• 제목/요약/키워드: Catechin Compounds

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DPPH Radical Scavenging Activity of Phenolic Compounds Isolated from the Stem Wood of Acer tegmentosum (산겨릅나무 목질부에서 분리한 페놀성 화합물의 DPPH 라디칼 소거활성)

  • Kwon, Dong-Joo;Kim, Jin-Kyu;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • 제39권1호
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    • pp.104-112
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    • 2011
  • There have been few reports on the constituents and biological activity of stem bark of $Acer$ $tegmentosum$, and no phytochemical and biological studies have been reported for stem wood of $A.$ $tegmentosum$. Two flavan 3-ols (1 and 2), three phenolic acid/alcohols (3~5), and two coumarins (6 and 7) were isolated from the stem wood of $A.$ $tegmentosum$ by repeated column chromatography. The structure of isolated compounds were identified as (+)-catechin (1), (-)-epicatechin (2), $p$-hydroxybenzaldehyde (3), syringic alcohol (4), $p$-tyrosol (5), scopoletin (6), and cleomiscosin A (7) on the basis of spectroscopic evidences such as $^1H$-NMR, $^{13}C$-NMR, 2D-NMR and MS spectrum. $p$-Hydroxybenzaldehyde (3), syringic alcohol (4), scopoletin (6), and cleomiscosin A (7) have not been reported from this plant so far. (+)-Catechin (1) and (-)-epicatechin (2) showed the higher 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity than butylated hydroxyanisole (BHA) used as a positive control.

Extractives of the Bark of Ash and Elm as Medicinal Hardwood Tree Species (약용 활엽수종인 물푸레나무와 느릅나무 수피의 추출성분)

  • Bae, Young-Soo;Kim, Jin-Kyu
    • Journal of the Korean Wood Science and Technology
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    • 제28권3호
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    • pp.62-69
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    • 2000
  • The bark of ash(Fraxinus rhynchophylla) and elm(Ulmus davidiana var. japonica) trees were collected, extracted with acetone-$H_2O$(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. The ash bark contained a large amount of coumarin derivatives such as aesculetin and aesculin in addition to trace amount of ligstroside and oleuropein. Most of the elm bark extractive were (+)-catechin and its glycosides such as (+)-catechin-7-O-xylopyranose and (+)-catechin-7-O-apiofuranose in addition to a small amount of procyanidin B-3, a dimeric (+)-catechin. NMR and FAB-MS spectrometric analyses were performed to characterize the structures of isolated phenolic compounds.

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LC-MS/MS Screening Method for Radical Scavenging Active Compounds in Extracts of Ulmus pumila Cortex (유근피 추출물의 radical 소거 활성 성분에 대한 LC-MS/MS 스크리닝 분석법)

  • Im, Do-Youn;Lee, Kyoung-In
    • Journal of Life Science
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    • 제30권11호
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    • pp.956-964
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    • 2020
  • The radical scavenging activity measurement system linked with liquid chromatography (LC) is a useful tool for identifying the radical scavenging active compound in a sample composed of numerous compounds such as plant extracts. Using this system, DPPH and ABTS radical scavenging activity were measured on extracts of Ulmus pumila cortex, which is known as an herbal medicine with antioxidant activity. Mass spectrometry (MS) was performed on the identified radical scavenging active compounds to identify the four components estimated to be procyanidin B2, procyanidin B3, catechin-7-O-β-D-apiofuranoside, and catechin-5-O-β-D-apiofuranoside, respectively. In order to compare the relative contents between extract samples, multiple reaction monitoring (MRM) mode analysis conditions were set for the four compounds in order to examine the possibility of comparing the content of radical scavenging active compounds in Ulmus pumila cortex extract using LC-MS/MS. As a result of the relative content comparison, it was found that the higher the ethanol concentration of the extraction solvent, the higher the content of radical scavenging active compounds. As with the results of measuring the radical scavenging activity of each extract, it was confirmed that the content difference of three of the compounds (all except the compound estimated as procyanidin B3) was not significantly observed in the extracts with an ethanol concentration of 50% or more.

Antiplatelet fraction from Ulmi cortex and its active components (유백피의 항혈전 활성 분획 및 유효성분에 관한 연구)

