Chemical Constituents and Cytotoxic Activities from the Stem of Maackia taiwanensis

Autor: Chi-Yun Lee, 李綺紜
Druh dokumentu: 學位論文 ; thesis
Popis: 96
Maackia taiwanensis Hoshi & Ohashi (Leguminosae) is a deciduous tree, endemic in Taiwan, up to 10 m high with greenish brown branchlets,distributed in Yangmingshan National Park and recently also found in Pingtung County. It has another common name, “Taiwan Dao-Huai”. The MeOH extract of the stem of this plant has shown cytotoxicity on high-throughput screening against MCF-7 cancer cell line and was partitioned into EtOAc, n-BuOH and H2O-soluble layers. The EtOAc-soluble layer showed cytotoxicity against MCF-7, NCI-H460 and SF-268 cancer cell lines. Investigation of the active EtOAc-soluble layer by column chromatography has led to the isolation of fifty compounds, including thirty-six flavonoids: (-)-maackicarpin (1), (-)-O-3’-secomaackicarpin (2), (-)-3-hydroxy-2,9-dimethoxypterocarpan (3), (-)-medicarpin (4), (-)-secundiflorol I (5), (-)-3,9-dihydroxypterocarpan (6), (-)-vesticarpan (7), (-)-2-hydroxymaackiain (8), (-)-maackiain (9), (-)-isoneorautenol (10), (-)-11b-hydroxy-11b,l-dihydromedicarpin (11), 2’,4’-dihydroxychalcone (12), isoliquiritigenin (13), (+)-ferreirin (14), (-)-4’,5,7-trihydroxyisoflavanone (15), 2’,4’-dihydroxy- dihydrochalcone (16), ?v?y?w?{??,2'',4''-trihydroxy-4-methoxydihydrochalcone (17), (+?y)-1-(2,4-dihydroxyphenyl)-3-hydroxy-3-(4’-hydroxyphenyl)-1-propanone (18), (+)-7-methoxyflavan-3,4-diol (19), (-)-trans-3-hydroxy-7-methoxy- flavanone (20), (-)-isobavachin (21), (-)-5-hydroxysophoranone (22), (+)-7-O-methylvestitol (23), (+)-4’-hydroxy-7-methoxyisoflavan (24), (-)- liquiritigenin (25), warangalone (26), osajin (27), formononetin (28), genistein (29), 8-???z???{dimethylallydaidzein (30), orobol (31), 2’,4’,7-trihydroxyisoflavone (32), 3’,4’,7-trihydroxyisoflavone (33), 3’-hydroxyformononetin (34), biochanin A (35) and 2’-hydroxyformonetin (36); seven benzenoids: trans-methyl ferulate (37), methyl 3-(3,4-dimethoxyphenyl)propenoate (38), methyl 3-(3,4,5-trimethoxyphenyl)acrylate (39), 4-hydroxybenzaldehyde (40), 4-hydroxybenzoic acid (41), vanillin (42) and syringaldehyde (43); three terpenoids: lupeol (44), a mixture of (24R)-6??-hydroxystigmasta-4-en-3-one (47) and (22E,24S)-6??-hydroxystigmasta-4,22-dien-3-one (48); two steroids: a mixture of ??-sitosterol (45) and stigmasterol (46); two lignan: (?b)-syringaresinol (49) and (-)-balanophonin (50). The structures of these compounds were elucidated by spectral analysis. Among the isolates, compounds 1 and 2 are new compounds. Compounds 1, 9, 26 and 27 showed cytotoxicities against MCF-7 cancer cell lines at 50μM；compounds 1, 2, 3, 4, 6, 7, 8, 9, 12, 13, 24, 26, 27 and 29 showed cytotoxicities against NCI-H460 cancer cell lines at 50μM；compounds 1 and 13 whatever at 10μM or 50μM both showed cytotoxicities against NCI-H460 cancer cell lines；compounds 1, 2, 3, 4, 6, 9, 12, 13, 26 and 27 showed cytotoxicities against SF-268 cancer cell lines at 50μM. Accroding to the above results, compounds 1, 9, 26 and 27 showed cytotoxicities against MCF-7,NCI-H460 and SF-268 cancer cell lines at 50μM. According to these data, compounds 1, 4, 12, 13, 27 show marginal cytotoxic activity against NCI-H460 and SF-268 cell lines.
Databáze: Networked Digital Library of Theses & Dissertations
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