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Dolabelladienols A–C, New Diterpenes Isolated from Brazilian Brown Alga Dictyota pfaffii

1
Departamento de Química, Universidad Nacional de Colombia, Cra. 30 N° 45-03, Bogotá D.C., Colombia
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Laboratório de Imunologia Clínica, Departamento de Imunologia, Instituto Oswaldo Cruz/FIOCRUZ, Av. Brasil 4365, Manguinhos, Pavilhão Leônidas Deane/409, Rio de Janeiro 21045-900, RJ, Brazil
3
Laboratório de Virologia Molecular e Biotecnologia Marinha, Programa de Pós-graduação em Ciências e Biotecnologia, Departamento de Biologia Celular e Molecular, Instituto de Biologia, Universidade Federal Fluminense, Niterói 24020-141, RJ, Brazil
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Departamento de Química Fundamental, Facultade de Ciencias and Centro de Investigaciones Científicas Avanzadas (CICA) Universidade da Coruña, 15071 A Coruña, Spain
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Laboratório de Difração de Raios X, Instituto de Química, Universidade Federal Fluminense, Niterói 24210-346, RJ, Brazil
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Laboratório Algamar, Departmento de Biologia Marinha, Instituto de Biologia, Universidade Federal Fluminense, Niterói 24020-141, RJ, Brazil
*
Authors to whom correspondence should be addressed.
Mar. Drugs 2014, 12(7), 4247-4259; https://doi.org/10.3390/md12074247
Received: 31 March 2014 / Revised: 27 June 2014 / Accepted: 30 June 2014 / Published: 23 July 2014
The marine brown alga Dictyota pfaffii from Atol das Rocas, in Northeast Brazil is a rich source of dolabellane diterpene, which has the potential to be used in future antiviral drugs by inhibiting reverse transcriptase (RT) of HIV-1. Reexamination of the minor diterpene constituents yielded three new dolabellane diterpenes, (1R*,2E,4R*,7S,10S*,11S*,12R*)10,18-diacetoxy-7-hydroxy-2,8(17)-dolabelladiene (1), (1R*,2E,4R*,7R*,10S*,11S*,12R*)10,18-diacetoxy-7-hydroxy-2,8(17)-dolabelladiene (2), (1R*,2E,4R*,8E,10S*,11S,12R*)10,18-diacetoxy-7-hydroxy-2,8-dolabelladiene (3), termed dolabelladienols A–C (13) respectively, in addition to the known dolabellane diterpenes (46). The elucidation of the compounds 13 was assigned by 1D and 2D NMR, MS, optical rotation and molecular modeling, along with the relative configuration of compound 4 and the absolute configuration of 5 by X-ray diffraction. The potent anti-HIV-1 activities displayed by compounds 1 and 2 (IC50 = 2.9 and 4.1 μM), which were more active than even the known dolabelladienetriol 4, and the low cytotoxic activity against MT-2 lymphocyte tumor cells indicated that these compounds are promising anti-HIV-1 agents. View Full-Text
Keywords: marine natural products; Dictyota pfaffii; dolabellane diterpenes; anti-HIV-1 marine natural products; Dictyota pfaffii; dolabellane diterpenes; anti-HIV-1
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Pardo-Vargas, A.; De Barcelos Oliveira, I.; Stephens, P.R.S.; Cirne-Santos, C.C.; De Palmer Paixão, I.C.N.; Ramos, F.A.; Jiménez, C.; Rodríguez, J.; Resende, J.A.L.C.; Teixeira, V.L.; Castellanos, L. Dolabelladienols A–C, New Diterpenes Isolated from Brazilian Brown Alga Dictyota pfaffii. Mar. Drugs 2014, 12, 4247-4259.

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