Andrena wilkella male bees discriminate between enantiomers of cephalic secretion components

Diastereomers of the spiroacetal, 2,8-dimethyl-1,7-dioxa-spiro[5.5]undecane, represent main components of the cephalic secretion from males of the solitary bee, Andrena wilkella. The major compound proved to be of high enantiomeric purity, showing (2S.6R.8S) configuration. Only, the naturally occurr...

Full description

Saved in:
Bibliographic Details
Published in:Journal of chemical ecology 1990-02, Vol.16 (2), p.429-441
Main Authors: Tengo, J. (Uppsala University, Farjestaden, Sweden), Agren, L, Baur, B, Isaksson, R, Liljefors, T, Mori, K, Konig, W, Francke, W
Format: Article
Language:English
Subjects:
ANDRENA
Andrena wilkella
Andrenidae
Animal and plant ecology
Animal, plant and microbial ecology
Animals
ATRAYENTES
ATTRACTIF
Autoecology
Biological and medical sciences
COMPORTAMIENTO
COMPORTEMENT
DOSAGE BIOLOGIQUE
ENSAYO BIOLOGICO
Fundamental and applied biological sciences. Psychology
Hymenoptera
ODEUR
OLOR
Protozoa. Invertebrata
SECRECION
SECRETION
SUECIA
SUEDE
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c364t-34193c5093508e3873830d2f9058c5f8e2d6627bbbfc71bc7a683bc84bd7b45f3
cites cdi_FETCH-LOGICAL-c364t-34193c5093508e3873830d2f9058c5f8e2d6627bbbfc71bc7a683bc84bd7b45f3
container_end_page 441
container_issue 2
container_start_page 429
container_title Journal of chemical ecology
container_volume 16
creator Tengo, J. (Uppsala University, Farjestaden, Sweden)
Agren, L
Baur, B
Isaksson, R
Liljefors, T
Mori, K
Konig, W
Francke, W
description Diastereomers of the spiroacetal, 2,8-dimethyl-1,7-dioxa-spiro[5.5]undecane, represent main components of the cephalic secretion from males of the solitary bee, Andrena wilkella. The major compound proved to be of high enantiomeric purity, showing (2S.6R.8S) configuration. Only, the naturally occurring enantiomer attracted patrolling males in the field; its antipode was behaviorally inactive and in a racemic mixture did not inhibit response. The (E,Z) diastereomers were also found to be almost inactive. EAG studies gave the same result as the behavioral tests. The biological function of the spiroacetal is discussed in view of the evolution of the mating behavior in A. wilkella
doi_str_mv 10.1007/BF01021775
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_15570531</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>15570531</sourcerecordid><originalsourceid>FETCH-LOGICAL-c364t-34193c5093508e3873830d2f9058c5f8e2d6627bbbfc71bc7a683bc84bd7b45f3</originalsourceid><addsrcrecordid>eNp90M9rFDEUwPEgit1WLx49SA4iIoy-l0x-zLGWVoWCB-1NGJLMi47OZLbJLMX_3iy71punQPLh8fJl7BnCWwQw795fAYJAY9QDtkFlZINK40O2AehsA1LiCTst5ScACG3VY3YiWqGlAtiwb-dpyJQcvxunXzRNjs9uIu6JCh_GEvI4j8mt-5v1jijxatM6LjPlwpfIA21_uGkMvFDIVB8SD8u8XRKltTxhj6KbCj09nmfs5ury68XH5vrzh08X59dNkLpdG9liJ4OCrq5kSVojrYRBxA6UDSpaEoPWwnjvYzDog3HaSh9s6wfjWxXlGXt1mLvNy-2OytrPdfX9bxItu9KjUgaUxApf_x-2Gm3tqLpK3xxoyEspmWK_rS1c_t0j9Pvs_b_sFb84zt35mYZ7-rdzBS-PwJXgpphdCmO5d9qiFSgqe35g0S29-54rufnSoWhlZ-QfuWaRZg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1461877559</pqid></control><display><type>article</type><title>Andrena wilkella male bees discriminate between enantiomers of cephalic secretion components</title><source>Springer LINK Archives</source><creator>Tengo, J. (Uppsala University, Farjestaden, Sweden) ; Agren, L ; Baur, B ; Isaksson, R ; Liljefors, T ; Mori, K ; Konig, W ; Francke, W</creator><creatorcontrib>Tengo, J. (Uppsala University, Farjestaden, Sweden) ; Agren, L ; Baur, B ; Isaksson, R ; Liljefors, T ; Mori, K ; Konig, W ; Francke, W</creatorcontrib><description>Diastereomers of the spiroacetal, 2,8-dimethyl-1,7-dioxa-spiro[5.5]undecane, represent main components of the cephalic secretion from males of the solitary bee, Andrena wilkella. The major compound proved to be of high enantiomeric purity, showing (2S.6R.8S) configuration. Only, the naturally occurring enantiomer attracted patrolling males in the field; its antipode was behaviorally inactive and in a racemic mixture did not inhibit response. The (E,Z) diastereomers were also found to be almost inactive. EAG studies gave the same result as the behavioral tests. The biological function of the spiroacetal is discussed in view of the evolution of the mating behavior in A. wilkella</description><identifier>ISSN: 0098-0331</identifier><identifier>EISSN: 1573-1561</identifier><identifier>DOI: 10.1007/BF01021775</identifier><identifier>PMID: 24263500</identifier><identifier>CODEN: JCECD8</identifier><language>eng</language><publisher>New York, NY: Springer</publisher><subject>ANDRENA ; Andrena wilkella ; Andrenidae ; Animal and plant ecology ; Animal, plant and microbial ecology ; Animals ; ATRAYENTES ; ATTRACTIF ; Autoecology ; Biological and medical sciences ; COMPORTAMIENTO ; COMPORTEMENT ; DOSAGE BIOLOGIQUE ; ENSAYO BIOLOGICO ; Fundamental and applied biological sciences. Psychology ; Hymenoptera ; ODEUR ; OLOR ; Protozoa. Invertebrata ; SECRECION ; SECRETION ; SUECIA ; SUEDE</subject><ispartof>Journal of chemical ecology, 1990-02, Vol.16 (2), p.429-441</ispartof><rights>1990 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c364t-34193c5093508e3873830d2f9058c5f8e2d6627bbbfc71bc7a683bc84bd7b45f3</citedby><cites>FETCH-LOGICAL-c364t-34193c5093508e3873830d2f9058c5f8e2d6627bbbfc71bc7a683bc84bd7b45f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=6818212$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24263500$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tengo, J. (Uppsala University, Farjestaden, Sweden)</creatorcontrib><creatorcontrib>Agren, L</creatorcontrib><creatorcontrib>Baur, B</creatorcontrib><creatorcontrib>Isaksson, R</creatorcontrib><creatorcontrib>Liljefors, T</creatorcontrib><creatorcontrib>Mori, K</creatorcontrib><creatorcontrib>Konig, W</creatorcontrib><creatorcontrib>Francke, W</creatorcontrib><title>Andrena wilkella male bees discriminate between enantiomers of cephalic secretion components</title><title>Journal of chemical ecology</title><addtitle>J Chem Ecol</addtitle><description>Diastereomers of the spiroacetal, 2,8-dimethyl-1,7-dioxa-spiro[5.5]undecane, represent main components of the cephalic secretion from males of the solitary bee, Andrena wilkella. The major compound proved to be of high enantiomeric purity, showing (2S.6R.8S) configuration. Only, the naturally occurring enantiomer attracted patrolling males in the field; its antipode was behaviorally inactive and in a racemic mixture did not inhibit response. The (E,Z) diastereomers were also found to be almost inactive. EAG studies gave the same result as the behavioral tests. The biological function of the spiroacetal is discussed in view of