Isolation of 5,7‑Dihydroxy, 6,8‑Dimethyl Flavanone from Syzygium aqueum with Its Antioxidant and Xanthine Oxidase Inhibitor Activities

Muhamad Insanu; Zelika Mega Ramadhania; Evelyne Nadia Halim; Rika Hartati; Komar Ruslan Wirasutisna

Isolation of 5,7‑Dihydroxy, 6,8‑Dimethyl Flavanone from Syzygium aqueum with Its Antioxidant and Xanthine Oxidase Inhibitor Activities

Articles

Abstract

Pharmacognosy Research,2018,10,1,60-63.

DOI:10.4103/pr.pr_59_17

Published:February 2018

Type:Original Article

Authors:

Author(s) affiliations:

Muhamad Insanu¹, Zelika Mega Ramadhania², Evelyne Nadia Halim¹, Rika Hartati¹, Komar Ruslan Wirasutisna¹

1 Department of Pharmaceutical Biology, School of Pharmacy, Institut Teknologi Bandung, Bandung, West Java, INDONESIA.

2 Department of Pharmaceutical of Biology, Faculty of Pharmacy, Universitas Padjadjaran, Bandung, West Java, INDONESIA.

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 CH₃COONa, the maximum wavelengths of band II moved to 340 and 339 nm, respectively. There was no change in wavelengths after addition CH₃COONa/H₃BO₃and 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.