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Studies On The Chemical Constituents And Biological Activities Of The Husks Of Xanthoceras Sorbifolia Bge.

Posted on:2007-04-29Degree:DoctorType:Dissertation
Country:ChinaCandidate:Z L LiFull Text:PDF
GTID:1114360185489168Subject:Natural medicinal chemistry
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Xanthoceras sorbifolia Bunge (Sapindaceae) is a plant widely distributed in Liaoning, Hebei and Shaanxi Province of China. Its wood of stem and branch, which is called "Wen Guan Mu", is used to treat rheumatism as a folk medicine in China. The extract of the seeds also has the activity of curing enuresis of children.From the 70% ethanol extract of the husks of Xanthoceras sorbifolia Bunge, 41 compounds were isolated by means of solvent partition, repeated column chromatography on silica gel and Sephadex LH-20, recrystallization. On the basis of physico-chemical properties and spectroscopic analysis, their structures were identified as follows. Tritepenoids: 21, 22-di-O-angeloyl-24-hydroxy-R1-barrigenol (1), 3-O-(3-O-α-L-arabinofuranosyl-2-O-β-D-galactopyranosyl)-β-D-glucuronopyra-nosyl-21, 22-di-O-angeloyl-R1-barrigenol (2), 21, 22-di-O-angeloyl-R1-barrigenol (3), 21-O-angeloyl-R1-barrigenol (4), 22-O-angeloyl-R1-barrigenol (5), R1-barrigenol (6), 16-O-acetyl-21-O-(4-O-angeloyl)-α-L-rhamnopyranosyl-barringtogenol C (7), 22-O-angeloyl-21-O-epoxyangeloyl-barringtogenol C(8), 21-O-(3, 4-di-O-angeloyl-β-D-fu-copyranosyl)-barringtogenol C (9), 21, 22-di-O-angeloyl-barringtogenol C (10), barringtogenol C (11), 28-O-β-D-glucopyranosyl-16-deoxybarringtogenol C (12), 16-deoxybarringtogenol C (13); Flavonoids: naringenin (14), eriodictyol (15), kaempferol (16), quercetin (17), rutin (18), 5, 7-dihydroxychromone (19); Coumari-ns: isofraxetin-6-O-β-D-glucopyranoside (20), cleomiscosin D (21), scopoletin (22), isofraxidin (23); Sterols: ergosterol peroxide (24), 9(11)dehydro-ergosterol peroxide (25),β-sitosierol (26), daucosterol (27),α-spinasterol (28),α-spinasterol-3-O-β-D-gl-ucopyranoside (29); Alkaloid: 2-methyl-6-(2', 3', 4'-trihydroxybutyl)-pyrazine (30); Organic acids and phenols: protocatechuic acid (31), protocatechuic acid ethyl ester(32), vanillic acid (33), 4-hydroxybenzaldehyde (34), 3, 4, 5-trimethoxybenzoic acid (35), 4-hydroxyphenylacetic acid (36), 2-hydroxy-6-methylbenzoic acid (37), succinic acid (38), tyrosol (39); Others: 1, 4-di-(2-cyanostyryl)benzene (40),1-O-methyl-myo-inositol (41).Among them, compounds 1, 2, 7, 8,12, 20, 30 were new compounds; compound 40 was a new natural product; compounds 4-6, 10-13, 15, 16, 18, 19, 22-27, 29, 32-39, 41 were firstly isolated from this genus.By MTT and SRB methods, the in vitro cytotoxicity activities against cancer cell lines of the triterpenoids isolated were assayed. Compound 2 showed moderate activity against several human cancer cell lines (HeLa, U87, SF-188, etc.); compound 1 was tested to possess the most strong activity against A375-S2 and Hela cell lines, with IC50 values of 4.2 and 0.2μg/ml, respectively; compound 13 displayed moderate activity with IC50 values of 23.5 and 20.6μg/ml against this two cell lines above; nevertheless, the compounds with the skeleton of R1-barrigenol did not show distinct cytotoxicity activity.The crude extract and fractions, along with compound 41 and eight triterpenoids were examined for their effects on the NGF-mediated neurite outgrowth from PC12D cells to evaluate their NGF-potentiating activities. The assay results indicated that the crude exact and fractions did not possess any potentiating activities; as for the compounds tested, compound 6 showed moderate activity with the 46%effect against the positive control at the concentration of 20μg/ml, compounds 3 and 5, which have the same skeleton with 6, also showed weak activities; compound 41 and the other triterpenoids showed no obvious activity in the assay.On the basis of references, a review was given on the structural categories, distribution, bioactivities, biosynthesis pathway and artificial synthesis methods, together with the studies on the structural elucidation of coumarinolignoids, a kind of compounds rarely occurring in nature.
Keywords/Search Tags:Xanthoceras sorbifolia Bunge, husks, triterpenoid, antitumor activity, NGF-potentiating activity, coumarinolignoid
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