Identification of (Z)-4-tridecene from defensive secretion of green lacewing, Chrysoperla carnea

Junwei Zhu; Rikard C. Unelius; Kye Chung Park; Samuel A. Ochieng; John J. Obrycki; Thomas C. Baker

doi:10.1023/A:1005587113469

Identification of (Z)-4-tridecene from defensive secretion of green lacewing, Chrysoperla carnea

Junwei Zhu, Rikard C. Unelius, Kye Chung Park, Samuel A. Ochieng, John J. Obrycki, Thomas C. Baker

Entomology

Research output: Contribution to journal › Article › peer-review

19 Scopus citations

Abstract

We report the identification of a defensive secretion from the green lacewing, Chrysoperla carnea. By using combined gas chromatography-electroantennographic detection (GC-EAD), we found one major compound in the solvent extract of this secretion that elicited a significant EAD response from the antenna. Based upon its characteristic fragments from gas chromatography-mass spectrometry (GC-MS) analysis, the compound was identified as a tridecene. Dimethyldisulfide derivatization suggested that a double bond was located between positions 4 and 5 in the carbon chain. Thus, the compound was tentatively identified as a 4-tridecene. Coinjection of the extract with a mixture of the Z or E form of the synthetic 4-tridecene revealed that the unknown was (Z)-4-tridecene. EAG dose-responses showed a direct correlation to dose. Single sensillum recordings from sensilla trichodea situated on the antennae suggested the presence of receptor neurons specifically responding to this compound. An arrestment behavior was observed when tested in the Y-tube olfactometer. Preliminary field trapping results indicate that the compound is an antagonist to attraction. The avoidance behavior of predatory ants, observed when tested with the synthetic compound of this secretion further suggested a defensive function.

Original language	English
Pages (from-to)	2421-2434
Number of pages	14
Journal	Journal of Chemical Ecology
Volume	26
Issue number	10
DOIs	https://doi.org/10.1023/A:1005587113469
State	Published - 2000

Bibliographical note

Funding Information:
Acknowledgments—The authors would like to express their thanks to Bess Lewis, Anna Keyte, and Brad Tucker for rearing the predatory insects and to Marcus Ruda for helping with the chemical synthesis. We also thank Tracey Pepper for assisting on scanning electron microscope at the ISU Bessey Microscopy Facility. This project was supported by a grant (98-72) from the Leopold Center for Sustainable Agriculture. Journal Paper No. J-18702 of the Iowa Agricultural and Home Economics Experiment Station, Ames, Iowa, Project No. 3437, and supported by Hatch Act and State of Iowa Funds.

Keywords

(Z)-4-tridecene
Alarm pheromone
Chrysoperla carnea
Chrysopidae
Defensive secretion
Electroantennography
Green lacewing
Neuroptera
Single sensillum recording

ASJC Scopus subject areas

Ecology, Evolution, Behavior and Systematics
Biochemistry

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10.1023/A:1005587113469

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@article{a88efecbe10b4c3383a4231e3c1438a3,

title = "Identification of (Z)-4-tridecene from defensive secretion of green lacewing, Chrysoperla carnea",

abstract = "We report the identification of a defensive secretion from the green lacewing, Chrysoperla carnea. By using combined gas chromatography-electroantennographic detection (GC-EAD), we found one major compound in the solvent extract of this secretion that elicited a significant EAD response from the antenna. Based upon its characteristic fragments from gas chromatography-mass spectrometry (GC-MS) analysis, the compound was identified as a tridecene. Dimethyldisulfide derivatization suggested that a double bond was located between positions 4 and 5 in the carbon chain. Thus, the compound was tentatively identified as a 4-tridecene. Coinjection of the extract with a mixture of the Z or E form of the synthetic 4-tridecene revealed that the unknown was (Z)-4-tridecene. EAG dose-responses showed a direct correlation to dose. Single sensillum recordings from sensilla trichodea situated on the antennae suggested the presence of receptor neurons specifically responding to this compound. An arrestment behavior was observed when tested in the Y-tube olfactometer. Preliminary field trapping results indicate that the compound is an antagonist to attraction. The avoidance behavior of predatory ants, observed when tested with the synthetic compound of this secretion further suggested a defensive function.",

keywords = "(Z)-4-tridecene, Alarm pheromone, Chrysoperla carnea, Chrysopidae, Defensive secretion, Electroantennography, Green lacewing, Neuroptera, Single sensillum recording",

author = "Junwei Zhu and Unelius, {Rikard C.} and Park, {Kye Chung} and Ochieng, {Samuel A.} and Obrycki, {John J.} and Baker, {Thomas C.}",

