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Abstract:

Fifteen illudalane sesquiterpenoids, alcyopterosins A-O (1-15) have been isolated from the subAntarctic soft coral Alcyonium paessleri which was collected at a depth of 200 m near the South Georgia Islands, and their structures were elucidated by spectroscopic techniques. Eight of these compounds (2, 3, 5-8, 10, and 13) are the first natural nitrate esters, while the other four (1, 4, 11, and 12) are chlorinated. These compounds are as well the first illudalane sesquiterpenoids to be isolated from the marine environement. Compounds 1, 3, 5, and 8 showeld mild cytotoxicity toward human tumor cell lines.

Registro:

Documento: Artículo
Título:Illudalane sesquiterpenoids from the soft coral Alcyonium paessleri: The first natural nitrate esters
Autor:Palermo, J.A.; Brasco, M.F.R.; Spagnuolo, C.; Seldes, A.M.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria Pabellón II, (1428) Buenos Aires, Argentina
Palabras clave:alcyopterosin A; alcyopterosin C; alcyopterosin E; alcyopterosin H; antineoplastic agent; illudalane; natural product; nitric acid derivative; sesquiterpenoid; unclassified drug; antineoplastic activity; article; cancer cell; chemical bond; controlled study; coral; drug cytotoxicity; drug isolation; drug structure; human; human cell; marine environment; nonhuman; nuclear Overhauser effect; proton nuclear magnetic resonance; structure analysis; Animals; Antarctic Regions; Cell Line; Cnidaria; Esters; Humans; Magnetic Resonance Spectroscopy; Molecular Structure; Nitrates; Sesquiterpenes; Spectroscopy, Fourier Transform Infrared
Año:2000
Volumen:65
Número:15
Página de inicio:4482
Página de fin:4486
DOI: http://dx.doi.org/10.1021/jo991740x
Título revista:Journal of Organic Chemistry
Título revista abreviado:J. Org. Chem.
ISSN:00223263
CODEN:JOCEA
CAS:Esters; Nitrates; Sesquiterpenes
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v65_n15_p4482_Palermo

Referencias:

  • Murakami, T., Tanaka, N., (1988) Prog. Chem. Org. Nat. Prod., 54, pp. 1-329. , and references therein
  • Nair, M.S.R., Takeshita, H., McMorris, T.C., Anchel, M., (1969) J. Org. Chem., 34, pp. 240-243
  • Nair, M.S.R., Anchel, M., (1972) Tetrahedron Lett., pp. 2753-2754
  • Ayer, W., McCaskill, R., (1980) Tetrahedron Lett., pp. 1917-1920
  • Donelly, D., O'Reilly, J., Polonsky, J., Van Eijk, G., (1982) Tetrahedron Lett., pp. 5451-5452
  • Arnone, A., Cardillo, R., Di Modugno, V., Nasini, G., (1989) J. Chem. Soc., Perkin Trans. 1, pp. 1995-2000
  • Arnone, A., Cardillo, R., Nasini, G., Vajna De Pava, O., (1991) J. Chem. Soc., Perkin Trans. 1, pp. 733-737
  • Becker, U., Anke, T., Sterner, O., (1994) Nat. Prod. Lett., 5, pp. 171-174
  • Fabian, K., Lorenzen, K., Anke, T., Johansson, M., Sterner, O., (1998) Z. Naturforsch. C: Biosci., 53, pp. 939-945
  • Clericuzio, M., Han, F., Pan, F., Pang, Z., Sterner, O., (1998) Acta Chem. Scand., 52, pp. 1333-1337
  • Pretsch, E., Seibl, J., Simon, W., Clerc, T., (1989) Tables of Spectral Data for Structure Determination of Organic Compounds, , Springer-Verlag: New York
  • Ohtani, I., Kusumi, T., Kashman, Y., Kakisawa, H., (1991) J. Am. Chem. Soc., 113, pp. 4092-4096

Citas:

---------- APA ----------
Palermo, J.A., Brasco, M.F.R., Spagnuolo, C. & Seldes, A.M. (2000) . Illudalane sesquiterpenoids from the soft coral Alcyonium paessleri: The first natural nitrate esters. Journal of Organic Chemistry, 65(15), 4482-4486.
http://dx.doi.org/10.1021/jo991740x
---------- CHICAGO ----------
Palermo, J.A., Brasco, M.F.R., Spagnuolo, C., Seldes, A.M. "Illudalane sesquiterpenoids from the soft coral Alcyonium paessleri: The first natural nitrate esters" . Journal of Organic Chemistry 65, no. 15 (2000) : 4482-4486.
http://dx.doi.org/10.1021/jo991740x
---------- MLA ----------
Palermo, J.A., Brasco, M.F.R., Spagnuolo, C., Seldes, A.M. "Illudalane sesquiterpenoids from the soft coral Alcyonium paessleri: The first natural nitrate esters" . Journal of Organic Chemistry, vol. 65, no. 15, 2000, pp. 4482-4486.
http://dx.doi.org/10.1021/jo991740x
---------- VANCOUVER ----------
Palermo, J.A., Brasco, M.F.R., Spagnuolo, C., Seldes, A.M. Illudalane sesquiterpenoids from the soft coral Alcyonium paessleri: The first natural nitrate esters. J. Org. Chem. 2000;65(15):4482-4486.
http://dx.doi.org/10.1021/jo991740x