Studies on the chemical constituents and biological activities from the stem and leaves of Beilschmiedia tsangii

• Main Authors: En-tzu Chou, 周恩慈
• Other Authors: Jih-Jung Chen
• Format: Others
• Language: zh-TW
• Published: 2006
• Online Access: http://ndltd.ncl.edu.tw/handle/33044322881364055640

碩士 === 大仁科技大學 === 製藥科技研究所 === 94 === Abstract Beilschmiedia tsangii Merr. (Lauraceae)1) is an evergreen tree, distributed in forests at low altitudes throughout southern Taiwan. Andiandric acids7), aporphine alkaloids4), bisbenzylisoquinoline alkaloids6), and arylpropanoids are widely distributed in plants of the genus Beilschmiedia. Some isolates exhibit biological activities, including antibacterial7) and antimalarial6) properties. However, the chemical constituents and biological activities of this plant have never been studied. Approximately 1000 species of Formosan plants have been screened for cytotoxicity, and B. tsangii was shown to be one of the active species. Investigation of CHCl3-soluble fraction of the stem of B. tsangii has led to the isolation of two new tetrahydrofuran-type lignans, beilschmin A (1) and beilschmin B (2), two new dihydrofuran-type lignan, beilschmin C (3) and beilschmin D (4), two new 1-phenylbutyl benzoates, tsangin A (5) and tsangin B (6), together with thirteen known compounds, including a tetrahydrofuran-type lignan, rel-(7S,8S,7’R,8’R)- 3,3’,4,4’,5,5’-hexamethoxylignan (7), seven steroids, β-sitosterol (8), β-sitostenone (9), 6α-hydroxystigmast-4-en-3-one (10), 6β-hydroxystigmast-4-en-3-one (11), 3β-hydroxystigmast-5-en-7-one (12), stigmast-4-en-3,6-dione (13) and ergosta-4,6,8(14),22-tetraen-3-one (14), a sesquiterpenoid, 2,6,11-tri- methyldodeca-2,6,10-triene (15), two benzaldehydes, vanillin (16) and 4-hydroxybenzaldehyde (17), a benzoquinone, α-tocopheryl quinone (18), and α-tocospiro B (19). In addition, investigation on the CHCl3-soluble fraction of the leaves of B. tsangii has led to the isolation of two new tetrahydrofuran-type lignans, beilschmin A (1) and beilschmin B (2), together with seven known compounds, including a tetrahydroxyfuran-type lignan, rel-(7S,8S,7’R,- 8’R)-3,3’,4,4’,5,5’-hexamethoxylignan (7), two steroids, β-sitosterol (8) and β-sitostenone (9), a benzoquinone, α-tocopheryl quinone (18), a triterpenoid, squalene (20), a tocopherone, α-tocopherol trimer B (21) and a aliphatic ester derivative, methyl linoleate (22). The structures of these new compounds were determined through spectral analyses. Among the isolates, compounds 1-3, 5, 6, 15, 18 and 19 exhibited cytotoxicities (IC50 values < 4 μg/mL) against P-388 and/or HT-29 cell lines in vitro. Compounds 1 and 2 also showed significant antitubercular activities in vitro (MIC = 2.5 and 7.5 μg/mL, respectively).