3,4-Dihydroxyhydrocinnamic acid (BioDeep_00000396444)

Main id: BioDeep_00000003369

 

human metabolite PANOMIX_OTCML-2023 blood metabolite


代谢物信息卡片


InChI=1/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13

化学式: C9H10O4 (182.057906)
中文名称: 3,4-二羟苯基丙酸, 二氢咖啡酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: c1(c(ccc(c1)CCC(=O)O)O)O
InChI: InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)

描述信息

3,4-Dihydroxyhydrocinnamic acid, also known as dihydrocaffeic acid (DHCA), is a metabolite product of the hydrogenation of caffeoylquinic acids, occurring in normal human biofluids, with potent antioxidant properties. DHCA has been detected in human plasma following coffee ingestion (PMID: 15607645) and is increased with some dietary sources, such as after ingestion of phenolic constituents of artichoke leaf extract (PMID: 15693705). Polyphenol-rich foods such as vegetables and fruits have been shown to significantly improve platelet function in ex vivo studies in humans (PMID: 16038718). Its antioxidant activity has been tested to reduce ferric iron in the ferric reducing antioxidant power (FRAP) assay, and it has been suggested that its catechol structure conveys the antioxidant effect in plasma and in erythrocytes (PMID: 11768243). 3,4-Dihydroxyhydrocinnamic acid is a microbial metabolite found in Bifidobacterium, Escherichia, Lactobacillus, and Clostridium (PMID: 28393285).
3,4-Dihydroxyhydrocinnamic acid (or Dihydrocaffeic acid, DHCA) is a metabolite product of the hydrogenation of caffeoylquinic acids, occurring in normal human biofluids, with potent antioxidant properties. DHCA has been detected in human plasma following coffee ingestion (PMID 15607645), and is increased with some dietary sources, such as after ingestion of phenolic constituents of artichoke leaf extract. (PMID 15693705) Polyphenol-rich foods such as vegetables and fruits have been shown to significantly improve platelet function in ex vivo studies in humans. (PMID 16038718) Its antioxidant activity has been tested to reduce ferric iron in the ferric reducing antioxidant power (FRAP) assay, and it has been suggested that its catechol structure convey the antioxidant effect in plasma and in erythrocytes. (PMID 11768243) [HMDB]. 3-(3,4-Dihydroxyphenyl)propanoic acid is found in red beetroot, common beet, and olive.
3-(3,4-dihydroxyphenyl)propanoic acid is a monocarboxylic acid that is 3-phenylpropionic acid substituted by hydroxy groups at positions 3 and 4. Also known as dihydrocaffeic acid, it is a metabolite of caffeic acid and exhibits antioxidant activity. It has a role as an antioxidant and a human xenobiotic metabolite. It is functionally related to a 3-phenylpropionic acid. It is a conjugate acid of a 3-(3,4-dihydroxyphenyl)propanoate.
3-(3,4-Dihydroxyphenyl)propionic acid is a natural product found in Liatris elegans, Polyscias murrayi, and other organisms with data available.
Dihydrocaffeic acid is a microbial metabolite of flavonoids, reduces phosphorylation of MAPK p38 and prevent UVB-induced skin damage. Antioxidant potential and anti-inflammatory activity[1].
Dihydrocaffeic acid is a microbial metabolite of flavonoids, reduces phosphorylation of MAPK p38 and prevent UVB-induced skin damage. Antioxidant potential and anti-inflammatory activity[1].

