Anti-HIV-1 Protease Activity of Compounds from Cassia garrettiana

Authors

  • Kingkan BUNLUEPUECH Faculty of Traditional Thai Medicine, Prince of Songkla University, Songkhla 90112
  • Supinya TEWTRAKUL Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Songkhla 90112
  • Chatchai WATTANAPIROMSAKUL Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Songkhla 90112

Keywords:

Anti-HIV-1 protease activity, longevity preparations, Cassia garrettiana, Thai plants

Abstract

For the purpose of discovering anti-HIV-1 agents from Thai plant preparations with a history of use in Thai traditional medicine as agents assisting health longevity, aqueous and ethanol extracts from 24 Thai plants were screened for their inhibitory activities against HIV-1 protease (PR) using an anti-HIV-1 PR assay. Five extracts (10 %), 3 ethanol and 2 water, from only 4 plants, Cassia garrettiana, Dioscorea bulbifera, Albizia procera, and Areca catechu, produced extracts with IC50 values of < 45 µg/ml. Thirty five extracts (90 %) had no detectable activity, with IC50 values >100 µg/ml. The ethanol extracts of Cassia garrettiana (heartwood), Areca catechu, and Dioscorea bulbifera were the most potent, with IC50 values of 15.6, 24.9, and 44.4 µg/ml, respectively. For the water extracts, the most potent activity was found in Albizia procera (bark) and Cassia garrettiana (heartwood), with IC50 values of 22.6 and 26.8 µg/ml, respectively. Pure compounds from ethanol extracts of Cassia garrettiana (heartwood) were separated to give 5 compounds, chrysophanol (1), piceatannol (2), aloe-emodin (3), emodin (4), and cassigarol E (5). Of the tested samples, piceatannol (2) showed the highest anti-HIV-1 PR activity (IC50 = 48.29 µM), whereas the % inhibition (mean±S.E.M., n=3) produced by 100 µM of cassigarol E (5), aloe-emodin (3), chrysophanol (1), and emodin (4) were only 27.64±3.8, 27.20±0.7, 26.66±0.6, and 4.52±1.9, respectively.

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References

S Tewtrakul, S Subhadhirasakul and P Rattanasuwan. HIV-1 protease inhibitory effects of some selected plants in Caesalpiniaceae and Papilionaceae families. Songklanakarin J. Sci. Tech. 2003; 25, 509-14.

N Boonyapraphatsara and A Chokchaicharoenporn. Thai Native Herbs. Vol IV (in Thai). Prachachon Press, Bangkok, 1998, p. 1-683.

S Yuenyongsawad, K Bunluepuech, C Wattanapiromsakul and S Tewtrakul. Anti-cancer activity of compounds from Bauhinia strychnifolia stem. Phytochem. Rev. 2014; 13, 511-24.

K Bunluepuech, C Wattanapiromsakul and S Tewtrakul. Anti-HIV-1 integrase activity of compounds from Cassia garrettiana heartwood. Songklanakarin J. Sci. Tech. 2013; 35, 665-9.

S Kaufmann. Protection against tuberculosis: cytokines, T cells, and macrophages. Ann. Rheum. Dis. 2002; 61, 54-8.

K García-Sosa, N Villarreal-Alvarez, P Lübben and ML Peña-Rodríguez. Chrysophanol, an antimicrobial anthraquinone from the root extract of Colubrina greggii. J. Mex. Chem. Soc. 2006; 50, 76-8.

Y Li, D Zhang and S Yu. A new stilbene from Cercis chinensis Bunge. J. Integr. Plant. Biol. 2005; 47, 1021-4.

S Kametani, A Kojima-Yuasa, H Kikusaki, DO Kennedy, M Honzawa and I Matsui-Yuasa. Chemical constituents of cape aloe and their synergistic growth-inhibiting effect on ehrlich ascites tumor cells. Biosci. Biotechnol. Biochem. 2007; 71, 1220-9.

S Yao, Y Lib and L Kong. Preparative isolation and purification of chemical constituents from the root of Polygonum multiflorum by high-speed counter-current chromatography. J. Chromatogr. A 2006; 1115, 64-71.

