Catechin is a flavan-3-ol, a type of secondary metabolite providing antioxidant roles in plants. It belongs to the subgroup of polyphenols called flavonoids.
The name of the catechin chemical family derives from catechu, which is the tannic juice or boiled extract of Mimosa catechu (Acacia catechu L.f).
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InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1 |
PFTAWBLQPZVEMU-DZGCQCFKSA-N |
O[C@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1ccc(O)c(O)c1 |
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Acacia mearnsii
(NCBI:txid139012)
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Found in
bark
(BTO:0001301).
Spray-dried aqueous extract of bark
See:
PubMed
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Uncaria gambir
(NCBI:txid43574)
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See:
PubMed
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antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
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plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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View more via ChEBI Ontology
(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1H-chromene-3,5,7-triol
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(+)-(2R,3S)-5,7,3',4'-Tetrahydroxyflavan-3-ol
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ChemIDplus
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(+)-3',4',5,7-Tetrahydroxy-2,3-trans-flavan-3-ol
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ChemIDplus
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(+)-Catechin
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KEGG COMPOUND
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(+)-Catechol
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ChemIDplus
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(+)-Cyanidan-3-ol
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ChemIDplus
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(2R,3S)-(+)-Catechin
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KEGG COMPOUND
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(2R,3S)-2-(3,4-dihydroxyphenyl)chromane-3,5,7-triol
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ChEBI
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(2R,3S)-Catechin
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KEGG COMPOUND
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(2R,3S)-catechin
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UniProt
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(2R-trans)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-Benzopyran-3,5,7-triol
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KEGG COMPOUND
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catechuic acid
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ChEBI
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Cianidanol
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KEGG COMPOUND
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Cyanidanol
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KEGG COMPOUND
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D-Catechin
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KEGG COMPOUND
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629
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DrugCentral
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C00000947
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KNApSAcK
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C06562
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KEGG COMPOUND
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Catechin
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Wikipedia
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CPD-1961
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MetaCyc
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HMDB0002780
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HMDB
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KXN
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PDBeChem
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LMPK12020001
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LIPID MAPS
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View more database links |
154-23-4
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CAS Registry Number
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KEGG COMPOUND
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154-23-4
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CAS Registry Number
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ChemIDplus
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92761
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Reaxys Registry Number
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Reaxys
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Weyant MJ, Carothers AM, Dannenberg AJ, Bertagnolli MM (2001) (+)-Catechin inhibits intestinal tumor formation and suppresses focal adhesion kinase activation in the min/+ mouse. Cancer research 61, 118-125 [PubMed:11196148] [show Abstract] Colorectal cancer is sensitive to dietary influences. Epidemiological data linking high intake of fruits and vegetables to decreased cancer risk have prompted the search for specific plant constituents implicated in tumor prevention. This task is difficult because of the complex chemical composition of plant foods and the multifactorial nature of carcinogenesis. Researchers are aided in this effort by the C57BL/6J-Min/+ (Min/+) mouse, an animal bearing a germline defect in Apc that is similar to the initiating genetic event in the majority of human colorectal cancers. In this study, we treated Min/+ mice with (+)-catechin, a phenolic antioxidant abundant in certain fruits. Administration of (+)-catechin in an AIN-76A diet at doses of 0.1 and 1% decreased the intestinal tumor number by 75 and 71%, respectively. Mechanistic studies linked this effect to (+)-catechin-induced