Sekizaki H, Yokosawa R, Chinen C, Adachi H, Yamane Y
Faculty of Pharmaceutical Sciences, Higashi Nippon Gakuen University, Hokkaido, Japan.
Biol Pharm Bull. 1993 Jul;16(7):698-701. doi: 10.1248/bpb.16.698.
Nineteen isoflavones were synthesized and their attracting activity to Aphanomyces euteiches zoospore were investigated. Isoflavones (1, 2, 4, 16 and 19) with an unsubstituted B ring were synthesized by the oxidation of corresponding 2'-hydroxychalcones with thallium (III) nitrate trihydrate in methanolic perchloric acid. A hydroxyl group at the C-5 position in isoflavones was necessary for strong attraction to A. euteiches zoospore. The introduction of an additional hydroxyl group at the C-7 or C-4' position strengthened the attracting activity. Moreover, the methylation of the C-7 hydroxyl group strengthened the attracting activity, but the methylation of the C-4' hydroxyl group slightly weakened it. The naturally occurring isoflavones (9 and 10), which were reported to possess estrogen activity, showed moderate attracting activity.
合成了19种异黄酮，并研究了它们对大豆疫霉游动孢子的吸引活性。通过在甲醇高氯酸中用三水硝酸铊（III）氧化相应的2'-羟基查耳酮，合成了具有未取代B环的异黄酮（1、2、4、16和19）。异黄酮C-5位的羟基对于对大豆疫霉游动孢子的强吸引力是必需的。在C-7或C-4'位引入额外的羟基增强了吸引活性。此外，C-7羟基的甲基化增强了吸引活性，但C-4'羟基的甲基化使其略有减弱。据报道具有雌激素活性的天然存在的异黄酮（9和10）表现出中等的吸引活性。
