Male-Produced Sex Pheromone of Tibraca limbativentris Revisited: Absolute Configurations of Zingiberenol Stereoisomers and their Influence on Chemotaxis Behavior of Conspecific Females
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 co...
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| Veröffentlicht in: | Journal of chemical ecology 2020, Vol.46 (1), p.1-9 |
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| creator | Blassioli-Moraes, M. C. Khrimian, A. Michereff, M. F. F. Magalhães, 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. |
| description | 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 (3
S
,6
S
,7
R
)-1,10-bisaboladien-3-ol (
1
) and (3
R
,6
S
,7
R
)-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 (3
S
,6
S
,7
R
) isomer
1
was essential for attraction of
T. limbativentris
females, but the minor (3
R
,6
S
,7
R
) isomer
2
was not, nor did it show synergistic/antagonistic effects when added to the major isomer. The (1
S
,6
S
,7
R
) and (1
R
,6
S
,7
R
) stereoisomers of sesquipepiritol also attracted
T. limbativentris
females. |
| doi_str_mv | 10.1007/s10886-019-01125-w |
| format | Article |
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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 (3
S
,6
S
,7
R
)-1,10-bisaboladien-3-ol (
1
) and (3
R
,6
S
,7
R
)-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 (3
S
,6
S
,7
R
) isomer
1
was essential for attraction of
T. limbativentris
females, but the minor (3
R
,6
S
,7
R
) isomer
2
was not, nor did it show synergistic/antagonistic effects when added to the major isomer. The (1
S
,6
S
,7
R
) and (1
R
,6
S
,7
R
) stereoisomers of sesquipepiritol also attracted
T. limbativentris
females.</description><identifier>ISSN: 0098-0331</identifier><identifier>EISSN: 1573-1561</identifier><identifier>DOI: 10.1007/s10886-019-01125-w</identifier><identifier>PMID: 31840210</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Agriculture ; Air entrainment ; Animals ; Behavior, Animal - drug effects ; Bioassays ; Biochemistry ; Biological Microscopy ; Biomedical and Life Sciences ; Chemotaxis ; Chromatography, Gas ; Configurations ; Ecology ; Entomology ; Entrainment ; Female ; Females ; Heteroptera - chemistry ; Heteroptera - metabolism ; Isomers ; Life Sciences ; Male ; Pheromones ; Sesquiterpenes ; Sesquiterpenes - chemistry ; Sesquiterpenes - pharmacology ; Sex ; Sex Attractants - chemistry ; Sex Attractants - pharmacology ; Sex pheromone ; Sexes ; Stereoisomerism ; Stereoisomers ; Volatile Organic Compounds - analysis ; Volatile Organic Compounds - chemistry</subject><ispartof>Journal of chemical ecology, 2020, Vol.46 (1), p.1-9</ispartof><rights>Springer Science+Business Media, LLC, part of Springer Nature 2019</rights><rights>Journal of Chemical Ecology is a copyright of Springer, (2019). All Rights Reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c375t-b8151a59e095f829c1b5b0fa3e5470a1b75e65b2486ef73e7067aa2ce0e26e793</citedby><cites>FETCH-LOGICAL-c375t-b8151a59e095f829c1b5b0fa3e5470a1b75e65b2486ef73e7067aa2ce0e26e793</cites><orcidid>0000-0003-3364-9677</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s10886-019-01125-w$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s10886-019-01125-w$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31840210$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Blassioli-Moraes, M. C.</creatorcontrib><creatorcontrib>Khrimian, A.</creatorcontrib><creatorcontrib>Michereff, M. F. F.</creatorcontrib><creatorcontrib>Magalhães, D. M.</creatorcontrib><creatorcontrib>Hickel, E.</creatorcontrib><creatorcontrib>de Freitas, T. F. S.</creatorcontrib><creatorcontrib>Barrigossi, J. A. F.</creatorcontrib><creatorcontrib>Laumann, R. A.</creatorcontrib><creatorcontrib>Silva, A. T.</creatorcontrib><creatorcontrib>Guggilapu, S. D.</creatorcontrib><creatorcontrib>Silva, C. C.</creatorcontrib><creatorcontrib>Sant’Ana, J.</creatorcontrib><creatorcontrib>Borges, M.</creatorcontrib><title>Male-Produced Sex Pheromone of Tibraca limbativentris Revisited: Absolute Configurations of Zingiberenol Stereoisomers and their Influence on Chemotaxis Behavior of Conspecific Females</title><title>Journal of chemical ecology</title><addtitle>J Chem Ecol</addtitle><addtitle>J Chem Ecol</addtitle><description>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 (3
