Cytosporin-related compounds from the marine-derived fungus Eutypella scoparia

Chemical investigation of the culture broth of the fungus Eutypella scoparia ICB-OBX, isolated from the marine pulmonate mollusc Onchidium sp., led to the finding of novel compounds 1 and 2, structurally related to angiotensin II binding inhibitors cytosporins, along with unrelated known nitrogen metabolites (compounds 3-5). The structure and the relative stereochemistry of the novel metabolites were assigned mainly by a detailed analysis of two-dimensional NMR techniques whereas the absolute stereochemistry was proposed by modified Mosher's method. Compound 2 contains an unusual cyclic carbonate functionality that is rare among natural products.     

Structure of onchidione, a bis-γ-pyrone polypropionate from a marine pulmonate mollusk

The chemical investigation of the marine pulmonate Onchidium sp. and of its defensive mucous secretion led us to the isolation of a novel polypropionate, onchidione (4), containing two γ-pyrone rings. The structure of 4 was elucidated by spectroscopic methods, mainly NMR techniques, and secured by X-ray analysis on a single crystal.