Planta Med 2006; 72 - P_092
DOI: 10.1055/s-2006-949892

A potent cytotoxic semisynthetic derivative of perezone with phenylglycine

RG Enríquez 1, D Alonso-Cortés 2, MC Lozada 3, EV Avila 4, JL Montiel 5, WF Reynolds 6, ML Villarreal 5
  • 1Instituto de Química, UNAM, Cd. Universitaria, Coyoacán, 04510, México, D. F
  • 2Centro de Investigación Biomédica del Sur IMSS, Argentina No 1, Xochitepec, Morelos México
  • 3Departamento de Sistemas Biológicos, UAM-Xochimilco, Calzada del Hueso 1100, Villa Quietud, Coyoacán, 04960, México, D.F
  • 4Departamento de Ciencias Biológicas, UAM-Iztapalapa, Av. San Rafael Atlixco 186, Vicentina, Iztapalapa, 09340, D. F, México
  • 5Universidad Autónoma del Estado de Morelos Av. Universidad 1001, 62210, Morelos, México
  • 6Deparment of Chemistry, University of Toronto, Ontario Canada

Perezone, is a naturally occurring quinone, first isolated in México (1852) from Perezia species and used in traditional medicine. We have isolated perezone from Perezia cuernavacana. This compound was reacted with methyl esthers of various amino acids. In particular, the phenylglycine esther derivative showed important cytotoxic activities against ovarian (ED50=4.0µg/mL), renal (ED50=0.86µg/mL), colon (ED50=0.82µg/mL) and nasopharyngeal (ED50=4.0µg/mL) cancer cell lines [1]. The chemical structure of this derivative was assessed by 13C an 1H NMR spectroscopy and X-ray crystallography [2].

The reaction scheme is given below

A biological screening has shown modification of the percentage of cells on cell cycle phases of the monocytic human cell line TPH1.

Acknowledgements: to: CONACYT of México (37821-N and 40959-Q); DGAPA of UNAM (IN232202).

References: 1. Alonso, D. (2003), M.Sc. Thesis. Cytotoxic effect of perezone derivatives. UAEM, Cuernavaca, Morelos. 2. Alducin, E. (1997), M.Sc. thesis. Analytic study of the reactivity of perezone. New heterocyclic derivatives of sulfur and nitrogen. UNAM, México.