Isolation of 5,7-Dihydroxy, 6,8-Dimethyl Flavanone from Syzygium aqueum with Its Antioxidant and Xanthine Oxidase Inhibitor Activities.
| Title: | Isolation of 5,7-Dihydroxy, 6,8-Dimethyl Flavanone from Syzygium aqueum with Its Antioxidant and Xanthine Oxidase Inhibitor Activities. |
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| Authors: | Insanu M; Department of Pharmaceutical Biology, School of Pharmacy, Institut Teknologi Bandung, Bandung, West Java, Indonesia.; Ramadhania ZM; Department of Pharmaceutical of Biology, Faculty of Pharmacy, Universitas Padjadjaran, Bandung, West Java, Indonesia.; Halim EN; Department of Pharmaceutical Biology, School of Pharmacy, Institut Teknologi Bandung, Bandung, West Java, Indonesia.; Hartati R; Department of Pharmaceutical Biology, School of Pharmacy, Institut Teknologi Bandung, Bandung, West Java, Indonesia.; Wirasutisna KR; Department of Pharmaceutical Biology, School of Pharmacy, Institut Teknologi Bandung, Bandung, West Java, Indonesia. |
| Source: | Pharmacognosy research [Pharmacognosy Res] 2018 Jan-Mar; Vol. 10 (1), pp. 60-63. |
| Publication Type: | Journal Article |
| Language: | English |
| Journal Info: | Publisher: Medknow Country of Publication: India NLM ID: 101558769 Publication Model: Print Cited Medium: Print ISSN: 0976-4836 (Print) Linking ISSN: 09748490 NLM ISO Abbreviation: Pharmacognosy Res Subsets: PubMed not MEDLINE |
| Imprint Name(s): | Original Publication: Mumbai : Medknow |
| Abstract: | Background: Syzygium aqueum Burm.f. Alston (water apple) belonging to Myrtaceae family was originated from tropical areas. It was traditionally used as a medicinal plant.; Objective: The objective of the study was to isolate the active compound from the methanolic extract of S. aqueum leaves.; Methods: Extraction was done using continuous extraction with methanol as a solvent. The extract was then fractionated using liquid-liquid extraction, vacuum liquid chromatography, and radial chromatography. Recrystallization was done for purification. The structure of the compound was determined by Ultraviolet-Visible and (1D and 2D) nuclear magnetic resonance (NMR) spectrometer.; Results: The isolate showed maximum wavelengths at 347 (band I) and 296 (band II) nm. After addition of NaOH and CH3 COONa, the maximum wavelengths of band II moved to 340 and 339 nm, respectively. There was no change in wavelengths after addition CH3 COONa/H3 BO3 and AlCl3. The 1H-NMR spectrum showed 16 protons, whereas 13C-NMR spectrum showed 15 carbons. Based on those data, the isolate was determined as 5,7-dihydroxy-6,8-dimethyl flavanone (demethoxymatteucinol). At a concentration of 100 and 50 μg/mL, it could inhibit 25.13% of xanthine oxidase (XO) activity and scavenge 11.87% of diphenyl-picrylhydrazyl, respectively.; Conclusion: Demethoxymatteucinol was isolated for the first time from S. aqueum and it had mild antioxidant and XO inhibitory activities.; Summary: One flavonoid compound, which 5,7-dihydroxy 6,8-dimethyl flavanone (demethoxymatteucinol), was isolated from the methanol extract of Syzygium aqueum. It had mild antioxidant and xanthine oxidase inhibitory activities. Abbreviations Used: CH3 COONa/H3 BO3: Natrium acetate/Boric acid; DPPH: Diphenyl-picrylhydrazyl, NMR: Nuclear Magnetic Resonance; ABTS: 2,2'-azinobis (3-ethyl-benzothiazline-6-sulfonic acid); AEAC: Ascorbic Acid Equivalent Antioxidant Capacity; UV-Vis: Ultraviolet-Visible; XO: Xanthine Oxidase; HSQC: Heteronuclear Single Quantum Coherence; HMBC: (Heteronuclear Multiple Bond Correlation). |
| Competing Interests: | There are no conflicts of interest. |
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| Contributed Indexing: | Keywords: Antioxidant; Myrtaceae; Syzygium aqueum; flavonoid |
| Entry Date(s): | Date Created: 20180324 Latest Revision: 20220316 |
| Update Code: | 20260130 |
| PubMed Central ID: | PMC5855375 |
| DOI: | 10.4103/pr.pr_59_17 |
| PMID: | 29568189 |
| Database: | MEDLINE |
Journal Article