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

Author: Pardo-Vargas Alonso   Oliveira Ingrid de Barcelos   Stephens Paulo Roberto Soares   Cirne-Santos Claudio Cesar   Paixão Izabel Christina Nunes de Palmer   Ramos Freddy Alejandro   Jiménez Carlos   Rodríguez Jaime   Resende Jackson Antonio Lamounier Camargos   Teixeira Valeria Laneuville   Castellanos Leonardo  

Publisher: MDPI

E-ISSN: 1660-3397|12|7|4247-4259

ISSN: 1660-3397

Source: Marine Drugs, Vol.12, Iss.7, 2014-07, pp. : 4247-4259

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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 (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.

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