W Li, K He, Y Li and Z Hou. Total Synthesis of (±)-Shegansu B, Gnetuhainin F, (±)-Maackin A and (±)-Cassigarol E. Acta Chim. Sinica 2005; 63, 1607-12.

Y Inamori, M Kubo, Y Kato, M Yasuda, K Baba and M Kozawa. The antifungal activity of stilbene derivative. Chem. Pharm. Bull. 1984; 132, 801-4.

K Yoshiyuki, M Maho, T Masahiko and B Kimiye. Antitumor and antimetastatic actions of anthrone-C-glucoside, cassialoin isolated from Cassia garrettiana heartwood in colon 26-bearing mice. Cancer Sci. 2008; 99, 2336-48.

N Matan, W Saengkrajang and N Matan. Antifungal activities of essential oils applied by dip-treatment on areca palm (Areca catechu) leaf sheath and persistence of their potency upon storage. Int. Biodeterior. Biodegradation 2011; 65, 212-6.

C Li and E Lin. Antiradical capacity and reducing power of different extraction method of Areca catechu seed. Afr. J. Biotechnol. 2010; 9, 7831-6.

AM Bhandare, AD Kshirsagar, NS Vyawahare, A Hadambar and VS Thorve. Potential analgesic, anti-inflammatory and antioxidant activities of hydroalcoholic extract of Areca catechu L. nut. Food. Chem. Toxicol. 2010; 48, 3412-7.

S Nantapap, C Loetchutinat, P Meepowpan, N Nuntasaen and W Pompimon. Antiproliferative effects of alkaloids isolated from the tuber of Stephania venosa via the induction of cell cycle arrest in mammalian cancer cell lines. Am. J. App. Sci. 2010; 7, 1057-65.

RN Yadava and P Tripathi. Chemical examination and anti-inflammatory action of the extract from the stem of Albizzia procera Benth. Res. J. Chem. Environ. 2000; 4, 57-60.

S Ignacimuthu, M Dhanasekaran and V Duraipandiyan. 2008. A Compound Methyl Tetradecahydro-phenanthrene-8a-carboxylate from Albizzia procera Bark with Anticancer Activity. Indian Patent. IN 2008CH02030 A20081121.

GA Potter, LH Patterson, E Wanogho, PJ Perry, PC Butler, T Ijazl, KC Ruparelia, JH Lamb, PB Farmer, LA Stanley and MD Burke. The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYP1B1. Br. J. Cancer 2002; 86, 774-8.

CL Clouser, J Chauhan, MA Bess, JL Oploo, D Zhou, S Dimick-Gray, LM Mansky and SE Patterson. Anti-HIV-1 activity of resveratrol derivatives and synergistic inhibition of HIV-1 by the combination of resveratrol and decitabine. Bioorg. Med. Chem. Lett. 2012; 22, 6642-46.

Z Ovesná, K Kozics, Y Bader, Y Saiko, N Handler, T Erker and T Szekeres. Antioxidant activity of resveratrol, piceatannol and 3,3',4,4',5,5'-hexahydroxy-trans-stilbene in three leukemia cell lines. Oncol. Rep. 2006; 16, 617-24.

K Ashikawa, S Majumdar, S Banerjee, AC Bharti, S Shishodia and BB Aggarwal. Piceatannol inhibits TNF-induced NF-kappaB activation and NF-kappaB-mediated gene expression through suppression of IkappaB alpha kinase and p65 phosphorylation. J. Immunol. 2002; 169, 6490-7.

M Cuccioloni, M Mozzicafreddo, L Bonfili, V Cecarini, AM Eleuteri and M Angeletti. Natural Occurring Polyphenols as Template for Drug Design. Focus on Serine Proteases. Chem. Biol. Drug Des. 2009. 74; 1-15.

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Published

2016-05-08

How to Cite

BUNLUEPUECH, K., TEWTRAKUL, S., & WATTANAPIROMSAKUL, C. (2016). Anti-HIV-1 Protease Activity of Compounds from Cassia garrettiana. Walailak Journal of Science and Technology (WJST), 13(10), 827–835. Retrieved from https://wjst.wu.ac.th/index.php/wjst/article/view/2090