Secondary Metabolites from The Active Antioxidant Fraction of The Stem Bark of Syzygium zeylanicum. L. DC.
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Abstract
Syzygium zeylanicum (L.) DC, known by the local community in South Sumatra, Indonesia, as jambu nasi-nasi. This plant has been used to treat various diseases including hypertension, diabetes, joint pain, headaches, and fever. The use of plants as medicine is closely related to their secondary metabolite content. This research is an experimental study aimed at determining the antioxidant activity of fractions from the stem bark of S.zeylanicum and isolating and determining the chemical structure of its active compounds. The fractionation of the dry powder of S. zeylanicum stem bark was carried out using a gradient extraction method with solvents n-hexane, ethyl acetate, and methanol. Each fraction was tested for antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH) method. The active antioxidant fractions were further isolated into pure compounds using chromatography techniques, and their chemical structures were identified through spectroscopy, including 1D and 2D Nuclear Magnetic Resonance (NMR). The antioxidant activity test results (IC50) for each fraction, namely n-hexane, ethyl acetate, and methanol, were 338.1: 114.1: and 88.71 µg/mL. The results of the separation of the ethyl acetate and methanol fractions using a chromatography column showed that the SE7 subfraction from the ethyl acetate fraction had the highest IC50, which is 83.25 µg/mL. The SE7 fraction was further separated by column chromatography until compound 1 was obtained as a white solid with an IC50 value of 62.22 µg/mL. Based on spectroscopic analysis including 1H-NMR, 13C-NMR, HSQC, HMBC and UV, compound 1 is proposed as 1-(4-isopropoxyphenyl)propane-1,2,3-triol
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References
1. Sies H. Oxidative Stress: Concept and Some Practical Aspects. Antioxidants. 2020: 10:9(9):852 - 857. Doi: 10.3390/antiox 9090852
2. Baek J, Lee MG. Oxidative stress and antioxidant strategies in dermatology. Redox Rep. 2016:21(4) 164 - 169.
3. Jahan S, Zahra A, Irum U, Iftikhar N, Ullah H. Protective effects of different antioxidants against cadmium induced oxidative damage in rat testis and prostate tissues. Syst Biol Reprod Med. 2014:60(4):199–205. Doi: 10.3109/19396368 .2014.912363
4. Ekin S, Bayramoglu M, Goktasoglu A, Ozgokce F, Kiziltas H. Antioxidant Activity of Aqueous And Ethanol Extracts of Crataegus Meyeri Pojark Leaves And Contents of Vitamin, Trace Element. J Chil Chem Soc. 2017:62(4):3661–3667.
5. Oktiansyah R, Juliandi B, Widayati KA, Juniantito V. Neuronal Cell Death and Mouse (Mus musculus) Behaviour induced by Bee Venom. trop Life Sci Res. 2018:29(2): 1-11. Doi: 10.21315/tlsr2018.29.2.1.
6. Nguyen VB, Wang Sl, Nguyen TH, Doan CT, Tran TN, Kuo YH. New Indications of Potential Rat Intestinal α-Glucosidase Inhibition By Syzygium zeylanicum (L.) and Its Hypoglycemic Effect In Mice. Res Chem Intermed. 2019:45(12):6061–6071. Doi: 10.1007/S11164-019-04019-4
7. Shilpa KJ, Krishnakumar G. Nutritional, Fermentation and Pharmacological Studies of Syzygium Caryophyllatum (L.) Alston and Syzygium Zeylanicum (L.) Dc Fruits. Cogent Food Agric. 2015:1(1): 1-13 Doi: 10.1080/23311932.2015.1018694
8. Potdar MB. Evaluation of Phytochemical, Antioxidant, Anti-Inflammatory Antimicrobial, Anti-Cancerous And Wound Healing Potential of Syzygium Zeylanicum. Ann Pharma Res. 2021:9(10):558–566.
