Identification and Synthesis of Leptotriene, a Unique Sesquiterpene Hydrocarbon from Males of the Leaffooted Bugs Leptoglossus zonatus and L. occidentalis
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| Format: | artículo biblioteca |
| Language: | English |
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ACS Publications
2022-07-25
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| Subjects: | Carbene compounds, Chemical structure, Chromatography, Ketones, Mixtures, |
| Online Access: | http://hdl.handle.net/10261/304967 http://dx.doi.org/10.13039/100000002 http://dx.doi.org/10.13039/501100007515 http://dx.doi.org/10.13039/501100014180 https://api.elsevier.com/content/abstract/scopus_id/85135941545 |
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dig-inia-es-10261-3049672024-05-15T20:42:07Z Identification and Synthesis of Leptotriene, a Unique Sesquiterpene Hydrocarbon from Males of the Leaffooted Bugs Leptoglossus zonatus and L. occidentalis Millar, Jocelyn G. Zou, Yunfan Hall, David R. Halloran, Sean Pajares, J. A. Ponce-Herrero, Laura Shates, Tessa Wilson, Houston Daane, Kent M. National Institutes of Health (US) Junta de Castilla y León Universidad de Valladolid Millar, Jocelyn G. [0000-0001-7639-9001] Pajares, J. A.[0000-0002-4682-8984] Wilson, Houston [0000-0001-7570-8618] Carbene compounds Chemical structure Chromatography Ketones Mixtures 9 Pág. The leaffooted bugs Leptoglossus zonatus and L. occidentalis (Hemiptera: Coreidae) cause substantial damage in tree nut crops in North America and pine seed orchards in North America and Europe, respectively. Sexually mature males of both species produce a number of aldehydes, esters, and sesquiterpenes, which are hypothesized to constitute an aggregation pheromone attractive to both sexes. Among the volatiles produced by males of both species, we identified a unique sesquiterpene hydrocarbon, given the common name "leptotriene" (5), which elicited strong responses from antennae of both sexes in electroantennogram assays. Here, we report its structure and its synthesis from (-)-(E)-β-caryophyllene (1). J.G.M., H.W., and K.M.D. gratefully acknowledge support for this work from the Almond Board of California and the California Pistachio Research Board. The 600 MHz Avance spectrometer was obtained with funding from National Science Foundation grant no. CHE-1626673, and the 700 MHz Avance III spectrometer was obtained with funds from National Institutes of Health grant no. S10 RR022981. J.A.P. and L.P.H. gratefully acknowledge support for this work from “Convenio de colaboración entre la Consejería de Fomento y Medio Ambiente de la Junta de Castilla y León y la Universidad de Valladolid para la realización de un estudio sobre plagas de perforadores de piñas en Pinus pinea L”. L.P.H. also acknowledges grants from the European Social Fund and from the Consejería de Educación de Castilla y León (JCyL) (ORDEN EDU/1100/2017). Peer reviewed 2023-03-30T08:05:35Z 2023-03-30T08:05:35Z 2022-07-25 artículo http://purl.org/coar/resource_type/c_6501 Journal of Natural Products 85(8): 2062–2070 (2022) 0163-3864 http://hdl.handle.net/10261/304967 10.1021/acs.jnatprod.2c00470 http://dx.doi.org/10.13039/100000002 http://dx.doi.org/10.13039/501100007515 http://dx.doi.org/10.13039/501100014180 35877168 2-s2.0-85135941545 https://api.elsevier.com/content/abstract/scopus_id/85135941545 en Instituto de Ciencias Forestales (ICIFOR) https://doi.org/10.1021/acs.jnatprod.2c00470 Sí open ACS Publications |
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Carbene compounds Chemical structure Chromatography Ketones Mixtures Carbene compounds Chemical structure Chromatography Ketones Mixtures |
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Carbene compounds Chemical structure Chromatography Ketones Mixtures Carbene compounds Chemical structure Chromatography Ketones Mixtures Millar, Jocelyn G. Zou, Yunfan Hall, David R. Halloran, Sean Pajares, J. A. Ponce-Herrero, Laura Shates, Tessa Wilson, Houston Daane, Kent M. Identification and Synthesis of Leptotriene, a Unique Sesquiterpene Hydrocarbon from Males of the Leaffooted Bugs Leptoglossus zonatus and L. occidentalis |
| description |
9 Pág. |
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National Institutes of Health (US) |
| author_facet |
National Institutes of Health (US) Millar, Jocelyn G. Zou, Yunfan Hall, David R. Halloran, Sean Pajares, J. A. Ponce-Herrero, Laura Shates, Tessa Wilson, Houston Daane, Kent M. |
| format |
artículo |
| topic_facet |
Carbene compounds Chemical structure Chromatography Ketones Mixtures |
| author |
Millar, Jocelyn G. Zou, Yunfan Hall, David R. Halloran, Sean Pajares, J. A. Ponce-Herrero, Laura Shates, Tessa Wilson, Houston Daane, Kent M. |
| author_sort |
Millar, Jocelyn G. |
| title |
Identification and Synthesis of Leptotriene, a Unique Sesquiterpene Hydrocarbon from Males of the Leaffooted Bugs Leptoglossus zonatus and L. occidentalis |
| title_short |
Identification and Synthesis of Leptotriene, a Unique Sesquiterpene Hydrocarbon from Males of the Leaffooted Bugs Leptoglossus zonatus and L. occidentalis |
| title_full |
Identification and Synthesis of Leptotriene, a Unique Sesquiterpene Hydrocarbon from Males of the Leaffooted Bugs Leptoglossus zonatus and L. occidentalis |
| title_fullStr |
Identification and Synthesis of Leptotriene, a Unique Sesquiterpene Hydrocarbon from Males of the Leaffooted Bugs Leptoglossus zonatus and L. occidentalis |
| title_full_unstemmed |
Identification and Synthesis of Leptotriene, a Unique Sesquiterpene Hydrocarbon from Males of the Leaffooted Bugs Leptoglossus zonatus and L. occidentalis |
| title_sort |
identification and synthesis of leptotriene, a unique sesquiterpene hydrocarbon from males of the leaffooted bugs leptoglossus zonatus and l. occidentalis |
| publisher |
ACS Publications |
| publishDate |
2022-07-25 |
| url |
http://hdl.handle.net/10261/304967 http://dx.doi.org/10.13039/100000002 http://dx.doi.org/10.13039/501100007515 http://dx.doi.org/10.13039/501100014180 https://api.elsevier.com/content/abstract/scopus_id/85135941545 |
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