Polyunsaturated hydrocarbons in the hemolymph: biosynthetic precursors of epoxy pheromones of geometrid and arctiid moths

Wang, Wei; Miyamoto, Takashi; Endo, Masao; Murakawa, Tatsuzo; Pu, Guan-Qin; Ando, Tetsu

doi:10.1016/s0965-1748(03)00002-x

Cited by 31 publications

(28 citation statements)

References 20 publications

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“…1 mg of monoenyl acetates and aldehydes in the Type I class and homoconjugated dienyl compounds in the Type II class can be detected. An RID records every type of compound, also at the level of 1 mg. Figure 12 shows the chromatograms of Type II pheromone components produced by an Arctiidae species, Spilosoma imparilis [178], indicating that all of the five components are easily separated by an ODS column. After this separation, the epoxy components were used for a subsequent analysis with a chiral column to determine their absolute configuration.…”

Section: Separation With a Chiral Columnsmentioning

confidence: 99%

Lepidopteran Sex Pheromones

Ando

Inomata

Yamamoto

2004

Topics in Current Chemistry

334

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: Separation With a Chiral Columnsmentioning

confidence: 99%

Lepidopteran Sex Pheromones

Ando

Inomata

Yamamoto

2004

Topics in Current Chemistry

334

289

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“…The alkene is transported to the pheromone gland and converted to (+)-disparlure by epoxidation . Polyene hydrocarbon precursors are present in the hemolymph of geometrid and arctiid moths, with the pheromone epoxide made in the pheromone gland (Wei et al 2003(Wei et al , 2004.…”

Section: Introductionmentioning

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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“…The type II pheromones are not produced de novo but are presumably derived from linolenic and linolic acids coming from plants (Rule and Roelofs, 1989), and the enzymatic process in a pheromone gland is only epoxidation (Miyamoto et al, 1999). Polyunsaturated hydrocarbons, which are precursors of epoxy pheromones and sometime pheromone components themselves, are expected to be produced outside the pheromone gland, probably in oenocytes or a fat body, and transported to the gland via the hemolymph (Howard and Blomquist, 2005;Jurenka, 2005;Wei et al, 2003).…”

Section: Introductionmentioning

confidence: 99%