Absolute configuration of volicitin, an elicitor of plant volatile biosynthesis from lepidopteran larvae

被引：54

作者：

Spiteller, D ^{[1
]}

Pohnert, G ^{[1
]}

Boland, W ^{[1
]}

机构：

[1] Max Planck Inst Chem Okol, D-07745 Jena, Germany

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 08期

关键词：

fatty acid amides; N-17-hydroxy-linolenoyl-L-glutamine; 1-phenyl-ethylisocyanate; stereochemistry;

D O I：

10.1016/S0040-4039(00)02290-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The absolute configuration of the hydroxylinolenoyl moiety of volicitin (17-hydroxylinolenoyl-L-glutamine) 1a/b from four lepidopteran larvae was determined by methanolysis and derivatisation of the resulting ester with (1R)-1 -phenyl-ethylisocyanate 3. The absolute configuration of the resulting (1'R)-17-(1'-phenyl-ethylcarbamoyloxy)-methyl linolenoates 4a/b followed from GLC comparison with synthetic references. Natural volicitin 1 from caterpillars of Spodoptera exigua, S. frugiperda, S. littoralis and Heliothis virescens (Noctuidae) exhibits a high ee (92-96%) and has a 17S configuration. (C) 2001 Elsevier Science Ltd. All rights reserved.

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页码：1483 / 1485

页数：3

相关论文

共 10 条

[1] An elicitor of plant volatiles from beet armyworm oral secretion [J].

Alborn, HT ;

Turlings, TCJ ;

Jones, TH ;

Stenhagen, G ;

Loughrin, JH ;

Tumlinson, JH .

SCIENCE, 1997, 276 (5314) :945-949

[2]

BJORKHEM I, 1971, J BIOL CHEM, V246, P7417

[3] JASMONIC ACID AND CORONATIN INDUCE ODOR PRODUCTION IN PLANTS [J].

BOLAND, W ;

HOPKE, J ;

DONATH, J ;

NUSKE, J ;

BUBLITZ, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (15) :1600-1602

[4] Coronatine, a bacterial phytotoxin, acts as a stereospecific analog of jasmonate type signals in tomato cells and potato tissues [J].

Greulich, F ;

Yoshihara, T ;

Ichihara, A .

JOURNAL OF PLANT PHYSIOLOGY, 1995, 147 (3-4) :359-366

[5] Induction of volatile biosynthesis in the Lima bean (Phaseolus lunatus) by leucine- and isoleucine conjugates of 1-oxo- and 1-hydroxyindan-4-carboxylic acid: Evidence for amino acid conjugates of jasmonic acid as intermediates in the octadecanoid signalling pathway [J].

Krumm, T ;

Bandemer, K ;

Boland, W .

FEBS LETTERS, 1995, 377 (03) :523-529

[6] Concerted biosynthesis of an insect elicitor of plant volatiles [J].

Paré, PW ;

Alborn, HT ;

Tumlinson, JH .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (23) :13971-13975

[7]

Pohnert G, 2000, EUR J ORG CHEM, V2000, P1821

[8] Synthesis of volicitin: a novel three-component Wittig approach to chiral 17-hydroxylinolenic acid [J].

Pohnert, G ;

Koch, T ;

Boland, W .

CHEMICAL COMMUNICATIONS, 1999, (12) :1087-1088

[9] Gut bacteria may be involved in interactions between plants, herbivores and their predators:: Microbial biosynthesis of N-acylglutamine surfactants as elicitors of plant volatiles [J].

Spiteller, D ;

Dettner, K ;

Boland, W .

BIOLOGICAL CHEMISTRY, 2000, 381 (08) :755-762

[10] Chiral silylation reagents for the determination of absolute configuration by NMR spectroscopy [J].

Weibel, DB ;

Walker, TR ;

Schroeder, FC ;

Meinwald, J .

ORGANIC LETTERS, 2000, 2 (15) :2381-2383