Glyco- and sphingophosphonolipids from the medusa Phyllorhiza punctata: NMR and ESI-MS/MS fingerprints

Chemistry and Physics of Lipids

Volumn 145, Issue 2, 2007, Pages 85-96

  de Souza, Lauro M ^a   Iacomini, Marcello ^a   Gorin, Philip A J ^a   Sari, Roger S ^a   Haddad, Maria A ^a   Sassaki, Guilherme L ^a  

^a FEDERAL UNIVERSITY OF PARANÁ   (Brazil)

Author keywords

Ceramide aminoethylphosphonate; ESI MS; Monogalactosyldiacylglycerol; NMR; Phyllorhiza punctata; Sulfoquinovosyldiacylglycerol

Indexed keywords

CERAMIDE DERIVATIVE; CERAMIDEAMINOETHYLPHOSPHONATE; FATTY ACID; GALACTOSYLDIACYLGLYCEROL; GLYCEROL DERIVATIVE; GLYCOPHOSPHONOLIPID; PHOSPHOLIPID; PHOSPHONIC ACID DERIVATIVE; SILICA GEL; SPHINGOPHOSPHONOLIPID; SULFOQUINOVOSYLDIGLYCERIDE; UNCLASSIFIED DRUG;

ANIMAL ANATOMY; ARTICLE; AUSTRALIA; BRAZIL; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; COLUMN CHROMATOGRAPHY; DINOFLAGELLATE; ELECTROSPRAY MASS SPECTROMETRY; ENDOSYMBIOSIS; GAS CHROMATOGRAPHY; HYDROLYSIS; INDONESIA; JELLYFISH; LIPID ANALYSIS; MEDUSA; MEMBRANE; MICROALGA; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PACIFIC OCEAN; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PHOTOSYNTHESIS; PHYLLORHIZA PUNCTATA; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

AMINOETHYLPHOSPHONIC ACID; ANIMALS; CERAMIDES; FATTY ACIDS; GALACTOLIPIDS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GLYCOLIPIDS; MAGNETIC RESONANCE SPECTROSCOPY; SCYPHOZOA; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

ANIMALIA; DINOPHYCEAE; PHYLLORHIZA PUNCTATA; SCYPHOZOA;

EID: 33846170845     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2006.11.001     Document Type: Article

References (46)