S
,6
S
,7
R
)-1,10-bisaboladien-3-ol (
1
) and (3
R
,6
S
,7
R
)-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 (3
S
,6
S
,7
R
) isomer
1
was essential for attraction of
T. limbativentris
females, but the minor (3
R
,6
S
,7
R
) isomer
2
was not, nor did it show synergistic/antagonistic effects when added to the major isomer. The (1
S
,6
S
,7
R
) and (1
R
,6
S
,7
R
) stereoisomers of sesquipepiritol also attracted
T. limbativentris
females.</description><subject>Agriculture</subject><subject>Air entrainment</subject><subject>Animals</subject><subject>Behavior, Animal - drug effects</subject><subject>Bioassays</subject><subject>Biochemistry</subject><subject>Biological Microscopy</subject><subject>Biomedical and Life Sciences</subject><subject>Chemotaxis</subject><subject>Chromatography, Gas</subject><subject>Configurations</subject><subject>Ecology</subject><subject>Entomology</subject><subject>Entrainment</subject><subject>Female</subject><subject>Females</subject><subject>Heteroptera - chemistry</subject><subject>Heteroptera - metabolism</subject><subject>Isomers</subject><subject>Life Sciences</subject><subject>Male</subject><subject>Pheromones</subject><subject>Sesquiterpenes</subject><subject>Sesquiterpenes - chemistry</subject><subject>Sesquiterpenes - pharmacology</subject><subject>Sex</subject><subject>Sex Attractants - chemistry</subject><subject>Sex Attractants - pharmacology</subject><subject>Sex pheromone</subject><subject>Sexes</subject><subject>Stereoisomerism</subject><subject>Stereoisomers</subject><subject>Volatile Organic Compounds - analysis</subject><subject>Volatile Organic Compounds - chemistry</subject><issn>0098-0331</issn><issn>1573-1561</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><recordid>eNp9kc1u1DAUhS0EokPhBVggS2zYhF7bcZywKyNaKhVR0bJhE9nOzYyrxJ7aybS8GY9XT6eAxIKFZUv-zo90CHnN4D0DUEeJQV1XBbAmH8ZlcfuELJhUomCyYk_JAqCpCxCCHZAXKV0DAK9q-ZwcCFaXwBksyK8vesDiIoZuttjRS7yjF2uMYQweaejplTNRW00HNxo9uS36KbpEv-HWJTdh94EemxSGeUK6DL53qzlmLPi0E_9wfuUMRvRhoJdTfgSXwogxUe07Oq3RRXrm-2FGb3Ocp8s1jmHSdzniI6711oW4M8rWaYPW9c7SExxz5fSSPOv1kPDV431Ivp98ulp-Ls6_np4tj88LK5ScClMzybRsEBrZ17yxzEgDvRYoSwWaGSWxkoaXdYW9EqigUlpzi4C8QtWIQ_Ju77uJ4WbGNLWjSxaHQXsMc2q54Epkrqoy-vYf9DrM0ed2mSp5mZuUMlN8T9kYUorYt5voRh1_tgza3a7tftc279o-7NreZtGbR-vZjNj9kfweMgNiD6T85VcY_2b_x_YePESx7Q</recordid><startdate>2020</startdate><enddate>2020</enddate><creator>Blassioli-Moraes, M. 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C. ; Khrimian, A. ; Michereff, M. F. F. ; Magalhães, 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.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c375t-b8151a59e095f829c1b5b0fa3e5470a1b75e65b2486ef73e7067aa2ce0e26e793</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Agriculture</topic><topic>Air entrainment</topic><topic>Animals</topic><topic>Behavior, Animal - drug effects</topic><topic>Bioassays</topic><topic>Biochemistry</topic><topic>Biological Microscopy</topic><topic>Biomedical and Life Sciences</topic><topic>Chemotaxis</topic><topic>Chromatography, Gas</topic><topic>Configurations</topic><topic>Ecology</topic><topic>Entomology</topic><topic>Entrainment</topic><topic>Female</topic><topic>Females</topic><topic>Heteroptera - chemistry</topic><topic>Heteroptera - metabolism</topic><topic>Isomers</topic><topic>Life Sciences</topic><topic>Male</topic><topic>Pheromones</topic><topic>Sesquiterpenes</topic><topic>Sesquiterpenes - chemistry</topic><topic>Sesquiterpenes - pharmacology</topic><topic>Sex</topic><topic>Sex Attractants - chemistry</topic><topic>Sex Attractants - pharmacology</topic><topic>Sex pheromone</topic><topic>Sexes</topic><topic>Stereoisomerism</topic><topic>Stereoisomers</topic><topic>Volatile Organic Compounds - analysis</topic><topic>Volatile Organic Compounds - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Blassioli-Moraes, M. 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C.</creatorcontrib><creatorcontrib>Sant’Ana, J.</creatorcontrib><creatorcontrib>Borges, M.