  • Kim, Dong-Seon;Yang, Won-Kyung;Sung, Yoon-Young;Lim, Sun Mi;Kim, Ho Kyoung
    • The Korea Journal of Herbology
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    • 제28권3호
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    • pp.39-44
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    • 2013
  • Objectives : The purpose of this study was to identify active fraction and components from antiplatelet Ulmi cortex extract. Methods : The 70% ethanol extract of Ulmi cortex was subjected to column chromatography over D101 resin and eluted with an 20% (W1), 30% (W2), 40% (W3), 50%(W4), 70% (W5), and 100% ethanol (W6) to yield 6 fractions. W6 was further fractioned and its active components were purified using semi-preparative HPLC. The isolated compounds were identified by MS and NMR, and their contents were simultaneously analyzed using HPLC/UV. Antiplatelet aggregation activities of the fractions and the compounds were evaluated using rat platelet-rich plasma in presence of collagen ($5{\mu}g/ml$), arachidonic acid (0.05 U/ml), or thrombin ($100{\mu}M$). Results : Among six fractions, W3 prominently inhibited platelet aggregation. At the concentration of $200{\mu}g/ml$, W3 strongly inhibited arachidonic acid- and collagen-induced platelet aggregations by 78.2% and 65.9%, respectivley, and weakly inhibited thrombin-inducded platelet aggregation by 32.6%. Catechin, epicatehin, and catechin-7-O-${\beta}$-D-glucopyranoside were isolated from W3 and their contents were revealed to be 15.1%, 0.87%, and 0.32%. Catechin and epicatechin at the concentrations of $100{\mu}M$ strongly inhibited collagen-induced platelet aggregation by 79.9% and 86.6%, respectively, but weakly inhibited arachidonic acid- and thrombin-induced platelet aggregations. Conclusions : A main active principle of anitplatelet Ulmi Cortex extract is W3 fraction, of which main active component is catechin considering its antiplatelet activity and content.

Isolation of Inhibitory Components on Tyrosinase Activity from the Bark of Paeonia moutan (목단피로부터 멜라닌 생성 억제성분의 분리)

  • Lee, Seung-Ho;Park, Ji-Soo;Kim, So-Young;Kim, Jin-Joon;Chung, See-Ryun
    • YAKHAK HOEJI
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    • 제42권4호
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    • pp.353-358
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    • 1998
  • The MeOH extract of the bark of Paeonia moutan showed potent inhibitory effect on the mushroom tyrosinase activity in vitro. The activity-guided fractionation of t he MeOH extract resulted in the isolation of three active compounds. The chemical structures of these compounds were elucidated by chemical and spectroscopic evidence as catechin, 1,2,3,6-tetra-O-galloyl-${\beta}$-D-glucose and 1,2,3,4,6-penta-0-galloyl-${\beta}$-D-glucose, respectively. Among them, the inhibitory activity by 1,2,3,6-tetra-galloyl-${\beta}$-D-glucose on mushroom tyrosinase was more potent $(IC_{50}=3.5\;{\mu}M)$ than that of kojic acid $(IC_{50}=8.7\;{\mu}M)$ ,but catechin enhanced the mushroom tyrosinase activity 50% in the concentration of 34.5M.

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The chemical structure of polyphenols isolated from cacao bean and their inhibitory effect on ACE (Cacao bean으로부터 분리된 polyphenol 성분의 화학구조분석과 ACE 저해효과)

  • Chang, Young-Youl;Yim, Moo-Hyun;Lee, Man-Chong
    • Applied Biological Chemistry
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    • 제41권1호
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    • pp.110-117
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    • 1998
  • Seven kinds of polyphenol compounds having ACE activities were isolated and purified by Sephadex LH-20, MCI-gel CHP-20, ${\um}-Bondapak\;C_{18}$ and Fuji-gel ODS $G_3$ sucessively from cacao bean(Ghana). The chemical structures of each compound were determined and identified using analyzers such as $^1H-NMR$, $^{13}C-NMR$, IR, MS, polarimeter and Elemental Analysis. Inhibition effects of isolated polyphenols on angiotensin converting enzyme (concerned with hypertension) were also observed. The results obtained were as follows,; The compounds isolated and identified were confirmed and determined as compound 1 [(+)-catechin], compound 2 [(-)-epicatechin], compound 3 [procyanidin B-1 : (-)-epicatechin-$(4{\beta}{\rightarrow}8)$-(+)catechin], compound 4 [procyanidin B-2 : (-)-epicatechin-$(4{\beta}{\rightarrow}8)$-(-)-epicatechin], compound 5 [procyanidin B-7 : (-)-epicatechin-$(4{\beta}{\rightarrow}6)$-(+)-catechin], campound 6 (procyanidin B-2,3,3'-O -digallate), compound 7 [cinnamtannin A-2 : (-)-epicatechin-$(4{\beta}{\rightarrow}8)$-(-)-epicatechin-$(4{\beta}{\rightarrow}8)$-(-)-epicatechin-$(4{\beta}{\rightarrow}8)$-(-)-epicatechin]. In the inhibition effect on ACE, procyanidin B-2,3,3'-O-digallate (compound 6) showed a higher value of 94.6% for ACE in $100\;{\um}M$ than other compounds such as (+)-catechin (compound 1), (-)-epicatechin (compound 2), procyanidin B-1 (compound 3), procyanidin B-2 (compound 4), procyanidin B-7 (compound 5) and cinnamtannin A-2 (compound 7) showing 67.9%, 61.9%, 88.6%, 82.5%, 72.2% and 82.3% for ACE, respectively. Inhibition of $4{\beta}{\rightarrow}8$ in coupling bond on the ACE enzyme was more effective than that of $4{\beta}{\rightarrow}6$. Procyanidin containing gallate inhibited more effectively than those containing not any. It was also observed that a lot of hydroxy group in the compounds increased the inhibitory effect.

