• Title/Summary/Keyword: Flavan-4-ol

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Inhibiory Effect of Novel Flavan-3-ol isolated Theobroma cacao L. Husk on Glucosyltransferase (Theobroma cacao L. 외피로부터 새로운 Flavan-3-ol 화합물의 Glucosyltransferase 저해효과)

  • An, Bong-Jeun;Kwon, Ik-Boo;Choi, Chung
    • Korean Journal of Food Science and Technology
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    • v.27 no.1
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    • pp.92-96
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    • 1995
  • In the course of our studies, novel flavan-3-ol structure isolated from Theobroma cacao L. husk was established by the thiolysis, desulfurization and spectroscopic method. The structure was identified for cinnamtannin A-2 containing the tetrameric epicatechin and molecular weight was [1153] by FAB-MS negative ion. The inhibitory effect on the glucosyltransferase activity was investigated. Cinnamtannin A-2 showed complete inhibition at 0.03 mM and inhibited on the glucosyltransferase noncompetitively. The hydroxyl group of flavan-3-ol was supposed to be the essential element for inhibition on the glucosyltransferase.

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Structure Determination of Glucosyltransferase Inhibitors from Cacao Bean Husk (Cacao Bean Husk로부터 Glucosyltransferase 저해물질 구조결정)

  • An, Bong-Jeun;Choi, Cheong
    • Applied Biological Chemistry
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    • v.37 no.6
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    • pp.498-502
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    • 1994
  • For glucosyltransferase(GTase) inhibitors, two flavan-3-ols were isolated from Theobroma cacao beam husk. They showed positive reaction with $anisaldehyde-H_2SO_4$ solution, $FeCl_3$ to be confirmed as dimeric flavan-3-ols on TLC and were identified as procyanidin B-1 [(-)-epicatechin-$(4{\beta}{\rightarrow}8)$-catechin] and procyanidin B-3 [(+)-catechin-$(4{\beta}{\rightarrow}8)$-catechin by spectroscopic analysis. Their inhibitory effect on glucosyltranaferase activity was also investigated and procyanidin B-1 showed 50% inhibition at 0.3 mM. They inhibited on the glucosyltransferasa noncompetitively and dimeric flavan-3-ol containing (-)-epicatechin had higer inhibitory activity.

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Chemotaxonomic Significance of Catechin 7-O-beta-D-apiofuranoside in Ulmus Species

  • KIM, Mi;LEE, Yong Jo;SHIN, Jae-Cheon;CHOI, Sun Eun
    • Journal of the Korean Wood Science and Technology
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    • v.48 no.6
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    • pp.888-895
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    • 2020
  • Ulmus genus has excellent various physiological activities, including anti-ulcer, antioxidant, antibacterial, anti-cancer, immunity, and homeostasis maintenance effects, and it is known to have many additional drug effects And one of reasons for these excellentbiological activities is a flavan-3-ol chemical group in Ulmus genus. In this study a new flavan-3-ol compound was identified in Ulmus davidiana var. japonica. A flavan-3-ol,(2R,3S)-7-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5-diol, named as catechin 7-O-beta-D apiofuranoside, was isolated from the stems and barks of Ulmus davidiana var. japonica for. suberosa, which is a species belonging to the genus Ulmus, growing throughout the Korea peninsula. The structure was elucidated by various spectroscopic methods including high-resolution TOF mass spectrometry, 1H-NMR and 13C-NMR spectrometry and comparison with chemical structures of defined compounds.

Inhibitory Effect of Flavan-3-ols Isolated from Oolong Tea on Xanthine Oxidase (우롱차로부터 분리된 Flavan-3-ol 화합물의 Xanthine Oxidase에 대한 저해 영향)

  • An, Bong-Jeun;Bae, Man-Jong;Choi, Chung
    • Korean Journal of Food Science and Technology
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    • v.28 no.6
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    • pp.1084-1088
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    • 1996
  • As a series of study for an anti-gout agent, two flavan-3-ols have been isolated from Oolong tea. They showed positive reaction in $anisaldehyde-H_2SO_4$ solution and $FeCl_3$, which were able to be confirmed in TLC with dimeric flavan-3-ols. The components were identified as procyanidin B-2 and procyanidin B-2-O-3, 3'-di-gallate by spectroscopic analysis. Their inhibitory effect on xanthine oxidase was also investigated and procyanidin B-2-O-3, 3'-digallate showed 60.6% inhibition at $50\;{\mu}mole$. The compound competitively inhibited the xantine oxidase and dimeric flavan-3-ols contanining gallate had higher inhibition activity.

