GC/FT-IR Analysis of Novel 4,6,9-Triene and 2,4,6,9-Tetraene Occurring in a Female Pheromone Gland of &amp;lt;i&amp;gt;Arctia plantaginis&amp;lt;/i&amp;gt; (Erebidae: Arctiinae)

Muraki, Yuta; Yamakawa, Rei; Yamamoto, Masanobu; Naka, Hideshi; Honma, Atsushi; Mappes, Johanna; Suisto, Kaisa; Ando, Tetsu

doi:10.4236/ajac.2017.810047

Cited by 6 publications

(8 citation statements)

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“…Many new epoxy compounds are expected to be found by further studies with these species. Table 2 shows new methyl-branched compounds (42)(43)(44)(45)(46)(47)(48)(49)(50) and unbranched compounds (51-60) that have been characterized in analytical studies on 14 species since 2003. In the case of methyl-branched hydrocarbons, 14 compounds had been previously recorded from several species in Lyonetiidae, Geometridae, and Erebidae, and two compounds (42 and 43) were added.…”

Section: Structures Of New Pheromones In Type IImentioning

confidence: 99%

“…A pheromone extract of the wood tiger moth, Arctia plantaginis (Erebidae: Arctiinae), included four pheromone components, A-D, with an unsaturated C 21 chain at a ratio of 30 : 3 : 5 : 1. 45) Comparing their mass spectra with those of synthetic standards, Z3,Z6,Z9-21:H and Δ1,Z3,Z6,Z9-21:H were assigned for Comps. A and C, respectively.…”

Section: Gc/ft-ir Analysismentioning

confidence: 99%

“…B and D are identified as E4,Z6,Z9-21:H (34) and Z2,E4,Z6,Z9-21:H (37), respectively. 45) The sensitivity of the GC/FT-IR is comparable to that of GC/ MS, and IR spectra offer some important information for structure determination that is difficult to obtain with mass spectra. In the future, it is expected that GC/FT-IR instruments will become widespread and be routinely used in many analytical studies on trace natural products, especially insect pheromones.…”

Section: Gc/ft-ir Analysismentioning

confidence: 99%

“…This building block is a useful bifunctional chiral synthon including a methyl branch, and it is possible to elongate the carbon chain. The block with a long chain was coupled with the 2-methyl block, and the produced acid moiety was esterified with (S)-2-methylpentan-3-ol synthesized from (S)valine to yield the ester pheromone (45). The advantage of starting with a chiral propylene oxide is that any type of building block can be prepared by modifying the Grignard reagent at the first reaction and the nucleophile of the S N 2 reaction.…”

Section: Enantioselective Synthesis Of Methyl-branched Pheromonesmentioning

confidence: 99%

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Semiochemicals containing lepidopteran sex pheromones: Wonderland for a natural product chemist

Ando

Yamamoto

2020

J. Pestic. Sci.

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Since the first identification of bombykol, sex pheromones of about 700 moth species have been elucidated. Additionally, field evaluations of synthetic pheromones and their related compounds have revealed the male attraction of another 1,300 species. These pheromones and attractants are listed on the web-sites, "Pheromone Database, Part I. " Pheromone components are classified according to their chemical structures into two major groups (Types I and II) and miscellaneous. Based on our previous review published in 2004, studies reported during the last two decades are highlighted here to provide information on the structure characteristics of newly identified pheromones, current techniques for structure determination, new enantioselective syntheses of methyl-branched pheromones, and the progress of biosynthetic research. Besides the moth sex pheromones, various pheromones and allomones from many arthropod species have been uncovered. These semiochemicals are being collected in the "Pheromone Database, Part II. " The chemical diversity provides a wonderland for natural product chemists.

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Section: Structures Of New Pheromones In Type IImentioning

confidence: 99%

Section: Gc/ft-ir Analysismentioning

confidence: 99%

Section: Gc/ft-ir Analysismentioning

confidence: 99%

Section: Enantioselective Synthesis Of Methyl-branched Pheromonesmentioning

confidence: 99%

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Semiochemicals containing lepidopteran sex pheromones: Wonderland for a natural product chemist

Ando

Yamamoto

2020

J. Pestic. Sci.

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“…Recent developments concerning the chemical defenses of the wood tiger moth have revealed the presence of two methopyraxines (2-sec-butyl-3-methoxypyrazine and 2-isobutyl-3-methoxypyrazine) that have a key role in predator deterrence Burdfield-Steel et al, 2018). By contrast, despite luring A. plantaginis males to pheromone traps during every field season, our knowledge of the compounds present in the pheromone blend(s) of A. plantaginis is only incipient (Muraki et al, 2017), with a number of microcompounds amongst the most prominent components. Pyrazines have been found in the pheromone blends of some insects, and seem to be particularly common in tiger moths (Rothschild et al, 1984;Guilford et al, 1987;Moore et al, 1990).…”

