Isolation, identification, and biosynthesis of compounds produced by male hairpencil glands of Heliothis virescens (F.) (Lepidoptera

Noctuidae)

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

Extracts of the intact hairpencil glands and hairs from the hairpencil glands of males of Heliothis virescens (F.) were analyzed by capillary gas chromatography (GC) and by GC-mass spectroscopy. These analyses indicated that hexadecanyl acetate (212.4 ng/male), hexadecanol (22.3 ng/male), (Z)-11-hexadecenyl acetate (3.5 ng/male), octadecanyl acetate (14.2 ng/male) octadecanol (7.5 ng/male), tetradecanoic acid (2.7 ng/male), hexadecanoic acid (22.3 ng/male), and octadecanoic acid (6.5 ng/male) were present in the extracts. These compounds also were found in volatiles released from the hairpencil glands. In addition, GC analysis using both polar and apolar capillary columns indicated that extracts of the glands and extracts of the hairs from the hairpencil glands contained small amounts of tetradecanyl acetate, (Z)-9-tetradecenyl acetate, tetradecanol, (Z)-7-hexadecenyl acetate, (Z)-9-hexadecenyl acetate, and (Z)-11-hexadecenol. No (Z)-9-tetradecenal was present. Studies indicated that titers of the compounds increased rapidly during the 36 hr after adult eclosion and then leveled off, being maintained at high levels until released when the glandular hairs were exposed. During exposure of the hair pencils substantial amounts of the compounds were released. In vivo application of 500 ng of suspensions of (Z)-11-hexadecenyl acetate, (E)-11-hexadecenyl acetate, (Z)-11-tetradecenyl acetate, or (E)-11-tetradecenyl acetate in dimethyl sulfoxide to the surface of the denuded hairpencil gland showed that biosynthesis proceeds to the alcohol via the acetate.

Original languageEnglish (US)
Pages (from-to)413-427
Number of pages15
JournalJournal of Chemical Ecology
Volume15
Issue number1
DOIs
StatePublished - Jan 1 1989

Fingerprint

Lepidoptera
Heliothis virescens
Biosynthesis
Noctuidae
acetate
Acetates
acetates
biosynthesis
Gas chromatography
hair
Gas Chromatography
hairs
Palmitic Acid
Myristic Acid
gas chromatography
Dimethyl Sulfoxide
extracts
Suspensions
Alcohols
Spectroscopy

All Science Journal Classification (ASJC) codes

  • Ecology, Evolution, Behavior and Systematics
  • Biochemistry

Cite this

@article{68038faa2ef0415b82e6244761798964,
title = "Isolation, identification, and biosynthesis of compounds produced by male hairpencil glands of Heliothis virescens (F.) (Lepidoptera: Noctuidae)",
abstract = "Extracts of the intact hairpencil glands and hairs from the hairpencil glands of males of Heliothis virescens (F.) were analyzed by capillary gas chromatography (GC) and by GC-mass spectroscopy. These analyses indicated that hexadecanyl acetate (212.4 ng/male), hexadecanol (22.3 ng/male), (Z)-11-hexadecenyl acetate (3.5 ng/male), octadecanyl acetate (14.2 ng/male) octadecanol (7.5 ng/male), tetradecanoic acid (2.7 ng/male), hexadecanoic acid (22.3 ng/male), and octadecanoic acid (6.5 ng/male) were present in the extracts. These compounds also were found in volatiles released from the hairpencil glands. In addition, GC analysis using both polar and apolar capillary columns indicated that extracts of the glands and extracts of the hairs from the hairpencil glands contained small amounts of tetradecanyl acetate, (Z)-9-tetradecenyl acetate, tetradecanol, (Z)-7-hexadecenyl acetate, (Z)-9-hexadecenyl acetate, and (Z)-11-hexadecenol. No (Z)-9-tetradecenal was present. Studies indicated that titers of the compounds increased rapidly during the 36 hr after adult eclosion and then leveled off, being maintained at high levels until released when the glandular hairs were exposed. During exposure of the hair pencils substantial amounts of the compounds were released. In vivo application of 500 ng of suspensions of (Z)-11-hexadecenyl acetate, (E)-11-hexadecenyl acetate, (Z)-11-tetradecenyl acetate, or (E)-11-tetradecenyl acetate in dimethyl sulfoxide to the surface of the denuded hairpencil gland showed that biosynthesis proceeds to the alcohol via the acetate.",
author = "Teal, {P. E.A.} and {Tumlinson, III}, {James Homer}",
year = "1989",
month = "1",
day = "1",
doi = "10.1007/BF02027801",
language = "English (US)",
volume = "15",
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journal = "Journal of Chemical Ecology",
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T1 - Isolation, identification, and biosynthesis of compounds produced by male hairpencil glands of Heliothis virescens (F.) (Lepidoptera

