| Spiroacetal biosynthesis in insects from Diptera to Hymenoptera: the Giant Ichneumon wasp Megarhyssa nortoni nortoni Cresson. | |
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MedLine Citation:
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PMID: 18841963 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Brett D Schwartz; Christopher J Moore; Fredrik Rahm; Patricia Y Hayes; William Kitching; James J De Voss |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2008-10-09 |
Journal Detail:
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Title: Journal of the American Chemical Society Volume: 130 ISSN: 1520-5126 ISO Abbreviation: J. Am. Chem. Soc. Publication Date: 2008 Nov |
Date Detail:
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Created Date: 2008-10-29 Completed Date: 2008-12-24 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 7503056 Medline TA: J Am Chem Soc Country: United States |
Other Details:
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Languages: eng Pagination: 14853-60 Citation Subset: IM |
Affiliation:
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Department of Chemistry, The University of Queensland, Brisbane, Australia. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Acetals
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isolation & purification,
metabolism* Animals Diptera / metabolism Female Gas Chromatography-Mass Spectrometry Hymenoptera / metabolism Oxygen / metabolism Spiro Compounds / isolation & purification, metabolism* Wasps / metabolism* |
| Chemical | |
Reg. No./Substance:
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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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