Isolation of six new flavonoids from Melicope triphylla.

Matsutake Higa, Megumi Imamura, Kanae Shimoji, Kazuhito Ogihara, Toshimasa Suzuka

College of Science, University of The Ryukyus, Nishihara, Okinawa 903-0213, Japan. matuhiga@sci.u-ryukyu.ac.jp

Chemical & pharmaceutical bulletin 2012

filter terms:

Six new flavonoids--5-hydroxy-3,8-dimethoxy-3',4':6,7-bismethylenedioxyflavone (1), 3,3',4',5-tetramethoxy-7-(3-methylbut-2-enyloxy)flavone (2), 7-(2-hydroxy-3-methylbut-3-enyloxy)-3,3',4',5-tetramethoxyflavone (3), 7-(2-hydroxy-3-methylbut-3-enyloxy)-3,5-dimethoxy-3',4'-methylenedioxyflavone (4), 7-(2-hydroxy-3-methylbut-3-enyloxy)-3,3',4',5,8-pentamethoxyflavone (5), and 7-(2-hydroxy-3-methylbut-3-enyloxy)-3,5,8-trimethoxy-3',4'-methylenedioxyflavone (6)--were isolated from the leaves of Melicope triphylla. In addition, six already known flavonoids were also detected: 5-hydroxy-3,6,7-trimethoxy-3',4'-methylenedioxyflavone (7), 5,7-dihydroxy-3,3',4',8-tetramethoxyflavone (8), 4',5-dihydroxy-3,3',7,8-tetramethoxyflavone (9), 3,5,6,7,8-pentamethoxy-3',4'-methylenedioxyflavone (10), 3,5,6,7-tetramethoxy-3',4'-methylenedioxyflavone (11), and 3,3',4',5,6,7,8-heptamethoxyflavone (12). The structures of the new compounds were established by spectroscopic methods. Compound 2 displayed ichthyotoxic activity against Japanese killifish (medaka in Japanese) (Oryzias latipes var.) at 10 ppm.

Citation

Matsutake Higa, Megumi Imamura, Kanae Shimoji, Kazuhito Ogihara, Toshimasa Suzuka. Isolation of six new flavonoids from Melicope triphylla. Chemical & pharmaceutical bulletin. 2012;60(9):1112-7