Sains Malaysiana 50(11)(2021): 3231-3239

http://doi.org/10.17576/jsm-2021-5011-07

Phytochemicals and Bioactivities of Syzygium filiforme var. filiforme

 (Fitokimia dan Bioaktiviti Syzygium filiforme var. filiforme)

MOHD HAFIZ AHMAD^1,3*, NORHAZANA NOR IZAN², NOR HADIANI ISMAIL³ & HUMERA NAZ⁴

¹Nanotechnology & Catalysis Research Centre (NANOCAT), University of Malaya, Block 3A, Inst. of Graduate Studies Building, 50603 Kuala Lumpur, Federal Territory, Malaysia

²Faculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor Darul Ehsan, Malaysia

³Atta-ur-Rahman Institute for Natural Produtcs Discovery (AuRIns), Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia

⁴Faculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia

Diserahkan: 3 Mei 2020/Diterima: 17 Mac 2021

ABSTRACT

Syzygium filiforme var. filiforme is a plant variety from dicotyledonous plant family (Myrtaceae). Phytochemical studies on S. filiforme var. filiforme stem bark have successfully isolated and characterized arjunolic acid (1), alphitolic acid (2), betulinic acid (3), ursolic acid (4), ursolic acid 3-methyl ester (5), β-sitosterol (6) and stigmasterol (7). The inhibitory activities against free radical, starch, and bacteria for major compounds were tested by using DPPH, α-glucosidase and minimum inhibitory and bacterial concentration assays, respectively. No promising antioxidant activity was shown on tested samples except methanolic crude extract. For antidiabetic activity, methanolic and dichloromethane crude extracts displayed potent activity compared to 1-deoxynojirimycin. Minimum inhibitory concentration (MIC) and minimum bacterial concentration (MBC) assays for antibacterial activity were evaluated on Escherichia coli, Staphylococcus aureus, and Bacillus subtilis. All crude extracts and major compounds displayed weak and no promising activities for MIC method, respectively. Meanwhile, for MBC method, hexane crude extract and compound 1 showed inhibition against B. subtilis.

Keywords: Antibacterial; antidiabetic; antioxidant; Myrtaceae; Syzygium filiforme var. filiforme

ABSTRAK

Syzygium filiforme var. filiforme adalah varieti tumbuhan daripada keluarga tumbuhan dicotyledonous (Myrtaceae). Kajian fitokimia pada kulit batang S. filiforme var. filiforme berjaya mengasingkan dan mencirikan asid arjunolik (1), asid alfitolik (2), asid betulinik (3), asid ursolik (4), asid ursolik 3-metil ester (5), β-sitosterol (6) dan stigmasterol (7). Aktiviti penghambatan terhadap radikal bebas, kanji dan bakteria untuk sebatian utama diuji dengan menggunakan DPPH, α-glukosidase dan uji kepekatan minimum dan kepekatan bakteria, masing-masing. Tiada aktiviti antioksidan yang menjanjikan pada sampel yang diuji kecuali ekstrak mentah metanolik. Untuk aktiviti antidiabetik, ekstrak mentah metanol dan diklorometana menunjukkan aktiviti yang kuat berbanding dengan 1-deoxynojirimycin. Kaedah kepekatan perencatan minimum (MIC) dan kepekatan bakteria minimum (MBC) untuk aktiviti antibakteria dinilai pada Escherichia coli, Staphylococcus aureus dan Bacillus subtilis. Semua ekstrak mentah dan sebatian utama masing-masing menunjukkan aktiviti lemah dan tidak menjanjikan untuk kaedah MIC. Sementara itu, untuk kaedah MBC, ekstrak mentah heksana dan sebatian 1 menunjukkan perencatan terhadap B. subtilis.

Kata kunci: Antibakteria; antidiabetik; antioksidan; Myrtaceae; Syzygium filiforme var. filiforme

RUJUKAN

Ajiboye, B.O., Ojo, O.A., Oyinloye, B.E., Akuboh, O., Okesola, M.A., Idowu, O. & Kappo, A.P. 2020. In vitro antioxidant and inhibitory activities of polyphenolic-rich extracts of Syzygium cumini (Linn) Skeels leaf on two important enzymes relevant to type II diabetes mellitus. Pakistan Journal of Pharmaceutical Sciences 33(2): 523-529.

Babu, T.M.C., Rajesh, S.S., Bhaskar, B.V., Devi, S., Rammohan, A., Sivaraman, T. & Rajendra, W. 2017. Molecular docking, molecular dynamics simulation, biological evaluation and 2D QSAR analysis of flavonoids from Syzygium alternifolium as potent anti-Helicobacter pylori agents. The Royal Society of Chemistry Advances 7(30): 18277-18292.

Bai, L.Y., Chiu, C.F., Chiu, S.J., Chen, Y.W., Hu, J.L., Wu, C.Y. & Weng, J.R. 2015. Alphitolic acid, an anti-inflammatory triterpene, induces apoptosis and autophagy in oral squamous cell carcinoma cells, in part, through a p53-dependent pathway. Journal of Functional Foods 18: 368-378.

