Abstract:
Four new sulfated asterosaponins, designated as cosmasterosides A [1], B [2], C [4], and D [5], have been isolated from the Atlantic starfish Cosmasterias lurida along with large amounts of the pentaglycoside ophidianoside F [3] and the minor component forbeside H [6], previously isolated from Ophidiaster ophidianus and Asterias forbesi, respectively. Cosmasteroside A [1] contains the same oligosaccharide chain as ophidianoside F [31 and a (2OS)-5α-cholesta- 9(11),24-diene-3β,6α,20-triol-3β-sulfated aglycone. Cosmasterosides B [2], C [4], and D [5] are based on the known aglycone, thornasterol A, and differ in the number and type of monosaccharide components of the carbohydrate chain. Cosmasteroside B [2] contains a novel oligosaccharide chain that differs from that of ophidianoside F [3] by the replacement of the quinovose unit attached to C-6 of the steroidal aglycone by glucose. The tetraglycosides cosmasterosides C [4] and D [5] are structurally related to ophidianoside F [3] and cosmasteroside B [2], respectively, by the loss of a terminal fucose unit. © 1994, American Chemical Society. All rights reserved.
Registro:
Documento: |
Artículo
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Título: | Starfish saponins, Part 2. Steroidal oligoglycosides from the starfish cosmasterias lurida |
Autor: | Roccatagliata, A.J.; Maier, M.S.; Seldes, A.M.; Iorizzi, M.; Minale, L. |
Filiación: | Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellón 2, 1428 Buenos Aires, Argentina Università degli Studi del Molise, 86100 Campobasso, Italy Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli “Federico II”, 80131 Napoli, Italy
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Palabras clave: | glycoside; saponin; steroid; article; asterias; drug isolation; drug structure; drug synthesis; Animal; Carbohydrate Sequence; Female; Glycosides; Magnetic Resonance Spectroscopy; Molecular Sequence Data; Oligosaccharides; Ovary; Saponins; Starfish; Support, Non-U.S. Gov't; Asterias; Asterias forbesii; Asteroidea; Ophidiaster ophidianus |
Año: | 1994
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Volumen: | 57
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Número: | 6
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Página de inicio: | 747
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Página de fin: | 754
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DOI: |
http://dx.doi.org/10.1021/np50108a010 |
Título revista: | Journal of Natural Products
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Título revista abreviado: | J. Nat. Prod.
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ISSN: | 01633864
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CAS: | Glycosides; Oligosaccharides; Saponins
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01633864_v57_n6_p747_Roccatagliata |
Referencias:
- Minale, L., Riccio, R., Zollo, F., Progress in the Chemistry of Organic Natural Products (1993), 62, p. 75. , Ed. by W. Herz, G.W. Kirby, W. Steglich, and Ch. Tamm, Springier Verlag, New York; Casapullo, A., Finamore, E., Minale, L., Zollo, F., Carré, J.B., Debitus, C., Laurent, D., Galdiero, F., (1993) J. Nat. Prod., 56, p. 105
- De Riccardis, F., Iorizzi, M., Minale, L., Riccio, R., Debitus, C., (1992) Tetrahedron Lett., 33, p. 1097
- Maier, M.S., Roccatagliata, A., Seldes, A.M., (1993) J. Nat. Prod., 56, p. 939
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- Riccio, R., Squillace-Greco, O., Minale, L., La Barre, S., Laurent, D., (1988) J. Nat. Prod., 51, p. 1003
- Findlay, J.A., He, Z.-Q., Blackwell, B., (1990) Can.J. Chem., 68, p. 1215
- Riccio, R., Iorizzi, M., Minale, L., Oshima, Y., Yasumoto, T., (1988) J. Chem.Soc., Perkin Trans., 1, p. 1337
- Krebs, H.C., Komori, T., Kawasaki, T., (1984) Liebigs Ann. Chem., p. 296
- Bruno, I., Minale, L., Pizza, C., Zollo, F., Riccio, R., Mellon, F., (1984) J. Chem. Soc., Perkin Trans., 1, p. 1875
- Gorin, P.A.J., Mazurek, M., (1975) Can. J. Chem., 53, p. 1212
- Finamore, E., Minale, L., Riccio, R., Rinaldo, G., Zollo, F., (1991) J. Org. Chem., 56, p. 1146
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Citas:
---------- APA ----------
Roccatagliata, A.J., Maier, M.S., Seldes, A.M., Iorizzi, M. & Minale, L.
(1994)
. Starfish saponins, Part 2. Steroidal oligoglycosides from the starfish cosmasterias lurida. Journal of Natural Products, 57(6), 747-754.
http://dx.doi.org/10.1021/np50108a010---------- CHICAGO ----------
Roccatagliata, A.J., Maier, M.S., Seldes, A.M., Iorizzi, M., Minale, L.
"Starfish saponins, Part 2. Steroidal oligoglycosides from the starfish cosmasterias lurida"
. Journal of Natural Products 57, no. 6
(1994) : 747-754.
http://dx.doi.org/10.1021/np50108a010---------- MLA ----------
Roccatagliata, A.J., Maier, M.S., Seldes, A.M., Iorizzi, M., Minale, L.
"Starfish saponins, Part 2. Steroidal oligoglycosides from the starfish cosmasterias lurida"
. Journal of Natural Products, vol. 57, no. 6, 1994, pp. 747-754.
http://dx.doi.org/10.1021/np50108a010---------- VANCOUVER ----------
Roccatagliata, A.J., Maier, M.S., Seldes, A.M., Iorizzi, M., Minale, L. Starfish saponins, Part 2. Steroidal oligoglycosides from the starfish cosmasterias lurida. J. Nat. Prod. 1994;57(6):747-754.
http://dx.doi.org/10.1021/np50108a010