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| Main Authors: | , , , , , , , , , |
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| Format: | Artículo científico |
| Language: | en |
| Published: |
Journal of natural products
2026
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| Subjects: | |
| Online Access: | https://pubmed.ncbi.nlm.nih.gov/41482996/ |
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Table of Contents:
- Cratenin, a Rare Oxylipin Marking Kleptopredation in Aeolid Nudibranchs. Quaini, Giulia Albiani, Federica Ziaco, Marcello Fioretto, Laura Follero, Olimpia Gallo, Carmela d'Ippolito, Giuliana Manzo, Emiliano Nuzzo, Genoveffa Fontana, Angelo Animals Molecular Structure Oxylipins Gastropoda Furans Marine mollusks of the order Nudibranchia produce a wide array of secondary metabolites that play key roles in predator-prey interactions and often exhibit remarkable bioactivity. In this study, a chemical investigation of the Mediterranean aeolid nudibranchs and led to the isolation and characterization of a novel oxylipin, designated cratenin (). This unique metabolite shows an unusual alkylated monosubstituted tetrahydrofuran (THF) moiety, a structural feature rarely encountered among marine natural products. The planar structure of was fully elucidated by high-resolution mass spectrometry (HRMS) and comprehensive 1D and 2D NMR spectroscopy, while the absolute configuration of the substituted THF ring was rigorously established by chemical degradation, derivatization, and NMR-based stereochemical comparison with known diasteromeric derivatives of (tetrahydrofuran-2-yl)methanol. The co-occurrence of cratenin () in the hydrozoan , a known prey of and other aeolid nudibranchs, strongly suggests its role as a semiochemical which mediates predator-prey interactions. The proposed biosynthetic origin of cratenin () from algal docosahexaenoic acid (DHA) further corroborates the hypothesis of dietary acquisition and provides compelling molecular evidence for kleptopredation, a sophisticated foraging behavior where nudibranchs consume prey that has recently ingested phytoplankton. In this view, this study reveals a clear metabolic and ecological link connecting phytoplankton, hydrozoans, and nudibranchs, underscoring the pivotal role of lipid-derived natural products in shaping chemical communication and interphyletic trophic interactions involving opisthobranchs.