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BMC Complementary Medicine and Therapies
Published in: BMC Complementary Medicine and Therapies 1/2020

Open Access 01-12-2020 | Gout | Research article

Xanthine oxidase inhibitory activity of a new isocoumarin obtained from Marantodes pumilum var. pumila leaves

Authors: Nor-Ashila Aladdin, Khairana Husain, Juriyati Jalil, Carla Wulandari Sabandar, Jamia Azdina Jamal

Published in: BMC Complementary Medicine and Therapies | Issue 1/2020

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Abstract

Background

In traditional Malay medicine, Marantodes pumilum (Blume) Kuntze (family Primulaceae) is commonly used by women to treat parturition, flatulence, dysentery, dysmenorrhea, gonorrhea, and bone diseases. Preliminary screening of some Primulaceae species showed that they possess xanthine oxidase inhibitory activity. Thus, this study aimed to investigate the xanthine oxidase inhibitory activity of three varieties of M. pumilum and their phytochemical compounds.

Method

Dichloromethane, methanol, and water extracts of the leaves and roots of M. pumilum var. alata, M. pumilum var. pumila, and M. pumilum var. lanceolata were tested using an in vitro xanthine oxidase inhibitory assay. Bioassay-guided fractionation and isolation were carried out on the most active extract using chromatographic techniques. The structures of the isolated compounds were determined using spectroscopic techniques.

Results

The most active dichloromethane extract of M. pumilum var. pumila leaves (IC50 = 161.6 μg/mL) yielded one new compound, 3,7-dihydroxy-5-methoxy-4,8-dimethyl-isocoumarin (1), and five known compounds, viz. ardisiaquinone A (2), maesanin (3), stigmasterol (4), tetracosane (5), and margaric acid (6). The new compound was found to be the most active xanthine oxidase inhibitor with an IC50 value of 0.66 ± 0.01 μg/mL, which was not significantly different (p > 0.05) from that of the positive control, allopurinol (IC50 = 0.24 ± 0.00 μg/mL).

