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Spiroacetal biosynthesis in insects from diptera to hymenoptera: The Giant Ichneumon wasp Megarhyssa nortoni nortoni Cresson

Schwartz, B.D. and Moore, C.J. and Rahm, F. and Hayes, P.Y. and Kitching, W. and De Voss, J.J. (2008) Spiroacetal biosynthesis in insects from diptera to hymenoptera: The Giant Ichneumon wasp Megarhyssa nortoni nortoni Cresson. Journal of the American Chemical Society, 130 (44). pp. 14853-14860.

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Article Link(s): http://dx.doi.org/10.1021/ja8036433

Publisher URL: http://pubs.acs.org/about.html

Abstract

The volatile components of the mandibular gland secretion generated by the Giant Ichneumon parasitoid wasp Megarhyssa nortoni nortoni Cresson are mainly spiroacetals and methyl ketones, and all have an odd number of carbon atoms. A biosynthetic scheme rationalizing the formation of these diverse components is presented. This scheme is based on the results of incorporation studies using 2H-labeled precursors and [18O]dioxygen. The key steps are postulated to be decarboxylation of β-ketoacid equivalents, β-oxidation (chain shortening), and monooxygenase-mediated hydroxylation leading to a putative ketodiol that cyclizes to spiroacetals. The generality of the role of monooxygenases in spiroacetal formation in insects is considered, and overall, a cohesive, internally consistent theory of spiroacetal generation by insects is presented, against which future hypotheses will have to be compared.

Item Type:Article
Additional Information:© American Chemical Society.
Keywords:Megarhyssa nortoni nortoni Cresson; giant ichneumon wasp; biosynthesis; spiroacetal; methyl ketones.
Subjects:Science > Zoology > Invertebrates > Insects
Science > Physiology > Insect biochemistry
Deposited On:02 Feb 2009 06:01
Last Modified:18 Apr 2011 03:52

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