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Animal Behavior Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Ecology Abstracts</collection><collection>Entomology Abstracts (Full archive)</collection><collection>Toxicology Abstracts</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Science Database (Alumni Edition)</collection><collection>ProQuest Pharma Collection</collection><collection>Public Health Database</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>Natural Science Collection</collection><collection>Earth, Atmospheric & Aquatic Science Collection</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>Engineering Research Database</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Materials Science Database</collection><collection>ProQuest Biological Science Collection</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Science Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biological Science Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Earth, Atmospheric & Aquatic Science Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central Basic</collection><collection>Genetics Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of chemical ecology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Blassioli-Moraes, M. C.</au><au>Khrimian, A.</au><au>Michereff, M. F. F.</au><au>Magalhães, D. M.</au><au>Hickel, E.</au><au>de Freitas, T. F. S.</au><au>Barrigossi, J. A. F.</au><au>Laumann, R. A.</au><au>Silva, A. T.</au><au>Guggilapu, S. D.</au><au>Silva, C. C.</au><au>Sant’Ana, J.</au><au>Borges, M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Male-Produced Sex Pheromone of Tibraca limbativentris Revisited: Absolute Configurations of Zingiberenol Stereoisomers and their Influence on Chemotaxis Behavior of Conspecific Females</atitle><jtitle>Journal of chemical ecology</jtitle><stitle>J Chem Ecol</stitle><addtitle>J Chem Ecol</addtitle><date>2020</date><risdate>2020</risdate><volume>46</volume><issue>1</issue><spage>1</spage><epage>9</epage><pages>1-9</pages><issn>0098-0331</issn><eissn>1573-1561</eissn><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 (3
S
,6
S
,7
R
)-1,10-bisaboladien-3-ol (
1
) and (3
R
,6
S
,7
R
)-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 (3
S
,6
S
,7
R
) isomer
1
was essential for attraction of
T. limbativentris
females, but the minor (3
R
,6
S
,7
R
) isomer
2
was not, nor did it show synergistic/antagonistic effects when added to the major isomer. The (1
S
,6
S
,7
R
) and (1
R
,6
S
,7
R
) stereoisomers of sesquipepiritol also attracted
T. limbativentris
females.</abstract><cop>New York</cop><pub>Springer US</pub><pmid>31840210</pmid><doi>10.1007/s10886-019-01125-w</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0003-3364-9677</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0098-0331 |
| ispartof | Journal of chemical ecology, 2020, Vol.46 (1), p.1-9 |
| issn | 0098-0331 1573-1561 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2327379366 |
| source | MEDLINE; SpringerLink Journals - AutoHoldings |
| subjects | Agriculture Air entrainment Animals Behavior, Animal - drug effects Bioassays Biochemistry Biological Microscopy Biomedical and Life Sciences Chemotaxis Chromatography, Gas Configurations Ecology Entomology Entrainment Female Females Heteroptera - chemistry Heteroptera - metabolism Isomers Life Sciences Male Pheromones Sesquiterpenes Sesquiterpenes - chemistry Sesquiterpenes - pharmacology Sex Sex Attractants - chemistry Sex Attractants - pharmacology Sex pheromone Sexes Stereoisomerism Stereoisomers Volatile Organic Compounds - analysis Volatile Organic Compounds - chemistry |
| title | Male-Produced Sex Pheromone of Tibraca limbativentris Revisited: Absolute Configurations of Zingiberenol Stereoisomers and their Influence on Chemotaxis Behavior of Conspecific Females |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-05T14%3A21%3A02IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Male-Produced%20Sex%20Pheromone%20of%20Tibraca%20limbativentris%20Revisited:%20Absolute%20Configurations%20of%20Zingiberenol%20Stereoisomers%20and%20their%20Influence%20on%20Chemotaxis%20Behavior%20of%20Conspecific%20Females&rft.jtitle=Journal%20of%20chemical%20ecology&rft.au=Blassioli-Moraes,%20M.%20C.&rft.date=2020&rft.volume=46&rft.issue=1&rft.spage=1&rft.epage=9&rft.pages=1-9&rft.issn=0098-0331&rft.eissn=1573-1561&rft_id=info:doi/10.1007/s10886-019-01125-w&rft_dat=%3Cproquest_cross%3E2327379366%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2342415145&rft_id=info:pmid/31840210&rfr_iscdi=true |