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Abstract:

From the water-insoluble lipid fraction of the chloroform/methanol/water extract of the gonads and body walls of the Patagonian starfish Allostichaster inaequalis, two new glucosylceramides (4 and 7) were isolated together with the known phalluside-1 (1) and two glucosylceramides (2 and 3) previously isolated from the starfish Cosmasterias lurida. The new compounds were characterized as (2 S, 3 R, 4 E, 8 E, 1 iOU)-1-(β D-glucopyranosyloxy)-3-hydroxy-2-[(R)-2-hydroxy-15-tetracosenoyl] amino-4,8,10-octadecatriene (4) and (2 S, 3 R, 4 E, 15 Z)-1-(β-D-glucopyranosyloxy)-3-hydroxy-2-[(R)-2-hydroxyhexadecanoyl] amino-4,15-docosadiene (7) by means of spectroscopic and chemical methods.

Registro:

Documento: Artículo
Título:Two novel glucosylceramides from gonads and body walls of the patagonian starfish Allostichaster inaequalis
Autor:Díaz de Vivar, M.E.; Seldes, A.M.; Maier, M.S.
Filiación:Facultad de Ciencias Naturales (Sede Puerto Madryn), Universidad Nacional de la Patagonia San Juan Bosco, Chubut 9120, Argentina
Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Buenos Aires 1428, Argentina
Palabras clave:Glucose; Methanol; Spectroscopic analysis; Body walls; Lipids; 1 (beta dextro glucopyranosyloxy) 3 hydroxy 2 (2 hydroxy 15 tetracosenoyl)amino 4,8,10 octadecatriene; 1 (beta dextro glucopyranosyloxy) 3 hydroxy 2 (2 hydroxyhexadecanoyl)amino 4,15 docosadiene; glucosylceramide; unclassified drug; glucosylceramide; article; Asterias; carbon nuclear magnetic resonance; chromatography; gonad; lipid analysis; nonhuman; proton nuclear magnetic resonance; spectroscopy; animal; chemistry; fast atom bombardment mass spectrometry; high performance liquid chromatography; isolation and purification; nuclear magnetic resonance; starfish; ultraviolet spectrophotometry; Allostichaster; Asterias; Asteroidea; Human echovirus 1; Vertebrata; Animals; Chromatography, High Pressure Liquid; Glucosylceramides; Gonads; Nuclear Magnetic Resonance, Biomolecular; Spectrometry, Mass, Fast Atom Bombardment; Spectrophotometry, Ultraviolet; Starfish
Año:2002
Volumen:37
Número:6
Página de inicio:597
Página de fin:603
DOI: http://dx.doi.org/10.1007/s11745-002-0938-7
Título revista:Lipids
Título revista abreviado:Lipids
ISSN:00244201
CODEN:LPDSA
CAS:Glucosylceramides
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00244201_v37_n6_p597_DiazdeVivar

Referencias:

