Two Phenolic Compounds from Chloroform Fraction of Syzygium Polycephalum MIQ. Stem Bark (Myrtaceae)

PDF
Full Text
Tukiran Tukiran, Andika Pramudya Wardhana, Nurul Hidajati, Kuniyoshi Shimizu

Abstract


Syzygium polycephalum (Kupa) is a plant of the Myrtaceae family which is one of the endemic plants in Indonesia, commonly called as Gowok. The chemical components of the plant have not been reported so far. This study is intended to know the molecular structures of isolated compounds of chloroform fraction from S. polycephalum stem bark.The steam bark of the plant is dried, powdered and macerated with methanol to yield methanolic extract. The methanolic extract was then conducted to fractionation using hexane and chloroform to obtain hexane and chloroform fractions. The chloroform fraction was further subjected to separation using column chromatography to obtain pure isolates and followed by measuring of their spectroscopic evidences. The isolation of chloroform fraction had led to the findings of two pure isolates. Their structures of isolates were elucidated by extensive spectroscopic methods and by comparison with the literature data to gain two phenolic compounds that are gallic acid and 3,4,3’-tri-O-methylellagic acid.

Keywords


3,4,3’-tri-O-methylellagic acid, gallic acid, Myrtaceae, phenolic compound, Syzygium polycephalum.

References


Anoop M.V. & Bindu A.R. (2014). Pharmacognostic and physico-chemical studies on leaves of Syzygium zeylanicum (L.) DC., International Journal of Pharmacognosy and Phytochemical Research, 6(4), 685-689.

Ariyanti, E. E., Rony, I., Lia, H., & Deden, M. (2012). Distribution of Syzygium spp. (klampok) in some areas of Bromo Tengger Semeru National Park, East Java. Proceeding of Society Indonesian Biodiversity International Conference, 1, 135142.

Baliga, Manjeshwar Shrinath, Harshith P. Bhat, Bantwal Raghavendra Vittaldas Baliga, Rajesh Wilson, & Princy Louis Palatty. (2011). Phytochemistry, traditional uses and pharmacology of Eugenia jambolana Lam. (black plum): A review, Food Research International, xxx: 1-14.doi: 10.1016/j.foodres.2011.02.007.

Barbosa, Luiz Claudio Almeida, Cleber José Silva, Róbson Ricardo Teixeira, Renata Maria Strozi Alves Meira, & Antônio Lelis Pinheiro. (2013). Chemistry and Biological Activities of Essential Oils from Melaleuca L. Species, Agric. Conspec. Sci. 78(1), 11-23.

Damle, Mrinalini & Nilam Dalavi. (2015). Development and validation of stability indicating HPLC method for determination of ellagic and gallic acids in jambul seeds (Syzygium cumini), International Journal of Applied Sciences and Biotechnology, 3(3): 434-438. doi: 10.3126./ijasbt.v3i3.12908.

De Bona K.S., Bonfanti G., Bitencourt P.E., da Silva T.P., Borges R.M., Boligon A., Pigatto A., Athayde M.L., & Moretto M.B. (2016). Protective effect of gallic acid and Syzygium cumini extract against oxidative stress-induced cellular injury in human lymphocytes, Drug Chem Toxicol., 39(3), 256-263.doi: 10.3109/01480545.2015.1084631.

Djipa CD, Delme´e M, and Quetin-Leclercq J. (2000). Antimicrobial activity of bark extracts of Syzygium jambos (L.) Alston (Myrtaceae). Journal of Ethnopharmacology, 71, 307-313.

Djoukeng, Jules Desire, Eliane Abou-Mansour, Leon Azefack Tapondjou, David Lontsi & Raffaele Tabacchi. (2007). Identification of ellagic acid derivatives from stem bark of Syzygium guineense (Myrtaceae), Natural Product Communications. 2, 1-6.

Edema M.O. & T.O. Alaga. (2012). Comparative evaluation of bioactive compounds in Hibiscus sabdariffa and Syzygium samarangense juice extracts. African Crop Science Journal, 20, 179 – 187.

Gao Y., Hu Q., & 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. doi: 10.5455/spatula.20120126062707.

Har, L.-W., & Ismail, I.S. (2012). Antioxidant activity, total phenolics and total flavonoid of Syzygium polyanthum (Wight) Walpleaves. Int. J. Med. Arom. Plants, 2(2), 219-228.

Hiranrat, Asadhawut (2010). Chemical constituents from Rhodomyrtus tomentosa (Aiton) Hassk and antibacterial activity, Thesis, Copyright of Prince of Songkla University.

Jemi, R., Wasrin Syafii, Fauzi Ferbianto, & Muhammad Hanafi. (2010). Sifat anti jamur kayu kupa (Syzygium polycephalum (Miq.)). Jurnal Ilmu dan Teknologi Kayu Tropis, 8, 93-110.

Khan, R.A., Khan, M.R., Sahreen, S., & Ahmed, M. (2012). Evaluation of phenolic contents and antioxidant activity of various solvent extracts of Sonchusasper (L.) Hill. Chemistry Central Journal, 6(12), 1-7.doi: 10.1186/1752-153X-6-12.

