Anti‐HIV‐1 Integrase Activity and Molecular Docking Study of Compounds from Caesalpinia sappan L. |
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| Authors: | Supinya Tewtrakul Prapaporn Chaniad Somsak Pianwanit Chatchanok Karalai Chanita Ponglimanont Orapun Yodsaoue |
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| Affiliation: | 1. Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat Yai, Songkhla, Thailand;2. Excellent Research Laboratory, Phytomedicine and Pharmaceutical Biotechnology Excellence Center, Faculty of Pharmaceutical Sciences, Prince of Songkla Univesity, Hat Yai, Songkhla, Thailand;3. Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, Thailand;4. Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla, Thailand |
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| Abstract: | Caesalpinia sappan L. (Caesalpiniaceae) has been traditionally used as blood tonic, expectorant, and astringent by boiling with water. Searching for HIV‐1 integrase (IN) inhibitors from this plant is a promising approach. The EtOH extract of C. sappan and its isolated compounds were tested for their anti‐HIV‐1 IN effect using the multiplate integration assay, and the active compounds were determined for their mechanisms by molecular docking technique. Extraction from the heartwoods and roots of C. sappan led to the isolation of nine compounds. Among the compounds tested, sappanchalcone (2) displayed the strongest effect against HIV‐1 IN with an IC50 value of 2.3 μM followed by protosappanin A (9, IC50 = 12.6 μM). Structure‐activity relationships of compounds from C. sappan were found, in which the vicinal hydroxyl moiety were essential for anti‐HIV‐1 IN effect of compounds 2 and 9 by binding with the amino acid residues Gln148 and Thr66 in the core domain of the HIV‐ 1 IN enzyme, respectively. Copyright © 2015 John Wiley & Sons, Ltd. |
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| Keywords: | anti‐HIV‐1 IN activity molecular docking Caesalpinia sappan Caesalpiniaceae |
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