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Open AccessCommunication
Int. J. Mol. Sci. 2014, 15(9), 16418-16429; doi:10.3390/ijms150916418

Flavonoids from Machilus japonica Stems and Their Inhibitory Effects on LDL Oxidation

1
Center, Seoul Cosmetics Co., Ltd., Incheon 443-749, Korea
2
Laboratory of Natural Products Chemistry, Graduate School of Oriental Medicinal Materials Biotechnology, Kyung Hee University, Yongin 446-701, Korea
3
National Research Laboratory of Lipid Metabolism & Atherosclerosis, KRIBB, Daejeon 305-806, Korea
4
Research & Development Center, GFC Co., Ltd., Suwon 443-813, Korea
5
Department of Herbal Crop Research, National Institute of Horticultural and Herbal Science, RDA, Eumseong 369-873, Korea
6
Cosmetic Business R&D Service Center, Graduate School, Ajou University, Suwon 443-749, Korea
*
Author to whom correspondence should be addressed.
Received: 21 July 2014 / Revised: 16 August 2014 / Accepted: 27 August 2014 / Published: 16 September 2014
(This article belongs to the Section Biochemistry, Molecular and Cellular Biology)
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Abstract

Stems of Machilus japonica were extracted with 80% aqueous methanol (MeOH) and the concentrated extract was successively extracted with ethyl acetate (EtOAc), normal butanol (n-BuOH), and water. Six flavonoids were isolated from the EtOAc fraction: (+)-taxifolin, afzelin, (−)-epicatechin, 5,3'-di-O-methyl-(−)-epicatechin, 5,7,3'-tri-O-methyl-(−)-epicatechin, and 5,7-di-O-methyl-3',4'-methylenedioxyflavan-3-ol. The chemical structures were identified using spectroscopic data including NMR, mass spectrometry and infrared spectroscopy. This is the first report of isolation of these six compounds from M. japonica. The compounds were evaluated for their diphenyl picryl hydrazinyl scavenging activity and inhibitory effects on low-density lipoprotein oxidation. Compounds 1 and 36 exhibited DPPH antioxidant activity equivalent with that of ascorbic acid, with half maximal inhibitory concentration (IC50) values of 0.16, 0.21, 0.17, 0.15 and 0.07 mM, respectively. The activity of compound 1 was similar to the positive control butylated hydroxytoluene, which had an IC50 value of 1.9 µM, while compounds 3 and 5 showed little activity. Compounds 1, 3, and 5 exhibited LDL antioxidant activity with IC50 values of 2.8, 7.1, and 4.6 µM, respectively. View Full-Text
Keywords: diphenyl picryl hydrazinyl; low-density lipoprotein-oxidation; flavonoid; Machilus japonica; NMR diphenyl picryl hydrazinyl; low-density lipoprotein-oxidation; flavonoid; Machilus japonica; NMR
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MDPI and ACS Style

Joo, S.-J.; Park, H.-J.; Park, J.-H.; Cho, J.-G.; Kang, J.-H.; Jeong, T.-S.; Kang, H.C.; Lee, D.-Y.; Kim, H.-S.; Byun, S.-Y.; Baek, N.-I. Flavonoids from Machilus japonica Stems and Their Inhibitory Effects on LDL Oxidation. Int. J. Mol. Sci. 2014, 15, 16418-16429.

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