Dissertation
Dissertation > Medicine, health > Chinese Medicine > Of Pharmacy > Pharmacology

Studies on the Chemical Constituents and Bioactivities of Sterculia Foetida L.

Author XiaPengFei
Tutor ZhangPeiCheng;YuDeQuan;ChenRuoZuo;LiShuai
School Peking Union Medical College , China
Course Medicinal Chemistry
Keywords Sterculiaceae family Sterculia Sterculia foetida flavonoid glucuronide chemical constituents biological activity
CLC R285
Type PhD thesis
Year 2009
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Sterculia foetida.L belongs to the sterculia genus of the family Sterculiaeace and is widely distributed in tropical area,such as India,Sri Lanka Vietnam,Thailand,Cambodia, Burma and Australia.About twenty-three species of them occurred in the southwestern and southern China,such as Kangle of Guangzhou province and Yaxian of Hainan province.S.foetida is used as aperient,diuretic and insect repellent in herbal medicine. Extracts of the leaves of S.foetida were reported to exhibit depressant activity on central nervous system and significant anti-inflammatory activity.This dessertation investigated chemical constituents of ethanolic extracts of the leaves of S.foetida and their bioactivities on several pharmacological models and synthesized baicalein-6-O-β-D-glucuronide and baicalein-6- O-β-D-glucoside so as to obtain a variety of flavonoid glucuronide compounds.The chemical constituents of the plants of the genus Sterculia were investigated systemicly for the first time.By using a variety of chromatographic techniques and spectroscopic methods,46(1-46) compounds were isolated and determined from the 95% ethanol extracts of the leaves of S.foetida,including 33 flavonoids,4 coumarins,6 organic acids and 3 sterides compounds.Among them,compounds 7-18 were isolated for the first time from this species and 1*-6* are new compounds,which as follows: hypolaetin 4’-methyl ether 8-O-β-D-glucuronide 2"-sulfate(1*),hypolaetin 3’-methyl ether 8-O-β-D- glucuronide 6"-methyl ester(2*),hypolaetin 8-O-β-D-glucuronide 6"-methyl ester(3*),hypolaetin 4’-methyl ether 3’-O-β-D-glucoside(4*),chrysoeriol 7-O-β-D-glucuronide 6"- methyl ester(5*),1,6-diferuloyl glucose(6*);the others were known compounds,including hypolaetin 8-O-β-D-glucuronide(7),hypolaetin 8-O-β-D-glucuronide 6"-ethyl ester(8),takakin 8-O-β-D-glucuronide(9),takakin 8-O-β-D-glucoside(10),takakin 7-O-β-D- glucoside(11),takakin 8-O-β-D-glucuronide 6"-methyl ester(12),isoscutellarein 8-O-β- D-glucuronide(13),isoscutellarein 8-O-β-D-glucuronide 6"-methyl ester(14),isoscute llarein 8-O-β-D-glucoside(15), isoscutellarein 8-O-β-D-glucuronide 6"-ethyl ester(16),chrysoeriol 7-O-β-D-glucuronide (17),chrysoeriol 7-O-β-D-glucuronide 6"-ethyl ester(18),luteolin 7-O-β-D-glucuronide (19),luteolin 7-O-β-D-glucoside(20),luteolin 7-O-β-D- glucuronide 6"-methyl ester(21), luteolin 7-O-β-D-glucuronide 6"-ethyl ester(22),apigenin-6,8-di-C-β-D-glucoside(23), apigenin 7-O-β-D-glucuronide 6"-ethyl ester(24),quercetin 3-O-β-D-glucoside(25), puerarin(26),5,7,8,3’-tetrahydroxy-4’-methoxy flavone(27), 5,7,8-tetrahydroxy-3’,4’-dimethoxyflavone(28),takakin(29),luteolin(30),chrysoeriol (31),apigenin(32),quercetin(33),scopolin(34),isofraxidin 7-O-β-D-glucoside(35), 5,7-dihydroxy-6-methoxy-7-O-β-D-glucosyl coumarin(36),fraxetin 7-O-β-D-glucoside (37),p-hydroxy benzcic acid(38),3,4-dihydroxybenzoic acid(39),p-coumaric acid(40), cis-p-coumaric acidβ-glucoside(41),trans-ferulic acidβ-glucoside(42),4-hydroxy-3,5-dimethoxy-benzoic acid 4-O-β-D-glucopyranosyloxy(43),5α,6β-Dihydroxy daucosterol(44),β-sitosterol(45),daucosterol(46)。At the same time,baicalein-6-O-β-D-glucoside(X6) and baicalein-6-O-β-D-glucuronide(X9) were synthesized from baicalein by acetylation, benzyl group protection,deacetylation,glycosylation and hydrogenolysis.Extracts evaluation:SF15%showed selective cytotoxicity against HCT-8 and Bel-7402 with IC50 values of 13.32 and 19.07μg/mL,SF30%indicated selective cytotoxicity against Bel-7402 with IC50 values of 37.72μg/mL,while,SF70%were active against HCT-8 and BGC-823 with IC50 values of 34.94 and 30.50μg/mL,respectively. SF15%,SF30%and SF70%showed obvious anti-flammatory activities against croton oil-induced rat ear edema.SF15%exhibited depressant activity on central nervous system with a sleeping rate of 57.1%at a concentration of 5 mg/kg.Compounds evaluation:Compounds 2* and 27 showed selective cytotoxicity against HCT-8,Compound 17 was active against Bel-7402 and BGC-823,Compound 22 indicated selective cytotoxicity against Bel-7402 and A549,while,Compound 19 exhibited selective cytotoxicity against A549.Compounds 2*,8,17,19 showed obvious anti-flammatory activities against croton oil-induced rat ear edema at 20 mg/kg.Compounds 18,19 exhibited inhibitory effect on release ofβ-glucuronidase rat polymorphous nuclear leukocytes activated by platelet activating factor(PAF) at a concentration of 10-5 M. Compound 30 showed protective effect against ECV304 endotheliocyte oxidative damage induced by H2O2 at a concentration of 3.91μg/mL.Besides,Compound 27 was active against endotheliocyte damage induced by hypoxemia in vitro.

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