Dolabelladienols A–C, New Diterpenes Isolated from Brazilian Brown Alga Dictyota pfaffii
AbstractThe 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. View Full-Text
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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.
Pardo-Vargas A, de Barcelos Oliveira I, Stephens PRS, Cirne-Santos CC, de Palmer Paixão ICN, Ramos FA, Jiménez C, Rodríguez J, Resende JALC, Teixeira VL, Castellanos L. Dolabelladienols A–C, New Diterpenes Isolated from Brazilian Brown Alga Dictyota pfaffii. Marine Drugs. 2014; 12(7):4247-4259.Chicago/Turabian Style
Pardo-Vargas, Alonso; de Barcelos Oliveira, Ingrid; Stephens, Paulo R.S.; Cirne-Santos, Claudio C.; de Palmer Paixão, Izabel C.N.; Ramos, Freddy A.; Jiménez, Carlos; Rodríguez, Jaime; Resende, Jackson A.L.C.; Teixeira, Valeria L.; Castellanos, Leonardo. 2014. "Dolabelladienols A–C, New Diterpenes Isolated from Brazilian Brown Alga Dictyota pfaffii." Mar. Drugs 12, no. 7: 4247-4259.