Planta Med 2006; 72(8): 757-761
DOI: 10.1055/s-2006-931587
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Two New Cassane-Type Diterpenes from Calliandra californica with Antituberculosis and Cytotoxic Activities

Rosalba Encarnación-Dimayuga1 , Jorge Agúndez-Espinoza1 , Abraham García2 , Guillermo Delgado2 , Gloria María Molina-Salinas3 , Salvador Said-Fernández3
  • 1Departamento de Agronomía, Universidad Autónoma de Baja California Sur, La Paz, México
  • 2Instituto de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, Coyoacán, México
  • 3Centro de Investigación Biomédica del Noreste, Instituto Mexicano del Seguro Social, Monterrey, México
Further Information

Publication History

Received: September 26, 2005

Accepted: February 17, 2006

Publication Date:
01 June 2006 (online)

Abstract

From the root of Calliandra californica two new cassane-type diterpenes were isolated and characterized, escobarine A (1) and B (2), which showed promising activities against two Mycobacterium tuberculosis strains. The microplate alamar blue assay was used to determine the minimum inhibitory concentrations (MIC) of 1 and 2 against M. tuberculosis H37Rv and the resistant CIBIN/UMF15 : 099 strains. The MIC of 1 against the resistant M. tuberculosis strain showed a value 8 times lower than that of rifampin. The structures of the bioactive constituents were established by extensive NMR data analyses (including 1D and 2D NMR). The relative configuration of 2 was confirmed by X-ray analysis and the absolute configurations of 1 and 2 were determined by the circular dichroism method. Additionally, 1 and 2 displayed remarkable cytotoxic activity when evaluated against five human tumor cell lines.

References

  • 1 Wiggins I L. Flora of Baja California. California; Stanford University Press 1980: p 703
  • 2 Encarnación-Dimayuga R. Medicina tradicional y popular de Baja California Sur. La Paz, México; Artes Gráficas de la UABCS 1992: p 75
  • 3 Christophersen C, Larsen C, Encarnacion-Dimayuga R. Medicina tradicional. Una fuente potencial de explotación de los recursos naturales. Copenhagen; the H. C. Ørsted Institute 1991: p 22-3
  • 4 Encarnacion-Dimayuga R, Ochoa N, Anthoni U, Christophersen C, Nielsen P H. Two new flavones from Calliandra californica .  J Nat Prod. 1994;  57 1307-9
  • 5 SMART . (5.625). Bruker AXS Inc Madison, WI; 2000
  • 6 Sheldrick G M. SHELXTL97, an integrated system for solving, refining and displaying crystal structures from diffraction data. Göttingen; University of Göttingen 1997
  • 7 International Tables for X-ray C rystallography. Vol. IV. Birmingham; Kynoch Press 1974
  • 8 Murillo-Alvarez J I, Encarnación D R, Franzblau S. Antimicrobial and cytotoxic activity of some medicinal plants from B.C.S. (México).  Pharm Biol. 2001;  39 445-9
  • 9 Molina-Salinas G M, Ramos-Guerra M C, Vargas-Villarreal J, Mata-Cárdenas B D, Becerril-Montes P, Said-Fernández S. Bactericidal activity of organic extracts from Flourensia cernua DC against sensitive and multidrug-resistant strains of Mycobacterium tuberculosis .  Arch Med Res. 2005;  36 45-9
  • 10 Franzblau S G, Witzig R S, McLaughlin J C, Torres P, Madico G, Hernandez A. et al . Rapid, low-technology MIC determination with clinical Mycobacterium tuberculosis isolates by using the microplate alamar blue assay.  J Clin Microbiol. 1998;  38 362-6
  • 11 Monks A, Scudiero D, Skehan P, Shoemaker R, Paull K, Vistica D. et al . Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines.  J Natl Cancer Inst. 1991;  83 757-66
  • 12 Barba B, Días J G, Goedken V L, Herz W, Domínguez X A. Unusual cassanes from Chamaecrista species.  Tetrahedron. 1992;  48 4725-32
  • 13 Nakanishi K, Berova N, Woody R W. Circular dichroism. Principles and applications. New York; VHC Publishers, Inc 1994: p 259-300
  • 14 Burkert U, Allinger N L. Molecular mechanics, ACS Monograph 177. Washington DC; American Chemical Society 1982

Dr. Rosalba Encarnación-Dimayuga

Departamento de Agronomía

Universidad Autónoma de Baja California Sur

A. P. 19-B

23080 La Paz B. C. S.

México

Phone: +52-1-612-123-8800-5130

Email: rosalba@uabcs.mx