• Title/Summary/Keyword: Catechin derivatives

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Determination of Amounts of Catechin and Caffeine in Green Tea Beverages (녹차음료에서의 카테킨 및 카페인 함량 조사)

  • Kim, Dae-Hwan;Lee, Myung-Jin;Kim, Yang-Hee;Ryu, Kyong-Sin;Lee, Ji-yeon;Park, Kwang-Hee
    • The Korean Journal of Food And Nutrition
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    • v.31 no.3
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    • pp.416-424
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    • 2018
  • The physiologically advantageous aspects of green tea have been identified recently and green tea has been a favorite drink of many people. Due to the increased awareness of green tea's positive effects on human health, the demand for foods containing green tea has increased. This has led to the development of diverse green tea-related beverages; thereby many companies in Korea have put a wide variety of manufactured green tea beverages on the market. However, the components within green tea beverages have not been examined in Korea yet. In this study, we investigated the contents of the physiologically functional materials found in green tea, such as catechin, catechin gallate, epicatechin, epicatechin gallate, epigallocatecin gallate, gallocatechin gallate and caffeine. Fifty-six green tea products purchased from the local grocery stores and cafes were analyzed using high performance liquid chromatography (HPLC) analysis. As a result, all tested products contained catechin and caffeine, although the amount of each component was largely different. The total amount of catechin derivatives in the manufactured green tea beverages purchased from cafes was 263.17 mg/L, while they were 61.99 mg/L in the beverages purchased from the local grocery stores. And, to the almost samples the amount of caffeine was proportional to the amount of catechin.

Bark Extractives of Several Populus Trees (몇가지 사시나무속 수종 수피의 추출성분)

  • Ham, Yeon-Ho;Kim, Jin-Kyu;Lee, Sang-Keuk;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.30 no.1
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    • pp.63-71
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    • 2002
  • The bark of P. alba × glandulosa, P. euramericana and P. nigra × maximounczii F1, several Populus trees, were collected, extracted with acetone-H2O(7:3, v/v), fractionated with hexane, chloroform and ethylacetate, and freeze dried to give some dark brown powder. Each fraction of the powder was chromatographed on a Sephadex LH-20 column using a series of aqueous methanol and ethanol-hexane mixture as eluents and then identified by thin layer chromatography using TBA and 6% acetic acid as developing solvents. The structures of the isolated compounds were characterized by 1H, 13C and 2D-NMR tools including mass spectrometry. Most of the compounds were flavonoids and salicin derivatives as follows: (+)-catechin, taxifolin, aromadendrin, eriodictyol, naringenin, sakuranetin, sakuranetin-5-O-𝛽-D-glucopyranoside, neosaturanin, salireposide, p-coumaric acid, and aesculin from P. alba × glandulosa, (+)-catechin, salireposide, populoside and salicortin from P. euramericana and (+)-catechin, quercetin, padmatin, salireposide, populoside and salicortin from P. nigra × maximounczii F1.

Determination of Several Phenolic Compounds in Cultivars of Grape in Korea (국내산 포도 품종의 주요 페놀계 화합물 함량 비교분석)

  • Chang, Seog-Won;Kim, Hyun-Ju;Song, Jeong-Hee;Lee, Ki-Yeol;Kim, Ik-Hwan;Rho, Yong-Taek
    • Food Science and Preservation
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    • v.18 no.3
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    • pp.328-334
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    • 2011
  • Natural polyphenolic compounds such as catechin, epicatechin derivatives, quercetin, and resveratrol, have been reported to have a wide range of biological activities against carcinogen and reactive oxygen species. The compounds can act together in synergy or can independently affect the activity. Contents of four compounds in different grape cultivar groups with different skin color were determined through HPLC. There were not significant differences in content of four phenolic compounds among the different skin color groups of the same grape cultivar groups, but were among different grape cultivars within the same skin color groups. Totally, contents of catechin, epicatechin derivatives were much higher than those of quercetin and resveratrol. In each skin color group, Campbell Early in Black, Seneka in Green, and Benigard in Red group showed highest contents, respectively. Nothing or a very small amount of four phenolic compounds was detected in some cultivars. This information would be useful for grape breeders and manufactures.

Effects of quercetin derivatives from mulberry leaves: Improved gene expression related hepatic lipid and glucose metabolism in short-term high-fat fed mice

