Chemoecology最新文献

{"title":"Isolation and identification of volatile compounds from a protein-based food lure: electrophysiological and behavioral responses of Bactrocera oleae adults","authors":"Aikaterini Psoma,&nbsp;Eirini Anastasaki,&nbsp;Georgios Partsinevelos,&nbsp;Panagiotis Milonas","doi":"10.1007/s00049-023-00388-w","DOIUrl":"10.1007/s00049-023-00388-w","url":null,"abstract":"<div><p>The olive fly, <i>Bactrocera oleae</i> (Rossi) (Diptera: Tephritidae), is the major insect pest for olive production in the Mediterranean basin and worldwide. Monitoring of its populations is vital for efficient management to avoid yield losses. Olive fly adults are attracted to protein-based food lures. Various protein-based lures are used either for monitoring olive fly populations or for pest management in combination with insecticides. We used two techniques, i.e., dynamic headspace (DHS) and solid-phase microextraction, (SPME) for headspace collection of volatile organic compounds (VOCs) emitted from a commercially available protein-based food lure to identify specific VOCs that attract the olive flies. The collected VOCs were identified with GC–MS and electroantennographically tested with GC–EAD. Both sampling methods isolated a substantial number of VOCs but certain compounds were detected by only one of the two methods. In SPME, more alkyl-substituted pyrazines were detected rather than in DHS. VOCs from various chemical classes provoked electroantennographic responses. Μature mated females gave more responses compared to virgin ones. Both age groups of <i>B. oleae</i> female adults showed electrophysiological responses to 2,5-dimethyl-pyrazine which had lower abundance than the major compound 2,3,5-trimethyl pyrazine. Selected compounds were tested in field trials for attraction of olive fly adults. The highest number of olive fly adults was caught with sticky traps baited with the terpene nonanal. The importance of the collection method in identifying VOCs that might contribute to better monitoring and management of olive fly populations in the field is discussed.</p></div>","PeriodicalId":515,"journal":{"name":"Chemoecology","volume":"33 5","pages":"99 - 112"},"PeriodicalIF":1.8,"publicationDate":"2023-07-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"6551524","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"环境科学与生态学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Changes to volatile profiles of arborvitae, Thuja occidentalis, from drought and insect infestation: olfactory cues for the cypress bark beetle, Phloeosinus aubei","authors":"Gábor Bozsik,&nbsp;Béla Péter Molnár,&nbsp;Michael J. Domingue,&nbsp;Gábor Szőcs","doi":"10.1007/s00049-023-00389-9","DOIUrl":"10.1007/s00049-023-00389-9","url":null,"abstract":"<div><p>The cypress bark beetle, <i>Phloeosinus aubei</i> (Coleoptera, Curculionidae, Scolytinae) prefers to build breeding galleries in decaying host trees. However, volatile cues specific to decaying or actively infested trees have not yet been reported. Any such information would be useful for the management of this invasive, wood-boring species that has become established across Europe in the temperate zone and is now a key pest of ornamental Cupressaceae in nurseries and urban landscapes. Our objective was to reveal key components in host volatiles specific to stressed trees, which could be potential signals for the pest of its suitability for colonisation. Volatile profiles of arborvitae, <i>Thuja occidentalis</i> ‘Smaragd’ suffering from either dehydration or fresh infestation of <i>P. aubei</i> was collected and compared to that samples from healthy control trees. Analyses of volatiles by gas chromatography coupled to an electroantennographic detector revealed substantial differences between healthy, dehydrated and infested trees. Structural elucidation of the major antennally active components revealed that both α-pinene and α-thujene were prevalent in the volatiles of infested trees, whilst α-thujone was the major component in volatiles of healthy trees. In volatiles collected from trunks housing fresh <i>P. aubei</i> female nuptial chambers, sharp increases of β-pinene, myrcene, limonene, and p-cymene were noticed, alongside trace amounts of camphene and fenchene. Volatiles collected from fresh frass showed a similar profile, but with a somewhat smaller amount of limonene. Fenchone was present in each type of volatiles, however, only in low amounts. Further studies should be directed to reveal the behavioural role of these components, which could be helpful in developing kairomone-based techniques for monitoring the flight of the pest in stands of scale-leafed trees.</p></div>","PeriodicalId":515,"journal":{"name":"Chemoecology","volume":"33 5","pages":"113 - 124"},"PeriodicalIF":1.8,"publicationDate":"2023-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s00049-023-00389-9.