9. Yumita A, Hikmawanti NPE, Hanani E, Saputri CW, Hanana PH, Ero JND, Marcelena M, Baytisani T, Sofiana FA, Shania AF, Saputri ESA, Islami FPN. Exploring the Polyphenol Contents and Antioxidant Capacity of the Leaf Extracts of Selected Indonesian Syzygium Species. Trop J Nat Prod Res. 2023:7(6):3119–3124.
10. Nguyen MT, Bui TBH, Pham VH, Tran MD, Nguyen QV. Syzygium zeylanicum (L.) Dc. Polyphenols Exhibit Anti-Diabetic Activity By Modulation of Acc1, Sglt1, And Glp-1 Genes and Restoration of Gut Microbiota In Overfeeding and High Glucose Exposure-Induced Diabetic Zebrafish. J Funct Foods. 2024:112 (1):105921-105931
11. Anoop MV, Bindu AR. In-Vitro Anti-Inflammatory Activity Studies on Syzygium zeylanicum (L.) Dc Leaves. Int J Pharma Res Rev. 2015:4(8): 18-27
12. Hamidah, Salni, Tanzerina N. Bioactive Compound of Syzygium zeylanicum Leaves Asthe Escherichia coli and Staphylococcus aureus Antibacterial. BIOVALENTIA Biol Res J E. 2017:3(1):2477–1392.
13. Elfita, Oktiansyah R, Mardiyanto, Widjajanti H, Setiawan A, Nasution SSA. Bioactive compounds of endophytic fungi Lasiodiplodia theobromae isolated from the leaves of Sungkai (Peronema canescens). Biointerface Res Appl Chem 2023:13(6). DOI: 10.33263/BRIAC136.530.
14. Nomi Y, Shimizu S, Sone Y, Truong Tuyet M, Pham Gia T, Kamiyama M. Isolation And Antioxidant Activity of Zeylaniin A, A New Macrocyclic Ellagitannin from Syzygium zeylanicum Leaves. J Agric Food Chem. 2012:60(41) : 10263-10269
15. Hamidah, Salni, Tanzerina N. Bioactive Compound of Syzygium zeylanicum Leaves Asthe Escherichia Coli And Staphylococcus Aureus Antibacterial. Biovalentia Biol Res J E. 2017:3(1).
16. Syarifah, Elfita, Widjajanti H, Setiawan A, Kurniawati Ar. Antioxidant and Antibacterial Activities of Endophytic Fungi Extracts of Syzygium zeylanicum. Sci Technol Indones. 2022:7(3).
17. Mayasani N, Hikmahtunnazila H, Lestari W, Roanisca O. Phytochemical Study of Syzygium zeylanicum Leaves Using Microwave Assisted Extraction Method ( Mae ). Pros Semin Nas Penelit Pengabdi Pada Masy. 2019:3:1–4.
18. Govindarajan M, Benelli G. Α-Humulene And Β-Elemene From Syzygium Zeylanicum (Myrtaceae) Essential Oil: Highly Effective And Eco-Friendly Larvicides Against Anopheles Subpictus, Aedes Albopictus, and Culex Tritaeniorhynchus (Diptera: Culicidae). Parasitol Res. 2016:115 (7): 2771–2778. Doi: 10.1007/S00436-016-5025-2
19. Rameshkumar Kb, Anu Aravind Ap, Vinodkumar Tg. Leaf Essential Oil Composition of Six Syzygium Species from The Western Ghats, South India. Rec Nat Prod. 2015:9(4): 592-596
20. Huong LT, Thinh BB, Hung NH, Phu HV., Hieu NC, Dai DN. Chemical Composition, Antimicrobial and Larvicidal Activities of Essential Oils of Two Syzygium Species From Vietnam. Braz J Biol. 2024:84 (1):1–9.
21. Oktiansyah R, Widjajanti H, Setiawan A, Nasution SSA, Mardiyanto M, Elfita. Antibacterial and antioxidant activity of endophytic fungi extract isolated from leaves of sungkai (Peronema canescens). Sci Technol Indonesia. 2023:8(2): 170–177. DOI: 10.26554/sti.2023.8.2.170-177.