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Structure Determination of Anti-plaque Agents for Prevention of Dental Caries from Cccao Bean Husk (Cacao Bean Husk로부터 분리한 충치 예방물질의 구조 결정)

  • 권익부;안봉전유주현이신영
    • KSBB Journal
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    • v.8 no.1
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    • pp.69-74
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    • 1993
  • For an anti-plaque agent, two flavan-3-ols isolated from Theobroma cacao bean husk showed positive reactions with $H_2SO_4$-anisaldehyde solution, $FeCl_3$, and were identified as monomeric, dimeric flavan-3-ots in TLC. They were (-)-epicatechin and procyanidin B-2(epicatechin-(4$\beta$$\rightarrow$8)-epicatechin). The structures were established by spectroscopic and chemical methods. (-)-Epicatechin had moderate inhibitory activity on GTase at concentration of 1.0mM while procyanidin B-2 showed complete inhibition activity at the same concentration. The hydroxyl group of flavan-3-ol was supposed to be the essential element for inhibition on GTase.

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Structural Elucidation of Epicatechin $(4{\rightarrow}7)$ 5,8,3'4'-tetrahydroxy-(2R,3R)-flavan-3-ol Isolated from the Bark of Korean Pine Tree (Pinus densifora)

  • Lim, Yoong-Ho;Yong, Yeun-Joong;Oh, Sung-Jin;Song, Hong-Keun
    • Applied Biological Chemistry
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    • v.41 no.4
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    • pp.265-269
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    • 1998
  • Several flavonoid dimers were isolated and elucidated from the bark of Korean pine tree (Pinus densiflora). One of them was postulated to be a compound, epicatechin $(4{\rightarrow}7)$ 5,8,3',4'-tetrahydroxy-(2R,3R)-flavan-3-ol, whose structural determination was carried out by diverse NMR techniques.

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Phenolic Compounds on the Leaves of Betula Platyphylla var. latifolia

  • Lee, Min-Won;Takashi Tanaka;Gen-Ichiro Nonaka;Hahn, Dug-Ryoung
    • Archives of Pharmacal Research
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    • v.15 no.3
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    • pp.211-214
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    • 1992
  • Chemical examination of Betula platyphylla var. latifolia afforded a novel diarylheptanoid named betulateraol, together with a phenylpropanoid (3, 4'-dihydroxypropio-phenone), flavan-3-ol [(+)-catechin] and its glycosides [(+)-catechin 5-O-$\beta$-glucopyranoside, (+)-catechin 7-0-$\beta$-D-glucopyranoside] and two proanthocyanidins (procyanidins B-1 and B-3).

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Tannins from Rubus coreanum

  • Lee, Yeon-Ah;Lee, Min-Won
    • Korean Journal of Pharmacognosy
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    • v.26 no.1
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    • pp.27-30
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    • 1995
  • Tannins were isolated from the stems of Rubus coreanum and identified as (-)-epicatechin, (+)-catechin, procyanidin B-4 and sanguiin H-4 by spectral analysis.

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Chemical Structure and Isolation of Novel Glucosyltransferase Inhibitor from Artocarpus heterophyllus folium (Jack Fruit 잎으로부터 새로운 Glucosyltransferase 저해물질 분리 및 화학구조)

  • An, Bong-Jeun
    • Korean Journal of Food Science and Technology
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    • v.29 no.6
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    • pp.1304-1308
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    • 1997
  • In the course of studies for anti-plaque agents, novel procyanidin structure isolated from Artocarpus heterophyllus folium was established by thiolysis and spectroscopic analysis. The chemical structure was identified for $(-)-epiafzelecin-(4{\beta}{\rightarrow}8)-afzelecin-(4{\alpha}-8)-catechin$ containing the trimeric flavan-3-ols and molecular weight was 833[M-H] by FAB-MS negative ion method. The inhibitory effect on the glucosyltransferase activity was investigated, novel compound showed complete inhibition at 1.0 mM and inhibited on the glucosyltransferase noncompetitively.

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