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

Raspotnig, Günther and Anderl, Felix and Kunert, Olaf and Schaider, Miriam and Brückner, Adrian and Schubert, Mario and Dötterl, Stefan and Fuchs, Roman and Leis, Hans-Jörg (2020) A Novel Class of Defensive Compounds in Harvestmen: Hydroxy-γ-Lactones from the Phalangiid Egaenus convexus. Journal of Natural Products, 83 (11). pp. 3278-3286. ISSN 0163-3864. https://resolver.caltech.edu/CaltechAUTHORS:20201020-123254097

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Abstract

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/acs.jnatprod.0c00277DOIArticle
ORCID:
AuthorORCID
Raspotnig, Günther0000-0002-6947-9406
Brückner, Adrian0000-0002-9184-8562
Schubert, Mario0000-0003-0278-4091
Additional Information:© 2020 American Chemical Society and American Society of Pharmacognosy. This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited. Received: May 20, 2020; Publication Date: October 16, 2020. This work was supported by the Austrian Science Fund (FWF), project number P29699-B25. We are particularly grateful to P. Föttinger and A. Bauer for their kind assistance in many laborious night excursions to collect specimens of Egaenus convexus and to I. Schäffler for supporting the preparative GC analyses. We thank G. Kunz for providing a photograph of a living specimen of Egaenus convexus. We further thank C. O. Kappe, D. Dallinger, and Y. Chen for their help regarding the initial steps in the synthesis of the β-hydroxy-γ-lactones. Author Contributions: G.R. and F.A. contributed equally to this work. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
FWF Der WissenschaftsfondsP29699-B25
Issue or Number:11
Record Number:CaltechAUTHORS:20201020-123254097
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20201020-123254097
Official Citation:A Novel Class of Defensive Compounds in Harvestmen: Hydroxy-γ-Lactones from the Phalangiid Egaenus convexus. Günther Raspotnig, Felix Anderl, Olaf Kunert, Miriam Schaider, Adrian Brückner, Mario Schubert, Stefan Dötterl, Roman Fuchs, and Hans-Jörg Leis. Journal of Natural Products 2020 83 (11), 3278-3286; DOI: 10.1021/acs.jnatprod.0c00277
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:106170
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:20 Oct 2020 20:22
Last Modified:25 Nov 2020 21:01

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