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Molecules 2002, 7(2), 112-118; doi:10.3390/70200112

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

* ,  and
Centre for Natural Products, SPIC Science Foundation, Guindy, Chennai - 600 032, India
* Author to whom correspondence should be addressed.
Received: 21 May 2001 / Revised: 19 December 2001 / Accepted: 21 December 2001 / Published: 28 February 2002
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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.
Keywords: Photooxygenation; tetranortriterpenoid; singlet oxygen; antifeedant Photooxygenation; tetranortriterpenoid; singlet oxygen; antifeedant
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Gopalakrishnan, G.; Pradeep Singh, N.D.; Kasinath, V. Photooxygenation of Nimonol, a Tetranortriterpenoid from Azadirachta indica. A. Juss.. Molecules 2002, 7, 112-118.

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