Identification of epoxyhenicosadiene and novel diepoxy derivatives as sex pheromone components of the clear-winged tussock moth Perina nuda

Four EAG-active components (A-D) were found in the solvent extract of virgin females of the clear-winged tussock moth, Perina nuda. The most abundant component (B, ca. 250 ng/female) was identified as (3Z,6S,7R,9Z)-6,7-epoxyhenicosa-3,9-diene by GC-MS analyses of the extract, chemical derivatization...

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Published in:Journal of chemical ecology 2002-03, Vol.28 (3), p.449-467
Main Authors: WAKAMURA, Sadao, ARAKAKI, Norio, YAMAZAWA, Hiroyuki, NAKAJIMA, Naoto, YAMAMOTO, Masanobu, ANDO, Tetsu
Format: Article
Language:English
Subjects:
6,7-Epoxyhenicosa-3,9-diene
Animal and plant ecology
Animal, plant and microbial ecology
Animals
Autoecology
Biological and medical sciences
Control
Epoxy Compounds - analysis
Epoxy Compounds - chemistry
Female
Females
Fundamental and applied biological sciences. Psychology
Gas Chromatography-Mass Spectrometry
Hypocala rostrata
Integrated pest control
Liquid chromatography
Lymantriidae
Male
Moths - physiology
Movement
Noctuidae
Orientation
Perina nuda
Phytopathology. Animal pests. Plant and forest protection
Protozoa. Invertebrata
Protozoa. Invertebrates
Sex Attractants - analysis
Sex Attractants - chemistry
Uranium
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container_issue 3
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container_title Journal of chemical ecology
container_volume 28
creator WAKAMURA, Sadao
ARAKAKI, Norio
YAMAZAWA, Hiroyuki
NAKAJIMA, Naoto
YAMAMOTO, Masanobu
ANDO, Tetsu
description Four EAG-active components (A-D) were found in the solvent extract of virgin females of the clear-winged tussock moth, Perina nuda. The most abundant component (B, ca. 250 ng/female) was identified as (3Z,6S,7R,9Z)-6,7-epoxyhenicosa-3,9-diene by GC-MS analyses of the extract, chemical derivatization, and comparative chiral HPLC. Minor components also elucidated were (3Z,9Z)-cis-6,7-epoxyicosa-3,9-diene, (A); (3R,45,6S,7R,9Z)-3,4-6,7-diepoxyhenicos-9-ene, (C); and its 3S,4R,6S,7R isomer, (D); with amounts of 0.4, 5, and 8 ng/female, respectively. Component B showed weak attractiveness to male moths in the field. The attractiveness was significantly enhanced by addition of component(s) C and/or D. No males were captured with either the antipode of component B or its mixtures with the minor components. In this field test, noctuid Hypocala rostrata males were also attracted with the synthetic P. nuda pheromone.
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The most abundant component (B, ca. 250 ng/female) was identified as (3Z,6S,7R,9Z)-6,7-epoxyhenicosa-3,9-diene by GC-MS analyses of the extract, chemical derivatization, and comparative chiral HPLC. Minor components also elucidated were (3Z,9Z)-cis-6,7-epoxyicosa-3,9-diene, (A); (3R,45,6S,7R,9Z)-3,4-6,7-diepoxyhenicos-9-ene, (C); and its 3S,4R,6S,7R isomer, (D); with amounts of 0.4, 5, and 8 ng/female, respectively. Component B showed weak attractiveness to male moths in the field. The attractiveness was significantly enhanced by addition of component(s) C and/or D. No males were captured with either the antipode of component B or its mixtures with the minor components. 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The most abundant component (B, ca. 250 ng/female) was identified as (3Z,6S,7R,9Z)-6,7-epoxyhenicosa-3,9-diene by GC-MS analyses of the extract, chemical derivatization, and comparative chiral HPLC. Minor components also elucidated were (3Z,9Z)-cis-6,7-epoxyicosa-3,9-diene, (A); (3R,45,6S,7R,9Z)-3,4-6,7-diepoxyhenicos-9-ene, (C); and its 3S,4R,6S,7R isomer, (D); with amounts of 0.4, 5, and 8 ng/female, respectively. Component B showed weak attractiveness to male moths in the field. The attractiveness was significantly enhanced by addition of component(s) C and/or D. No males were captured with either the antipode of component B or its mixtures with the minor components. In this field test, noctuid Hypocala rostrata males were also attracted with the synthetic P. nuda pheromone.</abstract><cop>New York, NY</cop><pub>Springer</pub><pmid>11944824</pmid><doi>10.1023/A:1014545309128</doi><tpages>19</tpages></addata></record>
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ispartof Journal of chemical ecology, 2002-03, Vol.28 (3), p.449-467
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1573-1561
language eng
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subjects 6,7-Epoxyhenicosa-3,9-diene
Animal and plant ecology
Animal, plant and microbial ecology
Animals
Autoecology
Biological and medical sciences
Control
Epoxy Compounds - analysis
Epoxy Compounds - chemistry
Female
Females
Fundamental and applied biological sciences. Psychology
Gas Chromatography-Mass Spectrometry
Hypocala rostrata
Integrated pest control
Liquid chromatography
Lymantriidae
Male
Moths - physiology
Movement
Noctuidae
Orientation
Perina nuda
Phytopathology. Animal pests. Plant and forest protection
Protozoa. Invertebrata
Protozoa. Invertebrates
Sex Attractants - analysis
Sex Attractants - chemistry
Uranium
title Identification of epoxyhenicosadiene and novel diepoxy derivatives as sex pheromone components of the clear-winged tussock moth Perina nuda
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