Planta Med 2005; 71(8): 711-716
DOI: 10.1055/s-2005-871224
Original Paper
Pharmacology
© Georg Thieme Verlag KG Stuttgart · New York

Norsecofriedelanes as Spasmolytics, Advances of Structure-Activity Relationships

Manasés González-Cortazar1 , 2 , 3 , Jaime Tortoriello2 , Laura Alvarez1
  • 1Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Cuernavaca, Morelos, México
  • 2Centro de Investigación Biomédica del Sur, Instituto Mexicano del Seguro Social (IMSS). Xochitepec, Morelos, México
  • 3This work was part of the Ph.D. thesis of M. G.-C., Programa de Doctorado en Ciencias (Química), Universidad Autónoma del Estado de Morelos, 2004
Further Information

Publication History

Received: October 11, 2004

Accepted: February 25, 2005

Publication Date:
04 August 2005 (online)

Abstract

Galphimia glauca has been used in Mexican traditional medicine as a remedy for the treatment of nervous excitement and other central nervous system disorders. Previous work has demonstrated the sedative, spasmolytic and anticonvulsant activities of an extract obtained from the aerial parts of this plant. A norsecotriterpene named galphimine B was found to be responsible for the sedative and spasmolytic activities. Activity-guided fractionation making use of the guinea pig ileum as an experimental system was used for the isolation of five compounds. They were identified as a new norsecotriterpene, galphimine J (2) and four known norsecotriterpenes (1, 3 - 5). Nine derivatives of 3 (5, 6 and 8 - 14) were obtained by chemical modification of the α,β-unsaturated lactone, the olefinic bonds on the A and E rings, the hydroxy groups on ring B, or a combination thereof, and a structure-activity correlation study was carried out. The results indicate the existence of a clear structure-activity relationship. They suggest the involvement of the double bond in the E ring as well as the hydroxy groups at C-4, C-6 and C-7 in biological activity and emphasize the relevance of a free OH group at C-6 and C-4.

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Dra. Laura Alvarez

Centro de Investigaciones Químicas

Universidad Autónoma del Estado de Morelos

Av. Universidad 1001

Cuernavaca

Morelos 62210

México

Phone: +52-777-329-7997

Fax: +52-777-329-7997

Email: lalvarez@intermor.net.mx