(+/-)-Catechin (BioDeep_00000398561)

Main id: BioDeep_00000000028

 

PANOMIX_OTCML-2023 Antitumor activity


代谢物信息卡片


2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol

化学式: C15H14O6 (290.079)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O
InChI: 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

描述信息

relative retention time with respect to 9-anthracene Carboxylic Acid is 0.345
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.348
(±)-Catechin (rel-Cianidanol) is the racemate of Catechin. (±)-Catechin has two steric forms of (+)-Catechin and its enantiomer (-)-Catechin. (+)-Catechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM. Anticancer, anti-obesity, antidiabetic, anticardiovascular, anti-infectious, hepatoprotective, and neuroprotective effects[1].
(±)-Catechin (rel-Cianidanol) is the racemate of Catechin. (±)-Catechin has two steric forms of (+)-Catechin and its enantiomer (-)-Catechin. (+)-Catechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM. Anticancer, anti-obesity, antidiabetic, anticardiovascular, anti-infectious, hepatoprotective, and neuroprotective effects[1].

同义名列表

5 个代谢物同义名

2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol; (+/-)-Catechin; rel-Cianidanol; rel-Catechuic acid; (±)-Catechin



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

220 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表


文献列表

  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Celia Bustos-Brito, Mariano Sánchez-Castellanos, Baldomero Esquivel, José S Calderón, Fernando Calzada, Lilian Yepez-Mulia, Angelina Hernández-Barragán, Pedro Joseph-Nathan, Gabriel Cuevas, Leovigildo Quijano. Structure, absolute configuration, and antidiarrheal activity of a thymol derivative from Ageratina cylindrica. Journal of natural products. 2014 Feb; 77(2):358-63. doi: 10.1021/np400964w. [PMID: 24502360]
  • An-Cheng Huang, Amelie Wilde, Johanna Ebmeyer, George K Skouroumounis, Dennis K Taylor. Examination of the phenolic profile and antioxidant activity of the leaves of the Australian native plant Smilax glyciphylla. Journal of natural products. 2013 Oct; 76(10):1930-6. doi: 10.1021/np4005163. [PMID: 24050300]
  • Dana Atrahimovich, Jacob Vaya, Soliman Khatib. The effects and mechanism of flavonoid-rePON1 interactions. Structure-activity relationship study. Bioorganic & medicinal chemistry. 2013 Jun; 21(11):3348-55. doi: 10.1016/j.bmc.2013.02.055. [PMID: 23623675]
  • Hassiba Aoudia, Nikoletta Ntalli, Nadhem Aissani, R Yahiaoui-Zaidi, Pierluigi Caboni. Nematotoxic phenolic compounds from Melia azedarach against Meloidogyne incognita. Journal of agricultural and food chemistry. 2012 Nov; 60(47):11675-80. doi: 10.1021/jf3038874. [PMID: 23136941]
  • Fedor Romanov-Michailidis, Florian Viton, René Fumeaux, Antoine Lévèques, Lucas Actis-Goretta, Maarit Rein, Gary Williamson, Denis Barron. Epicatechin B-ring conjugates: first enantioselective synthesis and evidence for their occurrence in human biological fluids. Organic letters. 2012 Aug; 14(15):3902-5. doi: 10.1021/ol3016463. [PMID: 22799566]
  • Myalowenkosy I Sabela, Njabulo J Gumede, Laura Escuder-Gilabert, Yolanda Martín-Biosca, Khirsna Bisetty, María-Jose Medina-Hernández, Salvador Sagrado. Connecting simulated, bioanalytical, and molecular docking data on the stereoselective binding of (±)-catechin to human serum albumin. Analytical and bioanalytical chemistry. 2012 Feb; 402(5):1899-909. doi: 10.1007/s00216-011-5636-5. [PMID: 22200924]
  • Zuzana Kyselova. Toxicological aspects of the use of phenolic compounds in disease prevention. Interdisciplinary toxicology. 2011 Dec; 4(4):173-83. doi: 10.2478/v10102-011-0027-5. [PMID: 22319251]
  • Andrew C Holloway, Simon W J Gould, Mark D Fielder, Declan P Naughton, Alison F Kelly. Enhancement of antimicrobial activities of whole and sub-fractionated white tea by addition of copper (II) sulphate and vitamin C against Staphylococcus aureus; a mechanistic approach. BMC complementary and alternative medicine. 2011 Nov; 11(?):115. doi: 10.1186/1472-6882-11-115. [PMID: 22093997]
