Reassignment of crispatene, isolation and chemical characterization of stachydrine, isolated from the marine mollusk Elysia crispata

Abstract

The molluscan genus Elysia Risso, 1818 (Sacoglossa) is composed of shell-less herbivore sea slugs. From these marine organisms, polyketides such as polypropynates have been isolated and showed cytotoxic, antibiotic, and antifungal, and antiviral properties. In this work, we reported the isolation, and structure elucidation of two compounds isolated from marine mollusk E. crispata. Both compounds isolated, crispatene (1) and stachydrine (2), were purified by HPLC. The chemical structure of compound (1) was reassigned through 1D and 2D NMR experiments and high-resolution electrospray ionization mass spectrometry (HRESIMS). On the other hand, this is the first time that compound (2) has been found in this species of mollusk or the marine environment, previously, (2) has only been found in terrestrial plants or bacteria in symbiosis with plants.

Graphical Abstract

Keywords:

• Gastropod
• Sacoglossa
• Elysia crispata
• polypropionates
• γ-pyrone

Acknowledgments

We thank the staff of NMR group (Daniela Briceño and Maria Núñez), Mass Spectrometry (Carlos Ibarra, Ana Angarita and Janeth Salas), IR (Liz Cubillán), Dr. Juan Alfonso and Dra. Soraya Silva (COEA), and Venezuelan Institute for Scientific Research (IVIC) for supporting this research.

Disclosure statement

Not potential conflict of interest was reported by the authors.

Correction Statement

This article has been republished with minor changes. These changes do not impact the academic content of the article.

Additional information

Funding

This work was financially supported by FONACIT (PEII-2012001567).