헛개나무 열매로부터 유용 화합물의 단리⋅동정 및 생리활성 평가

Isolation and Identification of Bioactive Compounds from the Fruits of Hovenia dulcis Thunb.

헛개나무 열매를 열수 추출 후 건조시킨 분말을 80% EtOH로 추출한 추출물을 농축하여 획득한 CHCl3, EtOAc 및 n-BuOH 가용성 획분을 실험재료로 silica gel 및 Sephadex LH-20 column chromatography를 반복 시행하여 화합물 1∼5를 단리하였다. UV-Vis, LC-ESI-MS (negative ion) 및 1 H-1 H COSY, DEPT, HMQC 및 HMBC 분석을 통해 화합물의 화학구조를 5-hydroxy-2-hydroxymethyl-4-pyrone (1), 5-hydroxy methyl-2- furaldehyde (2), 5-(3-acetylpropionate)methyl-2-furaldehyde (3), 3,5-dihydroxy-3,4,5,6-tetrahydro-2-pyranone (4) 및 (4-(3-ethoxy)- pyridyl)methanol-β-D-glucopyranoside (5)로 동정하였다. 화합물 1과 2의 DPPH radical-scavenging 활성(IC50, μM) 은 각각 19.48 ± 1.02 및 32.07 ± 1.64를 나타내었고, 화합물 1의 tyrosinase 저해 활성(IC50, μM)은 19.17 ± 0.72를나타내었다. 이번 실험을 통해, 헛개나무 열매에 함유된 화합물 1이 항산화 효능이 우수한 유용물질임을 확인하였으며, 대용차 개발 시 기능성 소재로서의 활용 가능성을 확인하였다.

This study was conducted to identify bioactive components with DPPH radical-scavenging and tyrosinase inhibitory activities from the fruits of Hovenia dulcis Thunb. The studies consisted of the extraction and solvent fractionation, and isolation of compounds 1~5 from chloroform, ethyl acetate and n-butanol-soluble fractions. Chemical structures were identified as 5-hydroxy-2-hydroxymethyl-4-pyrone (1), 5-hydroxymethyl-2-furaldehyde (2), 5-(3-acetylpropionate)-methyl-2-furaldehyde (3), 3,5-dihydroxy-3,4,5,6-tetrahydro-2-pyranone (4) and 4-(3-ethoxy)- pyridyl-methanol-β-D-glucopyranoside (5), respectively, using UV–visible spectrophotometry (UV-Vis), liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS), proton nuclear magnetic resonance ( 1 H-NMR), carbon-13 nuclear magnetic resonance (13C-NMR), 1 H-1 H correlated spectroscopy (COSY), distortionless enhancement by polarization transfer (DEPT), heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bonding connectivity (HMBC) spectral data. Compounds 1 and 2 showed moderate antioxidant effect with IC50 values of 19.48 ± 1.02 μM and 32.07 ± 1.64 μM in 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activity, respectively. In addition, compound 1 exhibited strong mushroom tyrosinase inhibitory activity with IC50 value of 19.17 ± 0.72 μM.