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Abstract:

A cocrystal, C15H22O3.C15H22O3, (I), obtained from Drimys winteri, is composed of two isomeric drimane sesquiterpene lactones, namely valdiviolide, (Ia), and 11-epivaldiviolide, (Ib), neither of which has been reported in the crystal form. Both diastereoisomers present three chiral centres at sites 5, 10 and 11, with an SSR sequence in (Ia) and an SSS sequence in (Ib). O-H⋯O hydrogen bonds bind molecules into chains running along [ 120] and the chains are in turn linked by π-π stacking interactions to define planar weakly interacting arrays parallel to (001). © 2014 International Union of Crystallography.

Registro:

Documento: Artículo
Título:Two drimane lactones, valdiviolide and 11-epivaldiviolide, in the form of a 1:1 cocrystal obtained from Drimys winteri extracts
Autor:Paz Robles, C.; Mercado, D.; Suarez, S.; Baggio, R.
Filiación:Departamento de Ciencias Quimicas y Recursos Naturales, Facultad de Ingenieria, Universidad de la Frontera, Temuco, Chile
Departamento de Quimica Inorganica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina
Gerencia de Investigacion y Aplicaciones, Centro Atomico Constituyentes, Comision Nacional de Energia Atomica, Buenos Aires, Argentina
Palabras clave:11-epivaldiviolide; cocrystal; Crystal structure; drimane lactone; Drimys winteri extracts; natural products; sesquiterpenes; valdiviolide; Chains; Esters; Hydrogen bonds; Stereochemistry; 11-epivaldiviolide; Co-crystals; drimane lactone; Drimys winteri extracts; Natural products; Sesquiterpenes; valdiviolide; Crystal structure; Drimys winteri; 11-epivaldiviolide; drimane; lactone; sesquiterpene; chemical structure; chemistry; Drimys; hydrogen bond; isolation and purification; isomerism; synthesis; X ray crystallography; Crystallography, X-Ray; Drimys; Hydrogen Bonding; Isomerism; Lactones; Molecular Structure; Sesquiterpenes
Año:2014
Volumen:70
Página de inicio:1112
Página de fin:1115
DOI: http://dx.doi.org/10.1107/S205322961402395X
Título revista:Acta Crystallographica Section C: Structural Chemistry
Título revista abreviado:Acta crystallogr., C Struct. Chem.
ISSN:20532296
CODEN:ACSCG
CAS:lactone, 1338-03-0; 11-epivaldiviolide; drimane; Lactones; Sesquiterpenes
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_20532296_v70_n_p1112_PazRobles

Referencias:

  • Allen, F.H., (2002) Acta Cryst. B, 58, pp. 380-388
  • Appel, H.H., Bond, R.P.M., Overton, K.H., (1963) Tetrahedron, 19, pp. 635-641
  • Bernstein, J., Davis, R.E., Shimoni, L., Chang, N.-L., (1995) Angew. Chem. Int. Ed. Engl., 34, pp. 1555-1573
  • Boeyens, J.C.A., (1978) J. Cryst. Mol. Struct., 8, pp. 317-320
  • Cremer, D., Pople, J.A., (1975) J. Am. Chem. Soc., 97, pp. 1354-1358
  • Escobar, C., Wittke, O., (1988) Acta Cryst. C, 44, pp. 154-156
  • Flack, H.D., (1983) Acta Cryst. A, 39, pp. 876-881
  • Janiak, C., (2000) J. Chem. Soc. Dalton Trans., pp. 3885-3898
  • Jansen, B.J., De Groot, A., (2004) Nat. Prod. Rep., 21, pp. 449-477
  • Kubo, I., Fujita, K., Lee, S., Ha, T., (2005) Phytother. Res., 19, pp. 1013-1017
  • Ley, S.V., Mahon, M., (1983) J. Chem. Soc. Perkin Trans., 1, pp. 1379-1381
  • Nakano, T., Villamizar, J., Maillo, M.A., (1998) J. Chem. Res. (S), pp. 560-561
  • (2009) CrysAlis PRO, , Oxford Diffraction Oxford Diffraction Ltd Abingdon, Oxfordshire, England
  • Paz Robles, C., Burgos, V., Suarez, S., Baggio, R., (2014) Acta Cryst. C, 70, pp. 1007-1010
  • Sakio, Y., Hirano, Y., Hayashi, M., Komiyama, K., Ishibashi, M., (2001) J. Nat. Prod., 64, pp. 726-731
  • Sheldrick, G.M., (2008) Acta Cryst. A, 64, pp. 112-122
  • Spek, A.L., (2009) Acta Cryst. D, 65, pp. 148-155

Citas:

---------- APA ----------
Paz Robles, C., Mercado, D., Suarez, S. & Baggio, R. (2014) . Two drimane lactones, valdiviolide and 11-epivaldiviolide, in the form of a 1:1 cocrystal obtained from Drimys winteri extracts. Acta Crystallographica Section C: Structural Chemistry, 70, 1112-1115.
http://dx.doi.org/10.1107/S205322961402395X
---------- CHICAGO ----------
Paz Robles, C., Mercado, D., Suarez, S., Baggio, R. "Two drimane lactones, valdiviolide and 11-epivaldiviolide, in the form of a 1:1 cocrystal obtained from Drimys winteri extracts" . Acta Crystallographica Section C: Structural Chemistry 70 (2014) : 1112-1115.
http://dx.doi.org/10.1107/S205322961402395X
---------- MLA ----------
Paz Robles, C., Mercado, D., Suarez, S., Baggio, R. "Two drimane lactones, valdiviolide and 11-epivaldiviolide, in the form of a 1:1 cocrystal obtained from Drimys winteri extracts" . Acta Crystallographica Section C: Structural Chemistry, vol. 70, 2014, pp. 1112-1115.
http://dx.doi.org/10.1107/S205322961402395X
---------- VANCOUVER ----------
Paz Robles, C., Mercado, D., Suarez, S., Baggio, R. Two drimane lactones, valdiviolide and 11-epivaldiviolide, in the form of a 1:1 cocrystal obtained from Drimys winteri extracts. Acta crystallogr., C Struct. Chem. 2014;70:1112-1115.
http://dx.doi.org/10.1107/S205322961402395X