22. Utomo DS, Kristiani E, Mahardika A. The Effect of Growth Location on Flavonoid, Phenolic, Chlorophyll, Carotenoid and Antioxidant Activity Levels In Horse Whip (Stachytarpheta Jamaicensis). Bioma. 2020:22(2):143–149.
23. Muharni, Elfita, Yohandini H, Julinar, Yasrina, Miranti. Chemical Constituents from Stem Bark of Flacourtia rukam Zoll. & Mor. and Their Antioxidant Activities. Sains Malaysiana. 2019:48(9):1899–1906
24. Zhang Q-W, Lin L-G, Ye W-C. Techniques For Extraction and Isolation of Natural Products: A Comprehensive Review. Chin Med. 2018:13(20): 1-26. Doi: 10.1186/S13020-018-0177-X
25. Iheanacho CM, Akubuiro PC, Oseghale IO, Imieje VO, Erharuyi O, Ogbeide KO, Jideonwo AN, Falodun A. Tropical J Phytochem and Pharmaceut Sci 2023: 2 (2), 65-69
26. Sabandar Cw, Jalil J, Ahmat N, Aladdin N-A, Nik Abdullah Zawawi Nk, Sahidin I. Anti-Inflammatory and Antioxidant Activity of Syzygium Polyanthum (Wight) Walp. Sains Malaysiana. 2022:51(5): 1475-1485.
27. Oktiansyah R, Elfita E, Widjajanti H, Setiawan A, Mardiyanto M, Nasution SSA. Antioxidant and Antibacterial Activity of Endophytic Fungi Isolated from The Leaves of Sungkai (Peronema canescens). Trop J Nat Prod Res. 2023:7(3):2596–2604.
28. Mehdizadeh L, Moghaddam M, Ganjeali A, Rahimmalek M. Phenolic Compounds, Enzymatic and Non-Enzymatic Antioxidant Activities of Mentha Piperita Modified By Zinc and Methyl Jasmonate Concentrations. Sci Hortic. 2024:329 (1): 1-10. https://doi.org/10.1016/j.scienta.2024.112980
29. Nguyen MT, Thi B, Maskey S, Tran MD, Nguyen QV. In Vitro and In Vivo Antioxidant and Antihyperglycemic Potentials of Phenolic Fractions of Syzygium Zeylanicum (L.) Dc Trunk-Bark. Food Sci Nutr. 2023:11(7):3875–3884.
30. Aung EE, Kristanti AN, Aminah NS, Takaya Y, Ramadhan R. Plant Description, Phytochemical Constituents And Bioactivities of Syzygium Genus: A Review. Open Chem. 2020 :18(1):1256–1281. Doi: 10.1515/chem-2020-0175
31. De AAN, De SEl, Nascimento DDS, Alves JM, Brito SK, DaSilva SRF. Revisiting The Nutritional and Functional Value and Health-Promoting Potential of Syzygium Species. J Funct Foods . 2024:118 (1):1062-1065.
32. Julizan N, Ishmayana S, Zainuddin A, Van HP, Kurnia D. Potential of Syzygnium Polyanthum As Natural Food Preservative: A Review. Foods. 2023:12(12): 2275-2299
33. Tarigan C, Pramastya H, Insanu M, Fidrianny I. Syzygium Samarangense: Review of Phytochemical Compounds and Pharmacological Activities. Biointerface Res Appl Chem. 2022:12(2):2084–2107.
34. Lundgren LN, Popoff T, Theander O, Napier RJ, Thomson RH, Tezuka T. Arylglycerol Glucosides from Pinus sylvestris. Vol. 36b, Acta Chemica Scandinavica. 1982. p. 695–9.
35. Metasari S, Elfita E, Muharni M, Yohandini H. Antioxidant Compounds From The Stem Bark of Syzygium Samarangvense L. Molekul. 2020:15(3): 175-183