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Gyrinidal: A Sesquiterpenoid Aldehyde from the Defensive Glands of Gyrinid Beetles
Three species of gyrinid beetles (Gyrinus ventralis, Dineutes hornii, and D. serrulatus) have been found to produce the nor-sesquiterpenoid aldehyde gyrinidal in the secretion of their pygidial defensive glands. This highly functionalized terpene is shown to be (E,E,E)-3,7-dimethyl-8,11-dioxo-2,6,9-...
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| Published in: | Proceedings of the National Academy of Sciences - PNAS 1972-05, Vol.69 (5), p.1208-1210 |
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| Main Authors: | , , |
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| Language: | English |
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| container_end_page | 1210 |
| container_issue | 5 |
| container_start_page | 1208 |
| container_title | Proceedings of the National Academy of Sciences - PNAS |
| container_volume | 69 |
| creator | Meinwald, J. Opheim, K. Eisner, T. |
| description | Three species of gyrinid beetles (Gyrinus ventralis, Dineutes hornii, and D. serrulatus) have been found to produce the nor-sesquiterpenoid aldehyde gyrinidal in the secretion of their pygidial defensive glands. This highly functionalized terpene is shown to be (E,E,E)-3,7-dimethyl-8,11-dioxo-2,6,9-dodecatrienal on the basis of spectral evidence and chemical degradation. While a very wide range of sesquiterpenoid structures occur in nature, gyrinidal appears to be the most highly oxidized acyclic sesquiterpene known. |
| doi_str_mv | 10.1073/pnas.69.5.1208 |
| format | article |
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This highly functionalized terpene is shown to be (E,E,E)-3,7-dimethyl-8,11-dioxo-2,6,9-dodecatrienal on the basis of spectral evidence and chemical degradation. 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While a very wide range of sesquiterpenoid structures occur in nature, gyrinidal appears to be the most highly oxidized acyclic sesquiterpene known.</description><subject>Aldehydes</subject><subject>Aldehydes - analysis</subject><subject>Aldehydes - isolation & purification</subject><subject>Aldehydes - metabolism</subject><subject>Animal Communication</subject><subject>Animal glands</subject><subject>Animals</subject><subject>Beetles</subject><subject>Chemicals</subject><subject>Chromatography</subject><subject>Chromatography, Gas</subject><subject>Chromatography, Thin Layer</subject><subject>Coleoptera</subject><subject>Female</subject><subject>Infrared Rays</subject><subject>Ketones - analysis</subject><subject>Ketones - isolation & purification</subject><subject>Ketones - metabolism</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Male</subject><subject>Mass Spectrometry</subject><subject>Mass spectroscopy</subject><subject>Nuclear magnetic resonance</subject><subject>Perianal Glands - analysis</subject><subject>Perianal Glands - metabolism</subject><subject>Pheromone glands</subject><subject>Physical Sciences: Chemistry</subject><subject>Protons</subject><subject>Secretion</subject><subject>Spectrum Analysis</subject><subject>Terpenes - analysis</subject><subject>Terpenes - isolation & purification</subject><subject>Terpenes - metabolism</subject><subject>Ultraviolet Rays</subject><issn>0027-8424</issn><issn>1091-6490</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1972</creationdate><recordtype>article</recordtype><recordid>eNp9kUtv1DAURi0EKkNhywIJyavuEq7jRxIkFtPSDkiVkHisLSe-Zlx54qmdVMy_J6MZyrBh5cV3zrWvP0JeMygZ1PzddjC5VG0pS1ZB84QsGLSsUKKFp2QBUNVFIyrxnLzI-Q4AWtnAGTkTEgTnYkG-rnbJD96a8J4u6TfM95MfMW1xiN7SZbC43lmkLsUNHddIP6LDIfsHpKtgBptpdPQ4gl4ijgHzS_LMmZDx1fE8Jz9urr9ffSpuv6w-Xy1vi57XrCkUMqucM9jyqu8FhwrA2b7jrqsBmOKojJUN651oRCdq1XYNs3UPsq470SE_Jx8Oc7dTt0Hb4zAmE_Q2-Y1JOx2N1_8mg1_rn_FBi0opJWf_4uineD9hHvXG5x7DvBfGKeuGiVZyCTNYHsA-xZwTusc7GOh9CXpfglatlnpfwiy8PX3ZI3789ZN87_1JT_2L_-XaTSGM-GucwTcH8C6PMf0lmaqB_wb596S5</recordid><startdate>19720501</startdate><enddate>19720501</enddate><creator>Meinwald, J.</creator><creator>Opheim, K.</creator><creator>Eisner, T.