Conclusion

This study suggests that the new compound 3,7-dihydroxy-5-methoxy-4,8-dimethyl-isocoumarin (1), which was isolated from the dichloromethane extract of M. pumilum var. pumila leaves, could be a potential xanthine oxidase inhibitor.
Literature
1.
2.
Stone BC. New and noteworthy Malesian Myrsinaceae III. On the genus Ardisia Sw. Borneo Proc Acad Nat Sci Philadelphia. 1989;141:263–306.
3.
Sunarno B. Revision of the genus Labisia (Myrsinaceae). Blumea. 2005;50(3):579–97.CrossRef
4.
Aladdin NA, Jamal JA, Talip N, Hamsani NAM, Rahman MRA, Sabandar CW, Muhammad K, Husain K, Jalil J. Comparative study of three Marantodes pumilum varieties by microscopy, spectroscopy and chromatography. Rev Bras Farmacogn. 2016;26(1):1–14.CrossRef
5.
Burkill IH. Dictionary of the Economic Products of the Malay Peninsula. Crown Agents of the Colonies, London, England. Vol. 2, 1935;1290.
6.
Zakaria M, Mohd MA. Traditional Malay medicinal plants. Kuala Lumpur: Fajar Bakti; 1994.
7.
Quattrocchi U. CRC world dictionary of medicinal and poisonous plants: common names, Scientific Names, Eponyms, Synonyms and Etymology. Roca Baton: CRC Press; 2012.CrossRef
8.
Runi SP. Studies on medicinal plant in Sarawak. In the seminar on medicinal and aromatic plants, Kuala Lumpur (Malaysia), 12-13 Sep 2000. Forest Research Institute Malaysia (FRIM); 2000.
9.
Singh GD, Ganjoo M, Youssouf MS, Koul A, Sharma R, Singh S, Sangwan PL, Koul S, Ahamad DB, Johri RK. Sub-acute toxicity evaluation of an aqueous extract of Labisia pumila, a Malaysian herb. Food Chem Toxicol. 2009;47(10):2661–5.CrossRef
10.
Norhaiza M, Maziah M, Hakiman M. Antioxidative properties of leaf extracts of a popular Malaysian herb Labisia pumila. J Med Plant Res. 2009;3:217–23.
11.
Mamat N, Jamal JA, Jantan I, Husain K. Xanthine oxidase inhibitory and DPPH radical scavenging activities of some Primulaceae species. Sains Malays. 2014;43(12):1827–33.CrossRef
12.
Khairul FK, Nurul HM, Zhari I. Antioxidative properties of various extract of Labisia pumila (Kacip Fatimah). Curr Trends Perspect. 2005;4:306–12.
13.
Karimi E, Jaafar HZ, Ahmad S. Phytochemical analysis and antimicrobial activities of methanolic extracts of leaf, stem and root from different varieties of Labisia pumila Benth. Molecules. 2011;16(6):4438–50.CrossRef
14.
Rahmi EP, Jamal JA, Kumolosasi E, Jalil J, Aladdin NA. Marantodes pumilum (Blume) Kuntze inhibited secretion of lipopolysaccharide- and monosodium urate crystal-stimulated cytokines and plasma prostaglandin E2. Pharmacogn Mag. 2017;13(Suppl. 3):S578–86.PubMedCentral
15.
Wan Omar WFN, Giribabu N, Karim K, Salleh N. Marantodes pumilum (Blume) Kuntze (Kacip Fatimah) stimulates uterine contraction in rats in post-partum period. J Ethnopharmacol. 2019;245:112175.CrossRef
16.
Jamal JA, Ramli N, Stanslas J, Husain K. Estrogenic activity of selected Myrsinaceae species in MCF-7 human breast cancer cells. Int J Pharm Pharm Sci. 2012;4:547–53.
17.
Pandey A, Bani S, Sangwan PL. Anti-obesity potential of gallic acid from Labisia pumila, through augmentation of adipokines in high fat diet induced obesity in C57BL/6 mice. Adv Res. 2014;2(10):556–70.CrossRef
18.
Choi H, Kim D, Kim JW, Ngadiran S, Sarmidi MR, Park CS. Labisia pumila extract protects skin cells from photoageing caused by UVB irradiation. J Biosci Bioeng. 2010;109:291–6.CrossRef
19.
Pihie AHL, Othman F, Zakaria ZA. Anticarcinogenic activity of Labisia pumila against 7,12-dimethylbenz(α) anthracene (DMBA)/croton oil-induced mouse skin carcinogenesis. Afr J Pharm Pharmaco. 2011;5:823–32.
20.
Ali Z, Khan IA. Alkyl phenols and saponins from the roots of Labisia pumila (Kacip Fatimah). Phytochemistry. 2011;72:2075–80.CrossRef
21.
Al-Mekhlafi NA, Shaari K, Abas F, Kneer R, Jeyaraj EJ, Stanslas J, Yamamoto N, Honda T, Lajis NH. Alkenylresorcinols and cytotoxic activity of the constituents isolated from Labisia pumila. Phytochemistry. 2012;80:42–9.CrossRef
22.
Avula B, Wang YH, Ali Z, Smillie TJ, Khan IA. Quantitative determination of triperpene saponins and alkenated-phenolics from Labisia pumila using an LC-UV/ELSD method and confirmation by LC-ESI-TOF. Planta Med. 2011;77(15):1742–8.CrossRef