  • Sun, Xufeng;Yamasaki, Masayuki;Katsube, Takuya;Shiwaku, Kuninori
    • Nutrition Research and Practice
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    • v.9 no.2
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    • pp.137-143
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    • 2015
  • BACKGROUND/OBJECTIVES: Mulberry leaves contain quercetin derivatives, which have the effects of reducing obesity and improving lipid and glucose metabolism in mice with obesity. It is not clear whether or not mulberry leaves can directly affect metabolic disorders, in the presence of obesity, because of the interaction between obesity and metabolic disorders. The aim of the current study was to assess the direct action of quercetin derivatives on metabolic disorders in non-obese conditions in short-term high-fat diet fed mice. MATERIALS/METHODS: C57BL/6N mice were fed a high-fat diet, supplemented with either 0% (control), 1%, or 3% mulberry leaf powder (Mul) or 1% catechin powder for five days. Anthropometric parameters and blood biochemistry were determined, and hepatic gene expression associated with lipid and glucose metabolism was analyzed. RESULTS: Body and white fat weights did not differ among the four groups. Plasma triglycerides, total cholesterol, and free fatty acids in the 1%, 3% Mul and catechin groups did not differ significantly from those of the controls, however, plasma glucose and 8-isoprostane levels were significantly reduced. Liver gene expression of gp91phox, a main component of NADPH oxidase, was significantly down-regulated, and PPAR-${\alpha}$, related to ${\beta}$-oxidation, was significantly up-regulated. FAS and GPAT, involved in lipid metabolism, were significantly down-regulated, and Ehhadh was significantly up-regulated. Glucose-metabolism related genes, L-PK and G6Pase, were significantly down-regulated, while GK was significantly up-regulated in the two Mul groups compared to the control group. CONCLUSIONS: Our results suggest that the Mul quercetin derivatives can directly improve lipid and glucose metabolism by reducing oxidative stress and enhancing ${\beta}$-oxidation. The 1% Mul and 1% catechin groups had similar levels of polyphenol compound intake ($0.4{\times}10^{-5}$ vs $0.4{\times}10^{-5}$ mole/5 days) and exhibited similar effects, but neither showed dose-dependent effects on lipid and glucose metabolism or oxidative stress.

Induction of Apoptosis of DK-5-62, a Novel (-)-Catechin Derivative Through MAPKs Signaling Pathway in HCT116 Cells

  • Guon, Tae Eun;Shin, Dong-Soo;Chung, Ha Sook
    • Journal of the Korean Chemical Society
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    • v.66 no.4
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    • pp.298-304
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    • 2022
  • The present study was designed to investigate the molecular mechanisms of DK-5-62, a novel (-)-catechin derivative on HCT116 human colorectal cancer cells. DK-5-62 inhibited the proliferation in dose- and time-dependent manner accompanied by the morphological changes. Effects of DK-5-62 appeared to be mediated by the induction of apoptosis, as manifested through DNA-binding dye Hoechst 33258 staining. Analysis of the mechanism of these events indicated that DK-5-62-treated cells exhibited an increased ratio of Bax/Bcl-2, resulting in the activation of caspase-9, caspase-3, and poly-ADP-ribose polymerase in a dose-dependent manner. Moreover, DK-5-62-induced apoptosis was accompanied by phosphorylation of the mitogen-activated protein kinase family, c-Jun N-terminal kinase, p38, and extracellular signal-regulated kinase. These results suggest that HCT116 cells are moderately sensitive to growth inhibition by DK-5-62 via apoptosis, as evidenced by activation of ERK/p38/Bcl-2 family signaling, as well as alteration in caspase-9 and caspase-3.

Characteristics of Microwave-assisted Extraction for Catechins from Grape Seed (포도씨 카테킨류의 마이크로웨이브 추출특성)

  • Lee, Eun-Jin;Choi, Sang-Won;Kim, Hyun-Ku;Kwon, Joong-Ho
    • Korean Journal of Food Science and Technology
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    • v.40 no.5
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    • pp.510-515
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    • 2008
  • Microwave energy was applied to the extraction of functional catechins from grape seed. The solvent, absolute ethanol, reached the boiling point when exposed for less than 3 min microwave treatment at 100 W. The effects of independent variables in microwave-assisted extraction (MAE), including microwave power (0-160W, $X_1$), ethanol concentration (0-100%, $X_2$) and extraction time (1-5 min, $X_3$), were investigated on each response variable ($Y_n$), and the contents of catechin and its derivatives were determined via response surface methodology, thereby allowing us to predict their optimal extraction conditions. The predicted maximal values of (+)-catechin, procyanidin $B_2$, (-)-epicatechin, and (-)-epicatechin gallate were 137.99, 72.78, 222.38, and 9.59 mg%, respectively, under different MAE conditions. The predicted extraction conditions for maximum catechin responses were as follows: 104.10 W of microwave power, 45.35% of EtOH, and 4.89 min of extraction time for (+)-catechin (137.99 mg%), 133.16 W, 46.16% and 4.49 min for procyanidin $B_2$ (72.78 mg%), 136.00 W, 41.37% and 4.39 min for (-)-epicatechin (222.38 mg%), 143.20 W, 37.51% and 1.88 min for (-)-epicatechin gallate (9.59 mg%), respectively. The contents of (+)-catechin, procyanidin 1B2 and (-)-epicatechin in MAE were similarly influenced by three independent variables, whereas (-)-epicatechin gallate was influenced less profoundly by ethanol concentration and extraction time.