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"6551793","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"环境科学与生态学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Leaf surface traits may influence host specificity in psyllids of Eucalyptus, Spondyliaspis cf. plicatuloides (Froggatt) and Glycaspis brimblecombei Moore (Hemiptera: Aphalaridae)","authors":"Privilege T. Makunde,&nbsp;Johannes C. Joubert,&nbsp;Bernard Slippers,&nbsp;Brett P. Hurley,&nbsp;Almuth Hammerbacher","doi":"10.1007/s00049-023-00387-x","DOIUrl":"10.1007/s00049-023-00387-x","url":null,"abstract":"<div><p><i>Spondyliaspis</i> cf. <i>plicatuloides</i> and <i>Glycaspis brimblecombei</i> (Hemiptera: Aphalaridae) are invasive insect pests of <i>Eucalyptus</i>, native to Australia. The insects feed on eucalypt sap, and both psyllid species exhibit clear preferences for different species and hybrids of <i>Eucalyptus</i>. The objective of this study was to identify the constitutive morphological and phytochemical characteristics underlying these host preferences. Four preferred and eight non-preferred eucalypt hosts were selected for evaluation. Thirteen leaf morphological features of the 12 eucalypts were analysed. The non-polar and polar metabolites in and on the surface of leaves of each eucalypt species were extracted, and their chemical composition was analysed using gas chromatography coupled with mass spectrometry. The leaf volatile profiles of hosts and non-hosts of <i>S</i>. cf. <i>plicatuloides</i> and <i>G. brimblecombei</i> did not differ sufficiently to explain the host choices of the two eucalypt psyllids. The leaf polar metabolite profiles of the susceptible hosts of the two psyllids differed significantly but did not explain the host preferences of the two psyllid species. However, preferred hosts of <i>S</i>. cf. <i>plicatuloides</i> and <i>G. brimblecombei</i> had some leaf morphological features and wax metabolites in common. Our results show that particular combinations of leaf morphological features and wax metabolites might influence the host choice of eucalypt-feeding lerp psyllids, but no traits explaining the differences in host-selection behaviour between <i>S</i>. cf. <i>plicatuloides</i> and <i>G. brimblecombei</i> were identified.</p></div>","PeriodicalId":515,"journal":{"name":"Chemoecology","volume":"33 3-4","pages":"83 - 98"},"PeriodicalIF":1.8,"publicationDate":"2023-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s00049-023-00387-x.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4935185","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"环境科学与生态学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"After chemo-metamorphosis: p-menthane monoterpenoids characterize the oil gland secretion of adults of the oribatid mite, Nothrus palustris","authors":"Günther Raspotnig,&nbsp;Michaela Bodner,&nbsp;David Fröhlich,&nbsp;Julia Blesl,&nbsp;Edith Stabentheiner,&nbsp;Olaf Kunert","doi":"10.1007/s00049-023-00386-y","DOIUrl":"10.1007/s00049-023-00386-y","url":null,"abstract":"<div><p>The oil gland secretion of the oribatid mite <i>Nothrus palustris</i> is known to show the phenomenon of juvenile–adult polymorphism, i.e., juvenile instars produce secretions predominated by geranial, whereas adults secrete dehydrocineole along with a number of chemically unidentified compounds. We here re-analyzed the secretions of adult <i>N. palustris</i> by GC–MS and NMR spectroscopy, eventually identifying the unknown compounds as <i>p</i>-menthane monoterpenoids. The major components were two isomeric 6-isopropenyl-3-methyl-cyclohex-3-en-1-yl formates (= <i>p</i>-1,8-menthadien-5-yl formates), which accounted for about 75% of the secretion. These were accompanied by five additional, only partly identified <i>p</i>-menthanes (or <i>p</i>-methane-derivatives), all of which represented minor or trace components. In addition, adult secretions contained two C₂₁-hydrocarbons, 1,12-heneicosadiene (major) and a heneicosatriene (minor). Menthane monoterpenoids represent a novel sub-class of terpene compounds in the oil gland secretions of Oribatida. In case of <i>N. palustris</i>, we assume that both geranial and <i>p</i>-menthane monoterpenoids arise via the mevalonate pathway which obviously shows a split at the level of geranyl pyrophosphate, leading to geranial in juveniles and to <i>p</i>-menthanes in adults. The significance of methane occurrence in oil glands as well as the taxonomic distribution of juvenile–adult polymorphism in oribatid oil gland secretions is discussed. The latter phenomenon—i.e., “chemo-metamorphosis” of secretions—is not known from early- and middle-derivative Oribatida nor from Astigmata, but appears to be more common in some derivative desmonomatan and brachypyline oribatid groups.</p></div>","PeriodicalId":515,"journal":{"name":"Chemoecology","volume":"33 3-4","pages":"71 - 82"},"PeriodicalIF":1.8,"publicationDate":"2023-07-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s00049-023-00386-y.