the evolution of the mating behavior in A. wilkella</description><subject>ANDRENA</subject><subject>Andrena wilkella</subject><subject>Andrenidae</subject><subject>Animal and plant ecology</subject><subject>Animal, plant and microbial ecology</subject><subject>Animals</subject><subject>ATRAYENTES</subject><subject>ATTRACTIF</subject><subject>Autoecology</subject><subject>Biological and medical sciences</subject><subject>COMPORTAMIENTO</subject><subject>COMPORTEMENT</subject><subject>DOSAGE BIOLOGIQUE</subject><subject>ENSAYO BIOLOGICO</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Hymenoptera</subject><subject>ODEUR</subject><subject>OLOR</subject><subject>Protozoa. Invertebrata</subject><subject>SECRECION</subject><subject>SECRETION</subject><subject>SUECIA</subject><subject>SUEDE</subject><issn>0098-0331</issn><issn>1573-1561</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1990</creationdate><recordtype>article</recordtype><recordid>eNp90M9rFDEUwPEgit1WLx49SA4iIoy-l0x-zLGWVoWCB-1NGJLMi47OZLbJLMX_3iy71punQPLh8fJl7BnCWwQw795fAYJAY9QDtkFlZINK40O2AehsA1LiCTst5ScACG3VY3YiWqGlAtiwb-dpyJQcvxunXzRNjs9uIu6JCh_GEvI4j8mt-5v1jijxatM6LjPlwpfIA21_uGkMvFDIVB8SD8u8XRKltTxhj6KbCj09nmfs5ury68XH5vrzh08X59dNkLpdG9liJ4OCrq5kSVojrYRBxA6UDSpaEoPWwnjvYzDog3HaSh9s6wfjWxXlGXt1mLvNy-2OytrPdfX9bxItu9KjUgaUxApf_x-2Gm3tqLpK3xxoyEspmWK_rS1c_t0j9Pvs_b_sFb84zt35mYZ7-rdzBS-PwJXgpphdCmO5d9qiFSgqe35g0S29-54rufnSoWhlZ-QfuWaRZg</recordid><startdate>19900201</startdate><enddate>19900201</enddate><creator>Tengo, J. (Uppsala University, Farjestaden, Sweden)</creator><creator>Agren, L</creator><creator>Baur, B</creator><creator>Isaksson, R</creator><creator>Liljefors, T</creator><creator>Mori, K</creator><creator>Konig, W</creator><creator>Francke, W</creator><general>Springer</general><scope>FBQ</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7QG</scope><scope>7QR</scope><scope>7SS</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>19900201</creationdate><title>Andrena wilkella male bees discriminate between enantiomers of cephalic secretion components</title><author>Tengo, J. (Uppsala University, Farjestaden, Sweden) ; Agren, L ; Baur, B ; Isaksson, R ; Liljefors, T ; Mori, K ; Konig, W ; Francke, W</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c364t-34193c5093508e3873830d2f9058c5f8e2d6627bbbfc71bc7a683bc84bd7b45f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1990</creationdate><topic>ANDRENA</topic><topic>Andrena wilkella</topic><topic>Andrenidae</topic><topic>Animal and plant ecology</topic><topic>Animal, plant and microbial ecology</topic><topic>Animals</topic><topic>ATRAYENTES</topic><topic>ATTRACTIF</topic><topic>Autoecology</topic><topic>Biological and medical sciences</topic><topic>COMPORTAMIENTO</topic><topic>COMPORTEMENT</topic><topic>DOSAGE BIOLOGIQUE</topic><topic>ENSAYO BIOLOGICO</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Hymenoptera</topic><topic>ODEUR</topic><topic>OLOR</topic><topic>Protozoa. Invertebrata</topic><topic>SECRECION</topic><topic>SECRETION</topic><topic>SUECIA</topic><topic>SUEDE</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tengo, J. (Uppsala University, Farjestaden, Sweden)</creatorcontrib><creatorcontrib>Agren, L</creatorcontrib><creatorcontrib>Baur, B</creatorcontrib><creatorcontrib>Isaksson, R</creatorcontrib><creatorcontrib>Liljefors, T</creatorcontrib><creatorcontrib>Mori, K</creatorcontrib><creatorcontrib>Konig, W</creatorcontrib><creatorcontrib>Francke, W</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Animal