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Suzuki, Takahisa; Haga, Kazuo; Tsutsumi, Tadaaki; Matsuyama, Shigeru

doi:10.1023/a:1005591214378

Cited by 7 publications

(5 citation statements)

References 13 publications

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“…( Z )-3-Octenal was also detected in the already mentioned ventral glands of Nematus sawfly larvae and, likewise, in the ventral glands of the Cladius, Priophorus, and Trichiocampus sawfly larvae . ( Z )-3-Decenoic acid is one compound of the anal secretion from different species of idolothripine thrips acting as a repellent . Furthermore, it has been reported as a sex pheromone in the furniture carpet beetle, Anthrenus flavipes LECONTE …”

Section: Introductionmentioning

confidence: 83%

Structure–Odor Relationships of (Z)-3-Alken-1-ols, (Z)-3-Alkenals, and (Z)-3-Alkenoic Acids

Lorber

Zeh

Regler

et al. 2016

J. Agric. Food Chem.

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( Z)-3-Unsaturated volatile acids, alcohols, and aldehydes are commonly found in foods and other natural sources, playing a vital role in the attractiveness of foods but also as compounds with chemocommunicative function in entomology. However, a systematic investigation of their smell properties, especially regarding humans, has not been carried out until today. To close this gap, the odor thresholds in air and odor qualities of homologous series of ( Z)-3-alken-1-ols, ( Z)-3-alkenals, and ( Z)-3-alkenoic acids were determined by gas chromatography-olfactometry. It was found that the odor qualities in the series of the ( Z)-3-alken-1-ols and ( Z)-3-alkenals changed, with increasing chain length, from grassy, green to an overall fatty and citrus-like, soapy character. On the other hand, the odor qualities of the ( Z)-3-alkenoic acids changed successively from cheesy, sweaty via plastic-like, to waxy in their homologous series. With regard to their odor potencies, the lowest thresholds in air were found for ( Z)-3-hexenal, ( Z)-3-octenoic acid, and ( Z)-3-octenal.

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Section: Introductionmentioning

confidence: 83%

Structure–Odor Relationships of (Z)-3-Alken-1-ols, (Z)-3-Alkenals, and (Z)-3-Alkenoic Acids

Lorber

Zeh

Regler

et al. 2016

J. Agric. Food Chem.

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“…( Z )‐3‐Dodecenoic acid is found in leaf extracts of the genus Vicia [36] and in essential oils of Cupressus sempervirens [37] and Hemizygia welwitschia [38] . It is also found in anal gland secretions of ants [39] and in indolothripine thrips, [40] as well as in gall thrips, where it may act as an alarm pheromone [41] . ( Z )‐3‐Decenoic acid has also been reported as a repellent in the anal glands of thrips, [40] in the defensive secretion of the rectal gland of the carrion beetle Necrodes surinamensis , [42] as a sex pheromone in the furniture carpet beetle Anthrenus flavipes , [43] and as part of the fatty acids of several Lactobacteriaceae [44] …”

Section: Resultsmentioning

confidence: 99%

“…Heliconius telesiphe belongs to the Erato clade and is involved in pupal mating. As shown in the TIC (Figure 24), the CSG extract consisted of a few compounds in higher concentrations, the main volatile (Z)-3-hexenyl butanoate (40), and some unknown higher terpene esters. In the volatile range again 1 occurred in moderate concentrations together with sulcatone (13), hexyl butanoate (41), some terpenes and short esters.…”

Section: Other Mimicry Groupsmentioning

confidence: 90%

“…[38] It is also found in anal gland secretions of ants [39] and in indolothripine thrips, [40] as well as in gall thrips, where it may act as an alarm pheromone. [41] (Z)-3-Decenoic acid has also been reported as a repellent in the anal glands of thrips, [40] in the defensive secretion of the rectal gland of the carrion beetle Necrodes surinamensis, [42] as a sex pheromone in the furniture carpet beetle Anthrenus flavipes, [43] and as part of the fatty acids of several Lactobacteriaceae. [44] The H. burneyi huebneri CSG extract consists mainly of these (Z)-3-alkenoates, hydrocarbons, some terpenes such as geranylgeraniol, phytol, and hexahydrofarnesylacetone, as well as macrolides and a few other fatty acid esters, mainly with 1butanol and 2-propanol.…”

