Literature DB >> 11607437

Sex pheromone for the brownbanded cockroach is an unusual dialkyl-substituted alpha-pyrone.

R E Charlton1, F X Webster, A Zhang, C Schal, D Liang, I Sreng, W L Roelofs.   

Abstract

Female brownbanded cockroaches, Supella longipalpa, emit a sex pheromone that attracts males from a distance. This pheromone was isolated and identified as 5-(2,4-dimethylheptanyl)-3-methyl-2H-pyran-2-one (which we refer to as supellapyrone), and its structure was confirmed by synthesis. A racemic blend of the synthetic compound elicited behavioral and electrophysiological responses comparable to the natural pheromone across a range of doses. This compound is not only a very different type of cockroach pheromone but also makes up an additional class of natural products--namely, 3,5-dialkyl-substituted alpha-pyrones.

Entities:  

Year:  1993        PMID: 11607437      PMCID: PMC47742          DOI: 10.1073/pnas.90.21.10202

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN: 0027-8424            Impact factor:   11.205


  13 in total

1.  Behavioral and electrophysiological evidence for volatile sex pheromones in Parcoblatta wood cockroaches.

Authors:  César Gemeno; Kirsten Snook; Nicole Benda; Coby Schal
Journal:  J Chem Ecol       Date:  2003-01       Impact factor: 2.626

2.  Unusual macrocyclic lactone sex pheromone of Parcoblatta lata, a primary food source of the endangered red-cockaded woodpecker.

Authors:  Dorit Eliyahu; Satoshi Nojima; Richard G Santangelo; Shannon Carpenter; Francis X Webster; David J Kiemle; Cesar Gemeno; Walter S Leal; Coby Schal
Journal:  Proc Natl Acad Sci U S A       Date:  2011-12-19       Impact factor: 11.205

Review 3.  Chemistry of sex attraction.

Authors:  W L Roelofs
Journal:  Proc Natl Acad Sci U S A       Date:  1995-01-03       Impact factor: 11.205

4.  Application of chiral gas chromatography with electroantennographic detection to the determination of the stereochemistry of a cockroach sex pheromone.

Authors:  W S Leal; X Shi; D Liang; C Schal; J Meinwald
Journal:  Proc Natl Acad Sci U S A       Date:  1995-02-14       Impact factor: 11.205

5.  New contact sex pheromone components of the German cockroach, Blattella germanica, predicted from the proposed biosynthetic pathway.

Authors:  Dorit Eliyahu; Satoshi Nojima; Kenji Mori; Coby Schal
Journal:  J Chem Ecol       Date:  2008-01-23       Impact factor: 2.626

6.  Behavioral and electrophysiological responses of the brownbanded cockroach, Supella longipalpa, to stereoisomers of its sex pheromone, supellapyrone.

Authors:  César Gemeno; Walter S Leal; Kenji Mori; Coby Schal
Journal:  J Chem Ecol       Date:  2003-08       Impact factor: 2.626

7.  Identification of cuticular lipids eliciting interspecific courtship in the German cockroach, Blattella germanica.

Authors:  Dorit Eliyahu; Satoshi Nojima; Sonja S Capracotta; Daniel L Comins; Coby Schal
Journal:  Naturwissenschaften       Date:  2008-01-09

8.  Male sex pheromone of cockroachEurycotis floridana (walker) (Blattidae, Polyzosteriinae): Role and composition of tergites 2 and 8 secretions.

Authors:  J P Farine; J L Le Quere; J Duffy; C Everaerts; R Brossut
Journal:  J Chem Ecol       Date:  1994-09       Impact factor: 2.626

9.  The male abdominal glands of Leucophaea maderae: chemical identification of the volatile secretion and sex pheromone function.

Authors:  Jean-Pierre Farine; Daniel Sirugue; Dehbia Abed-Vieillard; Claude Everaerts; Jean-Luc Le Quéré; Odile Bonnard; Remy Brossut
Journal:  J Chem Ecol       Date:  2007-01-03       Impact factor: 2.793

Review 10.  Stereochemical studies on pheromonal communications.

Authors:  Kenji Mori
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2014       Impact factor: 3.493

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