Mohanan, N., K.B. Vrinda, P. Padmesh, P.K. Suresh Kumar, Mathew Dan, S. Sreekumar, C.K. Biju, S.R. Suja, Smt. Rasiya Beegam, Shri. K.P. Pradeep Kumar, & Anil John. (2015). Jawaharlal Nehru Tropical Botanic Garden and Research Institute (JNTBGRI) Annual Report 2012-13 & 2014-15, 15-17.

Nurlaila, Ela. (2016). Identifikasi senyawa antioksidan hasil isolasi dari ekstrak kloroform kulit batang tumbuhan salam (Syzygium polyanthum), A Theses, Submitted to the Faculty of Mathematics and Natural Sciences (in partial fulfillment of the requirements for the Science Undergraduate Degree), Universitas Negeri Surabaya, Indonesia, 71-76.

Palanisamy, U.D., L.T. Ling, T. Manaharan, V. Sivapalan, T. Subramaniam, M.H. Helme & T. Masilamani. (2011). Standardized extract of Syzygium aqueum: a safe cosmetic Ingredient. International Journal of Cosmetic Science, 33(3), 269–275. doi: 10.1111/j.1468-2494.2010.00637.x.

Pranoti Belapurkar & Pragya Goyal. (2014). In vitro evaluation of phytochemical and antioxidant properties of Syzygium cumini leaves and their synergistic effect on its antimicrobial property. Int. J. Res.Pharm. Sci., 5, 254-258.

Preddy Victor. (2014). Cancer: oxidative Stress and dietary antioxidants. Chapter 10: The Indian blackberry (Jamun), antioxidant capacity, and cancer protection (authorized by Farrukh Aqil, Radha Munagala, Jeyaprakash Jeyabalan, Thwisha Joshi, Ramesh C. Gupta), 101.

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. & Raga, D.D. (2014). Triterpenes from the leaves of Syzygium polycephalum, S. cumini, and S. samarangense, Chemistry of Natural Compounds, 50(5), 942-944.

Reynertson, Kurt Allerslev. (2007). Phytochemical analysis of bioactive constituents from edible Myrtaceae fruits. A Dissertation Submitted to the Graduate Faculty in Biology in partial fulfillment of the requirements for the Degree of Doctor of Philosophy, The City University of New York.

Ruan, Z.P., Liang, L.Z., & Yi, M.L. (2008). Evaluation of the antioxidant activity of Syzygium cumini leaves. Molecules, 13, 2545-2556.doi: 10.3390/ molecules13102545.

Shilpa A. Wagh. (2010). Bioconversion of tannic acid to gallic acid by using fungal tannase, A Theses Submitted to the Division of Biochemical Sciences, National Chemical Laboratory, Pune – 411008 (India), 7-10.

Shubhi, Mehrotra, Kirar Vandana, Misra Kshipra, & Nandi Shoma Paul. (2013). Quantitative estimation of gallic acid in Rosa sinensis, Emblica officinalis, and Syzygium aromatocium by HPTLC. International Research Journal of Pharmacy, 4(7): 87-89. Doi: 10.7897/2230-8407.04719.

Sidney, Maliehe Tsolanku, Shandu Jabulani Siyabonga & Basson Albertus Kotze. (2015). The antibacterial and antidiarreal activities of the crude methanolic Syzygium cordatum [S.Ncik, 48 (UZ)] fruit pulp and seed extracts. Journal of Medicinal Plants Research, 9(33), 884-891. doi: 10.5897/JMPR2015.5789.

Simões-Pires CA, Vargas S, Marston A, Ioset JR, Paulo MQ, Matheeussen A, & Maes L. (2009). Ellagic acid derivatives from Syzygium cumini stem bark: investigation of their antiplasmodial activity. Natural Product Communications, 4(10), 1371- 1376.

Swami, Shrikant Baslingappa, Nayan Singh J. Thakor, Meghatai M. Patil, and Parag M. Haldankar. (2012). Jamun (Syzygium cumini (L.)): A review of its food and medicinal uses. Food and Nutrition Sciences, 3, 1100-1117. doi.org: 10.4236/fns.2012.38146.

Tukiran, Fitriyatul M., Nurul H. and Kuniyoshi S. (2016). A phenolic acid and its antioxidant activity from stem bark of chloroform fraction of Syzygium litorale (Blume) Amshoff (Myrtaceae). Molekul, 11(2), 180-189. doi: 10.20884/1.jm.2016.11.2.215.




DOI: http://dx.doi.org/10.20884/1.jm.2018.13.1.393

Metric logoArticle Metrics


This article has been viewed: 150 (times)
PDF file viewed / downloaded: 64 (times)

Refbacks

  • There are currently no refbacks.


Logo Unsoed

Molekul

Jurnal Ilmiah Kimia
Department of Chemistry, Faculty of Mathematics and Natural Sciences,
Universitas Jenderal Soedirman, Purwokerto, Indonesia

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