A Novel Class of Defensive Compounds in Harvestmen: Hydroxy-γ-Lactones from the Phalangiid Egaenus convexus

[Image: see text] When threatened, the harvestman Egaenus convexus (Opiliones: Phalangiidae) ejects a secretion against offenders. The secretion originates from large prosomal scent glands and is mainly composed of two isomers of 4-hydroxy-5-octyl-4,5-dihydro-3H-furan-2-one (1), a β-hydroxy-γ-lacton...

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Autores principales: Raspotnig, Günther, Anderl, Felix, Kunert, Olaf, Schaider, Miriam, Brückner, Adrian, Schubert, Mario, Dötterl, Stefan, Fuchs, Roman, Leis, Hans-Jörg
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society and American Society of Pharmacognosy 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7705963/
https://www.ncbi.nlm.nih.gov/pubmed/33064479
http://dx.doi.org/10.1021/acs.jnatprod.0c00277
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author Raspotnig, Günther
Anderl, Felix
Kunert, Olaf
Schaider, Miriam
Brückner, Adrian
Schubert, Mario
Dötterl, Stefan
Fuchs, Roman
Leis, Hans-Jörg
author_facet Raspotnig, Günther
Anderl, Felix
Kunert, Olaf
Schaider, Miriam
Brückner, Adrian
Schubert, Mario
Dötterl, Stefan
Fuchs, Roman
Leis, Hans-Jörg
author_sort Raspotnig, Günther
collection PubMed
description [Image: see text] When threatened, the harvestman Egaenus convexus (Opiliones: Phalangiidae) ejects a secretion against offenders. The secretion originates from large prosomal scent glands and is mainly composed of two isomers of 4-hydroxy-5-octyl-4,5-dihydro-3H-furan-2-one (1), a β-hydroxy-γ-lactone. The compounds were characterized by GC-MS of their microreaction derivatives, HRMS, and NMR. After the synthesis of all four possible stereoisomers of 1, followed by their separation by chiral-phase GC, the absolute configurations of the lactones in the Egaenus secretion was found to be (4S,5R)-1 (90%) and (4S,5S)-1 (10%). Hydroxy-γ-lactones represent a new class of exocrine defense compounds in harvestmen.
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spelling pubmed-77059632020-12-02 A Novel Class of Defensive Compounds in Harvestmen: Hydroxy-γ-Lactones from the Phalangiid Egaenus convexus Raspotnig, Günther Anderl, Felix Kunert, Olaf Schaider, Miriam Brückner, Adrian Schubert, Mario Dötterl, Stefan Fuchs, Roman Leis, Hans-Jörg J Nat Prod [Image: see text] When threatened, the harvestman Egaenus convexus (Opiliones: Phalangiidae) ejects a secretion against offenders. The secretion originates from large prosomal scent glands and is mainly composed of two isomers of 4-hydroxy-5-octyl-4,5-dihydro-3H-furan-2-one (1), a β-hydroxy-γ-lactone. The compounds were characterized by GC-MS of their microreaction derivatives, HRMS, and NMR. After the synthesis of all four possible stereoisomers of 1, followed by their separation by chiral-phase GC, the absolute configurations of the lactones in the Egaenus secretion was found to be (4S,5R)-1 (90%) and (4S,5S)-1 (10%). Hydroxy-γ-lactones represent a new class of exocrine defense compounds in harvestmen. American Chemical Society and American Society of Pharmacognosy 2020-10-16 2020-11-25 /pmc/articles/PMC7705963/ /pubmed/33064479 http://dx.doi.org/10.1021/acs.jnatprod.0c00277 Text en © 2020 American Chemical Society and American Society of Pharmacognosy This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Raspotnig, Günther
Anderl, Felix
Kunert, Olaf
Schaider, Miriam
Brückner, Adrian
Schubert, Mario
Dötterl, Stefan
Fuchs, Roman
Leis, Hans-Jörg
A Novel Class of Defensive Compounds in Harvestmen: Hydroxy-γ-Lactones from the Phalangiid Egaenus convexus
title A Novel Class of Defensive Compounds in Harvestmen: Hydroxy-γ-Lactones from the Phalangiid Egaenus convexus
title_full A Novel Class of Defensive Compounds in Harvestmen: Hydroxy-γ-Lactones from the Phalangiid Egaenus convexus
title_fullStr A Novel Class of Defensive Compounds in Harvestmen: Hydroxy-γ-Lactones from the Phalangiid Egaenus convexus
title_full_unstemmed A Novel Class of Defensive Compounds in Harvestmen: Hydroxy-γ-Lactones from the Phalangiid Egaenus convexus
title_short A Novel Class of Defensive Compounds in Harvestmen: Hydroxy-γ-Lactones from the Phalangiid Egaenus convexus
title_sort novel class of defensive compounds in harvestmen: hydroxy-γ-lactones from the phalangiid egaenus convexus
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7705963/
https://www.ncbi.nlm.nih.gov/pubmed/33064479
http://dx.doi.org/10.1021/acs.jnatprod.0c00277
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