Studies on zoospore attracting activity. II. Synthesis of isoflavones and their attracting activity to Aphanomyces euteiches zoospore.
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.
Sekizaki
H
H
Faculty of Pharmaceutical Sciences, Higashi Nippon Gakuen University, Hokkaido, Japan.
Yokosawa
R
R
Chinen
C
C
Adachi
H
H
Yamane
Y
Y
D002599:Chalcone / Q000737:chemistry*; D007529:Isoflavones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008745:Methylation; D009868:Oomycetes / Q000187:drug effects* / Q000502:physiology; D010084:Oxidation-Reduction; D013172:Spores, Fungal / Q000187:drug effects / Q000502:physiology
D007529:Isoflavones; D002599:Chalcone