Abstract
The zoanthids Palythoa caribaeorum and Protopalythoa variabilis are among the most abundant marine species along the Brazilian coast. We now report the isolation and structure elucidation of two unprecedented sulfonylated ceramides, palyosulfonoceramide A (1) and palyosulfonoceramide B (2) from specimens collected off Brazil’s northeastern coast. The structures of 1 and 2 were established using a combination of NMR analyses, including: evaluation of 1H, 13C, 1H–1H COSY, 1H–13C HSQC, 1H–13C HMBC, and 1H–15N HMBC NMR spectra, high-resolution mass spectrometry and chemical degradation. In addition, we also isolated the corresponding known ceramides, N-((2S,3R,4E,8E)-1,3-dihydroxyoctadeca-4,8-dien-2-yl)-hexadecanamide (3) and N-((2S,3R,4E)-1,3-dihydroxyoctadeca-4-en-2-yl)-hexadecanamide (4), which provided further support for the assignments of 1 and 2.
Highlights
Cnidarians are a highly diverse and chemically prolific group with over 11,000 species, including corals, jellyfishes and sea anemones [1,2]
We report on the isolation of a novel family of sulfonylated ceramides from extracts of Palythoa caribaeorum and Protopalythoa variabilis collected off Paracuru Beach in northeastern Brazil
Our approach focused on classical methods of extraction, fractionation, and compound purification
Summary
Cnidarians are a highly diverse and chemically prolific group with over 11,000 species, including corals, jellyfishes and sea anemones [1,2] They serve as the second most studied group for the isolation of marine natural products [3], surpassed only by Porifera. We report on the isolation of a novel family of sulfonylated ceramides from extracts of Palythoa caribaeorum and Protopalythoa variabilis collected off Paracuru Beach in northeastern Brazil. Lipids, due to their vast chemical characterization, are often overlooked as a source for new structural diversity. We describe the isolation of two unprecedented sulfonylated ceramides, designated as palyosulfonoceramide A (1) and palyosulfonoceramide B (2)
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