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

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

Use this link to cite:

http://hdl.handle.net/2183/19532

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

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Rodriguez2014-md12074247.pdf (757.65 KB)

Identifiers

URI: http://hdl.handle.net/2183/19532

Publication date

2014

Authors

Pardo-Vargas, Alonso

Barcelos Oliveira, Ingrid de

Stephens, Paulo Roberto Soares

Cirne-Santos, Claudio Cesar

Palmer Paixão, Izabel Christina Nunes de

Ramos, Freddy Alejandro

Jiménez, Carlos

Rodríguez, Jaime

Resende, Jackson Antonio Lamounier Camargos

Teixeira, Valeria Laneuville

Bibliographic citation

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.

Abstract

[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.