Section: Dennis-ray Mimicry Groupmentioning

confidence: 99%

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Variation of Clasper Scent Gland Composition of Heliconius Butterflies from a Biodiversity Hotspot

Ehlers,

Blow,

Szczerbowski

et al. 2023

ChemBioChem

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Male Heliconius butterflies possess two pheromone emitting structures, wing androconia and abdominal clasper scent glands. The composition of the clasper scent gland of males of 17 Heliconius and Eueides species from an overlapping area in Ecuador, comprising three mimicry groups, was investigated by GC/MS. The chemical signal serves as an anti‐aphrodisiac signal that is transferred from males to females during mating, indicating the mating status of the female to prevent them from harassment by other males. In addition, the odour may also serve in predator defence. There is potential for convergence driven by mimicry, although, such convergence might be detrimental for species recognition of the butterflies within the mimicry ring, making mating more difficult. More than 500 compounds were detected, consisting of volatile, semi‐volatile or non‐volatile compounds, including terpenes, fatty acid esters or aromatic compounds. Several novel esters were identified by GC/MS and GC/IR data, microderivatisation and synthesis, including butyl (Z)‐3‐dodecenoate and other (Z)‐3‐alkenoates, 3‐oxohexyl citronellate and 5‐methylhexa‐3,5‐dienyl (E)‐2,3‐dihydrofarnesoate. The secretions were found to be species specific, potentially allowing for species differentiation. Statistical analysis of the more than 500 compounds showed differentiation by phylogenetic clade and species, but not by mimicry group.

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“…Citronellic acid I is widespread in nature. The monounsaturated acid G was found in the thrips, Holurothrips morikawai [43]. Methyl-G occurs in secretions of the sternal glands from male cotton stainers (Dysdercus cingulatus) [44]; in Asian pears (Pyrus serotina) and flowers of Michelia champaca, it is accompanied by methyl-A [45] [46], and in carabao mangoes (Mangifera indica) by methyl-H [47].…”

Section: Methyl Ester Of J (Methyl-j) the Synthesis Of (S)-48-dimetmentioning

confidence: 99%

Composition of the Cloacal Gland Secretion of Tuatara, Sphenodon punctatus

Flachsbarth

Fritzsche

Weldon

et al. 2009

Chemistry & Biodiversity

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The lipophilic content of the cloacal gland secretion of the tuatara (Sphenodon punctatus) was investigated. GC/EI-MS Analysis of CH2Cl2 extracts of the secretions revealed triacylglycerols as major glandular constituents. Twelve major medium-chain fatty acids were found to be conjugated to glycerol in different combinations, resulting in complex mixtures. These acids were identified by transesterification and subsequent derivatization of natural samples, and their structures were verified by synthesis. The natural glycerides contain predominantly three of the following acids: octanoic (A), (E)- and (Z)-oct-4-enoic (B and C, resp.), (4E,6Z)-octa-4,6-dienoic (tuataric acid; D), (R)-2,6-dimethylheptanoic (E), (R)-2,6-dimethylhept-5-enoic (F), (Z)-dec-4-enoic (G), (4Z,7Z)-deca-4,7-dienoic (H), (R)-3,7-dimethyloct-6-enoic (I), (R)-4,8-dimethylnon-7-enoic (J), (2R,6S)-2,6,10-trimethylundec-9-enoic (K), and (2R,5E)-2,6,10-trimethylundeca-5,9-dienoic acids (L). Several additional acids, occurring in trace amounts only, were tentatively identified by MS. The elucidation of the absolute configuration of the acids was performed by GC on chiral phases. Individual tuatara show specific mixtures of glycerides with up to 100 components. The individual mixtures may permit individual recognition because the bouquets seem to be stable over years.

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Cited by 7 publications

References 13 publications

Structure–Odor Relationships of (Z)-3-Alken-1-ols, (Z)-3-Alkenals, and (Z)-3-Alkenoic Acids

Structure–Odor Relationships of (Z)-3-Alken-1-ols, (Z)-3-Alkenals, and (Z)-3-Alkenoic Acids

Variation of Clasper Scent Gland Composition of Heliconius Butterflies from a Biodiversity Hotspot

Composition of the Cloacal Gland Secretion of Tuatara, Sphenodon punctatus

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