Pyrogallol is a key component for xanthine oxidase inhibition by the leaves of Ammannia baecifera

Pyrogallol as XOD inhibitor of A. baecifera leaves

Authors

Abstract

Ammannia baecifera Linn is an important plant in traditional medication system of Bangladesh. In order to give the scientific clarification for using this plant in the treatment of gout, this study was designed to identify the xanthine oxidase (XO) inhibitors present in the extract of Ammannia baecifera leaves along with evaluating its antioxidant effect. First aqueous extract was prepared from leaves and then water insoluble part (WIP) was separated from water soluble part (WSP) as precipitate with ethanol. In DPPH and ABTS assays, WSP with rich amount of phenolic compound exhibited high radical scavenging activity than WIP. WSP also showed potent XO inhibition with IC50: 18.03 ± 1.65 μg/mL value.  Using different chromatographic techniques, the key XO inhibitor was isolated from WSP and identified as pyrogallol based on its different spectroscopic data.  In XO inhibition assay, pyrogallol (IC50: 11.67 ± 0.45 μg/mL) showed potent inhibitory effect as compared to a known XO inhibitor (allopurinol; IC50 = 27.35 ± 1.15 μg/mL) and it also displayed strong DPPH and ABTS radical scavenging effect. In addition, an inhibition kinetics study indicated that WSP and pyrogallol are mixed competitive inhibitors of XO. The overall results suggest that the presence of pyrogallol as XO inhibitor and free radical scavenger in Ammannia baecifera leaf justifies the traditional uses of this plant.

Keywords: Ammannia baecifera, Leaves, Xanthine oxidase, Pyrogallol, Inhibitor

Keywords:

Ammannia baecifera,, Leaves,, Xanthine oxidase,, Pyrogallol,, Inhibitor

DOI

https://doi.org/10.22270/jddt.v13i3.5994

Author Biographies

Md. Rowshanul Habib, Department of Biochemistry and Molecular Biology, University of Rajshahi, Rajshahi-6205, Bangladesh

Department of Biochemistry and Molecular Biology, University of Rajshahi, Rajshahi-6205, Bangladesh

Yasuhiro Igarashi, Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan

Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan

Tao Zhou, Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan

Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan

Md. Abdul Aziz, Department of Biochemistry and Molecular Biology, University of Rajshahi, Rajshahi-6205, Bangladesh

Department of Biochemistry and Molecular Biology, University of Rajshahi, Rajshahi-6205, Bangladesh

References

Choi HK, Mount DB, Reginato AM. Pathogenesis of gout. Ann Intern Med. 2005; 143:499–516. https://doi.org/10.7326/0003-4819-143-7-200510040-00009

Harrison R. Structure and function of xanthine oxidoreductase: where are we now? Free Radic Biol Med. 2002; 33:774–797. https://doi.org/10.1016/S0891-5849(02)00956-5

Orbán-Gyapai O, Lajter I, Hohmann J, Jakab G, Vasas A. Xanthine Oxidase Inhibitory Activity of Extracts Prepared from Polygonaceae Species. Phytother Res. 2014; 29:459-465. https://doi.org/10.1002/ptr.5275

Gout TR. Novel therapies for treatment of gout and hyperuricemia. Arthritis Res Ther. 2009; 11:236. 10.1186/ar2738

Forbes JM, Coughlan MT, Cooper ME. Oxidative stress as a major culprit in kidney disease in diabetes. Diabetes. 2008; 57:1446-1454. 10.2337/db08-0057

Hudaib MM, Tawaha KA, Mohammad MK, Assaf AM, Issa AY, Alali FQ, Aburjai TA, Bustanji YK. Xanthine oxidase inhibitory activity of the methanolic extracts of selected Jordanian medicinal plants. Pharmacogn Mag. 2011; 7:320-324. 10.4103/0973-1296.90413

Ghani A. Medicinal Plants of Bangladesh, Asiatic Society of Bangladesh, Dhaka, 2003; pp.90.

Parrotta JA. Healing Plants of Peninsular India. CABI publishing, USA, 2001; pp. 686–687. https://doi.org/10.1079/9780851995014.0000

Khare CP. Indian Medicinal Plants. Springer Private Limited, New Delhi, India, 2007: pp. 42–43. https://doi.org/10.1007/978-0-387-70638-2

Ray AB, Sarma BK, Singh UP. Medicinal Properties of Plants, Antifungal, antimicrobial and antiviral properties. International Book Distributing and Co, Charbagh, Lucknow, India, 2004.

