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J Chem Ecol

Title:		Male-Produced Sex Pheromone of Tibraca limbativentris Revisited: Absolute Configurations of Zingiberenol Stereoisomers and their Influence on Chemotaxis Behavior of Conspecific Females
Author(s):		Blassioli-Moraes MC; Khrimian A; Michereff MFF; Magalhaes DM; Hickel E; De Freitas TFS; Barrigossi JAF; Laumann RA; Silva AT; Guggilapu SD; Silva CC; Sant'Ana J; Borges M;
Address:		"Laboratorio de Semioquimicos, Embrapa Recursos Geneticos e Biotecnologia, Brasilia, DF, 70770-917, Brazil. Invasive Insect Biocontrol and Behavior Laboratory, USDA-ARS, NEA, Beltsville, MD, 20705, USA. Empresa de Pesquisa Agropecuaria e Extensao Rural de Santa Catarina - EPAGRI - Estacao Experimental de Itajai, Rod. Antonio Heil, 6.800 Itaipava, Itajai, SC, 88318-112, Brazil. Laboratorio de Etologia e Ecologia Quimica de Insetos, PPG-Fitotecnia, Universidade Federal do Rio Grande do Sul (UFRGS), Av. Bento Goncalves, 7712, Porto Alegre, RS, 91540-000, Brazil. Embrapa Arroz e Feijao, Rodovia GO 462, km 12, Santo Antonio de Goias, GO, 75375-000, Brazil. Faculdade de Agronomia e Medicina Veterinaria (FAV), Campus Darcy Ribeiro, Universidade de Brasilia, Brasilia, DF, 70910-900, Brazil. National Institutes of Health, National Institute of Diabetes and Digestive and Kidney Diseases, Laboratory of Bioorganic Chemistry, Bethesda, MD, 20892, USA. Laboratorio de Semioquimicos, Embrapa Recursos Geneticos e Biotecnologia, Brasilia, DF, 70770-917, Brazil. miguel.borges@embrapa.br"
Journal Title:		J Chem Ecol
Year:		2020
Volume:		20191216
Issue:		1
Page Number:		1 - 9
DOI:		10.1007/s10886-019-01125-w
ISSN/ISBN:		1573-1561 (Electronic) 0098-0331 (Linking)
Abstract:		"The rice stalk stink bug, Tibraca limbativentris, is an important rice pest in Brazil with a high invasive potential for Mexico and the USA. The sex pheromone of this species was previously identified as a combination of two stereoisomers of 1,10-bisaboladien-3-ol (zingiberenol), but the absolute configurations of these sesquiterpenes were not determined, neither were their effect(s) on T. limbativentris behavior evaluated. In this study, using two chiral columns, we compared retention times of the two natural 1,10-bisaboladien-3-ol stereoisomers from air-entrainment samples of male T. limbativentris with those of synthetic stereoisomers of 1,10-bisaboladien-3-ol. The results showed that T. limbativentris males produce (3S,6S,7R)-1,10-bisaboladien-3-ol (1) and (3R,6S,7R)-1,10-bisaboladien-3-ol (5) as their sex pheromone. Two new minor, male-specific components were also identified as cis and trans isomers of 2,10-bisaboladien-1-ol (sesquipiperitol). Y-tube olfactometer bioassays showed that the major (3S,6S,7R) isomer 1 was essential for attraction of T. limbativentris females, but the minor (3R,6S,7R) isomer 2 was not, nor did it show synergistic/antagonistic effects when added to the major isomer. The (1S,6S,7R) and (1R,6S,7R) stereoisomers of sesquipepiritol also attracted T. limbativentris females"
Keywords:		"Animals Behavior, Animal/*drug effects Chromatography, Gas Female Heteroptera/*chemistry/metabolism Male Sesquiterpenes/*chemistry/*pharmacology Sex Attractants/*chemistry/*pharmacology Stereoisomerism Volatile Organic Compounds/analysis/chemistry Attract;"
Notes:		"MedlineBlassioli-Moraes, M C Khrimian, A Michereff, M F F Magalhaes, D M Hickel, E de Freitas, T F S Barrigossi, J A F Laumann, R A Silva, A T Guggilapu, S D Silva, C C Sant'Ana, J Borges, M eng 304329/2017-7/Conselho Nacional de Desenvolvimento Cientifico e Tecnologico/ 307104/2018-4/Conselho Nacional de Desenvolvimento Cientifico e Tecnologico/ 2019/12/17 J Chem Ecol. 2020 Jan; 46(1):1-9. doi: 10.1007/s10886-019-01125-w. Epub 2019 Dec 16"