Chemical Constituents From Schima Crenata And Their Anti-inflammatory And Anti-tumor Activities

Schima crenata Korth belongs to the Theaceae family which distributed widely in Indochina Peninsula,Malaysian and Indonesia.The chemical constituents and biological activities of S.crenata have not been reported.Our previous studies revealed that triterpene saponins from Schima superb exhibited potent anti-inflammatory and anti-tumor activities.In the present study,a phytochemical investigation was undertaken to search for the active compounds from the ethanolic extract of S.crenata.As a result,40 compounds have been isolated from the 70%ethanolic extrat of S.crenata using various column chromatographic technologies?silica gel,Sephadex LH-20 and ODS column chromatographies?as well as semi-preparative HPLC.According to the physical and chemical properties as well as spectroscopic methods,they were identified to be 22?-O-angeloy-15?,16?,28-trihydroxyolean-12-en-3-one?SC-1?,16?-O-acetyl-22?-O-angeloy-15?,28-dihydroxyolean-12-en-3-one?SC-2?,28-O-acetyl-15?,16?,22?-trihydroxyolean-12-en-3-one?SC-3?,22?-O-angeloy-28-O-acetyl-3?,15?,16?-trihydroxyolean-12-en?SC-4?,22?-O-angeloy-15-O-acetyl-3?,16?-28?-trihydroxyolean-12-en?SC-5?,16?-O-acetyl-21?,22?-di-O-angeloy-R₁-barrigenol?SC-6?,16?-O-acetyl-21?-O-angeloy-22?-?2-methylbutanoyloxy?-R₁-barrigenol?SC-7?,harpullone?SC-8?,A₁-barrigenol?SC-9?,22?-O-angeloy-barrigenol A₁?SC-10?,28-O-angeloy-barrigenol A₁?SC-11?,21,22-di-O-angeloy R₁-barrigenol?SC-12?,sasanquasaponin??SC-13?,maetenoside B?SC-14?,schisusaponin B?SC-15?,?8S,8?E?-7?-en-dihydrocubebin?SC-16?,?8R,8?S,9S?-4,4?-dihydroxy-3,3?,9-trimethoxy-9,9?-epoxylignan?SC-17?,?8R,8?S,9R?-4,4?-dihydroxy-3,3?,9-trimethoxy-9,9?-epoxylignan?SC-18?,dihydrodehydrodiconiferyl alcohol 4?-O-acetate?SC-19?,tiruneesiin?SC-20?,dihydrodehydrodiconiferyl alcohol 4?-O-?-D-glucoside?SC-21?,rel-?7R,8S?-3,3?,5-trimethoxy-4?,7-epoxy-8,5?-neolignan-4,9,9?-triol 4-O-?-D-glucopyranoside?SC-22?,pinoresinol acetate?SC-23?,pinoresinol diacetate?SC-24?,?7S,8R?-1-[4-O-??-D-glucopyranosyl?-3-methoxyphenyl]-2-[4-?3-hydroxypropyl?-2,6-dimethoxyphenoxy]-1,3-propanediol?SC-25?,?7S,8S?-1-[4-O-??-D-glucopyranosyl?-3-methoxyphenyl]-2-[4-?3-hydroxypropyl?-2,6-dimethoxyphenoxy]-1,3-propanedio l?SC-26?,7S,8S-erythro-7,9,9?-trihydroxy-3,3?-dimethoxy-8-O-4?-neolignan-4-O-?-D-glucopyranosi de?SC-27?,tangeritin?SC-28?,melibentin?SC-29?,chrysophanic acid?SC-30?,methyl syringate4-O-?-L-rhamnopyranoside?SC-31?,4-O-?glycer-2-yl?-dihydroconiferylalcohol-10-O-?-D-mannopyranoside?SC-32?,dehydrozingerone?SC-33?,1,2,3-benzenetriol-1,3-diacetate?SC-34?,protocatechuic aldehyde?SC-35?,protocatechuic acid?SC-36?,3,4,5-trimethoxyphenyl1-O-?-D-apiofuranosyl-?1???6??-?-D-glucopyranoside?SC-37?,?-spinasterol?SC-38?,dibutyl phthalate?SC-39?,4-methylphenyl-1-thio-?-D-mannopyranoside?SC-40?.Among them,SC-1?7,SC-17?19 are ten new compounds,and SC-8?12,SC-16,SC-20?37,SC-39?40 were isolated from Schima genus for the first time.The in vitro anti-inflammatory activities for all compounds were evaluated in lipopolysaccharide?LPS?-stimulated RAW 264.7 macrophages.Compounds SC-3,SC-5,SC-6,SC-10,SC-11,SC-13,SC-14,SC-28 exerted more potent anti-inflammatory effects than positive control.In addition,the toxic concentration?C₀?of compounds SC-11 and SC-28 differs greatly from the anti-inflammatory activity(IC₅₀),which has the potential of structural modification as lead compounds.The cytotoxic activities of all compounds against the Hep G 2 cells were measured using3-?4,5-dimethylthiazol-2-yl?-2,5-diphenyl tetrazolium bromide?MTT?assay with cisplatin served as the positive control.Furthermore,the cytotoxic activities of triterpenoids against the He La,A549,MCF-7,MDA-MB-231,Lo Vo and A375 cells were determined by MTT assay.Compounds SC-7,SC-13 and SC-14 exhibited strong inhibitory activities.