Sex Pheromone of Japanese Giant Looper, Ascotis selenaria cretacea: Identification and Field Tests

Ando, Tetsu; Ohtani, Kazuya; Yamamoto, Masanobu; Miyamoto, Takashi; Qin, Xurong; Witjaksono, Witjaksono

doi:10.1023/b:joec.0000006683.58028.1e

Cited by 44 publications

(26 citation statements)

References 11 publications

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“…PBAN is also not involved in hydrocarbon pheromone production in the noctuid moth, Anticarsia gemmatalis, (Jeong 2003). In other species of moths producing type 2 pheromones, PBAN regulates epoxidation after the uptake of hydrocarbons in the pheromone gland (Ando et al 1997;Jurenka et al 2003). Recently, it was shown that PBAN could regulate the uptake of hydrocarbon into pheromone glands of geometrid moths (Wei et al 2004).…”

Section: Resultsmentioning

confidence: 99%

Identification and Biosynthetic Studies of the Hydrocarbon Sex Pheromone in Utetheisa ornatrix

et al. 2007

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The type II class of sex pheromones found in moths is composed of polyene hydrocarbons and their epoxides. Analysis of Utetheisa ornatrix females by gas chromatography-mass spectrometry and measurement of responses of male moths by coupled gas chromatography-electroantennogram detection confirmed the presence of large amounts of (Z,Z,Z)-1, 3,6,3,6,[9][10][11][12][13][14][15][16][17][18][19][20][21] and smaller amounts of (Z,Z,Z)-3,6,9-heneicosatriene (3,6,9-21:Hy). Both compounds were detected in pheromone glands of newly emerged adults, with low amounts found in the late pupal stage, indicating that sex pheromone biosynthesis started in the late pupal stage. In our population of females (several hundred sampled), approximately 90% produced the tetraene, 1,3,6,9-21:Hy, as the major component, while the other 10% produced only a large amount (1500-2000 ng) of 3,6,9-21:Hy, with no detectable amount of the tetraene. This result could indicate that two distinct populations are present in our original collection site in Florida. Decapitated female moths accumulated 3,6,9-21:Hy and 1,3,6,9-21:Hy compared to the same age normal females, indicating that female moths continuously produce pheromone. A pheromone biosynthesis activating neuropeptide (PBAN)-like neuropeptide did not affect sex pheromone production as indicated by injection of synthetic PBAN and decapitation of U. ornatrix female adults. When the labeled precursor, D4-9,12,15-18:acid, was injected into the early pupal stage, the most abundantly labeled hydrocarbons were 3,6,9-21:Hy and 1,3,6,9-21:Hy in the female adults. This result indicated that 3,6,9-21:Hy could be biosynthesized from linolenic acid through chain elongation and decarboxylation. To determine how 1,3,6,9-21:Hy is produced, D4-3,6,9-21:Hy was injected into pupae and monitored for incorporation of label. No label was incorporated into 1,3,6,9-21:Hy, although a large amount of triene, 3,6,9-21:Hy, was recovered in the pheromone gland. This indicates that U. ornatrix females do not use 3,6,9-21:Hy to produce 1,3,6,9-21:Hy, and the terminal double bond is introduced earlier in the biosynthetic pathway. RightsWorks produced by employees of the U.S. Government as part of their official duties are not copyrighted within the U.S. The content of this document is not copyrighted. Abstract The type II class of sex pheromones found in moths is composed of polyene hydrocarbons and their epoxides. Analysis of Utetheisa ornatrix females by gas chromatography-mass spectrometry and measurement of responses of male moths by coupled gas chromatography-electroantennogram detection confirmed the presence of large amounts of (Z,Z,Z)-1,3,6,9-heneicosatetraene (1,3,6,9-21:Hy) and smaller amounts of (Z,Z, Z)-3,6,9-heneicosatriene (3,6,9-21:Hy). Both compounds were detected in pheromone glands of newly emerged adults, with low amounts found in the late pupal stage, indicating that sex pheromone biosynthesis started in the late pupal stage. In our population of females (several hundred sampled), approximately ...