changes in integrin-mediated intestinal cell-survival signaling, including structural alteration of the actin cytoskeleton and decreased focal adhesion kinase (FAK) tyrosine phosphorylation. Immunoblot analysis of small intestine scrapings from Min/+ mice and Apc+/+ wild-type C57BL/6J littermates together with excised Min/+ adenomas showed increased expression of phosphorylated FAK in the macroscopically normal enterocytes of untreated Min/+ mice and adenomas. Confirming the relevance of this signaling pathway, treatment of Min/+ mice with (+)-catechin reduced the expression of phosphorylated FAK to a level similar to the wild-type littermate controls. Thus, the natural abundance and favorable bioavailability of (+)-catechin make it a promising addition to the list of potential colorectal cancer chemopreventive agents. | Bell JR, Donovan JL, Wong R, Waterhouse AL, German JB, Walzem RL, Kasim-Karakas SE (2000) (+)-Catechin in human plasma after ingestion of a single serving of reconstituted red wine. The American journal of clinical nutrition 71, 103-108 [PubMed:10617953] [show Abstract]
BackgroundRed wine consumption may decrease the risk of coronary heart disease through the actions of its constituent flavonoids. (+)-Catechin is an abundant flavonoid in red wine.ObjectiveThe objective was to determine changes in plasma (+)-catechin concentrations after ingestion of a single, moderate serving of dealcoholized red wine reconstituted with either water (DRW) or water and alcohol (ARW).DesignNine subjects (5 men, 4 women) ingested, in random order, 120 mL DRW on one day and 120 mL ARW on another day. Both the DRW and ARW contained 35 mg (121 micromol) free (+)-catechin. Blood samples were collected at 0, 0.5, 1, 2, 3, 4, and 8 h. Plasma was analyzed by gas chromatography-mass spectrometry for (+)-catechin after enzymatic release of sulfate and glucuronide conjugates.ResultsCalcium ions were needed to effectively hydrolyze (+)-catechin conjugates in plasma containing EDTA. Neither the ARW or DRW nor sex affected the area under the curve at 8 h, the maximum concentration (c(max)), or the time it took for plasma total (+)-catechin to reach maximum concentration (t(max)). Pooled mean (+/-SEM) values for the ARW and DRW were as follows: area under the curve, 306.1 +/- 29.5 nmol*h/L; c(max), 76.7 +/- 7.5 nmol/L; and t(max), 1.44 +/- 0.13 h. The half-life of (+)-catechin in plasma was significantly less (P = 0.038) after ingestion of the ARW (3.17 h) than after ingestion of the DRW (4.08 h).ConclusionsIncreases in plasma total (+)-catechin concentrations were not significantly different after single moderate servings of either the ARW or DRW. Alcohol in the ARW hastened the elimination of (+)-catechin from the plasma compartment. (+)-Catechin elimination may represent excretion or conversion to methylated derivatives. | Lotito SB, Fraga CG (1998) (+)-Catechin prevents human plasma oxidation. Free radical biology & medicine 24, 435-441 [PubMed:9438556] [show Abstract] Based on the recognized capacity of (+)-catechin (CTCH) to prevent free radical-mediated damage in different biological systems, its role in the protection of human plasma from oxidation was investigated. Samples of human blood plasma were incubated with 50 mM AAPH [2,2'-azobis-(2-amidinopropane) clorhidrate] or AMVN [2,2'-azobis(2,4-valeronitrile)], in the absence or the presence of CTCH (0.01 to 1 mM). Lipid oxidation was evaluated measuring the formation of 2-thiobarbituric acid reactive substances (TBARS). Alpha-tocopherol (AT), beta-carotene (BC), and CTCH were measured by reverse phase HPLC with electrochemical detection. TBARS formation was dependent on incubation time and on the nature of the azocompound, yielding 4.8 +/- 0.9, and 14.9 +/- 3.4 microM MDA, after 4 h, in AAPH and AMVN-exposed plasma, respectively. Plasma AT and BC were extensively depleted under these oxidant conditions. The addition of CTCH prevented or delayed the formation of TBARS, and the depletion of AT and BC in a dose dependent manner. This antioxidant effect was dependent on the concentration of CTCH and on the physical characteristics of the radical initiator. CTCH supplementation modified not only the lag time for the antioxidants depletion, but also the consumption rate. These results indicate that CTCH was an effective antioxidant in human blood plasma, delaying the consumption of endogenous lipid soluble antioxidants (AT and BC) and inhibiting lipid oxidation. | Brown S, Laird A, Liberman D, White DA (1993) The effect of (+)-catechin, a naturally occurring flavonoid, on benzopyrene oxidation by cells in culture. Biochemical Society transactions 21 ( Pt 3), 283S [PubMed:8224433] | Salama A, Berghöfer H, Mueller-Eckhardt C (1992) Detection of cell-drug (hapten)-antibody complexes by the gel test. Transfusion 32, 554-556 [PubMed:1502708] [show Abstract] Most drugs causing immunocytopenias do not bind firmly to the affected cells. Consequently, the drug-dependent antibodies in such cases are completely removed from their binding sites by conventional cell washing. It has recently been shown that such cell-drug-antibody complexes do survive the washing procedure, if the drug (metabolite) was included in the wash medium. The study reported here used the microtube gel test to reexamine the reactivity of different drug-dependent red cell antibodies: cefotaxime (n = 1), carbimazole (n = 1), cianidanol (n = 1), diclofenac (n = 3), penicillin (n = 3), and nomifensine (n = 10). Whether the drug tested binds (penicillin, cianidanol, carbimazole, and diclofenac) or does not bind (cefotaxime and nomifensine) firmly to the cells, the resultant cell-drug-antibody complex could be recognized on and/or in the gel after it was separated from the mixture containing the drug by means of centrifugation alone and without washing. It is concluded that the gel test might be of value not only for the detection of drug-dependent antibodies, but also for the analysis of subtle drug--cell interactions. |
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