  • Jarrod L Pollock, Lewis A Kogan, Andrea S Thorpe, William E Holben. (±)-catechin, a root exudate of the invasive centaurea stoebe lam. (Spotted knapweed) exhibits bacteriostatic activity against multiple soil bacterial populations. Journal of chemical ecology. 2011 Sep; 37(9):1044-53. doi: 10.1007/s10886-011-0005-6. [PMID: 21882071]
  • Ayaka Yoshida, Fumihiko Yoshino, Masahito Tsubata, Motoya Ikeguchi, Takeshi Nakamura, Masaichi-Chang-Il Lee. Direct assessment by electron spin resonance spectroscopy of the antioxidant effects of French maritime pine bark extract in the maxillofacial region of hairless mice. Journal of clinical biochemistry and nutrition. 2011 Sep; 49(2):79-86. doi: 10.3164/jcbn.10-103. [PMID: 21980222]
  • Nadine Saul, Kerstin Pietsch, Stephen R Stürzenbaum, Ralph Menzel, Christian E W Steinberg. Diversity of polyphenol action in Caenorhabditis elegans: between toxicity and longevity. Journal of natural products. 2011 Aug; 74(8):1713-20. doi: 10.1021/np200011a. [PMID: 21805983]
  • Sangaalofa T Clark, Wynand S Verwoerd. A systems approach to identifying correlated gene targets for the loss of colour pigmentation in plants. BMC bioinformatics. 2011 Aug; 12(?):343. doi: 10.1186/1471-2105-12-343. [PMID: 21849042]
  • Gustavo Scola, Danusa Conte, Patrícia Wilmsen Dalla-Santa Spada, Caroline Dani, Regina Vanderlinde, Claudia Funchal, Mirian Salvador. Flavan-3-ol compounds from wine wastes with in vitro and in vivo antioxidant activity. Nutrients. 2010 10; 2(10):1048-59. doi: 10.3390/nu2101048. [PMID: 22253995]
  • Sansa Dutta, Amit Basak, Swagata Dasgupta. Synthesis and ribonuclease A inhibition activity of resorcinol and phloroglucinol derivatives of catechin and epicatechin: Importance of hydroxyl groups. Bioorganic & medicinal chemistry. 2010 Sep; 18(17):6538-46. doi: 10.1016/j.bmc.2010.06.077. [PMID: 20692173]
  • Shail Kaushik, Harsh P Bais, Meredith L Biedrzycki, Lakshmannan Venkatachalam. Catechin is a phytototoxin and a pro-oxidant secreted from the roots of Centaurea stoebe. Plant signaling & behavior. 2010 Sep; 5(9):1088-98. doi: 10.4161/psb.5.9.11823. [PMID: 20505358]
  • Christina Ritter, Benno F Zimmermann, Rudolf Galensa. Chiral separation of (+)/(-)-catechin from sulfated and glucuronidated metabolites in human plasma after cocoa consumption. Analytical and bioanalytical chemistry. 2010 May; 397(2):723-30. doi: 10.1007/s00216-010-3542-x. [PMID: 20213173]
  • Harsh P Bais, L Venkatachalam, Meredith L Biedrzycki. Stimulation or Inhibition: Conflicting evidence for (+/-)-catechin's role as a chemical facilitator and disease protecting agent. Plant signaling & behavior. 2010 Mar; 5(3):239-46. doi: 10.4161/psb.5.3.10573. [PMID: 20023372]
  • Yukako Okazaki, Yunkyung Han, Mai Kayahara, Toshiro Watanabe, Hirofumi Arishige, Norihisa Kato. Consumption of curcumin elevates fecal immunoglobulin A, an index of intestinal immune function, in rats fed a high-fat diet. Journal of nutritional science and vitaminology. 2010; 56(1):68-71. doi: 10.3177/jnsv.56.68. [PMID: 20354349]
  • Vladimir Chobot, Christoph Huber, Guenter Trettenhahn, Franz Hadacek. (+/-)-catechin: chemical weapon, antioxidant, or stress regulator?. Journal of chemical ecology. 2009 Aug; 35(8):980-96. doi: 10.1007/s10886-009-9681-x. [PMID: 19701725]
  • Ryusuke Fudouji, Takashi Tanaka, Toshitugu Taguri, Yosuke Matsuo, Isao Kouno. Coupling reactions of catechins with natural aldehydes and allyl alcohols and radical scavenging activities of the triglyceride-soluble products. Journal of agricultural and food chemistry. 2009 Jul; 57(14):6417-24. doi: 10.1021/jf9010998. [PMID: 19537756]
