이질풀(Geranium thunbergii Sieb. et ZUCC)과 딱총나무(Sambucus williamsii var. coreana NAKAL)의 화학성분 및 생리활성에 관한 연구

Abstract

Geranium thunbergii Sieb. et ZUCC(Geraniaceae) is a perennial plant and is distributed in Korea, China, and Japan. In traditional medicine, the whole plants are used as an antihemorrhage, sterilization, diarrhea, and astringent. Previous phytochemical studies on this species afforded tannins and flavonoids, such as geraniin, corilagin, ellagic acid, gallic acid, quercetin, kaempferol, and kaempferol-7-rhamnoside. In an ongoing investigation into biologically active compounds from natural products, the EtOAc soluble fraction of methanol extract from G. thunbergii. showed significant antioxidative activity on the NBT superoxide scavenging assay and inhibitory effect on TNF-α induced hIL-6 production in the MG-63 cell. By means of the repeated column chromatography using silica gel, HP-20, Sephadex LH-20, LiChroprep RP-18, three flavonoids afzelin (1), quercetin 3-O-α- L-rhamnopyranoside (2), Kaempferol-3-O-α-rutinoside (3), three phenylic acids gallic acid(4), protocatechuic acid (5), gallic acid methyl ester (6) and one tannin Isocorilagin (7) were isolated. Their structures of compounds 1~7 were determined by chemical analysis, as well as, 1D- with 2D-NMR sepectroscopy. Among them, compounds 3 and 5~7 were isolated from this plant for the first time. In vitro cell cytotoxicity was evaluated by SRB method and compounds 1~6 showed no cytotoxic activity. Compound 4, 5 and 6 showed inhibitory effect on TNF-α induced hIL-6 production in the MG-63 cell. Therefore, compounds 4~6 may be developed for the anti-inflammatory agents and treatment of disease by overexpression of hIL-6. Korean Sambucus williamsii var. coreana(Caprifoliaceae) was plants usually used in popular medicine of Korea for prevention and treatment of bone diseases for thousands of years. A tree widely distributed in korea, china and japan, has been used for have been known to possess expelling the wind, remove dampness through diuresis, prompt blood flow, relieve pain activities, and have been used for rheumatic arthritis, lumbodynia, bone fracture and external hemorrhage, chemical investigation on this species has been seldom reported previously. However, chemical investigation on this species has been seldom reported previously. Only several lignans, phenolic acids, triterpenoids and steroids have been isolated until now, such as oleanolic acid, betulic acid, ursolic acid, vanillin, coniferyl alcohol, 4-hydroxybenzoic acid, 4-hydroxycinnamic acid, (-)-syringa- resinol, (-)-pinoresinol, (-)-dihydrodehydrodiconiferyl alchohol, stigmasterol. During our search for the phytochemical studies on Korean medicinal plants, seven triterpenoids, two sterols, nine lignans were isolated from the CH2Cl2- and EtOAc- soluble fraction of the stem bark of S. williamsii, through repetitive column chromatography method using silica gel, HP-20, Sephadex-LH 20 and RP-18. By analyses of spectroscopic data and comparison of their data with those of published values, the compounds were identified as α-amyrin-3-β-palmitate (8), 11-keto-α-ayrin palmitate (9), betulonic acid (10), oleanonic acid (11), betulinic acid (12), β-amyrin (13), ursolic acid latone (14), β-sitosterol (15), stigmasterol (16), (+)-pinoresinol (17), (-)-lariciresinol (18), (+)-lariciresinol (19), 8-hydroxy pinoresinol (20), (-)-olivil (21), (+)-medioresinol (22), (-)-Olivil 9-O-β- glucopyranoside (23), dihydrodehydrodiconiferyl alcohol 9'-O-β- glucoside (24), glochidioside (25). Among these compounds 8~11, 13, 14 and 19~25 were isolated from this plant for the first time. Among these isolates, the compounds 17, 18 and 21 in vitro using methods micro- dilution and MTT-assay of the experimental anti-fungal. The result express these compounds has different degree to the T. beigelii, M. furfur and C. albicans fungi cell to repress a function. So compounds 17, 18 and 21 cause to these fungis of the disease have a treatment function.