2,5-DialkyItetrahydrofurans, Common Components of the Cuticular Lipids of Lepidoptera

Schulz, Stefan; Beccaloni, George; Nishida, Ritsuo; Roisin, Yves; Vane‐Wright, R. I.; McNeil, Jeremy N.

doi:10.1515/znc-1998-1-219

Cited by 15 publications

(12 citation statements)

References 4 publications

(4 reference statements)

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“…The ion m/z 85 was predominant in the mass spectrum of the natural Me ester, in contrast to a reference mass spectrum of the x-1-methyl isomer methyl 6-methylheptanoate [36], leaving methyl 4-methylheptanoate as the most likely structure. The structure of ester E was, therefore, assigned to be 14methylheptadecyl 4-methylheptanote (5). The alcohol part of ester D (m/z 238) was identified similarly as 1-heptadecanol because both the TMS derivative as well as the pyridin-3-ylmethyl derivative revealed an unbranched chain (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…It serves important functions, such as preventing desiccation and unregulated water uptake [1] as well as various other tasks [2]. The dominating class of compounds constituting this wax layer in insects are hydrocarbons, varying largely in chain length, number of methyl branches, and number of double bonds [4], although other compounds, such as esters, alcohols, aldehydes, THFs [5], etc., occur as well [6] and can also carry information [7] [8]. The dominating class of compounds constituting this wax layer in insects are hydrocarbons, varying largely in chain length, number of methyl branches, and number of double bonds [4], although other compounds, such as esters, alcohols, aldehydes, THFs [5], etc., occur as well [6] and can also carry information [7] [8].…”

Section: Introductionmentioning

confidence: 99%

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Identification and Synthesis of Branched Wax‐type Esters, Novel Surface Lipids from the Spider Argyrodes elevatus (Araneae: Theridiidae)

Chinta

Goller

Uhl³

et al. 2016

Chemistry & Biodiversity

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The analysis of cuticular extracts from the kleptoparasitic spider Argyrodes elevatus revealed the presence of unusual esters, new for arthropods. These novel compounds proved to be methyl-branched long-chain fatty acid esters with methyl branches located either close or remote from the internally located ester group. The GC/MS analysis of the prosoma lipid blend from the male cuticle contained one major component, undecyl 2-methyltridecanoate (1). In contrast, four major wax-type esters, 2-methylundecyl 2,8-dimethylundecanoate (2), 2,8-dimethylundecyl 2,8-dimethylundecanoate (3), heptadecyl 4-methylheptanoate (4), and 14-methylheptadecyl 4-methylheptanoate (5), were identified in the lipid blend of female prosomata. Structure assignments were based on mass spectra, gas chromatographic retention indices, and microderivatization. Unambiguous proof of postulated structures was ensured by an independent synthesis of all five esters. Preferentially, odd-numbered carbon chains pointed to a distinct biosynthetic pathway, different from that of common fatty acids, because one or two C starter units are incorporated during the biosynthesis of all acid and alcohol building blocks present in the five esters. The striking sexual dimorphism together with the unique biosynthesis points to a function of the esters in chemical communication of the spiders, although no behavioral data are currently available to test this assumption.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Identification and Synthesis of Branched Wax‐type Esters, Novel Surface Lipids from the Spider Argyrodes elevatus (Araneae: Theridiidae)

Chinta

Goller

Uhl³

et al. 2016

Chemistry & Biodiversity

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“…The same is true for 2,5dialkyltetrahydrofurans such as 2-nonyl-5-octadecyltetrahydrofuran, commonly found on the cuticle of butterflies. [53] About 550 compounds of the 775 detected occurred at least three times within the samples, of which 360 were identified. The unknowns were, to a large extent, esters with a known acyl part or hydrocarbons, usually occurring in small amounts.…”

Section: Compound Identificationmentioning

confidence: 99%

Identification and Composition of Clasper Scent Gland Components of the Butterfly Heliconius erato and Its Relation to Mimicry

et al. 2021

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Dedicated to the memory of Wittko Francke.The butterfly Heliconius erato occurs in various mimetic morphs. The male clasper scent gland releases an anti-aphrodisiac pheromone and additionally contains a complex mixture of up to 350 components, varying between individuals. In 114 samples of five different mimicry groups and their hybrids 750 different compounds were detected by gas chromatography/ mass spectrometry (GC/MS). Many unknown components occurred, which were identified using their mass spectra, gas chromatography/infrared spectroscopy (GC/IR)-analyses, derivatization, and synthesis. Key compounds proved to be various esters of 3-oxohexan-1-ol and (Z)-3-hexen-1-ol with (S)-2,3-dihydrofarnesoic acid, accompanied by a large variety of other esters with longer terpene acids, fatty acids, and various alcohols. In addition, linear terpenes with up to seven uniformly connected isoprene units occur, e. g. farnesylfarnesol. A large number of the compounds have not been reported before from nature. Discriminant analyses of principal components of the gland contents showed that the iridescent mimicry group differs strongly from the other, mostly also separated, mimicry groups. Comparison with data from other species indicated that Heliconius recruits different biosynthetic pathways in a speciesspecific manner for semiochemical formation.

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“…When comparing the results in this study with a previous comprehensive study of CSGs by us (Estrada et al 2011), CSGs usually contain some compounds of higher volatility (RI < 1800) than those found in the wing androconia. They are embedded in a less volatile mixture of esters as well as cuticular alkanes and dialkyltetrahydrofurans (Schulz et al 1998).…”

Section: Wing Androconial Vs Clasper Scent Glands Compoundsmentioning

confidence: 99%

The Scent Chemistry of Heliconius Wing Androconia

et al. 2017

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Neotropical Heliconius butterflies are members of various mimicry rings characterized by diverse colour patterns. In the present study we investigated whether a similar diversity is observed in the chemistry of volatile compounds present in male wing androconia. Recent research has shown that these androconia are used during courting of females. Three to five wild-caught male Heliconius individuals of 17 species and subspecies were analyzed by GC/MS. Most of the identified compounds originate from common fatty acids precursors, including aldehydes, alcohols, acetates or esters preferentially with a C and C chain, together with some alkanes. The compounds occurred in species-specific mixtures or signatures. For example, octadecanal is characteristic for H. melpomene, but variation in composition between the individuals was observed. Cluster analysis of compound occurrence in individual bouquets and analyses based on biosynthetic motifs such as functional group, chain length, or basic carbon-backbone modification were used to reveal structural patterns. Mimetic pairs contain different scent bouquets, but also some compounds in common, whereas sympatric species, both mimetic and non-mimetic, have more distinct compound compositions. The compounds identified here may play a role in mate choice thus helping maintain species integrity in a butterfly genus characterized by pervasive interspecific gene flow.

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2,5-DialkyItetrahydrofurans, Common Components of the Cuticular Lipids of Lepidoptera

Cited by 15 publications

References 4 publications

Identification and Synthesis of Branched Wax‐type Esters, Novel Surface Lipids from the Spider Argyrodes elevatus (Araneae: Theridiidae)

Identification and Synthesis of Branched Wax‐type Esters, Novel Surface Lipids from the Spider Argyrodes elevatus (Araneae: Theridiidae)

Identification and Composition of Clasper Scent Gland Components of the Butterfly Heliconius erato and Its Relation to Mimicry

The Scent Chemistry of Heliconius Wing Androconia

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