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Abstract:

The γ-butyrolactone acid (1) and two known compounds, (-)-isomuronic acid and the tridepside gyrophoric acid, have been isolated from the lichen Punctelia microsticta. The structure and stereochemistry of compound 1 were determined on the basis of spectroscopic evidence and molecular modeling. Spectroscopic and physical data of 1 and (-)-dihydropertusaric acid, previously isolated from the lichen Pertusaria albescens, showed that both are the same compound, although for the latter the epimeric structure 2 has been proposed.

Registro:

Documento: Artículo
Título:A revised structure for (-)-dihydropertusaric acid, a γ-butyrolactone acid from the lichen Punctelia microsticta
Autor:Maier, M.S.; González Marimon, D.I.; Stortz, C.A.; Adler, M.T.
Filiación:Depto. de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Cuidad Universitaria, 1428 Buenos Aires, Argentina
Depto. de Ciencias Biológicas, Fac. de Ciencias Exactas y Naturales, Cuidad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:gamma butyrolactone; article; carbon nuclear magnetic resonance; chemical structure; lichen; mass spectrometry; molecular model; nonhuman; proton nuclear magnetic resonance; stereochemistry; Punctelia microsticta
Año:1999
Volumen:62
Número:11
Página de inicio:1565
Página de fin:1567
DOI: http://dx.doi.org/10.1021/np990110n
Título revista:Journal of Natural Products
Título revista abreviado:J. Nat. Prod.
ISSN:01633864
CODEN:JNPRD
CAS:gamma butyrolactone, 96-48-0
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01633864_v62_n11_p1565_Maier

Referencias:

  • Hoffmann, H.M.R., Rabe, J., (1985) Angew. Chem., Int. Ed. Engl., 24, pp. 94-100
  • Mulzner, J., Salimi, N., Hartl, H., (1993) Tetrahedron: Asymmetry, 4, pp. 457-471
  • Mulzer, J., Kattner, L., Strecker, A.R., Schroeder, C., Buschmann, J., Lehmann, C., Luger, P., (1991) J. Am. Chem. Soc., 113, pp. 4218-4229
  • Azevedo, M.B.M., Murta, M.M., Greene, A.E., (1992) J. Org. Chem., 57, pp. 4567-4569
  • Murta, M.M., Azevedo, M.B.M., Greene, A.E., (1993) J. Org. Chem., 58, pp. 7537-7541
  • Krog, H., (1994) Nord. J. Bot., 2, pp. 287-292
  • Bodo, B., Molho, D., (1980) Phytochemistry, 19, pp. 1117-1120
  • Huneck, S., Yoshimura, I., (1996) Identification of Lichen Substances, , Springer-Verlag: Berlin
  • Huneck, S., Tonsberg, T., Bohlmann, F., (1986) Phytochemistry, 25, pp. 453-459
  • Barone, V., Cossi, M., Tomasi, J., (1998) J. Comput. Chem., 19, pp. 404-417
  • Hussain, S.A.M.T., Ollis, W.D., Smith, C., Stoddart, J.F., (1975) J. Chem. Soc., Perkin Trans, 1, pp. 1480-1492
  • Kilpatrick, J.E., Pitzer, K.S., Spitzer, R., (1947) J. Am. Chem. Soc., 69, pp. 2483-2488
  • Eliel, E.L., Allinger, N.L., Angyal, S.J., Morrison, G.A., (1981) Conformational Analysis, , American Chemical Society: Washington, DC
  • Cremer, D., Pople, J.A., (1975) J. Am. Chem. Soc., 97, pp. 1354-1358
  • French, A.D., Dowd, M.K., Reilly, P.J., (1997) J. Mol. Struct. (THEOCHEM), 395-396, pp. 271-287
  • Gaudemer, A., (1977) Stereochemistry: Fundamentals and Methods, 1, pp. 44-136. , Kagan, H. B., Ed.; Georg Thieme: Stuttgart
  • Allinger, N.L., Yuh, Y.H., Lii, J.H., (1989) J. Am. Chem. Soc., 111, pp. 8551-8566
  • Haasnoot, C.A.G., De Leeuw, F.A.A.M., Altona, C., (1980) Tetrahedron, 36, pp. 2783-2792

Citas:

---------- APA ----------
Maier, M.S., González Marimon, D.I., Stortz, C.A. & Adler, M.T. (1999) . A revised structure for (-)-dihydropertusaric acid, a γ-butyrolactone acid from the lichen Punctelia microsticta. Journal of Natural Products, 62(11), 1565-1567.
http://dx.doi.org/10.1021/np990110n
---------- CHICAGO ----------
Maier, M.S., González Marimon, D.I., Stortz, C.A., Adler, M.T. "A revised structure for (-)-dihydropertusaric acid, a γ-butyrolactone acid from the lichen Punctelia microsticta" . Journal of Natural Products 62, no. 11 (1999) : 1565-1567.
http://dx.doi.org/10.1021/np990110n
---------- MLA ----------
Maier, M.S., González Marimon, D.I., Stortz, C.A., Adler, M.T. "A revised structure for (-)-dihydropertusaric acid, a γ-butyrolactone acid from the lichen Punctelia microsticta" . Journal of Natural Products, vol. 62, no. 11, 1999, pp. 1565-1567.
http://dx.doi.org/10.1021/np990110n
---------- VANCOUVER ----------
Maier, M.S., González Marimon, D.I., Stortz, C.A., Adler, M.T. A revised structure for (-)-dihydropertusaric acid, a γ-butyrolactone acid from the lichen Punctelia microsticta. J. Nat. Prod. 1999;62(11):1565-1567.
http://dx.doi.org/10.1021/np990110n