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Molecules 2001, 6(6), 551-556; doi:10.3390/60600551
Article

Photomediated Transformation of Salannin, 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: 6 December 2000 / Revised: 11 May 2001 / Accepted: 14 May 2001 / Published: 31 May 2001
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Abstract

Photolysis of Salannin (1), an important bioactive compound from Azadirachta indica A.Juss (Neem), affords Δ17-isosalanninolide (2), a hitherto unknown compound, along with isosalanninolide (3) and salanninolide (4). A probable mechanism has been suggested. While the mechanism of formation of 2 involves both a [4+2] cycloaddition and a [1,3] sigmatropic shift in the furan and D-rings, respectively, formation of 3 and 4 involves the decomposition of an ozonoide-like peroxide intermediate.
Keywords: Azadirachta indica; Salannin; cycloaddition; sigmatropic shift; antifeedant Azadirachta indica; Salannin; cycloaddition; sigmatropic shift; antifeedant
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Gopalakrishnan, G.; Pradeep Singh, N.D.; Kasinath, V. Photomediated Transformation of Salannin, a Tetranortriterpenoid from Azadirachta indica A. Juss. Molecules 2001, 6, 551-556.

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