Procyanidin B1 (BioDeep_00000017259)

Main id: BioDeep_00000003541

 

human metabolite PANOMIX_OTCML-2023 Endogenous PANOMIX-Anthocyanidin


代谢物信息卡片


(2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

化学式: C30H26O12 (578.1424196)
中文名称: 原花青素 B1, 原花青素B1
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: c1(cc2c(c(c1)O)[C@@H]([C@H]([C@H](O2)c1cc(c(cc1)O)O)O)c1c(cc(c2c1O[C@H]([C@H](C2)O)c1cc(c(cc1)O)O)O)O)O
InChI: InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26+,27+,28+,29+/m0/s1

描述信息

Procyanidin B1 is a proanthocyanidin consisting of (-)-epicatechin and (+)-catechin units joined by a bond between positions 4 and 8 respectively in a beta-configuration.. Procyanidin B1 can be found in Cinnamomum verum (Ceylon cinnamon, in the rind, bark or cortex), in Uncaria guianensis (cats claw, in the root), and in Vitis vinifera (common grape vine, in the leaf) or in peach. It has a role as a metabolite, an EC 3.4.21.5 (thrombin) inhibitor and an anti-inflammatory agent. It is a hydroxyflavan, a proanthocyanidin, a biflavonoid and a polyphenol. It is functionally related to a (-)-epicatechin and a (+)-catechin.
Procyanidin B1 is a natural product found in Quercus miyagii, Saraca asoca, and other organisms with data available.
See also: Garcinia mangostana fruit rind (part of); Maritime Pine (part of).
A proanthocyanidin consisting of (-)-epicatechin and (+)-catechin units joined by a bond between positions 4 and 8 respectively in a beta-configuration.. Procyanidin B1 can be found in Cinnamomum verum (Ceylon cinnamon, in the rind, bark or cortex), in Uncaria guianensis (cats claw, in the root), and in Vitis vinifera (common grape vine, in the leaf) or in peach.
Present in red wine. Procyanidin B1 is found in many foods, some of which are common bean, green bell pepper, common hazelnut, and guava.
Procyanidin B1 is found in alcoholic beverages. Procyanidin B1 is present in red win
Procyanidin B1 is a polyphenolic flavonoid isolated from commonly eaten fruits, binds to TLR4/MD-2 complex, and has anti-inflammatory activity.
Procyanidin B1 is a polyphenolic flavonoid isolated from commonly eaten fruits, binds to TLR4/MD-2 complex, and has anti-inflammatory activity.

同义名列表

45 个代谢物同义名

(2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol; (2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol; (4,8-BI-2H-1-BENZOPYRAN)-3,3,5,5,7,7-HEXOL, 2,2-BIS(3,4-DIHYDROXYPHENYL)-3,3,4,4-TETRAHYDRO-, (2R-(2.ALPHA.,3.ALPHA.,4.BETA.(2R*,3S*)))-; (4,8-BI-2H-1-BENZOPYRAN)-3,3,5,5,7,7-HEXOL, 2,2-BIS(3,4-DIHYDROXYPHENYL)-3,3,4,4-TETRAHYDRO-, (2R-(2alpha,3alpha,4beta(2R*,3S*)))-; (2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-8-yl]chromane-3,5,7-triol; [4,8-Bi-2H-1-benzopyran]-3,3,5,5,7,7-hexol, 2,2-bis(3,4-dihydroxyphenyl)-3,3,4,4-tetrahydro-, (2R,2R,3R,3S,4R)-; (4,8-BI-2H-1-BENZOPYRAN)-3,3,5,5,7,7-HEXOL, 2,2-BIS(3,4-DIHYDROXYPHENYL)-3,3,4,4-TETRAHYDRO-, (2R,2R,3R,3S,4R)-; (2R,2R,3R,3S,4R)-2,2-bis(3,4-dihydroxyphenyl)-3,3,4,4-tetrahydro-2H,2H-4,8-bichromene-3,3,5,5,7,7-hexol; (4,8-Bi-2H-1-benzopyran)-3,3,5,5,7,7-hexol, 2,2-bis(3,4-dihydroxyphenyl)-3,3,4,4-tetrahydro-; 2,2-Bis(3,4-dihydroxyphenyl)-3,3,4,4-tetrahydro-(4,8-Bi-2H-1-benzopyran)-3,3,5,5,7,7-hexol; (2R,2R,3R,3S,4R)-2,2-Bis(3,4-dihydroxyphenyl)-[4,8-bichromane]-3,3,5,5,7,7-hexaol; (2R,2R,3R,3S,4R)-2,2-Bis(3,4-dihydroxyphenyl)-[4,8-bichroman]-3,3,5,5,7,7-hexaol; PROCYANIDIN B1 (CONSTITUENT OF GRAPE SEEDS OLIGOMERIC PROANTHOCYANIDINS); PROCYANIDIN B1 (CONSTITUENT OF MARITIME PINE) [DSC]; cis,trans-4,8-Bi-(3,3,4,5,7-Pentahydroxyflavane); PROCYANIDIN B1 (CONSTITUENT OF MARITIME PINE); (-)-EPICATECHIN-(4.BETA.-8)-(+)-CATECHIN; 4,8-Bi-(3,3,4,5,7-Pentahydroxyflavane); (-)-EPICATECHIN-(4beta-8)-(+)-CATECHIN; Epicatechin-(4beta->8)-ent-epicatechin; Epicatechin-(4b->8)-ent-epicatechin; Epicatechin-(4β->8)-ent-epicatechin; Procyanidin B1, analytical standard; Epicatechin(4beta->8)catechin; XFZJEEAOWLFHDH-UKWJTHFESA-N; Epicatechin(4β->8)catechin; Epicatechin(4b->8)catechin; PROCYANIDIN B1, (+)-; Procyanidol oligomer; Procyanidin dimer B1; Proanthocyanidin B1; (+)-PROCYANIDIN B1; procyanidin-B-2; PROCYANIDOL B1; Procyanidin-B1; Procyanidin B1; Procyanidin B; ProcyanidinB1; Procyanidol D; Procyanidin D; Procyanidin; EC-(4b,8)-C; Endotelon; Epicatechin-(4beta-; 8)-ent-epicatechin