  • Georgina N Diaz Napal, María C Carpinella, Sara M Palacios. Antifeedant activity of ethanolic extract from Flourensia oolepis and isolation of pinocembrin as its active principle compound. Bioresource technology. 2009 Jul; 100(14):3669-73. doi: 10.1016/j.biortech.2009.02.050. [PMID: 19342224]
  • Min Hye Yang, Kee Dong Yoon, Young-Won Chin, Ju Hyun Park, Jinwoong Kim. Phenolic compounds with radical scavenging and cyclooxygenase-2 (COX-2) inhibitory activities from Dioscorea opposita. Bioorganic & medicinal chemistry. 2009 Apr; 17(7):2689-94. doi: 10.1016/j.bmc.2009.02.057. [PMID: 19303782]
  • Wei-Ming He, Yulong Feng, Wendy M Ridenour, Giles C Thelen, Jarrod L Pollock, Alecu Diaconu, Ragan M Callaway. Novel weapons and invasion: biogeographic differences in the competitive effects of Centaurea maculosa and its root exudate (+/-)-catechin. Oecologia. 2009 Apr; 159(4):803-15. doi: 10.1007/s00442-008-1234-4. [PMID: 19219462]
  • Stephen O Duke, Amy C Blair, Franck E Dayan, Robert D Johnson, Kumudini M Meepagala, Daniel Cook, Joanna Bajsa. Is (-)-catechin a novel weapon of spotted knapweed (Centaurea stoebe)?. Journal of chemical ecology. 2009 Feb; 35(2):141-53. doi: 10.1007/s10886-008-9587-z. [PMID: 19153796]
  • Vesna Rastija, Marica Medić-Sarić. QSAR study of antioxidant activity of wine polyphenols. European journal of medicinal chemistry. 2009 Jan; 44(1):400-8. doi: 10.1016/j.ejmech.2008.03.001. [PMID: 18403057]
  • Inderjit, Rajwant Kaur, Surinder Kaur, Ragan M Callaway. Impact of (+/-)-catechin on soil microbial communities. Communicative & integrative biology. 2009; 2(2):127-9. doi: 10.4161/cib.7744. [PMID: 19704908]
  • Ai-Lin Liu, Hai-Di Wang, Simon MingYuen Lee, Yi-Tao Wang, Guan-Hua Du. Structure-activity relationship of flavonoids as influenza virus neuraminidase inhibitors and their in vitro anti-viral activities. Bioorganic & medicinal chemistry. 2008 Aug; 16(15):7141-7. doi: 10.1016/j.bmc.2008.06.049. [PMID: 18640042]
  • Inderjit, Jarrod L Pollock, Ragan M Callaway, William Holben. Phytotoxic effects of (+/-)-catechin in vitro, in soil, and in the field. PloS one. 2008 Jul; 3(7):e2536. doi: 10.1371/journal.pone.0002536. [PMID: 18648546]
  • Wanxia Tang, Hideaki Hioki, Kenichi Harada, Miwa Kubo, Yoshiyasu Fukuyama. Antioxidant phenylpropanoid-substituted epicatechins from Trichilia catigua. Journal of natural products. 2007 Dec; 70(12):2010-3. doi: 10.1021/np0703895. [PMID: 18020420]
  • Márcia Reto, Maria Eduardo Figueira, Helder Mota Filipe, Cristina M M Almeida. Chemical composition of green tea (Camellia sinensis) infusions commercialized in Portugal. Plant foods for human nutrition (Dordrecht, Netherlands). 2007 Dec; 62(4):139-44. doi: 10.1007/s11130-007-0054-8. [PMID: 17899383]
  • Laura G Perry, Giles C Thelen, Wendy M Ridenour, Ragan M Callaway, Mark W Paschke, Jorge M Vivanco. Concentrations of the Allelochemical (+/-)-catechin IN Centaurea maculosa soils. Journal of chemical ecology. 2007 Dec; 33(12):2337-44. doi: 10.1007/s10886-007-9383-1. [PMID: 18030533]
  • Jun-Yup Jin, Sung-Hee Park, Jae-Hoon Bae, Ho-Chan Cho, Jeong-Geun Lim, Won Sun Park, Jin Han, Jin Ho Lee, Dae-Kyu Song. Uncoupling by (--)-epigallocatechin-3-gallate of ATP-sensitive potassium channels from phosphatidylinositol polyphosphates and ATP. Pharmacological research. 2007 Sep; 56(3):237-47. doi: 10.1016/j.phrs.2007.06.004. [PMID: 17656102]
  • Ana G Báidez, Pedro Gómez, José A Del Río, Ana Ortuño. Dysfunctionality of the xylem in Olea europaea L. Plants associated with the infection process by Verticillium dahliae Kleb. Role of phenolic compounds in plant defense mechanism. Journal of agricultural and food chemistry. 2007 May; 55(9):3373-7. doi: 10.1021/jf063166d. [PMID: 17394331]
  • J A van Meeuwen, M van den Berg, J T Sanderson, A Verhoef, A H Piersma. Estrogenic effects of mixtures of phyto- and synthetic chemicals on uterine growth of prepubertal rats. Toxicology letters. 2007 Apr; 170(2):165-76. doi: 10.1016/j.toxlet.2007.03.003. [PMID: 17428625]
