N-(15,16-Dihydroxylinoleoyl)-glutamine and N-(15,16-epoxylinoleoyl)-glutamine isolated from oral secretions of lepidopteran larvae

N-(15,16-Dihydroxylinoleoyl)-glutamine ( 1 ) and N-(15,16-epoxylinoleoyl)-glutamine ( 2 ) and were identified in the regurgitant of lepidopteran larvae ( Spodoptera exigua and Spodoptera frugiperda) by LC–MS. After methanolysis and derivatisation with MSTFA, the positions of the hydroxy groups of 1...

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Bibliographic Details
Published inTetrahedron Vol. 59; no. 2; pp. 135 - 139
Main Authors Spiteller, Dieter, Boland, Wilhelm
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 06.01.2003
Elsevier
Subjects
15,16-dihydroxylinoleate
15,16-epoxylinoleate
Chemistry
Chemistry, Organic
N-(15,16-dihydroxylinoleoyl)-glutamine
N-(15,16-epoxylinoleoyl)-glutamine
Physical Sciences
Science & Technology
Spodoptera exigua
15,16-epoxylinoleate
N-(15,16-dihydroxylinoleoyl)-glutamine
N-(15,16-epoxylinoleoyl)-glutamine
15,16-dihydroxylinoleate
Spodoptera exigua
ELICITOR
CYTOCHROME-P450
PLANT VOLATILES
HYDROXYLATION
EPOXIDATION
N-(15, 16-dihydroxylinoleoyl)-glutamine
BIOSYNTHESIS
POLYUNSATURATED FATTY-ACIDS
N-(5,16-epoxylinoleoyl)-glutamine
EPOXYEICOSATRIENOIC ACIDS
AMIDES
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Summary:N-(15,16-Dihydroxylinoleoyl)-glutamine ( 1 ) and N-(15,16-epoxylinoleoyl)-glutamine ( 2 ) and were identified in the regurgitant of lepidopteran larvae ( Spodoptera exigua and Spodoptera frugiperda) by LC–MS. After methanolysis and derivatisation with MSTFA, the positions of the hydroxy groups of 1 were identified by GC–MS. The structures of both conjugates were confirmed by synthesis. The N-acyl glutamines 1 and 2 were isolated from the regurgitant of the lepidopteran larvae Spodoptera exigua and Spodoptera frugiperda. The structures were confirmed by synthesis.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)01489-8