An Ellagic Acid Derivative and Its Antioxidant Activity of Stem Bark Extracts of Syzygium polycephalum Miq. (Myrtaceae)

https://doi.org/10.22146/ijc.25467

Tukiran Tukiran(1*), Andika Pramudya Wardana(2), Nurul Hidayati(3), Kuniyoshi Shimizu(4)

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Negeri Surabaya
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Negeri Surabaya
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Negeri Surabaya
(4) Department of Forests and Forest Products Sciences, Faculty of Agriculture, Kyushu University
(*) Corresponding Author

Abstract


The investigation of the Syzygium polycephalum Miq. (Myrtaceae) aimed to assess the phytochemical contents and antioxidant activity of the chloroform fraction. In this study, the fraction was obtained from methanol extract of S. polycephalum stem bark partitionated by chloroform. An ellagic acid derivative was successively isolated from the chloroform fraction. The molecular structure of isolated compound was elucidated and established as 3,4,3’-tri-O-methylellagic acid through extensive spectroscopic studies including UV-Vis, FTIR, NMR and LC-MS analyses and by comparison with literature data. The finding of the isolated compound is the first time from the plant, although the isolated compound previously have been found in the other Syzygium species such as S. cumini together with ellagic acid and 3,3’-di-O-methylellagic acid. The chloroform fraction, isolated compound, and vitamin C showed antioxidant activity against 2,2’-diphenyl-1-picrylhydrazyl (DPPH) with IC50 value of 163.6, 72.1, and 11.5 μg/mL, respectively.

Keywords


antioxidant; ellagic acid derivative; Myrtaceae; Syzygium polycephalum

Full Text:

Full Text PDF


References

[1] Janick, J., and Paull, R.E., 2008, The Encyclopedia of Fruit and Nuts, CABI Publisher, USA, 972.

[2] Ayyanar, M., and Subash-Babu, P., 2012, Syzygium cumini (L.) Skeels: A review of its phytochemical constituents and traditional uses, Asian Pac. J. Trop. Biomed., 2 (3), 240–246.

[3] Alma, M.H., Ertaş, M., Nitz, S., and Kollmannsberger, H., 2007, Chemical composition and content of essential oil from the bud of cultivated Turkish clove (Syzygium aromaticum L.), BioResources, 2 (2), 265–269.

[4] Gao, X., Wu, J., Zou, W., and Dai, Y., 2014, Two ellagic acids isolated from roots of Sanguisorba officinalis L. promote hematopoietic progenitor cell proliferation and megakaryocyte differentiation, Molecules, 19 (4), 5448–5458.

[5] Bhuiyan, M.N.I., Begum, J., Nandi, N.C., and Akter, F., 2010, Constituents of the essential oil from leaves and buds of clove (Syzigium caryophyllatum (L.) Alston), Afr. J. Plant. Sci., 4 (11), 451–454.

[6] Reddy, N.V.L.S., Priyanka, A.Y.K., and Raghavendra, N.M., 2012, Isolation and characterization of triterpenoids from bark of Syzygium alternifolium (Wight) Walp., Ann. Phytomed.,1 (2), 45–51.

[7] Har, L.W., and Ismail, I.S., 2012, Antioxidant activity, total phenolics and total flavonoid of Syzygium polyanthum (Wight) Walp. leaves, Int. J. Med. Arom. Plants, 2 (2), 219–228.

[8] Manaharan, T., Appleton, D., Cheng, H.M., and Palanisamy, U.D., 2012, Flavonoids isolated from Syzygium aqueum leaf extract as potential antihyperglycaemic agents, Food Chem., 132 (4), 1802–1807.

[9] Komuraiah, B., Chinde, S., Kumar, A.N., Srinivas, K.V.N.S., Venu, C., Kumar, J.K., Sastry, K.P., and Grover, P., 2014, Isolation of phytochemicals from anticancer active extracts of Syzygium alternifolium Walp. leaf, Pharmacogn. J., 6 (4), 83–85.

[10] Florido, H.B., and Cortiguerra, F.F., 2004, Research information series on ecosystems, J. Trop. For. Sci., 3, 1–10.

[11] Roosita, K., Kusharto, C.M., Sekiyama, M., Fachrurozi, Y., and Ohtsuka, R., 2008, Medicinal plants used by the villagers of a Sundanese community in West Java, Indonesia, J. Ethnopharmacol., 115 (1), 72–81.