Banerjee, A., Dasgupta, N. & De, B. 2005. In vitro study of antioxidant activity of Syzygium cumini fruit. Food Chemistry 90(4): 727-733.

Chagas, V.T., França, L.M., Malik, S. & Paes, A.M.d.A. 2015. Syzygium cumini (L.) skeels: A prominent source of bioactive molecules against cardiometabolic diseases. Frontiers in Pharmacology 6: 259-259.

Chandramu, C., Manohar, R.D., Krupadanam, D.G. & Dashavantha, R.V. 2003. Isolation, characterization and biological activity of betulinic acid and ursolic acid from Vitex negundo L. Phytotherapy Research: An International Journal Devoted to Pharmacological and Toxicological Evaluation of Natural Product Derivatives 17(2): 129-134.

Cock, I.E. & Cheesman, M. 2018. Plants of the genus Syzygium (Myrtaceae): A review on ethnobotany, medicinal properties and phytochemistry. In Bioactive Compounds of Medicinal Plants: Properties and Potential for Human Health, edited by Goyal, M.R. & Ayeleso, A. Florida: Apple Academic Press. pp. 35-84.

De Jesus Soares, J., da Silva Rosa, A., Motta, P.R., Cibin, F.W.S., Roehrs, R. & Denardin, E.L.G. 2019. Protective role of Syzygium cumini leaf extracts against paraquat-induced oxidative stress in superoxide-dismutase-deficient Saccharomyces cerevisiae strains. Acta Scientiarum Biological Sciences 41: e47139-e47139.

De-Eknamkul, W. & Potduang, B. 2003. Biosynthesis of β-sitosterol and stigmasterol in Croton sublyratus proceeds via a mixed origin of isoprene units. Phytochemistry 62(3): 389-398.

Djoukeng, J.D., Abou-Mansour, E., Tabacchi, R., Tapondjou, A.L., Bouda, H. & Lontsi, D. 2005. Antibacterial triterpenes from Syzygium guineense (Myrtaceae). Journal of Ethnopharmacology 101(1-3): 283-286.

Farag, F., Sasse, F., Hendrarto, B. & Izzati, M. 2009. Tree species composition and distribution in Sungai Lalang Forest Reserve, Selangor, Malaysia. The 10th International Seminar on Environment and Architecture 12(1): 29-34.

Faria, A.F., Marques, M.C. & Mercadante, A.Z. 2011. Identification of bioactive compounds from jambolao (Syzygium cumini) and antioxidant capacity evaluation in different pH conditions. Food Chemistry 126(4): 1571-1578.

Gaspar, R.S., da Silva, S.A., Stapleton, J., Fontelles, J.L.d.L., Sousa, H.R., Chagas, V.T., Alsufyani, S., Trostchansky, A., Gibbins, J.M. & Paes, A.M.d.A. 2020. Myricetin, the main flavonoid in Syzygium cumini leaf, is a novel inhibitor of platelet thiol isomerases PDI and ERp5. Frontiers in Pharmacology 10: 1678.

Güvenalp, Z., Kilic, N., Kazaz, C., Kaya, Y. & Demi̇rezer, L.Ö. 2006. Chemical constituents of Galium tortumense. Turkish Journal of Chemistry 30(4): 515-523.

Heng, R.K.J., Majid, N., Gandaseca, S. & Ahmed, O. 2013. Assessment of floristic composition in a rehabilitated forest, Sarawak, Malaysia. Borneo Journal of Resource Science and Technology 2: 60-66.

Hu, Y.K., Wang, L., Li, Y.Y., Li, M.J., Xu, W., Zhao, Y., Li, F. & Zhao, Y. 2018. Five new triterpenoids from Syzygium samarangense (Bl.) Merr. et Perry. Phytochemistry Letters 25: 147-151.

Ismail, I.S., Ismail, N. & Lajis, N. 2010. Ichthyotoxic properties and essential oils of Syzygium malaccense (Myrtaceae). Pertanika Journal of Science & Technology 18(1): 1-6.

Ito, H., Iwamori, H., Kasajima, N., Kaneda, M. & Yoshida, T. 2004. Kunzeanones A, B, and C: novel alkylated phloroglucinol metabolites from Kunzea ambigua. Tetrahedron 60(44): 9971-9976.

Kabra, S. & Patel, S. 2018. Total phenolics & flavonoid content of the leaves of Carica papaya & Syzygium cumini. World Journal of Pharmaceutical Research 7(14): 734-741.

Kim, D.H., Han, K.M., Chung, I.S., Kim, D.K., Kim, S.H., Kwon, B.M., Jeong, T.S., Park, M.H., Ahn, E.M. & Baek, N.I. 2005. Triterpenoids from the flower of Campsis grandiflora K. Schum. as human acyl-CoA: Cholesterol acyltransferase inhibitors. Archives of Pharmacal Research 28(5): 550-556.

