Download PDF
Planta Med 2007; 73(11): 1221-1224
DOI: 10.1055/s-2007-981589
Natural Product Chemistry
Letter
© Georg Thieme Verlag KG Stuttgart · New York

In vitro Antiviral Effect of Meroditerpenes Isolated from the Brazilian Seaweed Stypopodium zonale (Dictyotales)

Angelica Ribeiro Soares1 , 6 , Juliana Lourenço Abrantes2 , Thiago Moreno Lopes Souza3 , Carlos Frederico Leite Fontes3 , Renato Crespo Pereira4 , Izabel Christina de Palmer Paixão Frugulhetti5 , Valéria Laneuville Teixeira4
  • 1Programa de Pós-Graduação em Química Orgânica, Instituto de Química, Universidade Federal Fluminense, Niterói, RJ, Brazil
  • 2Programa de Pós-Graduação em Neuroimunologia, Instituto de Biologia, Universidade Federal Fluminense, Niterói, RJ, Brazil
  • 3Programa de Pós-graduação em Química Biológica, Instituto de Bioquímica Médica, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ, Brasil
  • 4Departamento de Biologia Marinha, Instituto de Biologia, Universidade Federal Fluminense, Niterói, RJ, Brazil
  • 5Departamento de Biologia Celular e Molecular, Instituto de Biologia, Universidade Federal Fluminense, Niterói, RJ, Brazil
  • 6Present Address: Núcleo de Estudos em Ecologia e Desenvolvimento Sócio-Ambiental de Macaé, Universidade Federal do Rio de Janeiro, Rua Rotary Club s/no, Bairro São José do Barreto, Macaé, RJ, Brazil
Further Information

Publication History

Received: April 20, 2007 Revised: July 11, 2007

Accepted: July 16, 2007

Publication Date:
23 August 2007 (online)

Also available at
    Permissions and Reprints

Abstract

The meroditerpenoids atomaric acid (1), epitaondiol (2) and the peroxylactone of 5′a-desmethyl-5′-acetylatomaric acid (3) were isolated from the Brazilian brown alga Stypopodium zonale collected in two localities (Búzios and Marataízes, RJ and ES States). These compounds showed strong anti-HSV-1 activity in vitro but neither of them inhibited the transcriptase reverse enzyme of HIV-1.

References

  • 1 Wessels M, König G M, Wright A D. A new tyrosine kinase inhibitor from the marine brown alga Stypopodium zonale .  J Nat Prod. 1999;  62 927-30.
    CrossrefPubMedGoogle Scholar
  • 2 Smit A J. Medicinal and pharmaceutical uses of seaweeds natural products: a review.  J Appl Phycol. 2004;  16 245-62.
    CrossrefPubMedGoogle Scholar
  • 3 Dorta E, Cueto M, Brito I, Darias J. New terpenoids from the brown alga Stypopodium zonale .  J Nat Prod. 2002;  65 1727-30.
    CrossrefPubMedGoogle Scholar
  • 4 Sánchez-Ferrando F, San-Martín A. Epitaondiol: The first polycyclic meroditerpenoid containing two fused six-membered rings forced into the twist-boat conformation.  J Org Chem. 1995;  60 1475-8.
    CrossrefPubMedGoogle Scholar
  • 5 González A G, Martin J D, Perez C, Rovirosa J, Tagle B, Clardy J. Isolation and X-ray structural determination of three new diterpenoids from the marine alga Taonia atomaria . Chem Lett 1984: 1649-52.
    Google Scholar
  • 6 Barbosa J P, Pereira R C, Abrantes J L, Cirne-Santos C C, Rebello M A, Frugulhetti I CPP. et al . In vitro antiviral diterpenes from the Brazilian brown alga Dictyota pfaffii .  Planta Med. 2004;  70 856-60.
    Article in Thieme ConnectPubMedGoogle Scholar
  • 7 Pereira H S, Leão-Ferreira L R, Moussatché N, Teixeira V L, Cavalcanti D N, Costa L J. et al . Effects of diterpenes isolated from the Brazilian marine alga Dictyota menstrualis on HIV-1 reverse transcriptase.  Planta Med. 2005;  71 1019-24.
    Article in Thieme ConnectPubMedGoogle Scholar
  • 8 Pereira H S, Leão-Ferreira L R, Moussatché N, Teixeira V L, Cavalcanti D N, Costa L J. et al . Antiviral activity of diterpenes isolated from the Brazilian marine alga Dictyota menstrualis against human immunodeficiency virus type 1 (HIV-1).  Antiviral Res. 2004;  64 69-76.
    CrossrefPubMedGoogle Scholar
  • 9 Cirne-Santos C C, Teixeira V L, Castello-Branco L R, Frugulhetti I C, Bou-Habib D C. Inhibition of HIV-1 replication in human primary cells by a dolabellane diterpene isolated from the marine algae Dictyota pfaffii .  Planta Med. 2006;  72 295-9.
    Article in Thieme ConnectPubMedGoogle Scholar
  • 10 González A G, Darias J, Martin J D, Norte M. Atomaric acid, a new component from Taonia atomaria .  Tetrahedron Lett. 1974;  45 3951-4.
    PubMedGoogle Scholar
  • 11 Lagrota M HC, Wigg M D, Santos M MG, Miranda M MFS, Camara F P, Couceiro J NSS. et al .Inhibitory activity of extracts of Alternanthera brasiliana (Amarantharaceae) against Herpes simplex virus. Phytother Res 1994 8: 358.
    Google Scholar
  • 12 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.  J Immunol Methods. 1983;  65 55-63.
    CrossrefPubMedGoogle Scholar
  • 13 Denizot F, Lang R. Rapid colorimetric assay for cell growth and survival. Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability.  J Immunol Methods. 1986;  89 271-7.
    CrossrefPubMedGoogle Scholar
  • 14 Reed J, Muench M. A simple method of estimating fifty per cent endpoints.  Am J Hyg. 1938;  27 493-7.
    PubMedGoogle Scholar
  • 15 Mishra V, Pandeya S N, Pannecouque C, Witvrouw M, De Clercq E. Anti-HIV activity of thiosemicarbazone and semicarbazone derivatives of (+/-)-3-menthone.  Arch Pharm (Weinheim). 2002;  335 83-6.
    CrossrefPubMedGoogle Scholar

Valéria Laneuville Teixeira

Departamento de Biologia Marinha

Instituto de Biologia

Universidade Federal Fluminense

Niterói

RJ

Brazil

Phone: +55-21-2629-2311

Fax: +55-21-2629-2292

Email: valerialaneuville@gmail.com

Email: gbmvalt@vm.uff.br

    www.thieme-connect.de/ejournals/toc/plantamedica