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4791223","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"环境科学与生态学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Gregarious mature male-specific volatiles and the semivolatile cuticular hydrocarbon fraction of the South American locust, Schistocerca cancellata","authors":"Karsten Seidelmann,&nbsp;Christiane Stahr","doi":"10.1007/s00049-023-00385-z","DOIUrl":"10.1007/s00049-023-00385-z","url":null,"abstract":"<div><p>The South American locust, <i>Schistocerca cancellata</i> (Serville 1838), is considered to be the most serious agricultural pest in Argentina and neighboring countries. The species is famous for the strong and pleasant aromatic scent of mature males in the gregarious phase. We identified this fragrance as a mixture of two main aromatic compounds, benzyl alcohol, and 2-phenylethanol. The male-specific volatiles are emitted almost exclusively from the abdomen. The release of the male volatiles is linked to sexual maturity and is influenced by the intensity of sexual competition between males. Consequently, a function of the volatiles as a gregarious mature male-emitted pheromone in the context of reproduction is obvious. No female-specific volatiles were found. Some compounds of the semivolatile fraction of the cuticular hydrocarbon (CHC) profile were also detected in the headspace of both sexes. This fraction of the CHCs of <i>S. cancellata</i> consists almost entirely of unbranched C23 to C31 alkanes. The profiles vary slightly between the sexes and differ from the reference profile of the prominent and well-studied species <i>S. gregaria</i>. Thus, semivolatile components of the CHCs may also play an important role in the short-range mate recognition system of the species.</p></div>","PeriodicalId":515,"journal":{"name":"Chemoecology","volume":"33 3-4","pages":"63 - 70"},"PeriodicalIF":1.8,"publicationDate":"2023-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s00049-023-00385-z.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4464791","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"环境科学与生态学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Straight-chain alkanes derived from leaf waxes stimulate feeding behaviors in a cucurbit leaf beetle, Aulacophora femolaris (Chrysomelidae, Coleoptera)","authors":"Ittetsu Kamata,&nbsp;Yoko Inui,&nbsp;Shoko Sakai","doi":"10.1007/s00049-023-00384-0","DOIUrl":"10.1007/s00049-023-00384-0","url":null,"abstract":"<div><p>The importance of plant cuticular waxes in plant–herbivore interactions has become an area of increasing interest, but it has been poorly explored in chrysomelid beetles, one of the most important groups of insect pests. In this study, we investigated the effects of cuticular wax on feeding behaviors of <i>Aulacophora femoralis</i> (Chyrosomelidae), a pest of Cucurbitaceae crops. We analyzed chemical compositions of leaf cuticular waxes using gas chromatography–mass spectrometry. The compositions were significantly different among plant species; in particular, host (<i>Cucumis maxima</i>, <i>C. pepo</i>, <i>C. sativus</i>, Cucurbitaceae) and non-host (<i>Pueraria lobata</i>, Fabaceae) leaves had distinctive compositions of cuticular waxes. We examined if the cuticular wax induces feeding behaviors based on a bioassay using filter papers treated with cuticular wax extract from host or non-host leaves, or a synthetic mixture of straight-chain alkanes (<i>n</i>-alkanes), major components of the host cuticular waxes shared among different host species. We found that the beetles frequently left bite marks on the filter papers treated with <i>n</i>-alkanes but less frequently on those treated with cuticular wax extracts of host leaves. These results indicate that leaf cuticular wax <i>n</i>-alkanes stimulate feeding behavior, but are not cues for host selection.</p></div>","PeriodicalId":515,"journal":{"name":"Chemoecology","volume":"33 3-4","pages":"55 - 61"},"PeriodicalIF":1.8,"publicationDate":"2023-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4211670","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"环境科学与生态学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Attraction of Pissodes castaneus (Coleoptera, Curculionidae) to Pinus taeda: laboratory and field evaluation","authors":"Gustavo Frensch,&nbsp;Scheila R. M. Zaleski,&nbsp;Renan R. Schorr,&nbsp;Liliane G. Dantas,&nbsp;Marina Krasniak,&nbsp;Sonia M. N. Lazzari,&nbsp;Beatriz H. L. N. S. Maia,&nbsp;Francisco A. Marques","doi":"10.1007/s00049-023-00383-1","DOIUrl":"10.1007/s00049-023-00383-1","url":null,"abstract":"<div><p>Coniferous trees of the genus <i>Pinus</i> (Pinaceae) are under continuous threats by numerous herbivorous insect species and pathogens attacking nearly all parts and tissues of the plants. To