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Research On The Chemical Constituents And Biological Activities Of Smilax Bockii Warb.

Posted on:2008-08-13Degree:DoctorType:Dissertation
Country:ChinaCandidate:J XuFull Text:PDF
GTID:1104360215464303Subject:Natural medicinal chemistry
Abstract/Summary:PDF Full Text Request
Smilax bockii Warb. (Liliaceae) is widely distributed in the south and the west ofChina and has been used as a folk herb to treat rheumatoid arthritis and womanailments.From the 70% ethanol extract of the roots of S. bockii Warb., 40 compounds wereisolated using chromatographic methods such as silica gel c.c., PTLC, Sephadex LH-20,polyamide c.c., HPLC etc. On the basis of IR, NMR, MS data and physico-chemicalevidences, the structures of the 40 compounds were identified as following: dioscin (1),methyl protodioscin (2), methyl proto-pb (3), 3β-hydroxypregna-5, 16-dien-20-one-3-O-α-L-rhamnopyranosyl(1→2)-[α-L-rhamnopyranosyl(1→4)]-β-D-glucopyranoside(4), 3β-hydroxypregna-5, 16-dien-20-one-3-O-α-L-rhamnopyranosyl(1→4)-α-L-rhamnopyranosyl(1→4)-[α-L-rhamnopyranosyl(1→2)]-β-D-glucopyranoside (5),kaempferol (6), kaempferol-7-O-α-L-rhamnoside (7), kaempferol-7-O-β-D-glucopyranoside (8), quercetin (9), quercitrin (10), rutin (11), isorhamnetin (12),isorhamnetin-3-O-β-D-glucopyranoside (13), isorhamnetin-3-O-α-L-rhamnopyranosyl(1→6)-β-D-glucopyranoside (14), dihydrokaempferol (15), engeletin (16), isoengeletin(17), 2-hydroxynaringenin-7-O-β-D-glucopyranoside (18), (—)-isolariciresinol 9'-carboxylic acid methyl ester (19), 7-hydroxymethyl-1, 4, 5-trihydroxynaphthalene-4-O-β-D-xylopyranosyl(1→6)-β-D-glucopyranoside (20), 3, 4-dihydroxyl-β-phenethanol-3-O-β-D-glucopyranoside (21), 1, 4-dihydroxy-2, 6-dimethoxyphenyl-4-O-β-D-glucopyranoside (22), arbutin (23), chlorogenic acid (24), chlorogenic acid methylester (25), chlorogenic acid n-butyl ester (26), caffeic acid (27), caffeic acid n-butylester (28), 5-O-p-coumaroyl quinic acid methyl ester (29), 4-hydroxybenzoic acid (30),isovanillic acid (31), protocatechuic acid (32), 3, 5-dimethoxy-4-hydroxy benzonic acid(33), n-butyl-β-D-fructopyranoside (34), n-butyl-a-D-fructofuranoside (35),hydroquinone (36), myoinositol (37), (3R)-dihydro-3-hydroxy-4, 4-dimethyl-2(3H)-furanone (38),β-sitosterol (39), daucosterol (40).Among them, compounds 19, 20 were new compounds; compound 5 was a newnatural product; compounds 6-8, 10, 12-14, 18, 19, 22, 24-33, 36-38 were isolated from the genus Smilax for the first time.We preliminarily screened the activities of S. bockii Warb. by different pharmaco-models, such as anti-inflammation, anti-dementia and antioxidation.The result of anti-inflammatory experiment in vitro using the SEAP assay showedthat the 70% ethanol extract of the roots of S. bockii Warb. suppressed the NF-κBactivation suggesting the extract has anti-inflammatory activity. The active part shouldbe the n-BuOH fraction. The crude extract and fractions, along with several majorcompounds were examined for their effects on the NGF-mediated neurite outgrowthfrom PC12D cells. The results indicated that the crude exact and fractions did notpossess any potential anti-dementia activities; The antioxidant experiment usingSOD-like method was tested and some flavonoids gave promising antioxidant activity.The treatment of Alzheimer's disease with nerve growth factor (NGF) and thenatural products with NGF-potentiating activity were reviewed based on the previousresearch.
Keywords/Search Tags:Smilax bockii Warb, chemical constituents, anti-inflammation, Nerve growth factor (NGF), SOD-like
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