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The Chemical Constituents From The Root And Stem Of Symplocos Laurina Wall

Posted on:2016-05-07Degree:MasterType:Thesis
Country:ChinaCandidate:L X XieFull Text:PDF
GTID:2284330461481885Subject:Medicinal chemistry
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Symplocos setchuensis Brand (Symplocaceae) is indigenous in southern China. Many species of this genus have been used as traditional herbal medicines for various ailments like leprosy, gynecological disorders, ulcers, malaria, nephritis, etc. Phytochemical investigations on Symplocos laurina Wall. reported occurrences of triterpenoid saponins, flavonoids, lignans and phenolic glycosides, etc, in which triterpenoid saponins are the main chemical constituents and also the main active ingredients. The genus Symplocos mainly contain chemical constituents which had been proved to have diverse biological activities, particularly anti-HIV activity, antitumor applications, antibacterial effect and inhibitory activities against phosphodiesterase, etc. At present, there are less domestic studies on chemical constituents andactivity ingredients of Sect. Palaeosymplocos Brand. The objective of in this review article is to study the triterpene acids constituents of Symplocos laurina Wall..the constituents were isolated by repeated chromatography with silica gel, Sephadex LH-20, ODS columns and semi-preparing liquid chromatography. The structures were elucidated by spectroscopic analysis. Twenty six compounds were obtained from theethanol extract of the stem and root of Symplocos laurina Wall. and identified as myo-inositol(2), oleanolic acid-3-acetate(3), erythrodiol-3-acetate(4), stigmasterol(5), a-spinasterol(6), vanillic acid(7), sucrose(8), maltose(9),5,4’-dihydroxy-7-Methoxy flavanone(10), Dihydrokaempferol(11), dihydro-kaempferide(12),4-Hydroxy-3-methoxy cinnamic acid(13), (2R,3R)-(-)-4’,5,7-trimethoxydihydroflavonol(14),19a-hydroxy-4-oxo-3,24-dinor-2,4-secours-12-en-2,28-dioic acid(15),19a-hydroxy-4-oxo-3,24-dinor-2,4-secoolean-12-en-2,28-dioic acid(16), negundonorin A(17),2a,3β,19α,23-tetrahydroxyurs-12-en-28-oic acid(18),2a,3β,19α,23-tetrahydroxy bearing-12-en-28-oic acid(19), 2α,3β,23-trihydroxyoic-12-en-28-oic acid(20),2a,3β,23-trihydroxybearing-12-en-28-oic acid(21),2a,3a,19a,23-tetrahydroxyurs-12-en-28-oic acid(22), 1β,2a,3β19a,23-pentahy droxyurs-12-en-28-oic acid(23), la,3β,19a,23-tetrahy droxyurs-12-en-28-oic acid(24), 3β,19a,23-trihydroxyoic-12-en-28-oic acid(25),3β,19a,23-trihydroxyurs-2-oxo-12-en-28-oic acid(27), Erythro-guaiacylglycerol-β-O-4’-dihydroconiferyl alcohol(27).Compound 15 is firstly obtained as new products and 23 are firstly obtained as natural products. Compounds 2,3-27 were isolated from this plant for the first time.Expect for the compounds 3,11,18 and 22, the other compounds were isolated from this Symplocaceae for the first time.Twenty-six compounds which include two sterols (compounds 5 and 6); three sugars (compounds 4,8,9); two phenolic compounds (compounds 7,13); a lignan compounds (compounds 27); four flavonoids (compounds 10,11,12,14), fourteen triterpenoids(compounds 3,4,15-26).Using [3H] tag liquid scintillation counting method to get PDE4 inhibitory activity of 12 compounds in vitro test. The PDE4 inhibitory activity tests showed one triterpenoid compound 3(oleanolic acid-3-acetate) have inhibitory activity against PDE4D2, with inhibitory rate of 85% at 10μM.
Keywords/Search Tags:Symplocos laurina Wall., chemical constituents, triterpene acids, anti-Inflammatory, phosphodiesterase 4 (PDE4)
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