title: Dolabelladienols A-C, new diterpenes isolated from Brazilian brown alga Dictyota pfaffii.
abstract: 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 (1-3) respectively, in addition to the known dolabellane diterpenes (4-6). The elucidation of the compounds 1-3 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.
authors: Departamento de Química, Universidad Nacional de Colombia, Cra. 30 N° 45-03, Bogotá D.C., Colombia. apardov@unal.edu.co.
authors: Alonso
authors: A
authors: Pardo-Vargas
authors: 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. izabeluff@gmail.com.
authors: Ingrid
authors: I
authors: de Barcelos Oliveira
authors: 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. izabeluff@gmail.com.
authors: Paulo Roberto Soares
authors: PR
authors: Stephens
authors: 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. izabeluff@gmail.com.
authors: Claudio Cesar
authors: CC
authors: Cirne-Santos
authors: 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. izabeluff@gmail.com.
authors: Izabel Christina Nunes
authors: IC
authors: de Palmer Paixão
authors: Departamento de Química, Universidad Nacional de Colombia, Cra. 30 N° 45-03, Bogotá D.C., Colombia. faramosr@unal.edu.co.
authors: Freddy Alejandro
authors: FA
authors: Ramos
authors: Departamento de Química Fundamental, Facultade de Ciencias and Centro de Investigaciones Científicas Avanzadas (CICA) Universidade da Coruña, 15071 A Coruña, Spain. carlos.jimenez@udc.es.
authors: Carlos
authors: C
authors: Jiménez
authors: Departamento de Química Fundamental, Facultade de Ciencias and Centro de Investigaciones Científicas Avanzadas (CICA) Universidade da Coruña, 15071 A Coruña, Spain. jaime.rodriguez@udc.es.
authors: Jaime
authors: J
authors: Rodríguez
authors: Laboratório de Difração de Raios X, Instituto de Química, Universidade Federal Fluminense, Niterói 24210-346, RJ, Brazil. jresende@id.uff.br.
authors: Jackson Antonio Lamounier Camargos
authors: JA
authors: Resende
authors: Laboratório Algamar, Departmento de Biologia Marinha, Instituto de Biologia, Universidade Federal Fluminense, Niterói 24020-141, RJ, Brazil. valerialaneuville@gmail.com.
authors: Valeria Laneuville
authors: VL
authors: Teixeira
authors: Departamento de Química, Universidad Nacional de Colombia, Cra. 30 N° 45-03, Bogotá D.C., Colombia. lcastellanosh@unal.edu.co.
authors: Leonardo
authors: L
authors: Castellanos
mesh_terms: D019380:Anti-HIV Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015497:HIV-1 / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D000459:Phaeophyceae / Q000378:metabolism*
chemical_list: C000601944:10,18-diacetoxy-7-hydroxy-2,8(17)-dolabelladiene; D019380:Anti-HIV Agents; D004224:Diterpenes; C000601945:dolabelladienol B