  • Kawano, Y., Higuchi, R., Isobe, R., Komori, T., Isolation and structure of six new cerebrosides (1988) Liebigs Ann. Chem., pp. 19-24
  • Kawano, Y., Higuchi, R., Isobe, R., Komori, T., Isolation and structure of two new ceramide lactosides (1988) Liebigs Ann. Chem., pp. 1181-1183
  • Higuchi, R., Natori, T., Komori, T., Isolation and characterization of acanthacerebroside B and structure elucidation of related, nearly homogeneous cerebrosides (1990) Liebigs Ann. Chem., pp. 51-55
  • Higuchi, R., Kagoshima, M., Komori, T., Structures of three new cerebrosides, astrocerebroside A, B, and C, and of related nearly homogeneous cerebrosides (1990) Liebigs Ann. Chem., pp. 659-663
  • Higuchi, R., Jhou, J.X., Inukai, K., Komori, T., Isolation and structure of six new cerebrosides, asteriacerebrosides A-F, and two known cerebrosides, astrocerebroside A and acanthacerebroside C (1991) Liebigs Ann. Chem., pp. 745-752
  • Higuchi, R., Inagaki, M., Togawa, K., Miyamoto, T., Komori, T., Isolation and structure of three new cerebrosides, CE-2b, CE-2c, and CE-2d, from the sea cucumber cucumaria echinata (1994) Liebigs Ann. Chem., pp. 79-81
  • Higuchi, R., Inagaki, M., Togawa, K., Miyamoto, T., Komori, T., Isolation and structure of cerebrosides from the sea cucumber pentacta australis (1994) Liebigs Ann. Chem., pp. 653-658
  • Jin, W., Rinehart, K.L., Jares-Erijman, E.A., Ophidiacerebrosides: Cytotoxic glycosphingolipids containing a novel sphingosine from a sea star (1994) J. Org. Chem., 59, pp. 144-147
  • Venkannababu, U., Bhandari, S.P.S., Garg, H.S., Regulosides A-C: Glycosphingolipids from the starfish pentaceraster regulus (1997) Liebigs Ann./Recueil, pp. 1245-1247
  • Babu, U.V., Bhandari, S.P.S., Garg, H.S., Temnosides A and B two new glycosphingolipids from the sea urchin temnopleurus toreumaticus of the Indian Coast (1997) J. Nat. Prod., 60, pp. 732-734
  • Agrawal, S., Garg, H.S., A novel sphingosine derivative from the sponge spirastrella inconstans (1994) J. Nat. Prod., 58, pp. 442-445
  • Li, H., Matsunaga, S., Fusetani, N., Halicylindrosides, antifungal and cytotoxic cerebrosides from the marine sponge halichondria cylindrata (1995) Tetrahedron, 51, pp. 2273-2280
  • Natori, T., Morita, M., Akimoto, K., Koezuka, Y., Agelasphins, novel antitumor and immunostimulatory cerebrosides from the marine sponge agelas mauritanus (1994) Tetrahedron, 50, pp. 2771-2784
  • Durán, R., Zubía, E., Ortega, M.J., Naranjo, S., Salvá, J., Phallusides, new glucosphingolipids from the ascidian phallusia fumigata (1998) Tetrahedron, 54, pp. 14597-14602
  • Chakrabarty, M., Balabyal, A., Barua, A., New ceramides from the hypotensive extract of a sea anemone, paracondylactis indicus (1994) J. Nat. Prod., 57, pp. 393-395
  • Ojika, M., Yoshino, G., Sakagami, Y., Novel ceramide 1-sulfates, potent DNA topoisomerase I inhibitors isolated from the bryozoa watersipora cucullata (1997) Tetrahedron Lett., 38, pp. 4235-4238
  • Shin, J., Seo, Y., Isolation of new ceramides from the gorgonian acabaria undulata (1995) J. Nat. Prod., 58, pp. 948-953
  • Schmidt, R.R., Recent developments in the synthesis of glycoconjugates (1989) Pure Appl. Chem., 61, pp. 1257-1270
  • Maier, M.S., Kuriss, A., Seldes, A.M., Isolation and structure of glucosylceramides from the starfish cosmasterias lurida (1998) Lipids, 33, pp. 825-827
  • Bligh, E.G., Dyer, W.J., A rapid method of total lipid extraction and purification (1959) Can. J. Biochem. Physiol., 37, pp. 911-917
  • Kates, M., (1986) Techniques of Lipidology 2nd edn., pp. 239-244. , Elsevier Science Publishers, Oxford
  • Gaver, R.C., Sweeley, C.C., Methods for methanolysis of sphingolipids and direct determination of long-chain bases by gas chromatography (1965) J. Am. Oil Chem. Soc., 42, pp. 294-298
  • Maier, M.S., Roccatagliata, A.J., Kuriss, A., Chludil, H., Seldes, A.M., Pujol, C.A., Damonte, E.B., Two new cytotoxic and virucidal trisulfated triterpene glycosides from the antarctic sea cucumber staurocucumis liouvillei (2001) J. Nat. Prod., 64, pp. 732-736
  • Vincenti, M., Guglielminetti, G., Cassani, G., Tonini, C., Determination of double bond position in diunsaturated compounds by mass spectrometry of dimethyl disulfide derivatives (1987) Anal. Chem., 59, pp. 694-699
  • Pretorius, Y.Y., Horn, D., The synthesis and stereochemistry of the straight-chain α-hydroxy-acids (1954) J. Chem. Soc., pp. 1460-1464
  • Julina, R., Herzig, T., Bernet, B., Vasella, A., Enantioselective synthesis of D-erythro-sphingosine and of ceramide (1986) Helv. Chim. Acta, 69, pp. 368-373
  • Kim, S.Y., Choi, Y., Huh, H., Kim, J., Kim, Y., Lee, H.S., New antihepatotoxic cerebrosides from lycium chinense fruits (1997) J. Nat. Prod., 60, pp. 274-276
  • Irie, A., Kubo, H., Hoshi, M., Glucosylceramide having a novel tri-unsaturated long-chain base from the spermatozoa of the starfish, asterias amurensis (1990) J. Biochem., 107, pp. 578-586
  • Breitmaier, E., (1987) Carbon-13 NMR Spectroscopy 3rd edn., pp. 108-116. , VCH, Weinheim

Citas:

---------- APA ----------
Díaz de Vivar, M.E., Seldes, A.M. & Maier, M.S. (2002) . Two novel glucosylceramides from gonads and body walls of the patagonian starfish Allostichaster inaequalis. Lipids, 37(6), 597-603.
http://dx.doi.org/10.1007/s11745-002-0938-7
---------- CHICAGO ----------
Díaz de Vivar, M.E., Seldes, A.M., Maier, M.S. "Two novel glucosylceramides from gonads and body walls of the patagonian starfish Allostichaster inaequalis" . Lipids 37, no. 6 (2002) : 597-603.
http://dx.doi.org/10.1007/s11745-002-0938-7
---------- MLA ----------
Díaz de Vivar, M.E., Seldes, A.M., Maier, M.S. "Two novel glucosylceramides from gonads and body walls of the patagonian starfish Allostichaster inaequalis" . Lipids, vol. 37, no. 6, 2002, pp. 597-603.
http://dx.doi.org/10.1007/s11745-002-0938-7
---------- VANCOUVER ----------
Díaz de Vivar, M.E., Seldes, A.M., Maier, M.S. Two novel glucosylceramides from gonads and body walls of the patagonian starfish Allostichaster inaequalis. Lipids. 2002;37(6):597-603.
http://dx.doi.org/10.1007/s11745-002-0938-7