</creator><general>National Academy of Sciences of the United States of America</general><general>National Acad Sciences</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>19720501</creationdate><title>Gyrinidal: A Sesquiterpenoid Aldehyde from the Defensive Glands of Gyrinid Beetles</title><author>Meinwald, J. ; Opheim, K. ; Eisner, T.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3718-6e1d6ffae932cc430200fdcb3fb700163e6ad581cf484b4769b81d7c0577b4be3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1972</creationdate><topic>Aldehydes</topic><topic>Aldehydes - analysis</topic><topic>Aldehydes - isolation & purification</topic><topic>Aldehydes - metabolism</topic><topic>Animal Communication</topic><topic>Animal glands</topic><topic>Animals</topic><topic>Beetles</topic><topic>Chemicals</topic><topic>Chromatography</topic><topic>Chromatography, Gas</topic><topic>Chromatography, Thin Layer</topic><topic>Coleoptera</topic><topic>Female</topic><topic>Infrared Rays</topic><topic>Ketones - analysis</topic><topic>Ketones - isolation & purification</topic><topic>Ketones - metabolism</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Male</topic><topic>Mass Spectrometry</topic><topic>Mass spectroscopy</topic><topic>Nuclear magnetic resonance</topic><topic>Perianal Glands - analysis</topic><topic>Perianal Glands - metabolism</topic><topic>Pheromone glands</topic><topic>Physical Sciences: Chemistry</topic><topic>Protons</topic><topic>Secretion</topic><topic>Spectrum Analysis</topic><topic>Terpenes - analysis</topic><topic>Terpenes - isolation & purification</topic><topic>Terpenes - metabolism</topic><topic>Ultraviolet Rays</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Meinwald, J.</creatorcontrib><creatorcontrib>Opheim, K.</creatorcontrib><creatorcontrib>Eisner, T.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Proceedings of the National Academy of Sciences - PNAS</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Meinwald, J.</au><au>Opheim, K.</au><au>Eisner, T.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Gyrinidal: A Sesquiterpenoid Aldehyde from the Defensive Glands of Gyrinid Beetles</atitle><jtitle>Proceedings of the National Academy of Sciences - PNAS</jtitle><addtitle>Proc Natl Acad Sci U S A</addtitle><date>1972-05-01</date><risdate>1972</risdate><volume>69</volume><issue>5</issue><spage>1208</spage><epage>1210</epage><pages>1208-1210</pages><issn>0027-8424</issn><eissn>1091-6490</eissn><abstract>Three species of gyrinid beetles (Gyrinus ventralis, Dineutes hornii, and D. serrulatus) have been found to produce the nor-sesquiterpenoid aldehyde gyrinidal in the secretion of their pygidial defensive glands. This highly functionalized terpene is shown to be (E,E,E)-3,7-dimethyl-8,11-dioxo-2,6,9-dodecatrienal on the basis of spectral evidence and chemical degradation. While a very wide range of sesquiterpenoid structures occur in nature, gyrinidal appears to be the most highly oxidized acyclic sesquiterpene known.</abstract><cop>United States</cop><pub>National Academy of Sciences of the United States of America</pub><pmid>4504334</pmid><doi>10.1073/pnas.69.5.1208</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0027-8424 |
| ispartof | Proceedings of the National Academy of Sciences - PNAS, 1972-05, Vol.69 (5), p.1208-1210 |
| issn | 0027-8424 1091-6490 |
| language | eng |
| recordid | cdi_crossref_primary_10_1073_pnas_69_5_1208 |
| source | PubMed Central (Open Access); JSTOR Archival Journals |
| subjects | Aldehydes Aldehydes - analysis Aldehydes - isolation & purification Aldehydes - metabolism Animal Communication Animal glands Animals Beetles Chemicals Chromatography Chromatography, Gas Chromatography, Thin Layer Coleoptera Female Infrared Rays Ketones - analysis Ketones - isolation & purification Ketones - metabolism Magnetic Resonance Spectroscopy Male Mass Spectrometry Mass spectroscopy Nuclear magnetic resonance Perianal Glands - analysis Perianal Glands - metabolism Pheromone glands Physical Sciences: Chemistry Protons Secretion Spectrum Analysis Terpenes - analysis Terpenes - isolation & purification Terpenes - metabolism Ultraviolet Rays |
| title | Gyrinidal: A Sesquiterpenoid Aldehyde from the Defensive Glands of Gyrinid Beetles |
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