同义名列表

46 个代谢物同义名

InChI=1/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13; 3,4-dihydroxyphenylpropionic acid, potassium salt; 3,4-dihydroxy-(6CI,7CI,8CI)Hydrocinnamic acid; 3-10-00-01517 (Beilstein Handbook Reference); 3-[3,4-bis(oxidanyl)phenyl]propanoic acid; 3,4-dihydroxy-(6CI,7CI,8CI)Hydrocinnamate; 3,4-DIHYDROXY-.BETA.-PHENYLPROPIONIC ACID; 3,4-Dihydroxy-beta-phenylpropionic acid; 3-(3,4-Dihydroxyphenyl)propanoic acid #; 3-(3,4-dihydroxyphenyl) propionic acid; 3,4-Dihydroxyhydrocinnamic acid, 98\\%; Benzenepropanoic acid, 3,4-dihydroxy-; 3-(3,4-Dihydroxyphenyl)propanoic acid; 3-(3,4-Dihydroxyphenyl)propionic acid; BF0C7A6D-A5FC-4B39-819E-5ECC037C0C39; 3,4-Dihydroxy-β-phenylpropionic acid; 3,4-Dihydroxy-b-phenylpropionic acid; 3-(3,4-DIHYDROXYPHENYL)PROPIONICACID; 3,4-Dihydroxy-beta-phenylpropionate; 3,4-Dihydroxy-benzenepropanoic acid; 3,4-Dihydroxybenzenepropanoic acid; Hydrocinnamic acid, 3,4-dihydroxy-; 3,4-Dihydroxybenzenepropionic acid; 3,4-dihydroxyphenylpropionic acid; 3-(3,4-dihydroxyphenyl)propanoate; 3-(3,4-Dihydroxyphenyl)propionate; 3,4-Dihydroxydihydrocinnamic acid; 3,4-dihydroxyhydro cinnamic acid; 3,4-Dihydroxy-β-phenylpropionate; 3,4-Dihydroxy-b-phenylpropionate; Hydrocinnamic acid,4-dihydroxy-; 3,4-dihydroxyhydrocinnamic acid; 3,4-Dihydroxybenzenepropanoate; 3,4-Dihydroxybenzenepropionate; 3,4-Dihydroxydihydrocinnamate; 3,4-Dihydroxyphenylpropionate; 3,4-Dihydroxyphenylpropanoate; 3,4-dihydroxyhydrocinnamate; Dihydrocaffeic acid; Hydrocaffeic acid; Dihydrocaffeate; Dihydrocafeate; Hydrocaffeate; 3,4-HPA; HYKOP; DHC



数据库引用编号

18 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)