Loganayaki N, Manian S. Antitumor activity of the methanolic extract of Ammannia baccifera L. against Dalton’s ascites lymphoma induced ascitic and solid tumors in mice. J Ethnopharmacol. 2012; 142:305–309. https://doi.org/10.1016/j.jep.2012.05.008

Loganayaki N, Siddhuraju P, Manian S. Antioxidant, anti-inflammatory and anti-nociceptive effects of Ammannia baccifera L. (Lythracceae), a folklore medicinal plant J Ethnopharmacol. 2012; 140:230– 233. https://doi.org/10.1016/j.jep.2012.01.001

Goodla L, Manubolu M, Pathakoti K, Jayakumar T, Sheu J, Fraker M, Tchounwou PB, Poondamalli PR. Protective Effects of Ammannia baccifera Against CCl4-Induced Oxidative Stress in Rats. Int J Environ Res Public Health. 2019; 16:1440. https://doi.org/10.3390/ijerph16081440

Upadhyay CH, Verma RK, Srivastava SK. Quantitative Determination of Bioactive 4-Hydroxy-a-Tetralone, Tetralone-4-O-b-D-Glucopyranoside and Ellagic Acid in Ammannia baccifera (Linn.) by Reversed-Phase High-Performance Liquid Chromatography. J Chromatogr Sci. 2013; 51:21–25. https://doi.org/10.1093/chromsci/bms099

Ranilla LG, Kwon YI, Apostolidis E, Shetty K. Phenolic compounds, antioxidant activity and in vitro inhibitory potential against key enzymes relevant for hyperglycemia and hypertension of commonly used medicinal plants, herbs and spices in Latin America. Bioresour Technol. 2010; 101:4676–4689. https://doi.org/10.1016/j.biortech.2010.01.093

Mohsen SM, Ammar ASM. Total phenolic contents and antioxidant activity of corn tassel extracts. Food Chem. 2009; 112:595–598. https://doi.org/10.1016/j.foodchem.2008.06.014

Cai Y, Luo Q, Sun M, Corke H. Antioxidant activity and phenolic compounds of 112 traditional Chinese medicinal plants associated with anticancer. Life Sci. 2014; 74:2157–2184. https://doi.org/10.1016/j.lfs.2003.09.047

Sweeney AP, Wyllie SG, Shalliker RA, Markham JL. Xanthine oxidase inhibitory activity of selected Australian native plants. J Ethnopharmacol. 2001; 75:273-277. https://doi.org/10.1016/S0378-8741(01)00176-3

Chiang HC, Lo YJ, Lu FJ. Xanthine oxidase inhibitors from the leaves of Alsophila spinulosa (Hook) Tryon. J Enzyme Inhib. 1994; 8: 61-71. https://doi.org/10.3109/14756369409040777

LD Kong, Z Abliz, CX Zhou, Li LJ, Cheng CH, Tan RX. Glycosides and xanthine oxidase inhibitors from Conyza bonariensis. Phytochemistry. 2001; 58:645-651. https://doi.org/10.1016/S0031-9422(01)00176-5

Nguyen MTT, Awale S, Tezuka Y, Tran LQ, Watanabe H, Kadota S. Xanthine oxidase inhibitors from the heartwood of Vietnamese Caesalpinia sappan. Chem Pharm Bull. 2005; 53: 984–988. https://doi.org/10.1248/cpb.53.984

Khan MTH, Lampronti I, Martello D, Bianchi N, Jabbar S, Choudhuri MSK, Datta BK, Gambari R. Identification of pyrogallol as an antiproliferative compound present in extracts from the medicinal plant Emblica officinalis: effects on in vitro cell growth of human tumor cell lines. Int J Oncol. 2002; 21:187-192. https://doi.org/10.3892/ijo.21.1.187

Djeridane A, Yousfi M, Nadjemi B, Boutassouna D, Stocker P, Vidal N. Antioxidant activity of some Algerian medicinal plants extracts containing phenolic compounds. Food Chemistry. 2006; 97:654–660. https://doi.org/10.1016/j.foodchem.2005.04.028

Lee OH, Lee BY, Lee J, Lee HB, Son JY, Park CS, Shetty K, Kim YC. Assessment of phenolics-enriched extract and fractions of olive leaves and their antioxidant activities. Bioresour Technol. 2009; 100:6107–6113. https://doi.org/10.1016/j.biortech.2009.06.059

Karimi E, Hawa Z, Jaafar E, Ahmad S. Phenolics and flavonoids profiling and antioxidant activity of three varieties of Malaysian indigenous medicinal herb Labisia pumila Benth. J Med Plants Res. 2011; 5:1200-1206.