T2 - Noctuidae)

AU - Teal, P. E.A.

AU - Tumlinson, III, James Homer

PY - 1989/1/1

Y1 - 1989/1/1

N2 - Extracts of the intact hairpencil glands and hairs from the hairpencil glands of males of Heliothis virescens (F.) were analyzed by capillary gas chromatography (GC) and by GC-mass spectroscopy. These analyses indicated that hexadecanyl acetate (212.4 ng/male), hexadecanol (22.3 ng/male), (Z)-11-hexadecenyl acetate (3.5 ng/male), octadecanyl acetate (14.2 ng/male) octadecanol (7.5 ng/male), tetradecanoic acid (2.7 ng/male), hexadecanoic acid (22.3 ng/male), and octadecanoic acid (6.5 ng/male) were present in the extracts. These compounds also were found in volatiles released from the hairpencil glands. In addition, GC analysis using both polar and apolar capillary columns indicated that extracts of the glands and extracts of the hairs from the hairpencil glands contained small amounts of tetradecanyl acetate, (Z)-9-tetradecenyl acetate, tetradecanol, (Z)-7-hexadecenyl acetate, (Z)-9-hexadecenyl acetate, and (Z)-11-hexadecenol. No (Z)-9-tetradecenal was present. Studies indicated that titers of the compounds increased rapidly during the 36 hr after adult eclosion and then leveled off, being maintained at high levels until released when the glandular hairs were exposed. During exposure of the hair pencils substantial amounts of the compounds were released. In vivo application of 500 ng of suspensions of (Z)-11-hexadecenyl acetate, (E)-11-hexadecenyl acetate, (Z)-11-tetradecenyl acetate, or (E)-11-tetradecenyl acetate in dimethyl sulfoxide to the surface of the denuded hairpencil gland showed that biosynthesis proceeds to the alcohol via the acetate.

AB - Extracts of the intact hairpencil glands and hairs from the hairpencil glands of males of Heliothis virescens (F.) were analyzed by capillary gas chromatography (GC) and by GC-mass spectroscopy. These analyses indicated that hexadecanyl acetate (212.4 ng/male), hexadecanol (22.3 ng/male), (Z)-11-hexadecenyl acetate (3.5 ng/male), octadecanyl acetate (14.2 ng/male) octadecanol (7.5 ng/male), tetradecanoic acid (2.7 ng/male), hexadecanoic acid (22.3 ng/male), and octadecanoic acid (6.5 ng/male) were present in the extracts. These compounds also were found in volatiles released from the hairpencil glands. In addition, GC analysis using both polar and apolar capillary columns indicated that extracts of the glands and extracts of the hairs from the hairpencil glands contained small amounts of tetradecanyl acetate, (Z)-9-tetradecenyl acetate, tetradecanol, (Z)-7-hexadecenyl acetate, (Z)-9-hexadecenyl acetate, and (Z)-11-hexadecenol. No (Z)-9-tetradecenal was present. Studies indicated that titers of the compounds increased rapidly during the 36 hr after adult eclosion and then leveled off, being maintained at high levels until released when the glandular hairs were exposed. During exposure of the hair pencils substantial amounts of the compounds were released. In vivo application of 500 ng of suspensions of (Z)-11-hexadecenyl acetate, (E)-11-hexadecenyl acetate, (Z)-11-tetradecenyl acetate, or (E)-11-tetradecenyl acetate in dimethyl sulfoxide to the surface of the denuded hairpencil gland showed that biosynthesis proceeds to the alcohol via the acetate.

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