note = "Funding Information: Acknowledgments—The authors would like to express their thanks to Bess Lewis, Anna Keyte, and Brad Tucker for rearing the predatory insects and to Marcus Ruda for helping with the chemical synthesis. We also thank Tracey Pepper for assisting on scanning electron microscope at the ISU Bessey Microscopy Facility. This project was supported by a grant (98-72) from the Leopold Center for Sustainable Agriculture. Journal Paper No. J-18702 of the Iowa Agricultural and Home Economics Experiment Station, Ames, Iowa, Project No. 3437, and supported by Hatch Act and State of Iowa Funds.",

year = "2000",

doi = "10.1023/A:1005587113469",

language = "English",

volume = "26",

pages = "2421--2434",

number = "10",

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T1 - Identification of (Z)-4-tridecene from defensive secretion of green lacewing, Chrysoperla carnea

AU - Zhu, Junwei

AU - Unelius, Rikard C.

AU - Park, Kye Chung

AU - Ochieng, Samuel A.

AU - Obrycki, John J.

AU - Baker, Thomas C.

N1 - Funding Information: Acknowledgments—The authors would like to express their thanks to Bess Lewis, Anna Keyte, and Brad Tucker for rearing the predatory insects and to Marcus Ruda for helping with the chemical synthesis. We also thank Tracey Pepper for assisting on scanning electron microscope at the ISU Bessey Microscopy Facility. This project was supported by a grant (98-72) from the Leopold Center for Sustainable Agriculture. Journal Paper No. J-18702 of the Iowa Agricultural and Home Economics Experiment Station, Ames, Iowa, Project No. 3437, and supported by Hatch Act and State of Iowa Funds.

PY - 2000

Y1 - 2000

N2 - We report the identification of a defensive secretion from the green lacewing, Chrysoperla carnea. By using combined gas chromatography-electroantennographic detection (GC-EAD), we found one major compound in the solvent extract of this secretion that elicited a significant EAD response from the antenna. Based upon its characteristic fragments from gas chromatography-mass spectrometry (GC-MS) analysis, the compound was identified as a tridecene. Dimethyldisulfide derivatization suggested that a double bond was located between positions 4 and 5 in the carbon chain. Thus, the compound was tentatively identified as a 4-tridecene. Coinjection of the extract with a mixture of the Z or E form of the synthetic 4-tridecene revealed that the unknown was (Z)-4-tridecene. EAG dose-responses showed a direct correlation to dose. Single sensillum recordings from sensilla trichodea situated on the antennae suggested the presence of receptor neurons specifically responding to this compound. An arrestment behavior was observed when tested in the Y-tube olfactometer. Preliminary field trapping results indicate that the compound is an antagonist to attraction. The avoidance behavior of predatory ants, observed when tested with the synthetic compound of this secretion further suggested a defensive function.

AB - We report the identification of a defensive secretion from the green lacewing, Chrysoperla carnea. By using combined gas chromatography-electroantennographic detection (GC-EAD), we found one major compound in the solvent extract of this secretion that elicited a significant EAD response from the antenna. Based upon its characteristic fragments from gas chromatography-mass spectrometry (GC-MS) analysis, the compound was identified as a tridecene. Dimethyldisulfide derivatization suggested that a double bond was located between positions 4 and 5 in the carbon chain. Thus, the compound was tentatively identified as a 4-tridecene. Coinjection of the extract with a mixture of the Z or E form of the synthetic 4-tridecene revealed that the unknown was (Z)-4-tridecene. EAG dose-responses showed a direct correlation to dose. Single sensillum recordings from sensilla trichodea situated on the antennae suggested the presence of receptor neurons specifically responding to this compound. An arrestment behavior was observed when tested in the Y-tube olfactometer. Preliminary field trapping results indicate that the compound is an antagonist to attraction. The avoidance behavior of predatory ants, observed when tested with the synthetic compound of this secretion further suggested a defensive function.

KW - (Z)-4-tridecene

KW - Alarm pheromone

KW - Chrysoperla carnea

KW - Chrysopidae

KW - Defensive secretion

KW - Electroantennography

KW - Green lacewing

KW - Neuroptera

KW - Single sensillum recording

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DO - 10.1023/A:1005587113469

M3 - Article

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SN - 0098-0331

VL - 26

SP - 2421

EP - 2434

JO - Journal of Chemical Ecology

JF - Journal of Chemical Ecology

IS - 10

ER -

Identification of (Z)-4-tridecene from defensive secretion of green lacewing, Chrysoperla carnea

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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