  • Julien Hamelet, Karine Demuth, Julien Dairou, Aurélie Ledru, Jean-Louis Paul, Jean-Marie Dupret, Jean-Maurice Delabar, Fernando Rodrigues-Lima, Nathalie Janel. Effects of catechin on homocysteine metabolism in hyperhomocysteinemic mice. Biochemical and biophysical research communications. 2007 Mar; 355(1):221-7. doi: 10.1016/j.bbrc.2007.01.142. [PMID: 17292331]
  • Balakrishnan Prithiviraj, Laura G Perry, Dayakar V Badri, Jorge M Vivanco. Chemical facilitation and induced pathogen resistance mediated by a root-secreted phytotoxin. The New phytologist. 2007; 173(4):852-860. doi: 10.1111/j.1469-8137.2006.01964.x. [PMID: 17286833]
  • Sumio Terada, Kikuo Ito, Akira Yoshimura, Naoto Noguchi, Takashi Ishida. [Constituents relating to anti-oxidative and alpha-glucosidase inhibitory activities in Yacon aerial part extract]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2006 Aug; 126(8):665-9. doi: 10.1248/yakushi.126.665. [PMID: 16880725]
  • Yukiho Takizawa, Toshimi Morita, Naoki Fujitsuka, Akiko Kido, Shouichirou Shindou, Hiroki Tomisawa, Yoshio Kase, Shuichi Takeda, Masaki Aburada, Keńtchi Miyamoto. Pharmacokinetics of TJ-8117(Onpi-to), a drug for renal failure (II): effects of food, repeated administration and renal failure to plasma concentration of [3H]-(-)epicatechin 3-O-gallate in rats. European journal of drug metabolism and pharmacokinetics. 2005 Jul; 30(3):175-80. doi: 10.1007/bf03190617. [PMID: 16250254]
  • Shan-Ling Hung, Yi-Yun Cheng, Ji-Lung Peng, Lien-Yu Chang, Tsung-Yun Liu, Yen-Ting Chen. Inhibitory effects of areca nut extracts on phagocytosis of Actinobacillus actinomycetemcomitans ATCC 33384 by neutrophils. Journal of periodontology. 2005 Mar; 76(3):373-9. doi: 10.1902/jop.2005.76.3.373. [PMID: 15857070]
  • Seung Joon Baek, Jong-Sik Kim, Felix R Jackson, Thomas E Eling, Michael F McEntee, Seong-Ho Lee. Epicatechin gallate-induced expression of NAG-1 is associated with growth inhibition and apoptosis in colon cancer cells. Carcinogenesis. 2004 Dec; 25(12):2425-32. doi: 10.1093/carcin/bgh255. [PMID: 15308587]
  • Takako Yokozawa, Takako Nakagawa. Inhibitory effects of Luobuma tea and its components against glucose-mediated protein damage. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2004 Jun; 42(6):975-81. doi: 10.1016/j.fct.2004.02.010. [PMID: 15110107]
  • Yukiho Takizawa, Hiroaki Nishimura, Takashi Morota, Hiroki Tomisawa, Shuichi Takeda, Masaki Aburada. Pharmacokinetics of TJ-8117 (Onpi-to), a drug for renal failure (I): Plasma concentration, distribution and excretion of [3H]-(-)epicatechin 3-O-gallate in rats and dogs. European journal of drug metabolism and pharmacokinetics. 2004 Apr; 29(2):91-101. doi: 10.1007/bf03190582. [PMID: 15230336]
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  • Pierre Kamnaing, Apollinaire Tsopmo, Eric A Tanifum, Marguerite H K Tchuendem, Pierre Tane, Johnson F Ayafor, Olov Sterner, Donna Rattendi, Maurice M Iwu, Brian Schuster, Cyrus Bacchi. Trypanocidal diarylheptanoids from Aframomum letestuianum. Journal of natural products. 2003 Mar; 66(3):364-7. doi: 10.1021/np020362f. [PMID: 12662093]
  • Harsh Pal Bais, Travis S Walker, Alan J Kennan, Frank R Stermitz, Jorge M Vivanco. Structure-dependent phytotoxicity of catechins and other flavonoids: flavonoid conversions by cell-free protein extracts of Centaurea maculosa (spotted knapweed) roots. Journal of agricultural and food chemistry. 2003 Feb; 51(4):897-901. doi: 10.1021/jf020978a. [PMID: 12568546]
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  • Harsh Pal Bais, Travis S Walker, Frank R Stermitz, Ruth A Hufbauer, Jorge M Vivanco. Enantiomeric-dependent phytotoxic and antimicrobial activity of (+/-)-catechin. A rhizosecreted racemic mixture from spotted knapweed. Plant physiology. 2002 Apr; 128(4):1173-9. doi: 10.1104/pp.011019. [PMID: 11950966]
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