A heterocyclic oxime from a fungus with anti-juvenile hormone activity

✍ Scribed by Manuela Castillo; Pilar Moya; Franck Couillaud; María Dolores Garcerá; Rafael Martínez-Pardo

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 129 KB
• Volume: 37
• Category: Article
• ISSN: 0739-4462
• DOI: 10.1002/(sici)1520-6327(1998)37:4<287::aid-arch4>3.0.co;2-o

✦ Synopsis

Two fractions obtained after chromatography of dichloromethane extract of Penicillium brevicompactum culture medium showed anti-juvenile hormone activity. One was active when assayed in vivo against Oncopeltus fasciatus third-instar nymphs, whereas the other showed a strong in vitro inhibition of JH III biosynthesis on Locusta migratoria corpora allata. A subfraction of the latter, constituting 97% of this fraction, is a main component that possessed the juvenile hormone biosynthesis inhibitory activity. Chemical characterization of this compound shows a sesquiterpene-like structure, molecular mass of 278.16185 daltons, corresponding to an empirical formula of C 15 H 22 N 2 O 3 named brevioxime. Evidence suggests that the final steps of JH III biosynthesis are the target of the active compound. Its effects may be compared with those of a known inhibitor of P-450-linked epoxidase, KK-42 (1-benzyl-5-[(E)-2,6-dimethyl-1,5-heptadienyl]imidazole), whose effects on L. migratoria corpora allata are also reported here for the first time. Arch.