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

Molecules

Geetha Gopalakrishnan¹  N. D. Pradeep Singh¹ 

[1] Centre for Natural Products, SPIC Science Foundation, Guindy, Chennai - 600 032, India

关键词: Photooxygenation;    tetranortriterpenoid;    singlet oxygen;    antifeedant;   

DOI  :  10.3390/70200112

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
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