Mar. Drugs 2012, 10(12), 2846-2860; doi:10.3390/md10122846
Article

Palyosulfonoceramides A and B: Unique Sulfonylated Ceramides from the Brazilian Zoanthids Palythoa caribaeorum and Protopalyhtoa variabilis

Jose Gustavo L. Almeida 1 email, Ana Isabel V. Maia 1 email, Diego V. Wilke 2 email, Edilberto R. Silveira 1 email, Raimundo Braz-Filho 1 , James J. La Clair 3 email, Leticia V. Costa-Lotufo 2,* email and Otília Deusdenia L. Pessoa 1 email
1 Department of Organic and Inorganic Chemistry, Federal University of Ceara, Fortaleza, CE, 60021-970, Brazil 2 Department of Physiology and Pharmacology, Federal University of Ceara, Fortaleza, CE, 60430-270, Brazil 3 Xenobe Research Institute, P.O. Box 3052, San Diego, CA 92163, USA
* Author to whom correspondence should be addressed.
Received: 11 September 2012; in revised form: 19 November 2012 / Accepted: 3 December 2012 / Published: 14 December 2012
(This article belongs to the Special Issue Marine Lipids)
PDF Full-text Download PDF Full-Text [927 KB, uploaded 14 December 2012 12:10 CET]
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-dihydroxy octadeca-4-en-2-yl)-hexadecanamide (4), which provided further support for the assignments of 1 and 2.
Keywords: zoanthids; Palythoa caribaeorum; Protopalythoa variabilis; sulfonylated ceramides

Supplementary Files

Article Statistics

Click here to load and display the download statistics.

Cite This Article

MDPI and ACS Style

Almeida, J.G.L.; Maia, A.I.V.; Wilke, D.V.; Silveira, E.R.; Braz-Filho, R.; La Clair, J.J.; Costa-Lotufo, L.V.; Pessoa, O.D.L. Palyosulfonoceramides A and B: Unique Sulfonylated Ceramides from the Brazilian Zoanthids Palythoa caribaeorum and Protopalyhtoa variabilis. Mar. Drugs 2012, 10, 2846-2860.

AMA Style

Almeida JGL, Maia AIV, Wilke DV, Silveira ER, Braz-Filho R, La Clair JJ, Costa-Lotufo LV, Pessoa ODL. Palyosulfonoceramides A and B: Unique Sulfonylated Ceramides from the Brazilian Zoanthids Palythoa caribaeorum and Protopalyhtoa variabilis. Marine Drugs. 2012; 10(12):2846-2860.

Chicago/Turabian Style

Almeida, Jose G.L.; Maia, Ana I.V.; Wilke, Diego V.; Silveira, Edilberto R.; Braz-Filho, Raimundo; La Clair, James J.; Costa-Lotufo, Leticia V.; Pessoa, Otília D.L. 2012. "Palyosulfonoceramides A and B: Unique Sulfonylated Ceramides from the Brazilian Zoanthids Palythoa caribaeorum and Protopalyhtoa variabilis." Mar. Drugs 10, no. 12: 2846-2860.

Mar. Drugs EISSN 1660-3397 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert