N-(17-acyloxy-acyl)-glutamines:: Novel surfactants from oral secretions of lepidopteran larvae

被引：24

作者：

Spiteller, D ^{[1
]}

Boland, W ^{[1
]}

机构：

[1] Max Planck Inst Chem Ecol, Dept Bioorgan Chem, D-07745 Jena, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 23期

关键词：

D O I：

10.1021/jo0342525

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-(17-Acyloxy-acyl)-glutamine conjugates such as N-(17-linolenoyloxy-linolenoyl)-glutamine (6), N-(17-linolenoyloxy-linoleoyl)-glutamine (7), N-(17-linoleoyloxy-linolenoyl)-glutamine (8), and N-(17-linoleoyloxy-linoleoyl)-glutamine (9) were identified as novel surfactants in the oral secretion of several lepidopteran larvae (S. exigua, S. littoralis, S. frugiperda, and H. virescens) by LC-MS/MS and chemical degradation. Authentic reference compounds were synthesized via a dissymmetric bis-Wittig approach and confirmed the assigned structures.

引用

页码：8743 / 8749

页数：7

共 25 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]

ASSELINEAU J, 1991, PROGR CHEM ORGANIC N, P1

[3] CYCLOPENTENE AND CYCLOHEXENE ANNULATION VIA COPPER-CATALYZED CONJUGATE ADDITION OF ACETAL-CONTAINING GRIGNARD-REAGENTS [J].

BAL, SA ;

MARFAT, A ;

HELQUIST, P .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (26) :5045-5050

[4]

BERGOMAZ R, 1986, Journal of the Lepidopterists' Society, V40, P131

[5] STRUCTURE OF EMULSIFYING SUBSTANCES IN SEVERAL INVERTEBRATES [J].

COLLATZ, KG ;

MOMMSEN, T .

JOURNAL OF COMPARATIVE PHYSIOLOGY, 1974, 94 (04) :339-352

[6]

Costa JT, 2001, ANN ENTOMOL SOC AM, V94, P480, DOI 10.1603/0013-8746(2001)094[0480:GFATFB]2.0.CO

[7]

[8] An herbivore elicitor activates the gene for indole emission in maize [J].

Frey, M ;

Stettner, C ;

Paré, PW ;

Schmelz, EA ;

Tumlinson, JH ;

Gierl, A .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2000, 97 (26) :14801-14806

[9] 2-(TRIMETHYLSILYL)ETHYL ESTERS AS CARBOXYL PROTECTING GROUP - APPLICATION IN SYNTHESIS OF (-)-(S)-CURVULARIN [J].

GERLACH, H .

HELVETICA CHIMICA ACTA, 1977, 60 (08) :3039-3044

[10] NOVEL HYDROXYICOSATETRAENOIC AND HYDROXYICOSAPENTAENOIC ACIDS AND A 13-OXO ANALOG - ISOLATION FROM A MIXTURE OF THE CALCAREOUS RED ALGAE LITHOTHAMNION-CORALLIOIDES AND LITHOTHAMNION-CALCAREUM OF BRITTANY WATERS [J].

GUERRIERO, A ;

DAMBROSIO, M ;

PIETRA, F .

HELVETICA CHIMICA ACTA, 1990, 73 (08) :2183-2189

← 1 2 3 →