Sex pheromone components of male Tirathaba mundella (Lepidoptera: Pyralidae)

Sasaerila, Yorianta; Gries, Regine; Gries, Gerhard; Khaskin, Grigori; King, Skip; Takács, Stephen; Hardi,

doi:10.1007/s00049-003-0233-5

Cited by 36 publications

(29 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The other components occur in both species and sexes, albeit in largely different concentrations. Hexahydrofarnesylacetone (18) has been reported several times from male scent organs of Lepidoptera, [35,[39][40][41] but pheromonal activity has not been shown so far. In addition, it serves as a phagostimulant of Bermuda grass to larvae of the fall armyworm, Spodoptera litoralis.…”

Section: Discussionmentioning

confidence: 99%

Aphrodisiac Pheromones from the Wings of the Small Cabbage White and Large Cabbage White Butterflies, Pieris rapae and Pieris brassicae

et al. 2009

View full text Add to dashboard Cite

The small and large cabbage butterflies, Pieris rapae and P. brassicae, are found worldwide and are of considerable economic importance. The composition of the male scent-producing organs present on the wings was investigated. More than 120 components were identified, but only a small portion proved to be male specific. Major components were the known beetle pheromone ferrulactone (1) in P. rapae and its previously unknown larger analogue, brassicalactone (2), in P. brassicae. The latter carries an additional isoprene unit and is closely related to 1. Other components present in larger amounts on male relative to female wings were hexahydrofarnesylacetone (18) and phytol (23). Brassicalactone (2) was fully characterized by synthesis of its various diastereomers by using ring-closing metathesis. A similar approach to ferrulactone (1) failed, presumably because of its smaller ring size. Instead, this compound was synthesized by using a modified literature procedure. The biological activity of the compounds in the extract was tested by coupled gas chromatographic-electroantennographic (GC-EAD) analysis, which showed that both macrolides and the other major components of the wings can be detected by the antennae of the conspecific female butterflies. Other detectable compounds included several alkanes, which are typical constituents of the butterfly cuticula, derivatives of phytol (23) and long-chain secondary alcohols. Finally, bioassays with males showed that the mixture of 1 (P. rapae) or 2 (P. brassicae) together with 18 and 23 applied to freshly eclosed males increased mating success compared to untreated males. Therefore, the two macrolides 1 and 2 are aphrodisiac pheromone components of male small and large cabbage white butterflies, respectively.

show abstract

Section: Discussionmentioning

confidence: 99%

Aphrodisiac Pheromones from the Wings of the Small Cabbage White and Large Cabbage White Butterflies, Pieris rapae and Pieris brassicae

et al. 2009

View full text Add to dashboard Cite

show abstract

“…In the case of E. excrescens, field observations of mating behavior confirmed a female flight straight toward a male in a swing-like pendulum flight (calling by the male) and indicated that the female was attracted to the male by visual cues from a long distance and by the male scent from a short distance in the final encounter [119]. As an exceptional instance, a sticky trap baited with a mixture of tetrahydropyran (5) and vanillin, male pheromone components of Tirathaba mundella (Pyralidae: Galleriinae), captured the females released in a screen cage, suggesting the activity for long-range female attraction [120]. Since female antennae response to male pheromones as well as male antennae are stimulated by female pheromones, the GC-EAD technique (see below) is also useful for the analysis of male pheromones [120,121].…”

Section: Male Sex Pheromonesmentioning

confidence: 99%

“…As an exceptional instance, a sticky trap baited with a mixture of tetrahydropyran (5) and vanillin, male pheromone components of Tirathaba mundella (Pyralidae: Galleriinae), captured the females released in a screen cage, suggesting the activity for long-range female attraction [120]. Since female antennae response to male pheromones as well as male antennae are stimulated by female pheromones, the GC-EAD technique (see below) is also useful for the analysis of male pheromones [120,121].…”

Section: Male Sex Pheromonesmentioning

confidence: 99%

Lepidopteran Sex Pheromones

Ando

Inomata

Yamamoto

2004

Topics in Current Chemistry

338

289

View full text Add to dashboard Cite

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.

show abstract

“…On the other hand, a 14-methyl derivative was synthesized starting from 1,12-dodecanediol (5), which was mono-brominated, and the remaining hydroxyl group was protected as a methoxymethyl (MOM) ether (6). The ylide derived from 6 was coupled with 2-hexanone to a C 18 alkenyl compound (7). After hydrogenation of the double bond in 7, deprotection of the MOM ether and successive oxidation produced an aldehyde (8) as for the 6-methyl derivative, Grignard coupling and oxidation produced 14-methyl-2-octadecanone, which showed almost the same 1 H NMR data as the 6-methyl derivative.…”

mentioning

confidence: 98%

“…While another 2-ketone, 6,10,14-trimethyl-2-pentadecanone (phytone), has been identified from male moths of Galleria melonella 6) and Tirathaba mundella, 7) methyl-branched 2-ketones have never been characterized as a sex pheromone produced by female moths. Some other structure-related insect sex pheromones are known, as follows: 3,11-dimethyl-2-heptacosanone 8) and 3,11-dimethyl-2-nonacosanone 9) of a cockroach (Blattella germanica, Dictyoptera), 10-methyl-2-tridecanone of a beetle (Diabrotica undecimpunctata howardi, Coleoptera), 10) and 6,12-dimethyl-2-pentadecanone of related species (D. balteata).…”

mentioning

confidence: 99%