Kuiate, J.R., Mouokeu, S., Wabo, H.K. & Tane, P. 2007. Antidermatophytic triterpenoids from Syzygium jambos (L.) Alston (Myrtaceae). Phytotherapy Research: An International Journal Devoted to Pharmacological and Toxicological Evaluation of Natural Product Derivatives 21(2): 149-152.

Lee, S.S., Lin, H.C. & Chen, C.K. 2008. Acylated flavonol monorhamnosides, α-glucosidase inhibitors, from Machilus philippinensis. Phytochemistry 69(12): 2347-2353.

Maliehe, T.S., Shandu, J.S., Basson, A.K., Simelane, M.B., Lazarus, G. & Singh, M. 2017. Pharmacodynamic and cytotoxicity effects of Syzygium cordatum {S Ncik, 48 (UZ)} fruit-pulp extract in gastrointestinal tract infections. Tropical Journal of Pharmaceutical Research 16(6): 1349-1355.

Manaharan, T., Appleton, D., Cheng, H.M. & Palanisamy, U.D. 2012. Flavonoids isolated from Syzygium aqueum leaf extract as potential antihyperglycaemic agents. Food Chemistry 132(4): 1802-1807.

Minh, N.P., Anh, N.H., Pha, P.T.L. & Bach, L.G. 2018. Effect of blanching, drying and preservation of dried wax apple (Syzygium samarangense) leaf tea. Research on Crops 19(4): 730-735.

Musabayane, C.T., Mahlalela, N., Shode, F.O. & Ojewole, J.A. 2005. Effects of Syzygium cordatum (Hochst.) [Myrtaceae] leaf extract on plasma glucose and hepatic glycogen in streptozotocin-induced diabetic rats. Journal of Ethnopharmacology 97(3): 485-490.

Nguyen, T.L., Rusten, A., Bugge, M.S., Malterud, K.E., Diallo, D., Paulsen, B.S. & Wangensteen, H. 2016. Flavonoids, gallotannins and ellagitannins in Syzygium guineense and the traditional use among Malian healers. Journal of Ethnopharmacology 192: 450-458.

Reynertson, K.A., Yang, H., Jiang, B., Basile, M.J. & Kennelly, E.J. 2008. Quantitative analysis of antiradical phenolic constituents from fourteen edible Myrtaceae fruits. Food Chemistry 109(4): 883-890.

Saleem, U., Ali, N. & Ahmad, B. 2016. Does Syzygium cumini possess significant pharmacological effects an overview. Newsletter 2: 26-29.

Savitha, R.C., Padmavathy, S. & Sundhararajan, A. 2011. In vitro antioxidant activities on leaf extracts of Syzygium malaccense (L.) merr and perry. Ancient Science of Life 30(4): 110-113.

Shen, S.C., Chang, W.C. & Chang, C.L. 2012. Fraction from wax apple [Syzygium samarangense (Blume) Merrill and Perry] fruit extract ameliorates insulin resistance via modulating insulin signaling and inflammation pathway in tumor necrosis factor α-treated FL83B mouse hepatocytes. International Journal of Molecular Sciences 13(7): 8562-8577.

Shinde, J., Taldone, T., Barletta, M., Kunaparaju, N., Hu, B., Kumar, S., Placido, J. & Zito, S.W. 2008. α-Glucosidase inhibitory activity of Syzygium cumini (Linn.) Skeels seed kernel in vitro and in Goto-Kakizaki (GK) rats. Carbohydrate Research 343(7): 1278-1281.

Swadhin, T.H., Islam, M.M. & Lima, K.A. 2019. Effect of different concentration of (Indole 3-Butyric Acid) on stem cutting of jamrul (Syzygium samarangense) at Patuakhali District under Dumki Upazila. Asian Journal of Research and Review in Agriculture 1(1): 36-44.

Teoh, W.Y., Sim, K.S., Richardson, M., Stella, J., Abdul Wahab, N. & Hoe, S.Z. 2013. Antioxidant capacity, cytotoxicity, and acute oral toxicity of Gynura bicolor. Evidence-Based Complementary and Alternative Medicine 2013: 1-10.

Ugbabe, G., Ezeunala, M., Edmond, I., Apev, J. & Salawu, O. 2010. Preliminary phytochemical, antimicrobial and acute toxicity studies of the stem, bark and the leaves of a cultivated Syzygium cumini Linn. (Family: Myrtaceae) in Nigeria. African Journal of Biotechnology 9(41): 6943-6747.

Zakaria, Z., Sufian, A., Ramasamy, K., Ahmat, N., Sulaiman, M., Arifah, A., Zuraini, A. & Somchit, M. 2010. In vitro antimicrobial activity of Muntingia calabura extracts and fractions. African Journal of Microbiology Research 4(4): 304-308.

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