23.
Karimi E, Jaafar HZ, Ghasemzadeh A, Ebrahimi M. Fatty acid composition, antioxidant and antibacterial properties of the microwave aqueous extract of three varieties of Labisia pumila Benth. Biol Res. 2015;48(1):9.CrossRef
24.
Stasiuk M, Kozubek A. Biological activity of phenolic lipids. Cell Mol Life Sci. 2010;67(6):841–60.CrossRef
25.
Chiang HC, Lo YJ, Lu FJ. Xanthine oxidase inhibitors from leaves of Alsophila spinulosa (hook) Tryon. J Enzym Inhib. 1994;8:61–71.CrossRef
26.
Cos P, Ying L, Calomme M, Hu JP, Cimanga K, Van Poel B, Pieters L, Vlietinck AJ, Berghe DV. Structure-activity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers. J Nat Prod. 1998;61:71–6.CrossRef
27.
Pacher P, Nivorozhkin A, Szabó C. Therapeutic effects of xanthine oxidase inhibitors: renaissance half a century after the discovery of allopurinol. Pharmacol Rev. 2006;58(1):87–114.CrossRef
28.
Rasaratnam I, Christophidis N. Gout: ‘a disease of plenty’. Aust Fam Physician. 1995;24:849–60.
29.
Stack A, Manolis AJ, Ritz E. Detrimental role of hyperuricemia on the cardio-Reno-vascular system. Curr Med Res Opin. 2015;31(Suppl. 2):21–6.CrossRef
30.
Johnson RJ, Kivlighn SD, Kim YG, Suga S, Fogo AB. Reappraisal of the pathogenesis and consequences of hyperuricemia in hypertension, cardiovascular disease, and renal disease. Am J Kidney Dis. 1999;33(2):225–34.CrossRef
31.
Ogino K, Hisatome I, Shigemasa C. Anti-hyperuricemic agents. Nihon Rinsho. 2003;61(1):197–201.PubMedCentral
32.
Unno T, Sugimoto A, Kakuda T. Xanthine oxidase inhibitors from the leaves of Lagerstroemia speciosa (L.) Pers. J. Ethnopharmacol. 2004;93(2):391–5.CrossRef
33.
Tapsell LC, Hemphill I, Cobiac L, Sullivan DR, Fenech M, Patch CS, Roodenrys S, Keogh JB, Clifton PM, Williams PG, Fazio VA, Inge KE. Health benefits of herbs and spices: the past, the present, the future. Med J Aust. 2006;185(4):S1–S24.PubMedCentral
34.
Costantino L, Albasini A, Rastelli G, Benvenuti S. Activity of polyphenolic crude extracts as scavengers of superoxide radicals and inhibitors of xanthine oxidase. Planta Med. 1992;58:342–4.CrossRef
35.
Iio M, Moriyama A, Matsumoto Y, Takaki N, Fukumoto M. Inhibition of xanthine oxidase by flavonoids by folate compounds and amethopterin. J Biol Chem. 1985;259:12–5.
36.
Liu HX, He MT, Tan HB, Gu W, Yang SX, Wang YH, Li L, Long CL. Xanthine oxidase inhibitors isolated from Piper nudibaccatum. Phytochem Lett. 2015;12:133–7.CrossRef
37.
Chang WS, Chiang HC. Structure-activity relationship of coumarins in xanthine oxidase inhibition. Anticancer Res. 1995;15(5B):1969–73.
38.
Zuo J, Zhang W, Jian H, Bou-Chacra N, Löbenberg R. Esculetin as bioactive marker: towards a rational scientific approach for the treatment of hyperuricemia using traditional Chinese medicine. Braz J Pharm Sci. 2020;56:e17827.CrossRef
39.
40.
Seruji NMU, Khong HY, Kutoi CJ. Antioxidant, anti-inflammatory, and cytotoxic activities of Garcinia nervosa (Clusiaceae). J Chem. 2013;2012:1–5.CrossRef
41.
Fukuyama Y, Kiriyama Y, Kodama M, Iwaki H, Hosozawa S, Aki S, Matsui K. Naturally occuring 5-lipoxygenase inhibitors. (VI. 1) structures of ardisiaquinones D, E, and F from Ardisiasieboldii. Chem Pharm Bull. 1995;43(8):1391–4.CrossRef
42.
Yan-Fang L, Jia L, Qiang S, Li-Hong H. Benzoquinones from Ardisia japonica with inhibitory activity towards human protein tyrosine phosphatase 1B (PTP1B). Chem Biodivers. 2007;4:961–5.CrossRef
43.
Forgo P, Kövér KE. Gradient enhanced selective experiments in the 1H NMR chemical shift assignment of the skeleton and side-chain resonances of stigmasterol, a phytosterol derivative. Steroid. 2004;69:43–50.CrossRef
44.
Kalegari M, Miguel MD, Dias JFG, Lordello ALL, Lima CP, Miyazaki CMS, Zanin SMW, Verdam MCS, Miguel OG. Phytochemical constituents and preliminary toxicity evaluation of leaves from Rourea induta planch. (Connaraceae). Braz. J Pharm Sci. 2011;47(3):635–42.
45.
46.
