Skip navigation
Skip navigation

Spiroacetal Biosynthesis in Insects. From Diptera to Hymenoptera: A Giant Ichneumon Wasp: Megarhyssa nortoni nortoni Cresson

Schwartz, Brett; Moore, Christopher J; Rahm, Fredrik; Hayes, Patricia Y; Kitching, William; De Voss, James Joseph

Description

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 using2H-labeled precursors and [18O]dioxygen. The key steps are postulated to be decarboxylation of β-ketoacid...[Show more]

dc.contributor.authorSchwartz, Brett
dc.contributor.authorMoore, Christopher J
dc.contributor.authorRahm, Fredrik
dc.contributor.authorHayes, Patricia Y
dc.contributor.authorKitching, William
dc.contributor.authorDe Voss, James Joseph
dc.date.accessioned2015-12-07T22:40:53Z
dc.identifier.issn0002-7863
dc.identifier.urihttp://hdl.handle.net/1885/24057
dc.description.abstractThe 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 using2H-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.
dc.publisherAmerican Chemical Society
dc.sourceJournal of the American Chemical Society
dc.subjectKeywords: Biochemical engineering; Biochemistry; Carboxylation; Ketones; Carbon atoms; Chain shortenings; Dioxygen; Diptera; Mandibular glands; Methyl ketones; Monooxygenase; Monooxygenases; Odd numbers; Volatile components; Organic compounds; acetone; oxygen; unsp
dc.titleSpiroacetal Biosynthesis in Insects. From Diptera to Hymenoptera: A Giant Ichneumon Wasp: Megarhyssa nortoni nortoni Cresson
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume130
dc.date.issued2008
local.identifier.absfor030502 - Natural Products Chemistry
local.identifier.ariespublicationu4222028xPUB30
local.type.statusPublished Version
local.contributor.affiliationSchwartz, Brett, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationMoore, Christopher J, QLD Department of Primary Industries and Fisheries
local.contributor.affiliationRahm, Fredrik, University of Queensland
local.contributor.affiliationHayes, Patricia Y, University of Queensland
local.contributor.affiliationKitching, William, University of Queensland
local.contributor.affiliationDe Voss, James Joseph, University of Queensland
local.description.embargo2037-12-31
local.bibliographicCitation.issue44
local.bibliographicCitation.startpage14853
local.bibliographicCitation.lastpage14860
local.identifier.doi10.1021/ja8036433
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
dc.date.updated2016-02-24T10:46:12Z
local.identifier.scopusID2-s2.0-55549137430
CollectionsANU Research Publications

Download

File Description SizeFormat Image
01_Schwartz_Spiroacetal_Biosynthesis_in_2008.pdf197.55 kBAdobe PDF    Request a copy


Items in Open Research are protected by copyright, with all rights reserved, unless otherwise indicated.

Updated:  22 January 2019/ Responsible Officer:  University Librarian/ Page Contact:  Library Systems & Web Coordinator