Behavior Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Entomology Abstracts (Full archive)</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Journal of chemical ecology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tengo, J. (Uppsala University, Farjestaden, Sweden)</au><au>Agren, L</au><au>Baur, B</au><au>Isaksson, R</au><au>Liljefors, T</au><au>Mori, K</au><au>Konig, W</au><au>Francke, W</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Andrena wilkella male bees discriminate between enantiomers of cephalic secretion components</atitle><jtitle>Journal of chemical ecology</jtitle><addtitle>J Chem Ecol</addtitle><date>1990-02-01</date><risdate>1990</risdate><volume>16</volume><issue>2</issue><spage>429</spage><epage>441</epage><pages>429-441</pages><issn>0098-0331</issn><eissn>1573-1561</eissn><coden>JCECD8</coden><abstract>Diastereomers of the spiroacetal, 2,8-dimethyl-1,7-dioxa-spiro[5.5]undecane, represent main components of the cephalic secretion from males of the solitary bee, Andrena wilkella. The major compound proved to be of high enantiomeric purity, showing (2S.6R.8S) configuration. Only, the naturally occurring enantiomer attracted patrolling males in the field; its antipode was behaviorally inactive and in a racemic mixture did not inhibit response. The (E,Z) diastereomers were also found to be almost inactive. EAG studies gave the same result as the behavioral tests. The biological function of the spiroacetal is discussed in view of the evolution of the mating behavior in A. wilkella</abstract><cop>New York, NY</cop><pub>Springer</pub><pmid>24263500</pmid><doi>10.1007/BF01021775</doi><tpages>13</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0098-0331
ispartof Journal of chemical ecology, 1990-02, Vol.16 (2), p.429-441
issn 0098-0331
1573-1561
language eng
recordid cdi_proquest_miscellaneous_15570531
source Springer LINK Archives
subjects ANDRENA
Andrena wilkella
Andrenidae
Animal and plant ecology
Animal, plant and microbial ecology
Animals
ATRAYENTES
ATTRACTIF
Autoecology
Biological and medical sciences
COMPORTAMIENTO
COMPORTEMENT
DOSAGE BIOLOGIQUE
ENSAYO BIOLOGICO
Fundamental and applied biological sciences. Psychology
Hymenoptera
ODEUR
OLOR
Protozoa. Invertebrata
SECRECION
SECRETION
SUECIA
SUEDE
title Andrena wilkella male bees discriminate between enantiomers of cephalic secretion components
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-02T10%3A54%3A55IST&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=Andrena%20wilkella%20male%20bees%20discriminate%20between%20enantiomers%20of%20cephalic%20secretion%20components&rft.jtitle=Journal%20of%20chemical%20ecology&rft.au=Tengo,%20J.%20(Uppsala%20University,%20Farjestaden,%20Sweden)&rft.date=1990-02-01&rft.volume=16&rft.issue=2&rft.spage=429&rft.epage=441&rft.pages=429-441&rft.issn=0098-0331&rft.eissn=1573-1561&rft.coden=JCECD8&rft_id=info:doi/10.1007/BF01021775&rft_dat=%3Cproquest_cross%3E15570531%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c364t-34193c5093508e3873830d2f9058c5f8e2d6627bbbfc71bc7a683bc84bd7b45f3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1461877559&rft_id=info:pmid/24263500&rfr_iscdi=true