Effect of the azetidine and azocine rings of okaramine B on insecticidal activity.
Four degraded okaramine B (2) products, 4',5'-dihydrookaramine B (3), two azetidine ring-opened compounds (4 and 5) and 1',2',4',5'-tetrahydrookaramine B (6), were prepared and their insecticidal activity was examined. Neither compounds 4 nor 5 showed such activity against silkworms, indicating that the azetidine ring moiety played an important role in the insecticidal activity. Moreover, both compounds 3 and 6 exhibited lower activity than 2, which means that the azocine ring moiety was indispensable to form the active conformation.
Shiono
Y
Y
Department of Applied Biological Chemistry, College of Agriculture, Osaka Prefecture University, Sakai, Japan.
Akiyama
K
K
Hayashi
H
H
D000470:Alkaloids / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D001384:Azetidines / Q000737:chemistry / Q000494:pharmacology*; D001392:Azocines / Q000737:chemistry / Q000494:pharmacology*; D012831:Bombyx / Q000187:drug effects; D026121:Indole Alkaloids; D007306:Insecticides / Q000737:chemistry / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D015394:Molecular Structure; D010407:Penicillium / Q000737:chemistry
D000470:Alkaloids; D001384:Azetidines; D001392:Azocines; D026121:Indole Alkaloids; D007306:Insecticides; C416703:okaramine B