Document Detail

Spiroacetal biosynthesis in insects from Diptera to Hymenoptera: the Giant Ichneumon wasp Megarhyssa nortoni nortoni Cresson.
MedLine Citation:
PMID:  18841963     Owner:  NLM     Status:  MEDLINE    
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 (2)H-labeled precursors and [(18)O]dioxygen. The key steps are postulated to be decarboxylation of beta-ketoacid equivalents, beta-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.
Brett D Schwartz; Christopher J Moore; Fredrik Rahm; Patricia Y Hayes; William Kitching; James J De Voss
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2008-10-09
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  130     ISSN:  1520-5126     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2008 Nov 
Date Detail:
Created Date:  2008-10-29     Completed Date:  2008-12-24     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  14853-60     Citation Subset:  IM    
Department of Chemistry, The University of Queensland, Brisbane, Australia.
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MeSH Terms
Acetals / isolation & purification,  metabolism*
Diptera / metabolism
Gas Chromatography-Mass Spectrometry
Hymenoptera / metabolism
Oxygen / metabolism
Spiro Compounds / isolation & purification,  metabolism*
Wasps / metabolism*
Reg. No./Substance:
0/Acetals; 0/Spiro Compounds; 7782-44-7/Oxygen

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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