Kaur C, Kapoor HC. Antioxidant activity and phenolic content of some Asian vegetables. Int J Food Sci Technol. 2002; 37:153–161. https://doi.org/10.1046/j.1365-2621.2002.00552.x

Shukla S, Mehtab A, Mehta P, Bajpai VK. Antioxidant ability and total phenolic content of aqueous leaf extract of Stevia rebaudiana Bert. Exp Toxicol Pathol. 2012; 64:807–811. https://doi.org/10.1016/j.etp.2011.02.002

Baruah K, Phong HPPD, Norouzitallab P, Defoirdt T, Bossier P. The gnotobiotic brine shrimp (Artemia franciscana) model system reveals that the phenolic compound pyrogallol protects against infection through its prooxidant activity. Free Radic Biol Med. 2015; 89:593-601. https://doi.org/10.1016/j.freeradbiomed.2015.10.397

Nazari H, Bakhshandeh N, Gholami M, Mehrzad J, Bineshian F. Anti-Candida activities and GC Mass analysis of seeds hydroalcohlic extract of Rumex obtusifolius. Jundishapur J Microbiol. 2017; 10:e13733. 10.5812/jjm.13733

Elzaawely AA, Xuan TD, Tawata S. Antioxidant and antibacterial activities of Rumex japonicus HOUTT. aerial parts. Biol Pharm Bull. 2005; 28:2225-2230. https://doi.org/10.1248/bpb.28.2225

Honda S, Fukuyama Y, Nishiwaki H, Masuda A, Masuda T. Conversion to purpurogallin, a key step in the mechanism of the potent xanthine oxidase inhibitory activity of pyrogallol. Free Radi Biol Med. 2017; 106:228–235. https://doi.org/10.1016/j.freeradbiomed.2017.02.037

Nguyen MT, Awale S, Tezuka Y, Ueda JY, Tran QI, Kadota S. Xanthine oxidase inhibitors from the flowers of Chrysanthemum sinense. Planta Med. 2006; 72:46−51. 10.1055/s-2005-873181

Day AJ, Bao Y, Morgan MR, Williamson G. Conjugation position of quercetin glucuronides and effect on biological activity. Free Radic Biol Med. 2000; 29:1234−1243. https://doi.org/10.1016/S0891-5849(00)00416-0

Nicolis E, Lampronti I, Dechecchi MC, Borgatti M, Tamanini A, Bianchi N, Vezzerri V, Mancini I, Giri MG, Rizzotti P, Gambari R, Cabrini G. Pyrogallol, an active compound from the medicinal plant Emblica officinalis, regulates expression of pro-inflammatory genes in bronchial epithelial cells. Int Immunopharmacol. 2008; 8:1672-1680. https://doi.org/10.1016/j.intimp.2008.08.001

Honda S, Masuda T. Identification of pyrogallol in the ethyl acetate-soluble part of coffee as the main contributor to its xanthine oxidase inhibitory activity. J Agric Food Chem. 2016; 64:7743–7749. https://doi.org/10.1021/acs.jafc.6b03339

Published

15-03-2023
Statistics
Abstract Display: 352
PDF Downloads: 295
PDF Downloads: 740

How to Cite

1.
Habib MR, Igarashi Y, Zhou T, Aziz MA. Pyrogallol is a key component for xanthine oxidase inhibition by the leaves of Ammannia baecifera: Pyrogallol as XOD inhibitor of A. baecifera leaves. J. Drug Delivery Ther. [Internet]. 2023 Mar. 15 [cited 2025 May 16];13(3):113-9. Available from: https://www.jddtonline.info/index.php/jddt/article/view/5994

How to Cite

1.
Habib MR, Igarashi Y, Zhou T, Aziz MA. Pyrogallol is a key component for xanthine oxidase inhibition by the leaves of Ammannia baecifera: Pyrogallol as XOD inhibitor of A. baecifera leaves. J. Drug Delivery Ther. [Internet]. 2023 Mar. 15 [cited 2025 May 16];13(3):113-9. Available from: https://www.jddtonline.info/index.php/jddt/article/view/5994