Planta Med 2004; 70(9): 856-860
DOI: 10.1055/s-2004-827235
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

In vitro Antiviral Diterpenes from the Brazilian Brown Alga Dictyota pfaffii

Jussara Pinheiro Barbosa1 , Renato Crespo Pereira2 , Juliana Lourenço Abrantes3 , Cláudio César Cirne dos Santos4 , Moacyr Alcoforado Rebello4 , Izabel Christina de Palmer Paixão Frugulhetti3 , Valéria Laneuville Teixeira2
  • 1Programa de Pós-graduação em Química Orgânica, Instituto de Química, Universidade Federal Fluminense, Niterói, RJ, Brazil
  • 2Departamento de Biologia Marinha, Instituto de Biologia, Universidade Federal Fluminense, Niterói, RJ, Brazil
  • 3Departamento de Biologia Celular e Molecular, Instituto de Biologia, Universidade Federal Fluminense, Niterói, RJ, Brazil
  • 4Instituto de Microbiologia Prof. Paulo de Góes, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ, Brazil
Further Information

Publication History

Received: December 12, 2003

Accepted: May 20, 2004

Publication Date:
23 September 2004 (online)

Abstract

Specimens of Dictyota pfaffii from Atol das Rocas, Northeast Brazil, afforded the rare dolabellane diterpene 10,18-diacetoxy-8-hydroxy-2, 6-dolabelladiene (1) and the new 10-acetoxy-8,18-dihydroxy-2,6-dolabelladiene (2). Reduction of 1 yielded 8,10,18-trihydroxy-2,6-dolabelladiene (3), also present in the crude extract of D. pfaffii. All three structures were assigned by 1D and 2D NMR spectral data. These substances showed strong anti-HSV-1 activity in vitro but only 3 inhibited the reverse transcriptase enzyme of HIV-1.

References

  • 1 Teixeira V L, Tomassini T, Fleury B G, Kelecom A. Dolastane and secodolastane diterpenes from the marine brown alga Dictyota cervicornis .  Journal of Natural Products. 1986;  49 570-5
  • 2 Teixeira V L, Tomassini T, Kelecom A. Cervicol, a further secodolastane diterpene from the marine brown alga Dictyota cervicornis .  Bulletin de la Societé Chimie Belgique. 1986;  95 263-7
  • 3 Teixeira V L, Almeida S AS, Kelecom A. Chemosystematic and biogeographic studies of the diterpenes from the marine brown alga Dictyota dichotoma .  Biochemical Systematic and Ecology. 1990;  18 87-92
  • 4 Teixeira V L, Cavalcanti D N, Pereira R C. Chemotaxonomic study of the diterpenes from the marine brown alga Dictyota menstrualis .  Biochemical Systematic and Ecology,. 2001;  29 313-6
  • 5 De-Paula J C, Pedrini A G, Pinheiro M D, Pereira R C, Teixeira V L. Chemical similarity between the brown algae Dictyota cervicornis and D. pardalis .  Biochemical Systematic and Ecology. 2001;  29 425-7
  • 6 Kelecom A, Teixeira V L. Dolastane diterpenes from the marine brown alga Dictyota cervicornis .  Phytochemistry. 1988;  27 2907-9
  • 7 Ireland C, Faulkner D J, Finer J, Clardy J. A novel diterpene from Dolabella californica .  Journal of the American Chemical Society. 1976;  98 4664-5
  • 8 Rodriguez A D, González E, Ramirez C. The structural chemistry, reactivity and total synthesis of dolabellane diterpenes.  Tetrahedron. 1998;  54 11 683-729
  • 9 Barbosa J P, Teixeira V L, Villaça R, Pereira R C, Abrantes J L, Frugulhetti I CPP. A dolabellane diterpene from the Brazilian brown alga Dictyota pfaffii.  Biochemical, Systematic and Ecology. 2003;  31 1451-3
  • 10 König G M, Wright A D, Sticher O, Angerhofer C K, Pezzuto J M. Biological activities of selected marine natural products.  Planta Medica. 1994;  60 532-7
  • 11 König G M, Wright A D, Franzblau G. Assessment of antimycobacterial activity of a series of mainly marine derived natural products.  Planta Medica. 2000;  66 337-42
  • 12 Durán R, Zubia E, Ortega M J, Salvá J. New diterpenoids from the alga Dictyota dichotoma .  Tetrahedron. 1997;  53 8675-88
  • 13 De Clercq E. Current lead natural products for the chemotherapy of human immunodeficiency virus (HIV) infection.  Medical Research Review. 2000;  20 323-49
  • 14 Jung M, Lee S, Kim H. Recent studies on natural products as anti-HIV agents.  Current Medical Chemistry. 2000;  7 649-61
  • 15 Hayashi K, Hayashi T H, Takeda Y. Antiviral activity of the 5, 6, 7-trimethoxyflavone and the antiherpes activity of acyclovir.  Journal of Antimicrobial Chemotherapy. 1977;  39 821-4
  • 16 Reed J, Muench M. A simple method of estimating 50 % endpoints.  American Journal of Virology. 1938;  27 492-97
  • 17 Hizi A, McGill C, Hughes H. Expression of soluble, enzimatically active, human immunodeficiency virus reverse transcriptase in Escherichia coli and analyses of mutants.  Proceedings of the Natural Academy of Science of the United States of America. 1988;  85 1218-22
  • 18 Ireland C, Faulkner D J. Diterpenes from Dolabella californica .  Journal of Organic Chemistry. 1977;  42 3157-62
  • 19 Tringali C, Piattelli M, Nicolosi G. Structure and conformation of new diterpenes based on the dolabellane skeleton from a Dictyota species.  Tetrahedron. 1984;  40 799-801

Valéria Laneuville Teixeira

Departamento de Biologia Marinha

Instituto de Biologia

P.O. Box 100.644

Universidade Federal Fluminense

Niterói, 24001-970

RJ

Brazil

Phone: +55-21-26292311

Fax: +55-21-26292292

Email: gbmvalt@vm.uff.br

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