1. Al-Moghrabi S., Allemand D., and Couret J.M. Fatty acids of the scleractinian coral Galaxea fascicularis: effect of light and feeding. J. Comp. Physiol. B 165 (1995) 183-192
2. Battey J.F., and Patton J.S. A re-evaluation of the role of the glycerol in carbon translocation in zooxanthellae-coelenterate symbiosis. Mar. Biol. 79 (1984) 27-38
3. Benson A.A. The plant sulfolipid. Adv. Lipid Res. 1 (1963) 387-394
4. Carlton J.T., and Geller J.B. Ecological roulette: the global transport of nonindigenous marine organisms. Science 261 (1993) 78-82
5. Dittmer L.C., and Lester R.L. A simple, specific spray for the detection of phospholipids on thin-layer chromatograms. J. Lipid Res. 15 (1964) 126-127
6. Duerden, J.E., 1902. West Indian madreporarian polyps. Mem. Nat. Acad. Sci. Washington VIII, 399-648 pls I-xxv text-figs. 1-18.
7. Frost D.J., and Gunstone F.D. The PMR analysis of non-conjugated alkenoic and alkynoic acids and esters. Chem. Phys. Lipids 15 (1975) 53-85
8. Graeve M., Kattner G., and Hagen W. Diet-induced changes in the fatty acid composition of Arctic herbivorous copepods: experimental evidence of trophic markers. J. Exp. Mar. Biol. Ecol. 182 (1994) 97-110
9. Graham W.M., Perry H.M., and Felder D.L. Ecological and Economic Implications of the Tropical Jellyfish, Phyllorhiza punctata, in the Northern Gulf of Mexico During the Summer of 2000 (2001), Marine Bioinvasions, New Orleans, Louisiana
10. Graham W.M., Martin D.L., Felder D.L., Asper V.L., and Perry H.M. Ecological and economic implications of a tropical jellyfish invader in the Gulf of Mexico. Biol. Invasions 5 (2003) 53-69
11. Haddad M.A., and Nogueira Jr. M. Reappearance and seasonality of Phyllorhiza punctata von Lendenfeld (Cnidaria, Scyphozoa, Rhizostomeae) medusae in southern Brazil. Revista Brasileira de Zoologia 23 (2006) 824-831
12. Harland A.D., Fixter L.M., Davies P.S., and Anderson R.A. Distribution of lipids between zooxanthellae and animal compartment in the symbiotic sea anemone Anemonia veridis: wax esters, triglycerides and fatty acids. Mar. Biol. 110 (1991) 13-19
13. Hiraga Y., Kaku K., Omoda D., Sugihara K., Hosoya H., and Hino M. A new digalactosyl diacylglycerol from a cultured marine Dinoflagellate Heterocapsa circularisquama. J. Nat. Prod. 65 (2002) 1494-1496
14. Hori T., and Sugita M. Sphingolipids in lower animals. Prog. Lipid Res. 32 (1993) 25-45
15. Itasaka O., Hori T., Sasahara K., Wakabayashi Y., Takahashi F., and Rhee H. Analysis of phospho- and phosphonosphingolipids by high-performance liquid chromatography. J. Biochem. 95 (1984) 1671-1675
16. Joseph J.D. Lipid composition of marine and estuarine invertebrates. Part II. Mollusca. Prog. Lipid Res. 21 (1982) 109-153
17. Kaneshiro E.S. Lipids of paramecium. J. Lipid Res. 28 (1987) 1241-1258
18. Kariotoglou D.M., and Mastronicolis S.K. Sphingophosphonolipids, phospholipids, and fatty acids from Aegean jellyfish Aurelia aurita. Lipids 36 (2001) 1255-1264
19. Kariotoglou D.M., and Mastronicolis S.K. Sphingophosphonolipid molecular species from edible mollusks and a jellyfish. Comp. Biochem. Phys. B 136 (2003) 27-44
20. Larson R.J., and Arneson A.C. Two medusae new to the coast of California: Carybdea marsupialis (Linnaeus, 1758), a cubozoa and Phyllorhiza punctata von Lendenfeld, 1884 a rhizostome scyphomedusa. Bull. Southern California Acad. Sci. 89 (1990) 130-136
21. Martin, J.C., Graham, W.M., 2001. Spatial variability of Phyllorhiza punctata (cnidaria: rhizostomeae) within large aggregations in lake Borgne, Louisiana. ASLO, Aquatic Sciences Meeting, Albuquerque.
22. Matsubara T. Distribution of the dienoic long chain bases in shell-fish sphingophoshponolipids. Chem. Phys. Lipids 14 (1975) 247-259
23. Matsubara T., and Hayashi A. Structural studies on glycolipids of shellfish. V. Gala-6 series glycosphingolipids of the marine snail, Chlorostoma argyrostoma turbinatum. J. Biochem. 99 (1986) 1401-1408
