LIPIDS FROM THE JELLYFISH Phyllorhiza punctata
SOUZA, L. M.; SARI, R. S.; IACOMINI, M.; GORIN, P. A. J. G; SASSAKI, G. L.
Depto. de Bioquímica e Biologia Molecular, Universidade Federal do Paraná,
CEP 81531-990, Curitiba-PR, Brazil.
email: lauro.bio@ufpr.br
The unusual jellyfish P. punctata collected in Guaratuba (PR – Brazil), has been investigated to identify its components. Since some of its lipids such as monogalactosyldiacylglicerol (MGD) and sulfoquinovosyldiacylglicerol (SQDG), seem to belong to the dinoflagellate (its symbiont), the medusa was submitted to a further analyses. The lyophilized medusa was thrice extracted with CHCl3-MeOH (2:1 v/v), 80ºC, 2 h. The extracts were combined and submitted to a fractionation on silica gel column eluted with CHCl3-MeOH mixtures with a gradual increase of MeOH, from 5% to 50%. 100 fractions were collected and chromatographed on TLC plates and visualized with orcinol-H2SO4, ninhydrin and Dittmer & Lester solution for phosphorus groups. Similar fractions were combined into 7, called F1, F2, and so on, which were analyzed by NMR spectroscopy, ESI-MS and CG-MS. Fraction F6 was amine and phosphorus positive on TLC, and gave 13C NMR spectrum with some signals comparable to those of sphingosine and was submitted to a 31P NMR analysis that gave a signal at d 21.26, close to the region of directly bound C-P such as 2-amnoethylphosphonate (2-AEP - d 19.66). There were also detected two 13C signals at d 35.3 and 33.8 JCP = 146 Hz. To confirm the structure, F6 was submitted to ESI-MS which gave a main ion at m/z 644 and its daughters at m/z 262, 280, 501, 520. The presence of palmitic acid (C16:0) as the main fatty acid of F6 confirmed the structure as being ceramide 2-aminoethylphosphonolipid (CAEP) found in other medusae. F7 was submitted to the same analyses and showed similar 13C and 31P NMR spectra with the same 13C signals at d 35.3 and 33.8 with JCP = 150 Hz, but it was amine negative on TLC. This fraction gave 2 main ESI-MS ions at m/z 800 and 910. The molecular ion and the presence of palmitic and stearic acids were not compatible to the CAEP structure, perhaps the structure contains another unknown group linked to the amine.
Supported by CNPq, Pronex-Carboidratos and Fundação Araraucária
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