Identification of sex pheromone of browntail moth,Euproctis chrysorrhoea (L.) (Lepidoptera: Lymantriidae)

Ba, Leonhardt; Vc, Mastro; Schwarz, M.; Jd, Tang; Re, Charlton; A, Pellegrini-Toole; Jd, Warthen; Cp, Schwalbe; Rt, Cardé

doi:10.1007/bf01395598

Cited by 17 publications

(13 citation statements)

References 7 publications

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“…3). The polyenyl 7,13,16,19-22 and 11,14,17-20 compounds containing an isobutyryl (isoBut) or 4-methylvaleryl (Me4-Val) ester function [53,54], which are produced by Lymantriidae species and might be derived from linolenic acid via chain elongation, are closely correlated to the Type II pheromones based on their biosynthetic origin.…”

Section: Type I Compounds With Unique Structuresmentioning

confidence: 99%

Lepidopteran Sex Pheromones

Ando

Inomata

Yamamoto

2004

Topics in Current Chemistry

339

289

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As a consequence of the diversity of Lepidoptera, including 150,000 described species, interesting species-specific sex pheromone systems are exhibited in this insect group. The quite varied pheromones, which have been identified from female moths of nearly 530 species from around the world, are classified into groups of Type I (75%), Type II (15%), and miscellaneous (10%), according to their chemical structures. Additionally, many pheromones produced by male moths and butterflies have been known. While new sex pheromones from about 70 lepidopteran species have been reported in the last five years utilizing GC-EAD, GC-MS, LC, and NMR, our information about the pheromones is still rudimentary, and these kinds of semiochemicals remain an exciting research target for natural product chemistry. In addition to the overview of their chemical structures, this chapter deals with current methods for their identification. Furthermore, an actual application of the synthetic pheromones for pest control is briefly introduced.

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Section: Type I Compounds With Unique Structuresmentioning

confidence: 99%

Lepidopteran Sex Pheromones

Ando

Inomata

Yamamoto

2004

Topics in Current Chemistry

339

289

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“…Some of the pheromone components of tussock moths, Euproctis spp. (Lepidoptera: Lymantriidae) are isobutyrate esters of various alcohols (Leonhardt et al 1991; Wakamura et al 1994; Yasuda et al 1995), which again points to the involvement of valine, this time furnishing the acid part. By replacing malonyl CoA as the starting unit, branched-chain amino acids also are involved in the biosynthesis of methylalkanes after being transformed to activated branched carboxylic acids.…”

Section: Discussionmentioning

confidence: 99%

Identification and Biosynthesis of Novel Male Specific Esters in the Wings of the Tropical Butterfly, Bicyclus martius sanaos

et al. 2014

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Representatives of the highly speciose tropical butterfly genus Bicyclus (Lepidoptera: Nymphalidae) are characterized by morphological differences in the male androconia, a set of scales and hair pencils located on the surface of the wings. These androconia are assumed to be associated with the release of courtship pheromones. In the present study, we report the identification and biosynthetic pathways of several novel esters from the wings of male B. martius sanaos. We found that the volatile compounds in this male butterfly were similar to female-produced moth sex pheromones. Components associated with the male wing androconial areas were identified as ethyl, isobutyl and 2-phenylethyl hexadecanoates and (11Z)-11-hexadecenoates, among which the latter are novel natural products. By topical application of deuterium-labelled fatty acid and amino acid precursors, we found these pheromone candidates to be produced in patches located on the forewings of the males. Deuterium labels from hexadecanoic acid were incorporated into (11Z)-11-hexadecenoic acid, providing experimental evidence of a Δ11-desaturase being active in butterflies. This unusual desaturase was found previously to be involved in the biosynthesis of female-produced sex pheromones of moths. In the male butterflies, both hexadecanoic acid and (11Z)-11-hexadecenoic acid were then enzymatically esterified to form the ethyl, isobutyl and 2-phenylethyl esters, incorporating ethanol, isobutanol, and 2-phenylethanol, derived from the corresponding amino acids L-alanine, L-valine, and L-phenylalanine.Electronic supplementary materialThe online version of this article (doi:10.1007/s10886-014-0452-y) contains supplementary material, which is available to authorized users.

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“…Synthetic sex pheromone would be useful to investigate the flight season and population trend of this species, even though further field evaluation studies will be needed to develop a formulation for optimum attraction. Leonhardt et al (1991), 2. Wakamura et al (1994); Ichikawa et al (1995), 3. this paper, 4.…”

Section: Discussionmentioning

confidence: 99%

“…Within this context, species belonging to the genus Euproctis (Lepidoptera: Lymantriidae) seem be unusual. Different compounds have been identified as sex pheromone in different species, and no common compound has been identified in this genus, even when minor related compounds are considered (Tan et al, 1984;Yasuda et al, 1994Yasuda et al, , 1995Leonhardt et al, 1991;Wakamura et al, 1994;Ichikawa et al, 1995).…”

Section: Introductionmentioning

confidence: 99%

Identification of novel sex pheromone components from a tussock moth, Euproctis pulverea

Wakamura¹,

Arakaki²,

Ono³

et al. 2001

Entomologia Exp Applicata

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Two EAG‐active compounds were found in the solvent extract of abdominal tips of virgin females of the tussock moth Euproctis pulverea (Leech) (Lepidoptera: Lymantriidae), and identified as (Z,Z,Z)‐11,14,17‐icosatrienyl isobutyrate and (Z,Z,Z)‐11,14,17‐icosatrienyl 4‐methylvalerate at 190 and 80 ng female−1, respectively, by means of GC‐MS analyses and chemical derivatization. Esters of n‐butyric acid, n‐valeric acid, n‐hexanoic acid and a methylheptanoic acid were also found at 3, 2, 0.4 and 9 ng female−1 as minor EAG‐inactive compounds. Two active compounds were also detected in the hexane extract of female anal tufts at 17 and 6 ng female−1, respectively. In Okinawa, the binary blend of the synthetic compounds attracted male moths to the sticky traps, but single compounds did not. The significance of these findings in relation to parasitism by Telenomus euproctidis (Hymenoptera: Scelionidae) is discussed.

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Identification of sex pheromone of browntail moth,Euproctis chrysorrhoea (L.) (Lepidoptera: Lymantriidae)

Cited by 17 publications

References 7 publications

Lepidopteran Sex Pheromones

Lepidopteran Sex Pheromones

Identification and Biosynthesis of Novel Male Specific Esters in the Wings of the Tropical Butterfly, Bicyclus martius sanaos

Identification of novel sex pheromone components from a tussock moth, Euproctis pulverea

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