Antiviral activity of diterpenes isolated from the Brazilian marine alga against human immunodeficiency virus type 1 (HIV-1)

Pereira, Helena de Souza; Leão-Ferreira, L.R.; Moussatché, Nissin; Teixeira, Valéria Laneuville; Cavalcanti, Diana Negrão; Costa, Luciana Jesus da; Diaz, Ricardo Sobhie; Frugulhetti, Izabel C.P.P.

doi:10.1016/j.antiviral.2004.06.006

Cited by 44 publications

(29 citation statements)

References 28 publications

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“…Research has proven marine organisms to be excellent sources of biologically active compounds with the potential to combat HIV [1]. In particular, terpenoids isolated from marine algae [1,3,4] have been described as anti-HIV-1 inhibitors.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2014

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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.

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Section: Introductionmentioning

confidence: 99%

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

et al. 2014

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“…Previous results have shown that the diterpenes, (6 R )-6-hydroxydichotoma-3,14-diene-1,17-dial, called pachydictyol A ( 1 ), and its acetate derivative, isopachydictyol A ( 2 ), as well as 6-Hydroxy-dichotomano-3,14-dieno-1,17-dial (called dichotomanol) ( 3 ), isolated form D. menstrualis , inhibit the human immunodeficiency virus type-1 (HIV-1) replication in vitro [22,23]. Moreover, their mechanisms of action and toxicity have been studied, and the results showed that such diterpenes do not induce any cytotoxicity or lethality in mice.…”

Section: Introductionmentioning

confidence: 99%

Antiplatelet and Anticoagulant Effects of Diterpenes Isolated from the Marine Alga, Dictyota menstrualis

et al. 2014

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Cardiovascular diseases represent a major cause of disability and death worldwide. Therapeutics are available, but they often have unsatisfactory results and may produce side effects. Alternative treatments based on the use of natural products have been extensively investigated, because of their low toxicity and side effects. Marine organisms are prime candidates for such products, as they are sources of numerous and complex substances with ecological and pharmacological effects. In this work, we investigated, through in vitro experiments, the effects of three diterpenes (pachydictyol A, isopachydictyol A and dichotomanol) from the Brazilian marine alga, Dictyota menstrualis, on platelet aggregation and plasma coagulation. Results showed that dichotomanol inhibited ADP- or collagen-induced aggregation of platelet-rich plasma (PRP), but failed to inhibit washed platelets (WP). In contrast, pachydictyol A and isopachydictyol A failed to inhibit the aggregation of PRP, but inhibited WP aggregation induced by collagen or thrombin. These diterpenes also inhibited coagulation analyzed by the prothrombin time and activated partial thromboplastin time and on commercial fibrinogen. Moreover, diterpenes inhibited the catalytic activity of thrombin. Theoretical studies using the Osiris Property Explorer software showed that diterpenes have low theoretical toxicity profiles and a drug-score similar to commercial anticoagulant drugs. In conclusion, these diterpenes are promising candidates for use in anticoagulant therapy, and this study also highlights the biotechnological potential of oceans and the importance of bioprospecting to develop medicines.

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“…8, 3.6 Hz, H-7), and 5.07 (1H, t, J=6. 6 Hz, H-13), were attributed to three trisubstituted double bonds. H-19b)], in combination with the heteronuclear multiple bond connectivity (HMBC) correlations from the hemiacetal methine proton to the oxymethylene carbon and from the hemiacetal methine and oxymethylene protons to the same two carbons at δ C 145.5 (C, C-1) and 46.9 (CH, C-2) (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Further isolation of compounds from the EtOAc-soluble portion of the EtOH extract of the brown alga Dictyota plectens was accomplished by repeated column chromatography with the aid of 1 H-NMR guided fractionation, affording three new xenicane-type diterpenes 4α-hydroxyisodictyohemiacetal (1), 4α-hydroxyisodictyoacetal (2), and 13,18-diacetoxy-4-hydroxyisodictyo-19-al (3), a new xenicane derivative, crenulidetype diterpene 4α-hydroxypachylactone (8), along with four known analogues (4)(5)(6)(7). The structures of known compounds were identified as isodictyohemiacetal (4), 12) isodictyoacetal (5), 13) (2S*,3S*,4R*,10R*,19R*)-19-deoxo-4-hydroxy-19-methoxydictyolactone (6), 5) and 4-hydroxydictyolactone (7) 14,15) by comparison of their 1 H-and 13 C-NMR spectroscopic and optical rotations with those reported in the literature (Fig.…”

Section: Resultsmentioning

confidence: 99%

Further New Xenicanes from a Chinese Collection of the Brown Alga <i>Dictyota plectens</i>

et al. 2015

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Four new xenicanes, namely 4α-hydroxyisodictyohemiacetal (1), 4α-hydroxyisodictyoacetal (2), 13,18-diacetoxy-4-hydroxyisodictyo-19-al (3), and 4α-hydroxypachylactone (8), were isolated from a Chinese collection of the brown alga Dictyota plectens, along with four known analogues (4-7). The structures of the new diterpenes were determined by extensive spectroscopic data analysis. All compounds were evaluated for their antiviral activities against human immunodeficiency virus type 1 (HIV-1) and the highly pathogenic avian influenza A (H5N1) virus, and inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in mouse peritoneal macrophages (PEMΦ).

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Antiviral activity of diterpenes isolated from the Brazilian marine alga against human immunodeficiency virus type 1 (HIV-1)

Cited by 44 publications

References 28 publications

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

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

Antiplatelet and Anticoagulant Effects of Diterpenes Isolated from the Marine Alga, Dictyota menstrualis

Further New Xenicanes from a Chinese Collection of the Brown Alga <i>Dictyota plectens</i>

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