Bidirectional Interactions between Green Tea (GT) Polyphenols and Human Gut Bacteria

  • Se Rin Choi;Hyunji Lee;Digar Singh;Donghyun Cho;Jin-Oh Chung;Jong-Hwa Roh;Wan-Gi Kim;Choong Hwan Lee
    • Journal of Microbiology and Biotechnology
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    • v.33 no.10
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    • pp.1317-1328
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    • 2023
  • Green tea (GT) polyphenols undergo extensive metabolism within gastrointestinal tract (GIT), where their derivatives compounds potentially modulate the gut microbiome. This biotransformation process involves a cascade of exclusive gut microbial enzymes which chemically modify the GT polyphenols influencing both their bioactivity and bioavailability in host. Herein, we examined the in vitro interactions between 37 different human gut microbiota and the GT polyphenols. UHPLC-LTQ-Orbitrap-MS/MS analysis of the culture broth extracts unravel that genera Adlercreutzia, Eggerthella and Lactiplantibacillus plantarum KACC11451 promoted C-ring opening reaction in GT catechins. In addition, L. plantarum also hydrolyzed catechin galloyl esters to produce gallic acid and pyrogallol, and also converted flavonoid glycosides to their aglycone derivatives. Biotransformation of GT polyphenols into derivative compounds enhanced their antioxidant bioactivities in culture broth extracts. Considering the effects of GT polyphenols on specific growth rates of gut bacteria, we noted that GT polyphenols and their derivate compounds inhibited most species in phylum Actinobacteria, Bacteroides, and Firmicutes except genus Lactobacillus. The present study delineates the likely mechanisms involved in the metabolism and bioavailability of GT polyphenols upon exposure to gut microbiota. Further, widening this workflow to understand the metabolism of various other dietary polyphenols can unravel their biotransformation mechanisms and associated functions in human GIT.

Structural Determination of Oxidation Products of Flavonoids in Alcoholic Aqueous Solution with Reactive Oxygen Species

  • Hirose, Yuko;Kakita, Mitsuko;Washizu, Toshiyuki;Matsugo, Seiichi
    • Journal of Photoscience
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    • v.9 no.2
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    • pp.424-426
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    • 2002
  • Recently, much attention has been paid to the physiological functions of flavonoids associated with their antioxidant properties. However, there was a lack of information on the molecular mechanism at which flavonoids play the antioxidative role. We have already studied on the oxidation of quercetin with hydrogen peroxide and sodium hypochlorite in alcoholic aqueous solution and determined the oxidation products. Through the structural analysis of the oxidation products, it was clarified that the hydroxyl group at C-3 in the C ring plays the important role in the antioxidative action of quercetin. Successively, rutin and (+)-catechin were oxidized with sodium hypochlorite and their mono- and di-chlorinated derivatives were obtained. These facts indicate that these flavonoids can directly scavenge hypochlorous acid and the active site in this scavenging reaction is not the hydroxyl group at C-3.

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Stilbenoids of Korean Pine (Pinus koraiensis) Inner Bark

  • Kwon, Dong-Joo;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.37 no.5
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    • pp.474-479
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    • 2009
  • Pinus koraiensis inner bark was collected and extracted with 95% ethanol. The extracts were concentrated and then sequentially fractionated using n-hexane, $CH_2Cl_2$, EtOAc, and $H_2O$ to be freeze dried. A portion of EtOAc fraction (6.6 g) was chromatographed on a Sephadex LH-20 column using aqueous methanol to isolate (+)-catechin (1), (-)-epicatechin (2), and trans-pinostilbenoside (3). Resveratrol (4) and trans-pinostilbene (5) were isolated by column chromatography using EtOH-hexane mixture after purification with aqueous methanol. The structures of these stilbenosides and flavans were characterized by spectroscopic tools using NMR and MS.

Extractives from the leaves of Thuja orientalis Linnaeus (측백나무(Thuja orientalis Linnaeus) 잎의 추출성분)

  • 이상극;김진규;함연호;배영수
    • Journal of Korea Foresty Energy
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    • v.21 no.1
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    • pp.56-64
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    • 2002
  • 2kg of the dried leaves of Thuja orientalis Linnaeus were ground, extracted with acetone-$H_2O$(7:3, v/v), concentrated, and fractionated with a series of hexane, $CH_2C1_2$ EtOAc and water on a separators funnel. Each fraction was freeze dried to give dark-brown powder and a EtOAc soluble portion. of the powder was chromatographed on a Sephadex LH-20 column using a series of aqueous methanol and ethanol-hexane mixture as eluents. Spectrometric analyses such as NMR and FAB-MS including TLC were performed to characterize the structures of isolated compounds. The leave of Thuja orientalis Linnaeus contained a large amount of flavononol derivatives such as quercetin-3-O-$\alpha$-L-rhamnopyranoside and myricetin-3-O-$\alpha$-L-rhamnopyranoside in addition to a small amount of flavan compounds such as (+)-catechin and (+)-gallocatechin. The antioxidative activities of each fractions and isolated compounds were done by DPPH radical scavenging test, and all of them were indicated strong antioxidative activities.

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