PYRROLIZIDINE ALKALOIDS IN THE ARCTIID MOTH HYALURGA-SYMA

dc.creatorTRIGO, JR
dc.creatorWITTE, L
dc.creatorBROWN, KS
dc.creatorHARTMANN, T
dc.creatorBARATA, LES
dc.date1993
dc.dateAPR
dc.date2014-12-16T11:33:56Z
dc.date2015-11-26T17:56:55Z
dc.date2014-12-16T11:33:56Z
dc.date2015-11-26T17:56:55Z
dc.date.accessioned2018-03-29T00:40:31Z
dc.date.available2018-03-29T00:40:31Z
dc.identifierJournal Of Chemical Ecology. Plenum Publ Corp, v. 19, n. 4, n. 669, n. 679, 1993.
dc.identifier0098-0331
dc.identifierWOS:A1993LA30500006
dc.identifier10.1007/BF00985000
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/58502
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/58502
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/58502
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1291359
dc.descriptionThe arctiid moth Hyalurga syma (subfamily Pericopinae) sequesters pyrrolizidine alkaloids (PAs) from its larval food plant Heliotropium transalpinum (Boraginaceae). Colorimetric quantification of total PAs in the larvae, pupae, and adults of Hyalurga revealed mean values of about 286-445 mug per individual (1.4-2.6% of dry weight). The PA mixtures found in the moth and its larval food plant were evaluated by GC-MS. Food-plant leaves were found to contain the diastereoisomeric retronecine esters indicine (IIIa), intermedine (IIIb), and lycopsamine (IIIc), and the heliotridine ester rinderine (IIId) only as minor constituents, whereas 3'-acetylrinderine (IVc) (68% of total PAs) and the respective 3'-acetyl esters of indicine (IVa) and intermedine (IVb) (both 17%) were the major alkaloids. Supinine (IIa) is detectable in traces only. The PA mixtures in eggs, larvae, pupae, and imagines of Hyalurga were identical: indicine, intermedine, and lycopsamine accompanied by considerable amounts of supinine and amabiline or coromandalinine (IIb/IIc) were the major components. Only larvae were found to store small quantities of a 3'-acetyl derivative. Rinderine and its 3'-acetyl ester were never found in the insects. Low concentrations of the arctiid-specific PA callimorphine (I) were present in larvae, pupae, and imagines. The differences in the PA patterns of the insects and their larval food plant suggest that Hyalurga is capable of modifying plant-derived PAs by inversion of the 7-OH configuration (conversion of the necine base heliotridine into retronecine), and perhaps the inversion of the 3'-OH [conversion of (+)-trachelanthic acid into (-)-viridifloric acid], although the possibility of a selective sequestration of the respective retronecine esters cannot be excluded. Some trials with the orb-weaving spider Nephila clavipes, a common neotropical predator, showed that both freshly emerged and field-caught adults of Hyalurga syma are liberated unharmed by the spider. The liberation could be related to the presence of PAs in the moths.
dc.description19
dc.description4
dc.description669
dc.description679
dc.languageen
dc.publisherPlenum Publ Corp
dc.publisherNew York
dc.relationJournal Of Chemical Ecology
dc.relationJ. Chem. Ecol.
dc.rightsfechado
dc.sourceWeb of Science
dc.subjectPYRROLIZIDINE ALKALOIDS
dc.subjectALKALOID SEQUESTRATION
dc.subjectALKALOID TRANSFORMATION
dc.subjectBORAGINACEAE
dc.subjectHELIOTROPIUM-TRANSALPINUM
dc.subjectHELIOTROPIUM-PERUVIANUM
dc.subjectLEPIDOPTERA
dc.subjectARCTIIDAE
dc.subjectPERICOPINAE
dc.subjectHYALURGA-SYMA
dc.subjectCHEMICAL DEFENSE
dc.subjectARANEIDAE
dc.subjectNEPHILA-CLAVIPES
dc.subjectORB-WEAVING SPIDER
dc.subjectBiosynthesis
dc.subjectTransformation
dc.subjectSequestration
dc.subjectLepidoptera
dc.subjectButterflies
dc.subjectInsects
dc.subjectSpider
dc.titlePYRROLIZIDINE ALKALOIDS IN THE ARCTIID MOTH HYALURGA-SYMA
dc.typeArtículos de revistas


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