Study On The Chemical Components Of Tribulus Terrestris Fruit And Four Microorganism

This dissertation is composed of six chapters.In the first chapter,a review about the chemical constituents and pharmacological effects of Tribulus terrestris was given.In chapters 2-6,chemical investigation on Tribulus terrestris L.and four microbe,inciuding Melanoleuca cognata,Boletus,Streptomycetaceae sp.YIM S03932,Streptomycetaceae sp.31339 was comprehensively.33 compounds,inclunding 1 new one,were isolated from the above mentiond Tribulus terrestris L.and four microbe by silica gel,reversed-phase（RP）,and Sephadex LH-20 column chromatographyies.Their structures were established on the basis of extensive spectroscopic analysis including 1D,2D NMR spectroscopy,MS,UV and IR spectroscopic methods.The type of isolated compounds includes acid amides,monoterpene,sterol,flavone,phenylpropanol,fatty acids,as well as other small molecules.Eleven compounds,inclunding 1 new one,were isolated from 75%methanol extract of the fruits of Tribulus terrestrer and identified as Tribulusmide D（1）,terrestriamide（2）,hecogenin（3）,25R-spirostan-4-ene-3,12-dione（4）,quercetin（5）,3,4’-dihydroxy-3’-methoxyphenylacetone（6）,p-hydroxybenzoic acid（7）,dibutyl phthalate（8）,（9Z,11E）-13-hydroxy-9,11-octadecadienoic acid（9）,（8E,12Z）-10-hydroxy-8,12-octadecadienoic acid（10）,myristic acid（11）.Compound5 showed antioxidant activities against DPPH,ABTS and OH free radicals with IC₅₀values of 1.202±0.13,0.011,0.32 mg/mL.Six known compounds were isolated from the culture of Melanoleuca cognata,namelyoleicacid（12）,methyllinoleate（13）（4S,5S,6Z,8E）-5-hydroxydeca-6,8-dien-4-olide（14）,p-hydroxyphenylethanol（15）,2,3-butanediol（16）,dibutyl phthalate（17）.The ethyl acetate extract of its fermentation broth had moderate scavenging activities on DPPH,ABTS and hydroxyl radical,and the IC₅₀was 0.371,0.220,0.093 mg/mL.Five known compounds were isolated from the culture of Boletus,namely（22E,24R）-ergosta-5,7,22-trien-3β-ol（18）,（22E,24R）-ergosta-7,22-diene-3β-ol（19）,9（Z）,12（Z）-octadecanedioenoic acid（20）,β-sitosterol（21）,stigmasterol（22）.The ethyl acetate extract of its fermentation broth had moderate scavenging activities on DPPH,ABTS and hydroxyl radical,and the IC₅₀was 0.287,0.325,0.161 mg/mL.Five known compounds were isolated from the culture of Streptomycetaceae YIM S03932,namely triglyceride linoleic acid（23）,triglyceride（24）,dibutyl phthalate（25）,β-sitosteryl-3-O-glucopyranoside（daucosterol）（26）,Macrolactin B（27）.The activity test results showed that compound 26 had a significant effect on DPPH(IC₅₀=1.218±0 04 mg/mL),ABTS(IC₅₀=0.37 mg/mL),and OH free radicals(IC₅₀=0.973 mg/mL)all exhibit certain antioxidant activity.Eight known compounds were isolated from the culture of Streptomycetaceae31339,namely 24-Methylenecycloartanol（28）,genistein（29）,β-sitosterol（30）,stigmasterol（31）,（3R,4R）-3,4-dihydroxy-3-methyl-pentan-2-one（32）,（3′S,4′R）-3′,4′-dihydroxy-3′-methyl-pentan-2′-one（33）.The activity test results showed that compound 28 had a better scavenging effect on OH radicals compared to DPPH and ABTS,with an IC₅₀ of 20.44±0.03 mg/mL,30.31±0.14 mg/mL and1.979±0.06 mg/mL;Compound 29 flavonoids showed good activity against three antioxidant tests,with IC₅₀ of 1.202±0.13 mg/mL,0.011 mg/mL,and 0.32 mg/mL,respectively;Compound 30:Sterol compounds generally have a better IC₅₀ of 0.036mg/mL for OH radicals.