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Scavenging Effects of Flavonoids on Paraquat Induced Toxicity (Paraquat 유독성에 대한 Flavonoid류의 독성경감효과)

  • 최병기;조내규
    • Environmental Analysis Health and Toxicology
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    • 제10권1_2호
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    • pp.47-54
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    • 1995
  • To investigate and evaluated the scavenging and antioxidative effects of various flavonoids on paraquat induced toxicity, in vivo and vitro tests of eight flavonoids (catechin, epocatechin, flavone, chrysin, apigenin, quercetin, morin and biochanin A) were carried out. The generation of reactive oxygen substances(ROS) in PMS-NADH system $H_2O_2$ induced hemolysis and lipidperoxidation to blood, NADPH dependent lipidperoxidation to liver and lung microsome by paraquat were studied.The results are summerized as follows; 1) In the concentration ranges from 3.3 to 9.8$\mu$M of catechin,epicatechin, quercetin and biochanin A removed the 50% of DPPH radical scavenging effects. 2) In the concentration ranges from 0.60 to 1.86 mM of catechin, epicatechin, quercetin and biochanin A showed the inhibitory and antioxidative activity on superoxide anion which gernerated in PMA-NADH system. 3) In the concentration ranges from 0.12 to 0.49mM of catechin, epicatechin, quercetin and biochanin A showed the inhibitory and antioxidative activity on H202 which generated in PMA-NADH system. 4) In the concentration ranges from 0.6 x10$^{-5}$ to 6.3 x 10$^{-5}$mM of catechin, epicatechin, flavone, chrysin, quercetin and morin showed the inhibitory and antioxidative activity on $H_2O_2$ induced hemolysis to blood 5) All flavonoids tested exhibited inhibitory and antioxidative effects on paraquat induced liver and tung microsomal lipidperoxidation. Therefore, all flavonoids evaluated showed the useful compounds for scavenger and antioxidant on paraquat induced toxicity.

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Inhibition Effect against Tyrosinase of Condensed Tannins from Korean Green Tea (한국산 녹차로부터 분리한 축합형 탄닌의 tyrosinase 저해효과)

  • Kim, Jin-Ku;Cha, Woen-Seup;Park, Joon-Hee;Oh, Sang-Lyong;Cho, Young-Je;Chun, Sung-Sook;Choi, Cheong
    • Korean Journal of Food Science and Technology
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    • 제29권1호
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    • pp.173-177
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    • 1997
  • For the utilizing of tannins in the functional foods and natural inhibitor against browning reaction by tyrosinase in foods, inhibition effect against tyrosinase of tannins from Korean green tea was determined. Acetone extract from Korean green tea showed inhibition effect against tyrosinase. The gallocatechin compounds showed higher inhibition effect than the catechin compounds. In terms of stereo isomers, (-)-epicatechin compounds had higher inhibition effect than the (+)-catechin compounds. The monomer had higher inhibition effect than the dimer.

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Chemical Analysis and Isolation of Antibacterial Compound from Ulmus Species (II) : Isolation and Chemical Structure of Antibacterial Compound (느릅나무 근피의 화학조성분 및 항균성 물질(II) : 항균성 물질의 단리 및 화학구조)

  • Kim, Chang-Soon;Lee, Jung-Myoung;Choi, Chang-Ok;Park, Soung-Bae;Eom, Tae-Jin
    • Journal of the Korean Wood Science and Technology
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    • 제31권1호
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    • pp.16-21
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    • 2003
  • The methanol extractives from root bark of Ulmus davidiana var japonica nakai were fractionated with n-hexane, ethyl ether, ethyl acetate and waster, the water soluble fraction was also fractionated with silicagel column chromatograhy. The chemical structure of purifided compounds were identified with UV, IR, 1H-NMR and 13C-NMR spectra and the antibacterial activities also were investigated. Two different antibacterial compounds (compound A and B) were fractionated with silicagel chromatography and TLC. Compounds B was identified as a catechin rahmnoside. The both of compounds had antibacterial activity on Staphylococcus aureus and Salmonella typhimurium.

Phenolic Compounds from the Rachis of Cedrela sinensis

  • Yu, Young-Beob;Lee, Jong-Ho;Choi, Jae-Sue;Ok, Kwang-Dae;Park, Jong-Cheol
    • Korean Journal of Pharmacognosy
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    • 제27권3호
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    • pp.219-223
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    • 1996
  • From the rachis of Cedrela sinensis A. Juss., methyl gallate, quercitrin, bis-(p-hydroxyphenyl)ether, adenosine, isoquercitrin, rutin, (+)-catechin and (-)-epicatechin were isolated and characterized by spectral data.

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