- 學位論文
細齒水蛇麻化學成分與抗結核活性之研究
Chemical Constituents and Antitubercular Activity from Fatoua pilosa
摘要
細齒水蛇麻 (Fatoua pilosa Gaud.)為桑科，多年生草本植物，主要分布於台灣、菲律賓、摩鹿加群島和新幾內亞。在台灣產植物活性成分之一系列研究，發現F. pilosa植物之全草甲醇萃取物，對Mycobacterium tuberculosis H37Rv標準菌種，具有抗結核活性，而Fatoua屬植物全世界只有三種，其化學成分及生物活性均未被報告過。 將本植物之甲醇萃取物進行分配，得到乙酸乙酯及水層，針對乙酸乙酯層進行研究，迄今分離得到六個新coumarins，分別為: (+)-fatouain A (1), (-)-fatouain B (2), (+)-fatouain C (3), (-)-fatouain D (4), (+)-fatouain E (5), (-)-fatouain F (6)，另外四個新bis-coumarins，分別為: (+)-fatouain G (7), (+)-fatouain H (8), fatouain I (9), fatouapilosin (10)，還有18個已知化合物，其中3個為simple coumarins: umbelliferone (11), scopoletin (12), phellodenol-A (13)，6個為furanocoumarins: psoralen (14), bergapten (15), S-(+)-marmesin (16), S-(+)-rutaretin methyl ether (17), S-(+)-rutaretin (18), 2’,3’-dehydromarmesin (19)，1個為pyranocoumarin: xanthyletin (20)，3個為chaclones: isobavachalcone (21), kanzonol C (22), (E)-1-[2,4-dihydroxy-3-(3-methyl-2-butenyl)phenyl]-3- (2,2-dimethyl-8-hydroxy-2H-benzopyran-6-yl)-2-propen-1-one (23)，1個為ben- zenoid: syringaldehyde (24)，1個為quinone: α-tocopheryl quinone (25)，1個為triterpenoid: lupeol (26)，2個為steroids: a mixture of β-sitosterol (27) and stigamasterol (28)。所有化合物之結構均經各種光譜分析或化學誘導，予以確認。 scopoletin (12), isobavachalcone (21) and (E)-1-[2,4-dihydroxy-3-(3-methyl- 2-butenyl)-phenyl]-3-(2,2-dimethyl-8-hydroxy-2H-benzopyran-6-yl)-2-propen-1- one (23)，對Mycobacterium tuberculosis H37Rv，呈現抑制作用，MICs值分別為: 42.1, 17.6, 30.0 μg/ mL。
並列摘要
Fatoua pilosa Gaud. (Moraceae) is a small perennial herb, which distributed in Taiwan, Philippine, Moluccas and New Guinea. In a series of studies on the active constituents of Formosan plants, the methanolic extract of the whole plant of this species showed antitubercular activity against Mycobacterium tuberculosis H37Rv in vitro. There are only three species of Fatoua in the world. The chemical constituents and bioactivities of Fatoua plants have never been conducted. The methanolic extract of whole plant of this species was partitioned into EtOAc and H2O-soluble fractions. Investigation of EtOAc-soluble fraction led to the isolation of six new coumarins: (+)-fatouain A (1), (-)-fatouain B (2), (+)-fatouain C (3), (-)-fatouain D (4), (+)-fatouain E (5), (-)-fatouain F (6) and four new bis-coumarins: (+)-fatouain G (7), (+)-fatouain H (8), fatouain I (9), fatouapilosin (10), along with eighteen known compounds, including three simple coumarins: umbelliferone (11), scopoletin (12), phellodenol-A (13), six furanocoumarins: psoralen (14), bergapten (15), S-(+)-marmesin (16), S-(+)-rutaretin methy1 ether (17), S-(+)-rutaretin (18), 2’,3’-dehydromarmesin (19), one pyranocoumarin: xanthyletin (20), three chaclones: isobavachalcone (21), kanzonol C (22), (E)-1-[2,4-dihydroxy-3-(3-methyl-2-butenyl)phenyl]-3-(2,2-di- methyl-8-hydroxy-2H-benzopyran-6-yl)-2-propen-1-one (23), one benzenoid: syringaldehyde (24), one quinone: α-tocopheryl quinone (25), one triterpenoid: lupeol (26), two steroids: a mixture of β-sitosterol (27) and stigamasterol (28). The structures of these compounds were elucidated by spectral analysis or by chemical derivation. Scopoletin (12), isobavachalcone (21) and (E)-1-[2,4-dihydroxy-3-(3-methyl- 2-butenyl)-phenyl]-3-(2,2-dimethyl-8-hydroxy-2H-benzopyran-6-yl)-2-propen-1- one (23) showed antituburcular acivity aganist Mycobacterium tuberculosis H37Rv in vitro with MIC values: 42.1, 17.6 and 30.0 μg/ mL, respectively.