Section: Components Of Chemical Defenses Could Have a Dual Function Imentioning

confidence: 99%

Multimodal Aposematic Signals and Their Emerging Role in Mate Attraction

et al. 2018

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Chemically defended animals often display conspicuous color patterns that predators learn to associate with their unprofitability and subsequently avoid. Such animals (i.e., aposematic), deter predators by stimulating their visual and chemical sensory channels. Hence, aposematism is considered to be "multimodal." The evolution of warning signals (and to a lesser degree their accompanying chemical defenses) is fundamentally linked to natural selection by predators. Lately, however, increasing evidence also points to a role of sexual selection shaping warning signal evolution. One of the species in which this has been shown is the wood tiger moth, Arctia plantaginis, which we here put forward as a promising model to investigate multimodality in aposematic and sexual signaling. A. plantaginis is an aposematic diurnal moth which exhibits sexually dimorphic coloration as well as sex-limited polymorphism in part of its range. The anti-predator function of its coloration and, more recently, its chemical defenses (even when experimentally decoupled from the visual signals), has been well-demonstrated. Interestingly, recent studies have revealed differences between the two male morphs in mating success, suggesting a role of coloration in mate choice or attraction, and providing a possible explanation for its sexual dimorphism in coloration. Here, we: (1) review the lines of evidence showing the role of predation pressure and sexual selection in the evolution of multimodal aposematic signals in general, and in the wood tiger moth in particular;(2) establish gaps in current research linking sexual selection and predation as selective pressures on aposematic signals by reviewing a sample of the literature published in the last 30 years; (3) highlight the need of identifying suitable systems to address simultaneously the effect of natural and sexual selection on multimodal aposematic signals; and (4) propose directions for future research to test how aposematic signals can evolve under natural and sexual selection.

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Identification of a unique three‐component sex pheromone produced by the tea black tussock moth, Dasychira baibarana (Lepidoptera: Erebidae: Lymantriinae)

Magsi

Cai

et al. 2022

Pest Management Science

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BACKGROUND: The tea black tussock moth Dasychira baibarana Matsumura is a devastating pest in tea plantations that causes substantial economic losses. Presently, there is no effective method to control this pest other than pesticide application. The identified sex pheromone of D. baibarana could be used for detecting and monitoring this pest. RESULTS: Gas chromatography-electroantennogram detection showed that D. baibarana male moth antennae responded strongly to three components in the female sex pheromone gland, which were identified as: (3Z,6Z)-cis-9,10-epoxyhenicosa-3,6-diene (Z3,Z6,epo9-21:H) (I), (3Z,6Z,11E)-cis-9,10-epoxyhenicosa-3,6,11-triene (Z3,Z6,epo9,E11-21:H) (II) and (3Z,6Z)-henicosa-3,6-dien-11-one (Z3,Z6-21:11-one) (III). Dasychira baibarana uses a unique composition of an epoxydiene, epoxytriene, and dienone with the same 3,6-dienyl motif as its sex pheromone. The epoxytriene and dienone were not previously characterized as insect pheromone components. Electroantennogram analysis showed that each synthetic compound strongly stimulated male antennae, and compounds II and III elicited stronger responses than compound I. A wind tunnel bioassay and field trapping experiments proved that, ternary blends of compounds I-III attracted D. baibarana. Efficient attraction was achieved with a rubber septum baited with 500 ∼g of a mixture of compounds I-III at the ratio 25:20:55. CONCLUSION: The three identified compounds elicited an electroantennogram response in D. baibarana male moth antennae, and a mixture of the three components at the ratio 25:20:55 attracted D. baibarana male moths in a wind tunnel assay and field trapping experiments. This blend could be used for integrated management of D. baibarana in tea plantations.

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GC/FT-IR Analysis of Novel 4,6,9-Triene and 2,4,6,9-Tetraene Occurring in a Female Pheromone Gland of <i>Arctia plantaginis</i> (Erebidae: Arctiinae)

Abstract: Fifteen subspecies of the wood tiger moth, Arctia plantaginis (Lepidoptera: Erebidae: Arctiinae), have been recorded in the Northern Hemisphere. An analysis of crude pheromone extracts by GC equipped with an electroantennographic (EAG) detector showed four EAG-active components (Comps.

Cited by 6 publications

References 16 publications

Semiochemicals containing lepidopteran sex pheromones: Wonderland for a natural product chemist

Semiochemicals containing lepidopteran sex pheromones: Wonderland for a natural product chemist

Multimodal Aposematic Signals and Their Emerging Role in Mate Attraction

Identification of a unique three‐component sex pheromone produced by the tea black tussock moth, Dasychira baibarana (Lepidoptera: Erebidae: Lymantriinae)

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