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De Lampasona, M.E.P.; De Fenik, I.S.; Catalán, C.A.N.; Dartayet, G.H.; Gros, E.G.; Cerda-García-Rojas, C.M.; Mora-Pérez, Y.; Joseph-Nathan, P. "Constituents of the essential oil of lippia integrifolia (Griseb.) Hieron. (Verbenaceae)" (1999) Acta Horticulturae. 500:81-88
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Abstract:

The essential oil of Lippia integrifolia was analysed by capillary GC interfaced with MS. The main constituents were isolated by using column chromatography and reversed-phase liquid chromatography and their structures established by spectroscopic methods. The major constituent of the oil is lippifoli-l(6)-en-5-one (4), a ketone based on a new sesquiterpene skeleton named lippifoliane. Ketone 4 biogenetically derives from integrifolian-1,5-dione (2), which is also a constituent of the oil. In addition to several known mono and sesquiterpenes the following new sesquiterpenes were identified: trans-humul-9(E)-en-2,6-dione (8); 4,5-seco-african-4,5-dione (9); 1,6-cis-and 1,6-trans-lippifolian-1α-o1-5-one (5) and (6) respectively; lippifoli-1(6)-en-4α-o1-5-one (7) and the sesquiterpenes 10 - 12 whose structures and conformations are discussed.

Registro:

Documento: Artículo
Título:Constituents of the essential oil of lippia integrifolia (Griseb.) Hieron. (Verbenaceae)
Autor:De Lampasona, M.E.P.; De Fenik, I.S.; Catalán, C.A.N.; Dartayet, G.H.; Gros, E.G.; Cerda-García-Rojas, C.M.; Mora-Pérez, Y.; Joseph-Nathan, P.
Filiación:Inst. de Qca. Org., Fac. de Bqca Qca y Farmacia, Univ. Nac. de Tucumán, Ayacucho 491, Tucumán 4000, Argentina
Depto de Qca. Org., Fac. de Ciencias Exactas y Naturales, Univ. de Buenos Aires, Pab. 2 Ciudad Universitaria, 1428, Buenos Aires, Argentina
Departamento de Química, Centra de Investigación y de Estudios, Avanzados Instituto Politécnico Nacional, Apartado 14-740, México, D.F., 07000, Mexico
Palabras clave:Essential oil; Sesquiterpenes; Stereochemistry; Structure; Verbenaceae
Año:1999
Volumen:500
Página de inicio:81
Página de fin:88
DOI: http://dx.doi.org/10.17660/ActaHortic.1999.500.10
Título revista:Acta Horticulturae
Título revista abreviado:Acta Hortic.
ISSN:05677572
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_05677572_v500_n_p81_DeLampasona

Referencias:

  • Catalan, C.A., Iglesias, D.A., Retamar, J., Iturraspe, J., Dartayet, G.H., Gros, E., A sesquiterpene diketone from Lippia integrifolia (1983) Phytochemistry, 22, pp. 1507-1508
  • Catalan, C.A., De Fenik, J.S., Dartayet, G.H., Gros, E., Integrifolian-l,5-dione and a revised structure for " africanone", biogenetically related sesquiterpene from Lippia integrifolia (1991) Phytochemistry, 30, pp. 1323-1326
  • Catalan, C.A.N., De Fenik, J.S., De Arriazu, P.J., Kokke, W.C.M.C., 4,5-seco-african-4,5-dione from Lippia integrifolia (1992) Phytochemistry, 31, pp. 4025-4026
  • Catalan, C.A., De Fenik, J.S., Cerda-García-Rojas, C.M., Mora-Pérez, Y., Joseph-Nathan, P., Total assignment of the 13C NMR spectra of integrifolian-l,5-dione and derivatives by 2D spectroscopy (1993) Spectroscopy, 11, pp. 1-8
  • Catalan, C.A.N., De Lampasona, M.P., De Fenik, J.S., Cerda-García-Rojas, C.M., Joseph-Nathan, P., Structure and Conformation of a Humulendione from Lippia integrifolia (1993) Journal of Natural Products, 56, pp. 381-385
  • Catalan, C.A.N., De Lampasona, M.P., De Fenik, J.S., Cerda-García-Rojas, C.M., Mora-Pérez, Y., Joseph-Nathan, P., Minor Constituents of Lippia integrifolia (1994) Journal of Natural Products, 57, pp. 206-210
  • Catalan, C.A.N., De Lampasona, M.P., Cerda-García-Rojas, C.M., Joseph-Nathan, P., Trace Constituents of Lippia integrifolia (1995) Journal of Natural Products, 58, pp. 1713-1717
  • Dartayet, G., Catalan, C.A., Rater, J.A., Gros, E.G., Sesquiterpenoids from Lippia integrifolia -africanone-, a tricyclic sesquiterpene ketone (1984) Phytochemistry, 23, pp. 688-689
  • Toursarkissian, M., (1980) Plantas Medicinales de la Argentina. Sus Nombres Botánicos, Vulgares, Usos y Distribución Geográfica, p. 135. , Editorial Hemisferio Sur, Buenos Aires

Citas:

---------- APA ----------
De Lampasona, M.E.P., De Fenik, I.S., Catalán, C.A.N., Dartayet, G.H., Gros, E.G., Cerda-García-Rojas, C.M., Mora-Pérez, Y.,..., Joseph-Nathan, P. (1999) . Constituents of the essential oil of lippia integrifolia (Griseb.) Hieron. (Verbenaceae). Acta Horticulturae, 500, 81-88.
http://dx.doi.org/10.17660/ActaHortic.1999.500.10
---------- CHICAGO ----------
De Lampasona, M.E.P., De Fenik, I.S., Catalán, C.A.N., Dartayet, G.H., Gros, E.G., Cerda-García-Rojas, C.M., et al. "Constituents of the essential oil of lippia integrifolia (Griseb.) Hieron. (Verbenaceae)" . Acta Horticulturae 500 (1999) : 81-88.
http://dx.doi.org/10.17660/ActaHortic.1999.500.10
---------- MLA ----------
De Lampasona, M.E.P., De Fenik, I.S., Catalán, C.A.N., Dartayet, G.H., Gros, E.G., Cerda-García-Rojas, C.M., et al. "Constituents of the essential oil of lippia integrifolia (Griseb.) Hieron. (Verbenaceae)" . Acta Horticulturae, vol. 500, 1999, pp. 81-88.
http://dx.doi.org/10.17660/ActaHortic.1999.500.10
---------- VANCOUVER ----------
De Lampasona, M.E.P., De Fenik, I.S., Catalán, C.A.N., Dartayet, G.H., Gros, E.G., Cerda-García-Rojas, C.M., et al. Constituents of the essential oil of lippia integrifolia (Griseb.) Hieron. (Verbenaceae). Acta Hortic. 1999;500:81-88.
http://dx.doi.org/10.17660/ActaHortic.1999.500.10