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Section: Resultsmentioning

confidence: 99%

Identification and Biosynthetic Studies of the Hydrocarbon Sex Pheromone in Utetheisa ornatrix

et al. 2007

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“…Three monoepoxides derived from Z3,Z6,Z9-trienes elute in the order of 6,7-, 3,4-, and 9,10-epoxides [9]. The former two isomers are sufficiently separated on the high polar column, while the elution of the latter two isomers overlaps [71]. For each positional isomer of diepoxides derived from the Z3,Z6,Z9-trienes, two diastereomeric )-isomers, i.e., 3,4-6,7-diepoxides with a 3S,4R,6R,7S configuration, 6,7-9,10-diepoxides with a 6S,7R,9R,10S configuration, 3,4-9,10-diepoxides with a 3S,4R,9R,10S configuration, and their antipodes] elute faster than the isomers with a configuration orienting two epoxy rings to the same face [(S * ,R * ,S * ,R * )-isomers].…”

Section: Identification Of Type II Componentsmentioning

confidence: 98%

“…Combining the data from ten other species, which were tentatively determined by field tests of synthetic epox-ides, the overview of their stereochemistry indicates that the S,R configuration has been assigned for the epoxy ring more frequently than the R,S configuration and that no 9,10-epoxides with 9R,10S configuration have been found. The female of A. s. cretacea exceptionally produce a racemic pheromone, while the male is attracted more by an optically pure sample with a 3R,4S configuration [71].…”

Section: Structures Of Pheromones In Type IImentioning

confidence: 99%

“…The kinds of available chiral columns and their resolution capabilities are described later. Table 3 shows the absolute configuration of some natural pheromones as analyzed by chiral chromatography and the attractive activity of synthetic epoxides in the field [67,[71][72][73][74][75][76]. Interestingly, males were not always effectively attracted by the synthetic epoxide despite exhibiting the same configuration as produced by the corresponding females.…”

Section: Structures Of Pheromones In Type IImentioning

confidence: 99%

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Lepidopteran Sex Pheromones

Ando

Inomata

Yamamoto

2004

Topics in Current Chemistry

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332

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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“…Recently, we identified one protein (AscrPBP1) grouped in Cluster C from the antennae of the Japanese giant looper, Ascotis selenaria cretacea, 10) whose mating communication is mediated with (Z,Z,Z)-3,6,9-nonadecatriene and cis-3,4-epoxy-(Z,Z)-6,9-nonadecadiene. 11,12) This is the first identification of PBP from a species in the family of Geometridae, and no other OBPs of the insects producing Type II pheromones have been reported. Furthermore, since many lepidopteran insects produce multiple PBPs, we designed primers with reference to conserved regions in some PBPs of Clusters A and B to examine other proteins in A. s. cretacea antennae.…”

Section: Identification Of a New Pheromone-binding Protein In The Antmentioning

confidence: 89%

Identification of a New Pheromone-Binding Protein in the Antennae of a Geometrid Species and Preparation of Its Antibody to Analyze the Antennal Proteins of Moths Secreting Type II Sex Pheromone Components

Watanabe

Tabunoki

Miura

et al. 2009

Bioscience, Biotechnology, and Biochemistry

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Sex Pheromone of Japanese Giant Looper, Ascotis selenaria cretacea: Identification and Field Tests

Cited by 44 publications

References 11 publications

Identification and Biosynthetic Studies of the Hydrocarbon Sex Pheromone in Utetheisa ornatrix

Identification and Biosynthetic Studies of the Hydrocarbon Sex Pheromone in Utetheisa ornatrix

Lepidopteran Sex Pheromones

Identification of a New Pheromone-Binding Protein in the Antennae of a Geometrid Species and Preparation of Its Antibody to Analyze the Antennal Proteins of Moths Secreting Type II Sex Pheromone Components

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