Inhibition of HIV-1 Reverse Transcriptase and Protease by Phlorotannins from the Brown Alga Ecklonia cava

Mi-Jeong Ahn; Kee-Dong Yoon; So-Young Min; Ji Suk Lee; Jeong Ha Kim; Tae Gyun Kim; Seung Hee Kim; Nam-Gil Kim; Hoon Huh; Jinwoong Kim

doi:10.1248/bpb.27.544

Regular Articles

Inhibition of HIV-1 Reverse Transcriptase and Protease by Phlorotannins from the Brown Alga Ecklonia cava

Mi-Jeong Ahn, Kee-Dong Yoon, So-Young Min, Ji Suk Lee, Jeong Ha Kim, Tae Gyun Kim, Seung Hee Kim, Nam-Gil Kim, Hoon Huh, Jinwoong Kim

Author information

Mi-Jeong Ahn
College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University, Korea
Kee-Dong Yoon
College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University, Korea
So-Young Min
College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University, Korea
Ji Suk Lee
Research Group of Pain and Neuroscience in Vision 2000 Project, East-West Medical Research Institute, Kyung Hee University
Jeong Ha Kim
Department of Biological Sciences, Institute of Natural Sciences, Sungkyunkwan University
Tae Gyun Kim
National Institute of Toxicological Research, Korea Food and Drug Administration, Korea
Seung Hee Kim
National Institute of Toxicological Research, Korea Food and Drug Administration, Korea
Nam-Gil Kim
Department of Aquaculture, Gyeongsang National University, Korea
Hoon Huh
College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University, Korea
Jinwoong Kim
College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University, Korea

Keywords: Ecklonia cava, 8,8′-bieckol, 8,4′′′-dieckol, HIV-1 reverse transcriptase, noncompetitive inhibition, protease

JOURNAL FREE ACCESS

2004 Volume 27 Issue 4 Pages 544-547

DOI https://doi.org/10.1248/bpb.27.544

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Abstract

The bioassay-directed isolation of a marine brown alga, Ecklonia cava, afforded four phlorotannin derivatives, eckol (1), 8,8′-bieckol (2), 8,4′′′-dieckol (3), and phlorofucofuroeckol A (4). Among these compounds, 2 and 3 exhibited an inhibitory effect on human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) and protease. Specifically, they inhibited the RT more potently than the protease. The inhibitory activity of compound 2 (IC₅₀, 0.51 μM) against HIV-1 RT was comparable to that of nevirapine (IC₅₀, 0.28 μM), a reference compound. An enzyme kinetic assay showed that this compound inhibited the RNA-dependent DNA synthesis activity of HIV-1 RT noncompetitively against dUTP/dTTP with a K_i value of 0.78 μM. With respect to the homopolymeric template/primer, (rA)_n(dT)₁₅, 8,8′-bieckol (2) displayed an uncompetitive type of inhibition (K_i, 0.23 μM).

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