Lin HC, Tsai SH, Chen CS, Chang YC, Lee CM, Lai ZY, Lin CM. Structure-activity relationship of coumarin derivatives on xanthine oxidase-inhibiting and free radical-scavenging activities. Biochem Pharmacol. 2008;75(6):1416–25.CrossRef
47.
Fais A, Era B, Asthana S, Sogos V, Medda R, Santana L, Uriarte E, Matos MJ, Delogu F, Kumar A. Coumarin derivatives as promising xanthine oxidase inhibitors. Int J Biol Macromol. 2018;120(A):1286–93.CrossRef
48.
Masuoka N, Nihei K, Masuoka T, Kuroda K, Sasaki K, Kubo I. The inhibition of uric acid formation catalyzed by xanthine oxidase properties of the alkyl caffeates and cardol. J Food Res. 2012;1(3):257–62.CrossRef
49.
Luxita S, Zarrin A. The role of xanthine oxidase inhibiting foods in therapeutic management of hyperuricemia and gout. Int J Res Soc Sci. 2018;8(11):253–67.
50.
Lin J, Chen S, Li S, Lu M, Li Y, Su Y. Efficacy and safety of Chinese medicinal herbs for the treatment of hyperuricemia: a systematic review and meta-analysis. Evid Based Complement Altern Med. 2016;2016:2146204.
51.
52.
Becker MA, Jolly M. Hyperuricemia and associated diseases. Rheum Dis Clin N Am. 2006;32:275–93.CrossRef
53.
Ali N, Mahmood S, Islam F, Rahman S, Haque T, Islam S, Rahman S, Haque N, Mosaib G, Perveen R, Jhanum FA. Relationship between serum uric acid and hypertension: a cross-sectional study in Bangladeshi adults. Sci Rep. 2019;9:9061.CrossRef
54.
Liu B, Wang T, Zhao HN, Yue WW, Yu HP, Liu CX, Yin J, Jia RY, Nie HW. The prevalence of hyperuricemia in China: a meta-analysis. BMC Public Health. 2011;11:823.CrossRef
55.
Ali N, Perveen R, Rahman S, Mahmood S, Rahman S, Islam S, Haque T, Sumon AH, Kathak RR, Molla NH, Islam F, Mohanto NC, Nurunnabi SM, Ahmed S, Rahman M. Prevalence of hyperuricemia and the relationship between serum uric acid and obesity: a study on Bangladeshi adults. PLoS One. 2018;13(11):e0206850.CrossRef
56.
Guan S, Tang Z, Fang X, Wu X, Liu H, Wang C, Hou C. Prevalence of hyperuricemia among Beijing post-menopausal women in 10 years. Arch Gerontol Geriat. 2016;64:162–6.CrossRef
57.
Hak EA, Choi HK. Menopause, postmenopausal hormone use and serum uric acid levels in US women – the third national health and nutrition examination survey. Arthritis Res Ther. 2008;10:R116.CrossRef
58.
Hairi HA, Mohd Sofi NS, Khodari SN, Jamal JA, Mohamed IN, Shuid AN. Therapeutic effects of Labisia pumila on estrogen-deficiency related disorders: an evidence-based review. Int J Pharmacol. 2016;12(5):451–60.CrossRef
59.
Giaze TR, Shuid AN, Soelaiman IN, Muhammad N, Jamal JA, Fauzi MB, Mohamed N. Comparative anti-osteoporotic properties of the leaves and roots of Marantodes pumilum var. alata in postmenopausal rat model. J Tradit Complement Med. 2019;9(4):393–400.CrossRef
60.
Dharmani M, Kamarulzaman K, Giribabu N, Choy KW, Aladdin NA, Jamal JA, Mustafa MR. Effect of Marantodes pumilum Blume (Kuntze) var. alata on β-cell function and insulin signalling in ovariectomised diabetic rats. Phytomedicine. 2019;65:153101.CrossRef
61.
Dianita R, Jantan I, Jalil J, Amran AZ. Effects of Labisia pumila var. alata extracts on the lipid profile, serum antioxidant status and abdominal aorta of high-cholesterol diet rats. Phytomedicine. 2016;23(8):810–7.CrossRef
62.
Manshor NM, Razali N, Jusoh RR, Asmawi MZ, Mohamed N, Zainol S, Altaf E, Dewa A. Vasorelaxant effect of water fraction of Labisia pumila and its mechanisms in spontaneously hypertensive rats aortic ring preparation. Int J Cardiol Hypertens. 2020;4:100024.CrossRef
63.
Rajana, Nooreen Z, Bushra U, Jyotshna, Bawankule DU, Shanker K, Ahmad A, Tandon S. Standardization and xanthine oxidase inhibitory potential of Zanthoxylum armatum fruits. J Ethnopharmacol. 2019;230:1–8.CrossRef
Metadata
Title
Xanthine oxidase inhibitory activity of a new isocoumarin obtained from Marantodes pumilum var. pumila leaves
Authors
Nor-Ashila Aladdin
Khairana Husain
Juriyati Jalil
Carla Wulandari Sabandar
Jamia Azdina Jamal
Publication date
01-12-2020
Publisher
BioMed Central
Published in
BMC Complementary Medicine and Therapies / Issue 1/2020
Electronic ISSN: 2662-7671
DOI
https://doi.org/10.1186/s12906-020-03119-8

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