defend themselves, pine trees produce large amounts of oleoresin that is accumulated in a highly developed network of specialized resin ducts, which are distributed in the wood, bark, and needles. Such defense reactions in pines can be induced by the attack of herbivores. The banded pine weevil, <i>Pissodes castaneus</i> (De Geer, 1775) (Coleoptera, Curculionidae), is an important pest of <i>Pinus</i> in Brazil, where it has been an invasive species since 2001. The female lays its eggs under the tree bark of trees and the larvae feed in the phloem of the trunk and branches, interrupting the sap circulation and eventually causing its death. In the present study, we conducted detailed GC–MS analyses of volatiles emitted by twigs of <i>Pinus taeda L</i>. We analyzed how the attack by <i>P. castaneus</i> males and females affects the volatile pattern emitted by the twigs. When comparing volatiles produced by healthy plants and by female- and male-attacked <i>P. taeda</i>, qualitative and quantitative differences were detected, as the decreased production of limonene, germacrene D and (<i>E</i>)-caryophyllene and the increase of α-pinene. Laboratory bioassays showed that plants attacked by male and female <i>P. castaneus</i> were more attractive to the insects. Understanding about what compounds may attract or repel the insects may help in the development of more effective traps, as well as preventing stress to avoid infestation.</p></div>","PeriodicalId":515,"journal":{"name":"Chemoecology","volume":"33 1-2","pages":"45 - 54"},"PeriodicalIF":1.8,"publicationDate":"2023-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4424661","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"环境科学与生态学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Cuticular hydrocarbon profiles in velvet ants (Hymenoptera: Mutillidae) are highly complex and do not chemically mimic their hosts","authors":"Federico Ronchetti,&nbsp;Thomas Schmitt,&nbsp;Marcello Romano,&nbsp;Carlo Polidori","doi":"10.1007/s00049-023-00382-2","DOIUrl":"10.1007/s00049-023-00382-2","url":null,"abstract":"<div><p>Although recognition using cuticular chemistry is important for host–parasite interactions within aculeate Hymenoptera, cuticular hydrocarbon (CHC) profiles of only a few host–parasite pairs were characterized and compared. One largely neglected family in this context is the Mutillidae (velvet ants), whose species are ectoparasitoids of bees and wasps. In our study, we characterized and compared the CHC profiles of five species of Mutillidae and seven host species. The CHC profile of velvet ants differed among species and included large proportions of <i>n</i>-alkanes and methyl-branched alkanes. Alkenes were much less abundant in the CHC profiles of three species of velvet ants compared with their hosts, while the other two species possess a much lower abundance of methyl-branched alkanes than their hosts. Both the number of peaks and compound diversity were generally higher in velvet ants compared with their hosts. Thus, CHC profiles of parasitoids did not show signs of mimicry when compared with their hosts. In dyadic encounters between one species of velvet ant and its host bee species, the parasitoid mainly avoided interacting, while aggression by the host was rare. Our results suggest that velvet ants did not evolve chemical mimicry, perhaps in accordance with their wide host spectrum which would limit chemical specialization. However, the reduction of alkenes in social bee-attacking species and the reduction of methyl-branched alkanes in social wasp-attacking species may favour host nest invasion, since these two CHC classes are known to be important in nestmate recognition for social bees and wasps, respectively. A larger, phylogeny-corrected comparison of Mutillidae and hosts may help clarifying the evolution of the CHC profile of these parasitoids.\u0000</p></div>","PeriodicalId":515,"journal":{"name":"Chemoecology","volume":"33 1-2","pages":"29 - 43"},"PeriodicalIF":1.8,"publicationDate":"2023-05-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s00049-023-00382-2.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4979542","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"环境科学与生态学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"The variability of iridomyrmecin, the venom of the Argentine ant, in its native and invasive ranges","authors":"Isabel Salado,&nbsp;Paloma Álvarez-Blanco,&nbsp;Raphaël Boulay,&nbsp;Olivier Blight,&nbsp;Sílvia Abril,&nbsp;Xim Cerdá,&nbsp;Elena Angulo","doi":"10.1007/s00049-023-00381-3","DOIUrl":"10.1007/s00049-023-00381-3","url":null,"abstract":"<div><p>The Argentine ant is one of the five worst invasive ants. Recently it has been shown that one of the main compounds of its pygidial gland, iridomyrmecin, is used as a venom against competitors and enemies. Here, we explore the variability in the