16 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。



文献列表

  • David S Goldstein, Patti Sullivan, Abraham Corrales, Risa Isonaka, Janna Gelsomino, Jamie Cherup, Genessis Castillo, Courtney Holmes. Multiple catechols in human plasma after drinking caffeinated or decaffeinated coffee. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2021 Nov; 1185(?):122988. doi: 10.1016/j.jchromb.2021.122988. [PMID: 34731744]
  • Maizatul Hasyima Omar, Rocío González Barrio, Gema Pereira-Caro, Tahani Mazyad Almutairi, Alan Crozier. In vitro catabolism of 3',4'-dihydroxycinnamic acid by human colonic microbiota. International journal of food sciences and nutrition. 2021 Jun; 72(4):511-517. doi: 10.1080/09637486.2020.1850650. [PMID: 33238790]
  • Nils Mertens, Thomas Heymann, Marcus A Glomb. Oxidative Fragmentation of Aspalathin Leads to the Formation of Dihydrocaffeic Acid and the Related Lysine Amide Adduct. Journal of agricultural and food chemistry. 2020 Nov; 68(46):13111-13120. doi: 10.1021/acs.jafc.9b07689. [PMID: 32023062]
  • Shenli Wang, Beatriz Sarriá, Raquel Mateos, Luis Goya, Laura Bravo-Clemente. TNF-α-induced oxidative stress and endothelial dysfunction in EA.hy926 cells is prevented by mate and green coffee extracts, 5-caffeoylquinic acid and its microbial metabolite, dihydrocaffeic acid. International journal of food sciences and nutrition. 2019 May; 70(3):267-284. doi: 10.1080/09637486.2018.1505834. [PMID: 30185085]
  • Mariana M Oliveira, Bianca A Ratti, Regina G Daré, Sueli O Silva, Maria da Conceição T Truiti, Tânia Ueda-Nakamura, Rachel Auzély-Velty, Celso V Nakamura. Dihydrocaffeic Acid Prevents UVB-Induced Oxidative Stress Leading to the Inhibition of Apoptosis and MMP-1 Expression via p38 Signaling Pathway. Oxidative medicine and cellular longevity. 2019; 2019(?):2419096. doi: 10.1155/2019/2419096. [PMID: 30800206]
  • Gema Baeza, Eva-Maria Bachmair, Sharon Wood, Raquel Mateos, Laura Bravo, Baukje de Roos. The colonic metabolites dihydrocaffeic acid and dihydroferulic acid are more effective inhibitors of in vitro platelet activation than their phenolic precursors. Food & function. 2017 Mar; 8(3):1333-1342. doi: 10.1039/c6fo01404f. [PMID: 28229135]
  • Siyu Wang, Joon Hyuk Suh, Xi Zheng, Yu Wang, Chi-Tang Ho. Identification and Quantification of Potential Anti-inflammatory Hydroxycinnamic Acid Amides from Wolfberry. Journal of agricultural and food chemistry. 2017 Jan; 65(2):364-372. doi: 10.1021/acs.jafc.6b05136. [PMID: 28008757]
  • Pei Wang, Huadong Chen, Yingdong Zhu, Jennifer McBride, Junsheng Fu, Shengmin Sang. Oat avenanthramide-C (2c) is biotransformed by mice and the human microbiota into bioactive metabolites. The Journal of nutrition. 2015 Feb; 145(2):239-45. doi: 10.3945/jn.114.206508. [PMID: 25644343]
  • Felix Aladedunye, Roman Przybylski. Phosphatidylcholine and dihydrocaffeic acid amide mixture enhanced the thermo-oxidative stability of canola oil. Food chemistry. 2014 May; 150(?):494-9. doi: 10.1016/j.foodchem.2013.10.165. [PMID: 24360481]
  • Aya Fujimoto, Miyuki Inai, Toshiya Masuda. Chemical evidence for the synergistic effect of a cysteinyl thiol on the antioxidant activity of caffeic and dihydrocaffeic esters. Food chemistry. 2013 Jun; 138(2-3):1483-92. doi: 10.1016/j.foodchem.2012.11.073. [PMID: 23411271]
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  • Chi Chun Wong, Walter Meinl, Hans-Rudolf Glatt, Denis Barron, Angélique Stalmach, Heike Steiling, Alan Crozier, Gary Williamson. In vitro and in vivo conjugation of dietary hydroxycinnamic acids by UDP-glucuronosyltransferases and sulfotransferases in humans. The Journal of nutritional biochemistry. 2010 Nov; 21(11):1060-8. doi: 10.1016/j.jnutbio.2009.09.001. [PMID: 19954949]
  • Gary Williamson, Michael N Clifford. Colonic metabolites of berry polyphenols: the missing link to biological activity?. The British journal of nutrition. 2010 Oct; 104 Suppl 3(?):S48-66. doi: 10.1017/s0007114510003946. [PMID: 20955650]
  • Fernanda M F Roleira, Christophe Siquet, Elizabeta Orrù, E Manuela Garrido, Jorge Garrido, Nuno Milhazes, Gianni Podda, Fátima Paiva-Martins, Salette Reis, Rui A Carvalho, Elisiário J Tavares da Silva, Fernanda Borges. Lipophilic phenolic antioxidants: correlation between antioxidant profile, partition coefficients and redox properties. Bioorganic & medicinal chemistry. 2010 Aug; 18(16):5816-25. doi: 10.1016/j.bmc.2010.06.090. [PMID: 20650639]
  • Hye-Jin Kim, Seon-Min Jeon, Mi-Kyung Lee, Yun-Young Cho, Eun-Young Kwon, Jin Hee Lee, Myung-Sook Choi. Comparison of hesperetin and its metabolites for cholesterol-lowering and antioxidative efficacy in hypercholesterolemic hamsters. Journal of medicinal food. 2010 Aug; 13(4):808-14. doi: 10.1089/jmf.2009.1320. [PMID: 20553191]
  • Daniele Del Rio, Angelique Stalmach, Luca Calani, Alan Crozier. Bioavailability of coffee chlorogenic acids and green tea flavan-3-ols. Nutrients. 2010 08; 2(8):820-33. doi: 10.3390/nu2080820. [PMID: 22254058]
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  • Philippe A Guy, Mathieu Renouf, Denis Barron, Christophe Cavin, Fabiola Dionisi, Sunil Kochhar, Serge Rezzi, Gary Williamson, Heike Steiling. Quantitative analysis of plasma caffeic and ferulic acid equivalents by liquid chromatography tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2009 Dec; 877(31):3965-74. doi: 10.1016/j.jchromb.2009.10.006. [PMID: 19879819]
  • Dimitra Hadjipavlou-Litina, Thomas Garnelis, Constantinos M Athanassopoulos, Dionissios Papaioannou. Kukoamine A analogs with lipoxygenase inhibitory activity. Journal of enzyme inhibition and medicinal chemistry. 2009 Oct; 24(5):1188-93. doi: 10.1080/14756360902779193. [PMID: 19772491]
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