Planta Med 2009; 75(14): 1520-1522
DOI: 10.1055/s-0029-1185834
Pharmacology
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Antiproliferative Activity of the Diterpenes Jatrophone and Jatropholone and Their Derivatives

Cristina Theoduloz1 , Jaime A. Rodríguez1 , Mariano Pertino2 , Guillermo Schmeda-Hirschmann2
  • 1Departamento de Ciencias Básicas Biomédicas, Facultad de Ciencias de la Salud, Universidad de Talca, Casilla 747, Talca, Chile
  • 2Laboratorio de Química de Productos Naturales, Instituto de Química de Recursos Naturales, Universidad de Talca, Casilla 747, Talca, Chile
Further Information

Publication History

received January 19, 2009 revised April 21, 2009

accepted May 28, 2009

Publication Date:
26 June 2009 (online)

Abstract

The antiproliferative activity of the diterpenes jatropholone A and B, 16 semi-synthetic derivatives thereof, and that of jatrophone and its three derivatives was assessed on human cell cultures. The cells used comprised normal lung fibroblasts (MRC-5), gastric adenocarcinoma (AGS), leukemia (HL-60), lung cancer (SK‐MES‐1), and bladder carcinoma (J82). Jatropholone A (1) was inactive against all the tumor cell lines; however, its acetylation rendered a compound with antiproliferative activity. The epimeric jatropholone B (8) was active against all the cancer cell lines, and its derivatives presented different effects on the selected cell lines. While jatrophone (19) showed strong anticancer activity, its derivatives 9β,13α-dihydroxyisabellione and 13α-hydroxy-9β-acetoxyisabellione were less active.

References

  • 1 Kupchan S M, Sigel C W, Matz M J, Gilmore C J, Bryan R F. Structure and stereochemistry of jatrophone, a novel macrocyclic diterpenoid tumor inhibitor.  J Am Chem Soc. 1976;  98 2295-2300
  • 2 Taylor M D, Smith I IIAB, Furst G T, Gunasekara S P, Bevelle C A, Cordell G A, Farnsworth N R, Kupchan S M, Uchida H, Branford A R, Dailey Jr R G, Sneden A T. New antileukemic jatrophone derivatives from Jatropha gosypiifolia: structural and stereochemical assignment through nuclear magnetic resonance spectroscopy.  J Am Chem Soc. 1983;  105 3177-3183
  • 3 Taylor M D, Smith III A B, Malamas M S. Jatrophone, jatrophone derivatives, and analogues. Conformation and reactions with propanethiol.  J Org Chem. 1983;  48 4257-4261
  • 4 Pertino M, Schmeda-Hirschmann G, Rodríguez J A, Theoduloz C. Gastroprotective effect and cytotoxicity of diterpenes from the Paraguayan crude drug “yagua rova” (Jatropha isabelii).  J Ethnopharmacol. 2007;  111 553-559
  • 5 Pertino M, Schmeda-Hirschmann G, Rodríguez J A, Theoduloz C. Gastroprotective effect and cytotoxicity of semisynthetic jatropholone derivatives.  Planta Med. 2007;  73 1095-1100
  • 6 Pertino M, Schmeda-Hirschmann G, Santos L S, Rodriguez J A, Theoduloz C. Biotransformation of jatrophone by Aspergillus niger ATCC 16404.  Z Naturforsch B. 2007;  62 275-279
  • 7 Bahmanyar S, Ye W, Dickman P W, Nyren O. Long-term risk of gastric cancer by subsite in operated and unoperated patients hospitalized for peptic ulcer.  Am J Gastroenterol. 2007;  102 1185-1191
  • 8 Valderrama J A, González M F, Pessoa-Mahana D, Tapia R A, Fillion H, Pautet F, Rodríguez J A, Theoduloz C, Schmeda-Hirschmann G. Studies on quinones. Part 41: synthesis and cytotoxity of isoquinoline-containing polycyclic quinones.  Bioorg Med Chem. 2006;  14 5003-5011

Dr. Guillermo Schmeda-Hirschmann

Laboratorio de Química de Productos Naturales
Instituto de Química de Recursos Naturales
Universidad de Talca

Casilla 747

Talca

Chile

Phone: + 56 71 20 02 88

Fax: + 56 71 20 04 48

Email: schmeda@utalca.cl