns are bergenin (1), ardisicrenoside I (2)*, ardisicrenoside J (3)*, ardisicrenoside K (4)*, ardisiacrispin A (5), ardisiacrispin B (6), ardisicrenoside B (7), ardisicrenoside A (8), ardisicrenoside D (9), ardisicrenoside M (10)*, ardisicrenoside C (11), ardisicrenoside L (12)*, ardisicrenoside H (13), ardisicrenoside G (14), 3B-0-{p-D-xylopyranosyl-(1- 2)-B-D-glucopyranosyl-(l - 4)-[(B-D-glucopyranosyl-(l -2)]-a-L-arabinopyranosyl}-16a, 28-dihydroxy-olean-12-en-30-aldehyde(15), 3p, 16a-dihydroxy-30-methoxy-28, 30-epoxy-olean-12-en (16), 2, 4, 6-trihydroxybenzoic acid (17), ardisicrenoside P (18)*, 3p-0-[p-D-glucopyranosyl-(l -* 2)-a-L-arabinopyranosyl] cyclamiretin A(19), 3p-O-[p-D-glucopyranosyl-(1-4)-a-L-arabuiopyranosyl] cyclamiretin A(20), 3B-0-[B-D-xylopyranosyl-(l -2)-p-D-glucopyranosyl-(1-4)-a-L-arabinopyranosyl] cyclamiretin A(21), 3B-0-[a-L-rhamnopyranosyl-(1 - 2)-B-D-glucopyranosyl-(1 - 4) -a-L-arabinopyranosyl] cyclamiretin A (22), ardisicrenoside N (23) *, ardisicrenoside 0 (24) *, respectively. Compound 2, 3, 4,10,12,18,23 and 24 are new, compound 15-17 and 19-22 were isolated for the first time from Ardisia genus.The 29 compounds from Bulbophyllum odoratissimum Lindl. are 2, 2'-dihydroxy-3, 3'-dimethoxy-4, 5-methylenedioxybibenzyl (1)*, 3'-hydroxy-3, 5'-dimethoxy-4, 5-methylenedioxybibenzyl (2)*, 2, 3'-dihydroxy-3-methoxy-4, 5-methylenedioxybibenzyl (3), 3', 3-dihydroxy-4, 5-methylenedioxybibenzyl (4), 3'-hydroxy-3-methoxy-4, 5-methylenedioxybibenzyl (5), 2-hydroxy-5-methoxy-3, 4, 3', 4'-dimethylenedioxybibenzyl (6), 5'-hydroxy-5-methoxy-2, 2'-oxrpin-3, 4-methylenedioxybibenzyl (7), 4, 5'-dihydroxy-3, 3'-dimethoxybibenzyl (8), 4, 5'-dihydroxy-3, 3', 5-trimethoxybibenzyl (9), batatasin III(10), 3'-hydroxy-3, 5-dimethoxybibenzyl (11), 2'-(3", 5"-dunethoxy-4"-hydroxybenzyl)-3'-hydroxy-2', 3'-dihydro-4H-pyrano [5', 6'-i]2-hydroxy-5-methoxyphenanthrene (12)*, 2,7-dihydroxy-3, 4-dimethoxyphenanthrene(13), 2, 5-dihydroxy-3, 4-dimethoxyphenanthrene (14), 2, 7-dihydroxy-4-methoxyphenanthrene (IS), 2, 7-dihydroxy-3, 4-dimethoxy-9, 10-dihydrophenanthrene(16), 2, 7-dihydroxy-4-methoxy-9, 10-dihydrophenanthrene (17), 2, 7-dihydroxy-3, 4, 6-trimethoxy-9, 10-dihydrophenanthrene (18), 4, 5-dihydroxy-2, 3-dihydroindenespiro-3'-methoxy-4', 5'-methylenedioxy-3', 5'-diene-cyclohex-2'-one (19)*, (+)-lyoniresinol-3a-O-B-D-glucopyranoside (20), 3-hydroxyphenethyl alcohol 3-O-(6'-O-p-D-apioruranosyl)-p-D-glucopyranoside (21)*, 3-methoxyphenethyl alcohol 4-O-B-D-glucopyranoside (22), 3, 5-dimethoxyphenethyl alcohol 4-0-p-D-glucopyranoside (23), syringin (24), p-hydroxy-phenylpropionic acid (25), p-hydroxyphenylpropionic methyl ester (26), 3-methoxy-4-hydroxycinnamic aldehyde (27), 4-hydroxy-2, 6-dimethoxybenzaldehyde (28), orsellinic ethyl ester (29), respectively. 1,2,12,19 and 21 are new compounds, 8, 9,14,17,18, 20, 22-29 were isolated from Bulbophyllum genus for the first time.Among the 53 compounds, triterpenoid saponins from A. crenata Sims showed potent activity against Pyricularia oryzae, however, bibenzyls, phenanthrenes and dihydrophenanthrenes from Bulbophyllum odoratissimum Lindl. had relatively very weak activity.MTT method was also used to test the cytotoxic activity of these compounds on MCF-7, NCI-H460 and SF-268 cancer cell lines recommended by NCI. Triterpenoid saponins from A. crenata Sims also showed strong cytotoxic activities. Bibenzyl, phenanthrene and dihydrophenanthrene from B. odoratissimum Lindl. were inactive except that 3'-hydroxy-3-methoxy-4, 5-methylenedioxybibenzyl (5) and 5'-hydroxy-5-methoxy-2, 2'-oxrpin-3, 4- methylenedioxybibenzyl(7) had relatively weak activity. The cytotoxicity on HepG2 and Hep3B cell lines, two kinds of human li...
Keywords/Search Tags:Pryculara oryzae, Ardisia crenata Sims, Bulbophyllum odoratissimum Lindl., triterpenoid saponins, bibenzyls, phenanthrenes, dihydrophenanthrenes, cytotoxic activity, MTT method, structure-activity relationship, inhibitory effect of NO production
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