Biological activity of (3 R,5 S,6 R)- and (3 S,5 R,6 S)-3,5-dimethyl-6-(methylethyl)-3,4,5,6-tetrahydropyran-2-one, a pheromone of Macrocentrus grandii (Goidanich) (Hymenoptera

Braconidae)

Paul D. Swedenborg, Richard L. Jones, Hui Qiang Zhou, Injae Shin, Hung Wen Liu

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

In a previous study we reported identification of (3 R*,5 S*,6 R*)-3,5-dimethyl-6-(methylethyl)-3,4,5,6-tetrahydropyran-2-one as a component of the pheromone of Macrocentrus grandii Goidanich. The lactone was present in male and female wasps, and laboratory and field bioassays demonstrated that both sources of the lactone elicit flight initiation, upwind anemotaxis, and casting in male wasps. In the present study, the synthetic (3 R,5 S,6 R)- and (3 S,5 R,6 S)-lactone enantiomers (RSR and SRS, respectively) were bioassayed for biological activity. In wind tunnel studies the SRS enantiomer elicited flight initiation, upwind anemotaxis, and casting by male wasps comparable to lactone derived from male and female wasps. Flight response to the RSR enantiomer averaged 14 percent of the SRS enantiomer. No specific ratio of the stereoisomers was found more attractive than the SRS enantiomer alone. Field studies demonstrated the SRS enantiomer was active alone in attracting male wasps. When paired with (Z)-4-tridecenal (a previously identified female-derived sex pheromone), the SRS enantiomer yielded a synergistic response comparable to (Z)-4-tridecenal plus female-derived lactone.

Original languageEnglish
Pages (from-to)3373-3380
Number of pages8
JournalJournal of Chemical Ecology
Volume20
Issue number12
DOIs
Publication statusPublished - 1994 Dec 1

Fingerprint

Macrocentrus grandii
Wasps
Hymenoptera
Enantiomers
Pheromones
enantiomers
Lactones
Braconidae
Bioactivity
pheromone
wasp
pheromones
bioactive properties
lactones
flight
Sex Attractants
Stereoisomerism
Casting
sex pheromone
wind tunnel

All Science Journal Classification (ASJC) codes

  • Ecology, Evolution, Behavior and Systematics
  • Biochemistry

Cite this

@article{780ad18626804e6384391d8596959a7a,
title = "Biological activity of (3 R,5 S,6 R)- and (3 S,5 R,6 S)-3,5-dimethyl-6-(methylethyl)-3,4,5,6-tetrahydropyran-2-one, a pheromone of Macrocentrus grandii (Goidanich) (Hymenoptera: Braconidae)",
abstract = "In a previous study we reported identification of (3 R*,5 S*,6 R*)-3,5-dimethyl-6-(methylethyl)-3,4,5,6-tetrahydropyran-2-one as a component of the pheromone of Macrocentrus grandii Goidanich. The lactone was present in male and female wasps, and laboratory and field bioassays demonstrated that both sources of the lactone elicit flight initiation, upwind anemotaxis, and casting in male wasps. In the present study, the synthetic (3 R,5 S,6 R)- and (3 S,5 R,6 S)-lactone enantiomers (RSR and SRS, respectively) were bioassayed for biological activity. In wind tunnel studies the SRS enantiomer elicited flight initiation, upwind anemotaxis, and casting by male wasps comparable to lactone derived from male and female wasps. Flight response to the RSR enantiomer averaged 14 percent of the SRS enantiomer. No specific ratio of the stereoisomers was found more attractive than the SRS enantiomer alone. Field studies demonstrated the SRS enantiomer was active alone in attracting male wasps. When paired with (Z)-4-tridecenal (a previously identified female-derived sex pheromone), the SRS enantiomer yielded a synergistic response comparable to (Z)-4-tridecenal plus female-derived lactone.",
author = "Swedenborg, {Paul D.} and Jones, {Richard L.} and Zhou, {Hui Qiang} and Injae Shin and Liu, {Hung Wen}",
year = "1994",
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Biological activity of (3 R,5 S,6 R)- and (3 S,5 R,6 S)-3,5-dimethyl-6-(methylethyl)-3,4,5,6-tetrahydropyran-2-one, a pheromone of Macrocentrus grandii (Goidanich) (Hymenoptera : Braconidae). / Swedenborg, Paul D.; Jones, Richard L.; Zhou, Hui Qiang; Shin, Injae; Liu, Hung Wen.

In: Journal of Chemical Ecology, Vol. 20, No. 12, 01.12.1994, p. 3373-3380.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Biological activity of (3 R,5 S,6 R)- and (3 S,5 R,6 S)-3,5-dimethyl-6-(methylethyl)-3,4,5,6-tetrahydropyran-2-one, a pheromone of Macrocentrus grandii (Goidanich) (Hymenoptera

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AU - Swedenborg, Paul D.

AU - Jones, Richard L.

AU - Zhou, Hui Qiang

AU - Shin, Injae

AU - Liu, Hung Wen

PY - 1994/12/1

Y1 - 1994/12/1

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AB - In a previous study we reported identification of (3 R*,5 S*,6 R*)-3,5-dimethyl-6-(methylethyl)-3,4,5,6-tetrahydropyran-2-one as a component of the pheromone of Macrocentrus grandii Goidanich. The lactone was present in male and female wasps, and laboratory and field bioassays demonstrated that both sources of the lactone elicit flight initiation, upwind anemotaxis, and casting in male wasps. In the present study, the synthetic (3 R,5 S,6 R)- and (3 S,5 R,6 S)-lactone enantiomers (RSR and SRS, respectively) were bioassayed for biological activity. In wind tunnel studies the SRS enantiomer elicited flight initiation, upwind anemotaxis, and casting by male wasps comparable to lactone derived from male and female wasps. Flight response to the RSR enantiomer averaged 14 percent of the SRS enantiomer. No specific ratio of the stereoisomers was found more attractive than the SRS enantiomer alone. Field studies demonstrated the SRS enantiomer was active alone in attracting male wasps. When paired with (Z)-4-tridecenal (a previously identified female-derived sex pheromone), the SRS enantiomer yielded a synergistic response comparable to (Z)-4-tridecenal plus female-derived lactone.

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