[12] Ragasa, C.Y., Torres, O.B., Shen, C.C., Lachica, M.K.E.G., Sulit, A.B., Chua, D.B.D.L., Ancheta, A.D.M., Ismail, C.J.B., Bernaldez, F.T.E., and Raga, D.D., 2014, Triterpenes from the leaves of Syzygium polycephalum, S. cumini, and S. samarangense, Chem. Nat. Compd., 50 (5), 942–944.

[13] Jemi, R., Syafii, W., Febrianto, F., and Hanafi, M., 2010, Sifat anti jamur kayu kupa (Syzygium polycephalum (Mig), JITKT, 8 (2), 93–110.

[14] Braca, A., De Tommasi, N., Di Bari, L., Pizza, C., Politi, M., and Morelli, I., 2001, Antioxidant principles from Bauhinia terapotensis, J. Nat. Prod., 64(7), 892-895.

[15] Khan, R.A., Khan, M.R., Sahreen, S., and Ahmed, M., 2012, Evaluation of phenolic contents and antioxidant activity of various solvent extracts of Sonchus asper (L.) Hill, Chem. Cent. J., 6 (1), 12.

[16] Reynertson, K.A., 2007, Phytochemical analysis of bioactive constituents from edible Myrtaceae fruits, Dissertation, City University of New York, America, 1-121.

[17] Pojchaijongdee, Nuch., 2006, Chemical constituents and biological activity of Phyllanthus reticulatus Poir. leaves, Thesis, Silpakorn University, Thailand.

[18] Hiranrat, A., 2010, Chemical constituents from Rhodomyrtus tomentosa (Aiton) Hassk and antibacterial activity, Thesis, Prince of Songkla University, Thailand.

[19] Gao, Y., Hu, Q., and Li, X., 2012, Chemical composition and antioxidant activity of essential oil from Syzygium samarangense (BL.) Merr.et Perry flower-bud, Spatula DD, 2 (1), 23–33.

[20] Benherlal, P.S., 2010. Investigation on bioactive phytochemicals of Jamun (Syzygium cumini) fruit, Thesis, Cochin University of Science and Technology, India.

[21] Djoukeng, J.D., Abou-Mansour, E., Tapondjou, L.A., Lontsi, D., and Tabacchi, R., 2007, Identification of ellagic acid derivatives from stem bark of Syzygium guineense (Myrtaceae), Nat. Prod. Commun., 2, 1–6.

[22] Ruan, Z.P., Zhang, L.L., and Lin, Y.M., 2008, Evaluation of the antioxidant activity of Syzygium cumini leaves, Molecules, 13 (10), 2545–2556.

[23] Shan, B., Cai, Y.Z., Sun, M., and Corke, H., 2005, Antioxidant capacity of 26 spices extracts and characterization of their phenolic constituents, J. Agric. Food Chem., 53 (20), 7749–7759.

[24] Nakhuru, K.S., Gogoi, J., Pfoze, N.L., Chattopadhyay, P., and Veera, V., 2014, Comparative studies on phytoconstituents, total phenolic content and free radical scavenging potential of some of the traditionally used medicinal plants of North East India, Int. J. Pharm. Sci. Res., 29 (1), 66–170.

[25] Rojano, B., Saez, J., Schinella, G., Quijano, J., Vélez, E., Gil, A., and Notario, R., 2008, Experimental and theoretical determination of the antioxidant properties of isoespintanol (2-isopropyl-3,6-dimethoxy-5-methylphenol), J. Mol. Struct., 877 (1-3), 1–6.

[26] Wootton-Beard, P.C., Moran, A., and Ryan, L., 2011, Stability of the total antioxidant capacity and total polyphenol content of 23 commercially available vegetable juices before and after in vitro digestion measured by FRAP, DPPH, ABTS and Folin–Ciocalteu methods, Food Res. Int., 44 (1), 217–224.

[27] Siti-Azima, M., Noriham, A., and Manshoor, N., 2014, Anthocyanin content in relation to the antioxidant activity and colour properties of Garcinia mangostana peel, Syzigium cumini and Clitoria ternatea extracts, Int. Food Res. J., 21 (6), 2369–2375.



DOI: https://doi.org/10.22146/ijc.25467

Article Metrics

Abstract views : 4869 | views : 4602


Copyright (c) 2017 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 


Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.