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Photooxygenation of Nimonol, a Tetranortriterpenoid from Azadirachta indica. A. Juss.

Author(s): Geetha Gopalakrishnan | N. D. Pradeep Singh | V. Kasinath

Journal: Molecules ISSN 1420-3049
Volume: 7; Issue: 2; Start page: 112; Date: 2002;
Original page

Keywords: Photooxygenation | tetranortriterpenoid | singlet oxygen | antifeedant

ABSTRACT
Nimonol (1), a tetranortriterpenoid isolated from the leaves of Azadirachta indica A. Juss (Meliaceae), upon photolysis undergoes both Diels-Alder and ene reactions with singlet oxygen at different sites leading to 14,15,20,21-diepoxy-23-nimonolactone (3), along with nimonolide (4), which have been well-characterised. The novelty of the reported reactions lies in hitherto unreported formation of an α-epoxide in the ring D in tetranortriterpenoids. The photoproduct 4 exhibited antifeedancy comparable to that of azadirachtin-A, the most potent antifeedant constituent isolated from neem.