24. Meyers P.A. Fatty acids and hydrocarbons of Caribbean corals. Proceedings of the 3rd International Coral Reef Symposium. Florida, USA (1977) 529-536
25. Meyers P.A. Polyunsaturated fatty acids in coral: indicators of nutritional sources. Mar. Biol. Lett. 1 (1979) 69-75
26. Moschidis M.C. Phosphonolipids. Prog. Lipid Res. 23 (1985) 223-246
27. Mukhamedova Kh.S., and Glushenkova A.I. Natural phosphonolipids. Chem. Nat. Compd. 36 (2000) 329-341
28. Muscatine L. Symbiosis of hydra and algae-extracellular products of the algae. Comp. Biochem. Physiol. B 16 (1965) 77-84
29. Muscatine L. Glycerol excretion by symbiotic algae from corals and Tridacna and its control by the host. Science 156 (1967) 516-519
30. Nakhel I.C., Mastronicolis S.K., and Meimaroglou S.M. Phospho- and phosphonolipids of the Aegean pelagic scyphomedusa Pelagia noctiluca. Biochim. Biophys. Acta 958 (1988) 300-307
31. Papina M., Meziane T., and van Woesik R. Symbiotic zooxanthellae provide the host-coral Montipora digitata with polyunsaturated fatty acids. Comp. Biochem. Physiol. B 135 (2003) 533-537
32. Parrish C.C., Bodennec G., and Gentien P. Haemolytic glycoglycerolipids from Gymnodinium species. Phytochemistry 47 (1998) 783-787
33. Rippingale M.G.B.S., and Kelly S.J. Reproduction and survival of Phyllorhiza punctata (Cnidaria: Rhizostomeae) in a seasonally fluctuating salinity regime in Western Australia. Mar. Freshwater Res. 46 (1995) 1145-1151
34. Rouser G., Kritchevsky G., Heller D., and Lieber E. Lipid composition of beef brain, beef liver and sea anemone: two approaches to quantitative fractionation of complex lipid mixtures. J. Am. Oil Chem. Soc. 40 (1963) 425-454
35. Sassaki G.L., Gorin P.A.J., and Iacomini M. Characterization of a lyso-galactolipid, C-2 or C-3 O-acyl trigalactosylglycerol isomers, obtained from the lichenized fungus Dictyonema glabratum. FEMS Microbiol. Lett. 194 (2001) 155-158
36. Sassaki G.L., Gorin P.A.J., Tischer C.A., and Iacomini M. Sulfonoglycolipids from the lichenized basidiomycete Dictyonema glabratum: isolation, NMR, and ESI-MS approaches. Glycobiology 11 (2001) 345-351
37. Sassaki G.L., Machado M.J., Tischer C.A., Gorin P.A.J., and Iacomini M. Glycosyldiacylglycerolipids from the lichen Dictyonema glabratum. J. Nat. Prod. 62 (1999) 844-847
38. Silveira F.L., and Cornelius P.F.S. Novas observações sobre medusas (Cnidária, Scyphozoa, Rhisostomeae) no Nordeste e Sul do Brasil (New observations on medusas in the northeast and south Brazil). Acta Biol. Leopoldensia 22 (2000) 9-18
39. Skipski V.P. Thin layer chromatography of neutral glycolipids. Meth. Enzymol. 35 (1985) 396-425
40. Smith J.D. Replacement of ethanolamine phosphate by 3-aminopropylphosphonate in the phospholipids of Tetrahymena. Arch. Biochem. Biophys. 206 (1981) 420-423
41. Smith J.D. Effect of dimethylaminoethylphosphonate on phospholipid metabolism in Tetrahymena. Biochim. Biophys. Acta 878 (1986) 450-453
42. Watanabe Y., Nakajima M., Hoshino T., Jayasimhulu K., Brooks E.E., and Kaneshiro E.S. A novel sphingophosphonolipid head group 1-hydroxy-2-aminoethyl phosphonate in Bdellovibrio stolpii. Lipids 36 (2001) 513-519
43. Yasumoto T., Underdal B., Aune T., Hormazabal V., Skulberg O.M., and Oshima Y. In: Granéli E., Sundstrom B., Edler L., and Anderson D.M. (Eds). Toxic Marine Phytoplankton (1990), Elsevier, New York 436-440
44. Yonge C.M. The significance of the relationships between corals and zooxanthellae. Nature 128 (1931) 309-310
45. Zhukova N.V., and Aizdaicher N.A. Fatty acid composition of 15 species of marine microalgae. Phytochemistry 39 (1995) 351-356
46. Zhukova N.V., and Titlyanov E.A. Fatty acid variations in symbiotic dinoflagellates from Okinawan corals. Phytochemistry 62 (2003) 191-195