quantities of iridomyrmecin of individual workers, along a range of locations pertaining to both its native and invasive ranges, in order to know whether its venom could have contributed to the differential invasion success of European supercolonies. We specifically compared the amount of iridomyrmecin among supercolonies in the native range and among three invasive supercolonies: the Main supercolony (the most extended worldwide), the Corsican and the Catalonian supercolonies (both with a restricted distribution in Europe). Our main result is that the variability of the iridomyrmecin is very high. Looking at mean values, we found that the amount of iridomyrmecin of the Main supercolony was the lowest while the highest corresponded to the Corsican supercolony, with the Catalonian and the native range supercolonies having intermediate values. However, variability in the values within each supercolony was similar between supercolonies. This suggests that the success of a given invasive supercolony may not be explained by higher quantities of this defensive compound. Our results open the way for exploring the connection between defensive compounds and the invasion success of this global invader.</p></div>","PeriodicalId":515,"journal":{"name":"Chemoecology","volume":"33 1-2","pages":"17 - 27"},"PeriodicalIF":1.8,"publicationDate":"2023-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s00049-023-00381-3.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4428660","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"环境科学与生态学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Chemical and evolutionary analysis of the scent gland secretions of two species of Gonyleptes Kirby, 1819 (Arachnida: Opiliones: Laniatores)","authors":"Matheus Lima Silva Vieira,&nbsp;Marcos Ryotaro Hara,&nbsp;Amanda Cruz Mendes,&nbsp;Rodrigo Hirata Willemart,&nbsp;Aline Bertinatto Cruz,&nbsp;Deborah Yara Alves Cursino dos Santos,&nbsp;Miriam Sannomiya","doi":"10.1007/s00049-023-00380-4","DOIUrl":"10.1007/s00049-023-00380-4","url":null,"abstract":"<div><p>The subfamily Gonyleptinae is the second largest in Gonyleptidae, harboring over 100 species. Gonyleptinae is polyphyletic, nestled in the clade K92, and despite its richness, several species of that subfamily have not had their chemicals of the defensive secretions analyzed. Among these are <i>Gonyleptes curticornis</i> (Mello-Leitão, 1940) and <i>G. horridus</i> Kirby, 1819, the latter being particularly important, because it is the type species of the genus, which in turn names the subfamily Gonyleptinae. <i>Gonyleptes horridus</i> is also used in many phylogenetic analyses, be it using morphological or molecular data. The chemical study of the secretions of these two species by GC–MS and ¹H NMR showed the presence of 1-(6-isopropyl-3,4-dihydro-2H-pyran-2-yl)-methylbutanone, 1-(6-isopropyl-3,4-dihydro-2H-pyran-2-yl) isobutanone and 4-methyl-1-hepten-3-one in both species. On the other hand, 4-methyl-1-hexen-3-one was observed only in <i>G. curticornis</i>, and 7-methyl-2-octanol is exclusive of <i>G. horridus</i>. All vinyl-ketones identified have already been described for Gonyleptidae. We ran an Ancestral Character State Reconstruction (ASR) analysis under three different conditions to infer the evolution of the identified compounds (based on modified characters of a previous study) and their chemical nature (multistate character, either as alkylphenol, benzoquinone or vinyl-ketone) on a modified Gonyleptidae phylogeny. Our results corroborate previous studies that alkylphenol is the ancestral most condition, changing to benzoquinone in the ancestor of Gonyleptidae or even earlier in a grassatorean ancestor depending on the analysis. Vinyl-ketones are a synapomorphy of K92. We briefly discuss character codifications and use of weights of ASR analyses of specific compounds, which were inconclusive. 1-(6-isopropyl-3,4-dihydro-2H-pyran-2-yl) isobutanone is shared by both <i>Gonyleptes</i> species and described for the genus <i>Sodreana</i> Mello-Leitão, 1922. 1-(6-(1-methyl-propyl)3,4-dihydro-2H-pyran-2yl)2-methylbutanone and 4-methyl-1-hepten-3-one are also shared by both <i>Gonyleptes</i> species and described for <i>Moreiranula saprophila</i>. From a taxonomic standpoint, combinations of specific compounds might help to diagnose supraspecific groups but given our limited sample, such decision should be taken with care and further tested. Finally, 7-methyl-2-octanol is described for the first time in Gonyleptidae, emphasizing the chemical diverse nature in the K92 clade.</p></div>","PeriodicalId":515,"journal":{"name":"Chemoecology","volume":"33 1-2","pages":"1 - 15"},"PeriodicalIF":1.8,"publicationDate":"2023-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4568103","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"环境科学与生态学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}