Abstract:
A new triterpene glycoside, patagonicoside A (1), has been isolated from the sea cucumber Psolus patagonicus and its structure has been elucidated by 1D and 2D NMR (1H-, 13C-, 1H-1H COSY, HETCOR, COLOC and NOESY spectra), FAB-MS and chemical evidence. Compound 1 is a disulfated tetrasaccharide with a new aglycon moiety. Patagonicoside A (1) exhibits considerable antifungal activity against the pathogenic fungus Cladosporium cucumerinum. © 2001 Elsevier Science Ltd. All rights reserved.
Registro:
Documento: |
Artículo
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Título: | Patagonicoside A: A novel antifungal disulfated triterpene glycoside from the sea cucumber Psolus patagonicus |
Autor: | Murray, A.P.; Muniaín, C.; Seldes, A.M.; Maier, M.S. |
Filiación: | Departamento De Química Orgánica, Facultad De Ciencias Exactas Y Naturales, Ciudad Universitaria, Pabellón 2, 1428 Buenos Aires, Argentina Departamento De Química, Universidad Nacional del Sur, Avda. Alem 1253, 8000 Bahía Blanca, Argentina Museo Argentino De Ciencias Naturales Bernardino Rivadavia, Av. A. Gallardo 470, 1405 Buenos Aires, Argentina
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Palabras clave: | Antifungal activity; Glycosides; Holothuroidea; Psolus patagonicus; Triterpenes; antifungal agent; glycoside; patagonicoside a; triterpenic glycoside; unclassified drug; antifungal activity; article; carbon nuclear magnetic resonance; Cladosporium cucumerinum; controlled study; desulfurization; dose response; drug isolation; drug structure; echinoderm; mass spectrometry; nonhuman; priority journal; proton nuclear magnetic resonance |
Año: | 2001
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Volumen: | 57
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Número: | 47
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Página de inicio: | 9563
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Página de fin: | 9568
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DOI: |
http://dx.doi.org/10.1016/S0040-4020(01)00970-X |
Título revista: | Tetrahedron
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Título revista abreviado: | Tetrahedron
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ISSN: | 00404020
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CODEN: | TETRA
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v57_n47_p9563_Murray |
Referencias:
- Kalinin, V.I., Anisimov, M.M., Prokofieva, N.G., Avilov, S.A., Afiyatullov, Sh.Sh., Stonik, V.A., Biological activities and biological role of triterpene glycosides from holothuroidea (Echinodermata) (1996) Echinoderm Studies, 5, pp. 139-181. , Jangoux, M., Lawrence, J. M., Eds.; Balkema: Rotterdam
- Maier, M.S., Roccatagliata, A.J., Kuriss, A., Chludil, H., Seldes, A.M., Pujol, C.A., Damonte, E.B., (2001) J. Nat. Prod., 64, pp. 732-736
- Kalinin, V.I., Avilov, S.A., Kalinina, E.Y., Korolkova, O.G., Kalinovsky, A.I., Stonik, V.A., Riguera, R., Jimenez, C., (1997) J. Nat. Prod., 60, pp. 817-819
- Kalinin, V.I., Kalinovskii, A.I., Stonik, V.A., (1985) Khim. Prirod. Soedin., 2, pp. 212-217
- Garneau, F.-X., Simard, J.-L., Harvey, O., ApSimon, J.W., Girard, M., (1983) Can. J. Chem., 61, pp. 1465-1471
- Kalinin, V.I., Kalinovskii, A.I., Stonik, V.A., Dmitrnok, P.S., El'kin, Y.N., (1989) Khim. Prirod. Soedin., 3, pp. 361-368
- Maier, M.S., Kuriss, A., Seldes, A.M., (1998) Lipids, 33, pp. 825-827
- Roccatagliata, A.J., Maier, M.S., Seldes, A.M., (1998) J. Nat. Prod., 61, pp. 370-374
- Kitagawa, I., Kobayashi, M., Inamoto, T., Fuchida, M., Kyogoku, Y., (1985) Chem. Pharm. Bull., 33, pp. 5214-5224
- Kitagawa, I., Kobayashi, M., Hori, M., Kyogoku, Y., (1989) Chem. Pharm. Bull., 37, pp. 61-67
- Kitagawa, I., Kobayashi, M., Wha Son, B., Suzuki, S., Kyogoku, Y., (1989) Chem. Pharm. Bull., 37, pp. 1230-1234
- Miyamoto, T., Togawa, K., Higuchi, R., Komori, T., Sasaki, T., (1990) Liebigs Ann. Chem., pp. 453-460
- Björndal, H., Lindberg, B., Svensson, S., (1967) Carbohyd. Res., 5, pp. 433-440
- Kalinin, V.I., Volkova, O.V., Likhatskaya, G.N., Prokofieva, N.G., Agafonova, I.G., Anisimov, M.M., Kalinovsky, A.I., Stonik, V.A., (1992) J. Nat. Toxins, 1, pp. 17-30
- Rodriguez, J., Castro, R., Riguera, R., (1991) Tetrahedron, 47, pp. 4753-4762
- Kitagawa, I., Nishino, T., Kobayashi, M., Kyogoku, Y., (1981) Chem. Pharm. Bull., 29, pp. 1951-1956
- Bhatnagar, S., Dudouet, B., Ahond, A., Poupat, C., Thoison, O., Clastres, A., Laurent, D., Potier, P., (1985) Bull. Soc. Chim. Fr., Part 2, 1, pp. 124-129
- Kitagawa, I., Yamanaka, H., Kobayashi, M., Nishino, T., Yosioka, I., Sugawara, T., (1978) Chem. Pharm. Bull., 26, pp. 3722-3731
- Kitagawa, I., Nishino, T., Kobayashi, M., Matsuno, T., Akutsu, H., Kyogoku, Y., (1981) Chem. Pharm. Bull., 29, pp. 1942-1950
- Homans, A.L., Fuchs, A., (1970) J. Chromatogr., 51, pp. 327-329
- Hostettmann, K., Hostettmann, M., Marston, A., (1986) Preparative Chromatography Techniques, pp. 23-26. , Springer: Berlin
Citas:
---------- APA ----------
Murray, A.P., Muniaín, C., Seldes, A.M. & Maier, M.S.
(2001)
. Patagonicoside A: A novel antifungal disulfated triterpene glycoside from the sea cucumber Psolus patagonicus. Tetrahedron, 57(47), 9563-9568.
http://dx.doi.org/10.1016/S0040-4020(01)00970-X---------- CHICAGO ----------
Murray, A.P., Muniaín, C., Seldes, A.M., Maier, M.S.
"Patagonicoside A: A novel antifungal disulfated triterpene glycoside from the sea cucumber Psolus patagonicus"
. Tetrahedron 57, no. 47
(2001) : 9563-9568.
http://dx.doi.org/10.1016/S0040-4020(01)00970-X---------- MLA ----------
Murray, A.P., Muniaín, C., Seldes, A.M., Maier, M.S.
"Patagonicoside A: A novel antifungal disulfated triterpene glycoside from the sea cucumber Psolus patagonicus"
. Tetrahedron, vol. 57, no. 47, 2001, pp. 9563-9568.
http://dx.doi.org/10.1016/S0040-4020(01)00970-X---------- VANCOUVER ----------
Murray, A.P., Muniaín, C., Seldes, A.M., Maier, M.S. Patagonicoside A: A novel antifungal disulfated triterpene glycoside from the sea cucumber Psolus patagonicus. Tetrahedron. 2001;57(47):9563-9568.
http://dx.doi.org/10.1016/S0040-4020(01)00970-X