Effect of the azetidine and azocine rings of okaramine B on insecticidal activity

Biosci Biotechnol Biochem. 2000 Jul;64(7):1519-21. doi: 10.1271/bbb.64.1519.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / pharmacology*
  • Animals
  • Azetidines / chemistry
  • Azetidines / pharmacology*
  • Azocines / chemistry
  • Azocines / pharmacology*
  • Bombyx / drug effects
  • Indole Alkaloids
  • Insecticides / chemistry
  • Insecticides / pharmacology*
  • Magnetic Resonance Spectroscopy / methods
  • Molecular Structure
  • Penicillium / chemistry

Substances

  • Alkaloids
  • Azetidines
  • Azocines
  • Indole Alkaloids
  • Insecticides
  • okaramine B