Planta Med 2007; 73(3): 292-295
DOI: 10.1055/s-2007-967108
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Evaluation of Antifungal and DNA-Damaging Activities of Alkaloids from Branches of Porcelia macrocarpa

João Henrique G. Lago1 , Mariana H. Chaves2 , Mariane Cruz C. Ayres2 , Débora G. Agripino3 , Maria Cláudia M. Young3
  • 1Centro de Ciências e Humanidades, Universidade Presbiteriana Mackenzie, São Paulo, SP, Brazil
  • 2Departamento de Química, Universidade Federal do Piauí, Teresina, PI, Brazil
  • 3Seção de Fisiologia e Bioquímica de Plantas, Instituto de Botânica, São Paulo, SP, Brazil
Further Information

Publication History

Received: July 17, 2006

Accepted: December 22, 2006

Publication Date:
12 March 2007 (online)

Abstract

Bioactivity-guided fractionation of the alkaloidal fractions of the CH2Cl2 extract from branches of Porcelia macrocarpa using mutant yeast strains of Saccharomyces cerevisiae and fungi Cladosporium cladosporioides and C. sphaerospermum led to the isolation of bioactive alkaloids: two tetrahydrobenzylisoquinolines (1 and 2), two aporphines (3 and 4), one proaporphine (5), one oxoaporphine (6), four azantraquinones (7 - 10) and four azafluorenones (11 - 14). The alkaloids cleistopholine (7) and 6-methoxycleistopholine (8) showed the highest fungitoxic activity while the mixture of 6- and 7-methoxyonychine (12 + 13) and 6,7-dimethoxyonychine (14) showed a weak DNA-damaging potential.

References

  • 1 Chaves M H, Roque N F. Acetogenins from Porcelia macrocarpa: stereochemical determination of 2-alkyl-3-hydroxy-4-methyl-γ-lactones by 13C NMR spectroscopy.  Phytochemistry. 1997;  44 523-8.
  • 2 Brochini C B, Nuñez C V, Moreira I C, Roque N F, Chaves M H, Martins D. Identificação de componentes de óleos voláteis: análise espectroscópica de misturas de sesquiterpenos.  Quim Nova. 1999;  22 37-40.
  • 3 Chaves M H, Lago J HG, Roque N F. Macrocarpane, a new sesquiterpene skeleton from the leaves of Porcelia macrocarpa .  J Braz Chem Soc. 2003;  14 16-9.
  • 4 Chaves M H, Roque N F. Amides and lignanamides from Porcelia macrocarpa .  Phytochemistry. 1997;  46 879-81.
  • 5 Chaves M H, Freitas A, Roque N F, Cavalheiro A J. Separação e identificação de constituintes químicos polares dos galhos de Porcelia macrocarpa .  Quim Nova. 2000;  23 307-9.
  • 6 Chaves M H, Santos L A, Lago J HG, Roque N F. Alkaloids from Porcelia macrocarpa .  J Nat Prod. 2001;  64 240-2.
  • 7 Chaves M H, Roque N F, Ayres M CC. Steroids and flavonoids of Porcelia macrocarpa .  J Braz Chem Soc. 2004;  15 608-13.
  • 8 Danelutte A P, Lago J HG, Young M CM, Kato M J. Antifungal prenylated hydroquinones and flavanones from Piper crassinervium .  Phytochemistry. 2003;  64 555-9.
  • 9 Lago J HG, Ramos C S, Casanova D CC, Morandin A A, Bergamo D CB, Bolzani V da S. et al . Benzoic acid derivatives from Piper species and their fungitoxic potential against Cladosporium cladosporioides and Cladosporium sphaerospermum .  J Nat Prod. 2004;  49 1783-8.
  • 10 Homans A L, Fuchs A. A direct bioautography on thin layer chromatograms as a method for detecting fungitoxic substances.  J Chromatogr. 1970;  51 327-9.
  • 11 Rahalison L, Hamburger M, Monod M, Frenk E, Hostettmann K. Antifungal tests in phytochemical investigations - comparison of bioautographic methods using phytopatogenic and human pathogenic fungi.  Planta Med. 1994;  60 41-4.
  • 12 Silva R V, Navickiene H MD, Kato M J, Bolzani V da S, Méda C, Young M CM. et al . Antifungal amides from Piper arboreum and Piper tuberculatum .  Phytochemistry. 2002;  59 521-7.
  • 13 Rex J H, Pfaller M A, Walsh T J, Chaturvedi V, Espinel-Ingroff A, Ghannoum M A. et al . Antifungal susceptibility testing: practical aspects current challenges.  Clin Microbiol Rev. 2001;  14 643-58.
  • 14 Gunatilaka A AL, Kingston D GI, Johnson R K. Mechanism-based isolation and structures of some anticancer active natural products.  Pure Appl Chem. 1994;  66 2219-22.
  • 15 Bolzani V da S, Gunatilaka A AL, Kingston D GI. Bioactive and other bioactive alkaloids from Cassia leptophylla .  Tetrahedron. 1995;  51 5929-34.
  • 16 Woo S H, Sun N J, Cassady J M, Snapka R M. Inhibition of topoisomerase II by liriodenine.  Biochem Pharmacol. 1997;  54 467-73.
  • 17 Woo S H, Sun N J, Cassady J M, Snapka R M. Topoisomerase II inhibition by aphorphine alkaloids.  Biochem Pharmacol. 1999;  57 1141-5.
  • 18 Bracher F. Polycyclic aromatic alkaloids 10. Annonaceous alkaloids with antifungal activity.  Arch Pharm. 1994;  327 371-5.
  • 19 Peterson J R, Zjawidny K J, Liu S, Hufford C D, Clark A M, Rogers R D. Copyrine alkaloids: synthesis, spectroscopic characterization, and antimycotic/amtimycobacterial activity of A- and B-ring-functionalized sampangines.  J Med Chem. 1992;  35 4069-77.
  • 20 Hufford C D, Liu S, Clark A M. Anticandidal activity of eupolauridine and onycine, alkaloids from Cleistopholis patens .  J Nat Prod. 1987;  50 961-4.

Prof. Dr. João Henrique G. Lago

Centro de Ciências e Humanidades

Universidade Presbiteriana Mackenzie

CEP 01302-907

São Paulo

SP

Brazil

Phone: +55-151-121-148-145

Email: joaolago@iq.usp.br

    >