• Title/Summary/Keyword: Caffeoylquinic acid derivatives

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Characterization of Anti-Advanced Glycation End Products (AGEs) and Radical Scavenging Constituents from Ainsliaea acerifolia (단풍취의 최종당화산물 생성 저해 및 라디칼 소거 물질의 동정)

  • Jeong, Gyeng Han;Kim, Tae Hoon
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.46 no.6
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    • pp.759-764
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    • 2017
  • Reactive oxygen species (ROS) and advanced glycation end products (AGEs) are valuable therapeutic targets for the regulation of diabetic complications. Activity-guided isolation of the ethylacetate (EtOAc)-soluble portion of 70% ethanolic extract from aerial parts of Ainsliaea acerifolia was performed, followed by AGE formation inhibition assay for the characterization of four dicaffeoylquinic acid derivatives of a previously known structure, methyl 3,5-di-O-caffeoyl-epi-quinate (1), 3,5-di-O-caffeoyl-epi-quinic acid (2), 4,5-di-O-caffeoyl-quinic acid (3), and methyl 4,5-di-O-caffeoyl-quinate (4). The structures of these compounds were confirmed by interpretation of nuclear magnetic resonance (NMR, $^1H-$, $^{13}C-NMR$, two-dimensional NMR) and mass spectroscopic data. Among the isolates, the major secondary metabolites, 3,5-di-O-caffeoyl-epi-quinic acid (2) and 4,5-di-O-caffeoyl-quinic acid (3) showed the most potent inhibitory effects against AGE formation with $IC_{50}$ values of $0.6{\pm}0.1{\mu}M$ and $0.4{\pm}0.1{\mu}M$, respectively. Furthermore, all isolated dicaffeoylquinic acid derivatives were evaluated for their radical scavenging activities using 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical, and compound 3 exhibited the most potent inhibitory effect in a concentration-dependent manner. This result suggests that the caffeoylquinic acid dimers isolated from A. acerifolia might be beneficial for the prevention of diabetic complications and related diseases.

Topical or oral treatment of peach flower extract attenuates UV-induced epidermal thickening, matrix metalloproteinase-13 expression and pro-inflammatory cytokine production in hairless mice skin

  • Kwak, Chung Shil;Yang, Jiwon;Shin, Chang-Yup;Chung, Jin Ho
    • Nutrition Research and Practice
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    • v.12 no.1
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    • pp.29-40
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    • 2018
  • BACKGROUND/OBJECTIVES: Ultraviolet radiation (UV) is a major cause of skin photoaging. Previous studies reported that ethanol extract (PET) of Prunus persica (L.) Batsch flowers (PPF, peach flowers) and its subfractions, particularly the ethylacetate (PEA) and n-butanol extracts (PBT), have potent antioxidant activity and attenuate the UV-induced matrix metalloproteinase (MMP) expression in human skin cells. In this study, we investigated the protective activity of PPF extract against UV-induced photoaging in a mouse model. MATERIALS/METHODS: Hairless mice were treated with PET or a mixture of PEA and PBT either topically or orally along with UV irradiation. Histological changes and biochemical alterations of mouse skin were examined. Major phenolic compounds in PPF extract were analyzed using an ACQUITY UPLC system. RESULTS: The overall effects of topical and oral treatments with PPF extract on the UV-induced skin responses exhibited similar patterns. In both experiments, the mixture of PEA and PBT significantly inhibited the UV-induced skin and epidermal thickening, while PET inhibited only the UV-induced epidermal thickening. Treatment of PET or the mixture of PEA and PBT significantly inhibited the UV-induced MMP-13 expression, but not type I collagen expression. Topical treatment of the mixture of PEA and PBT with UV irradiation significantly elevated catalase, superoxide dismutase (SOD) and glutathione-peroxidase (GPx) activities in the skin compared to those in the UV irradiated control group, while oral treatment of the mixture of PEA and PBT or PET elevated only catalase and SOD activities, but not GPx. Thirteen phytochemical compounds including 4-O-caffeoylquinic acid, cimicifugic acid E and B, quercetin-3-O-rhamnoside and kaempferol glycoside derivatives were identified in the PPF extract. CONCLUSIONS: These results demonstrate that treatment with PET or the mixture of PEA and PBT, both topically or orally, attenuates UV-induced photoaging via the cooperative interactions of phenolic components having anti-oxidative and collagen-protective activities.