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

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

82 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

  • Jian-Nan Ma, Xu Feng, Cheng-Bin Shan, Yue Ma, Zhan-Yuan Lu, De-Jian Zhang, Chao-Mei Ma. Quantification and purification of procyanidin B1 from food byproducts. Journal of food science. 2022 Nov; 87(11):4905-4916. doi: 10.1111/1750-3841.16358. [PMID: 36303405]
  • Jixiao Zhu, Manqin Fu, Jian Gao, Guoyu Dai, Qiunong Guan, Caigan Du. Upregulation of Thioredoxin Reductase 1 Expression by Flavan-3-Ols Protects Human Kidney Proximal Tubular Cells from Hypoxia-Induced Cell Death. Antioxidants (Basel, Switzerland). 2022 Jul; 11(7):. doi: 10.3390/antiox11071399. [PMID: 35883890]
  • Ze-Hua Liu, Bo Li. Procyanidin B1 and p-Coumaric Acid from Highland Barley Grain Showed Synergistic Effect on Modulating Glucose Metabolism via IRS-1/PI3K/Akt Pathway. Molecular nutrition & food research. 2021 09; 65(18):e2100454. doi: 10.1002/mnfr.202100454. [PMID: 34342938]
  • Fangfang Tie, Jifei Wang, Yuexin Liang, Shujun Zhu, Zhenhua Wang, Gang Li, Honglun Wang. Proanthocyanidins Ameliorated Deficits of Lipid Metabolism in Type 2 Diabetes Mellitus Via Inhibiting Adipogenesis and Improving Mitochondrial Function. International journal of molecular sciences. 2020 Mar; 21(6):. doi: 10.3390/ijms21062029. [PMID: 32188147]
  • V Lavelli, P S C Sri Harsha. Microencapsulation of grape skin phenolics for pH controlled release of antiglycation agents. Food research international (Ottawa, Ont.). 2019 05; 119(?):822-828. doi: 10.1016/j.foodres.2018.10.065. [PMID: 30884721]
  • Tao Li, Qili Li, Weiguo Wu, Yong Li, De-Xing Hou, Hua Xu, Baodong Zheng, Shaoxiao Zeng, Yang Shan, Xiangyang Lu, Fangming Deng, Si Qin. Lotus seed skin proanthocyanidin extract exhibits potent antioxidant property via activation of the Nrf2-ARE pathway. Acta biochimica et biophysica Sinica. 2019 Jan; 51(1):31-40. doi: 10.1093/abbs/gmy148. [PMID: 30544155]
  • Carmen Tatiana Cuadrado-Silva, Maria Ángeles Pozo-Bayón, Coralia Osorio. Targeted Metabolomic Analysis of Polyphenols with Antioxidant Activity in Sour Guava (Psidium friedrichsthalianum Nied.) Fruit. Molecules (Basel, Switzerland). 2016 Dec; 22(1):. doi: 10.3390/molecules22010011. [PMID: 28025550]
  • Marco Fumagalli, Enrico Sangiovanni, Urska Vrhovsek, Stefano Piazza, Elisa Colombo, Mattia Gasperotti, Fulvio Mattivi, Emma De Fabiani, Mario Dell'Agli. Strawberry tannins inhibit IL-8 secretion in a cell model of gastric inflammation. Pharmacological research. 2016 09; 111(?):703-712. doi: 10.1016/j.phrs.2016.07.028. [PMID: 27473819]
  • Andoni Zuriarrain, Juan Zuriarrain, Ana Isabel Puertas, María Teresa Dueñas, Miren Ostra, Iñaki Berregi. Polyphenolic profile in cider and antioxidant power. Journal of the science of food and agriculture. 2015 Nov; 95(14):2931-43. doi: 10.1002/jsfa.7036. [PMID: 25475490]
  • Tuba Esatbeyoglu, Victor Wray, Peter Winterhalter. Isolation of dimeric, trimeric, tetrameric and pentameric procyanidins from unroasted cocoa beans (Theobroma cacao L.) using countercurrent chromatography. Food chemistry. 2015 Jul; 179(?):278-89. doi: 10.1016/j.foodchem.2015.01.130. [PMID: 25722166]
  • Stefanie Wiese, Tuba Esatbeyoglu, Peter Winterhalter, Hans-Peter Kruse, Stephanie Winkler, Achim Bub, Sabine E Kulling. Comparative biokinetics and metabolism of pure monomeric, dimeric, and polymeric flavan-3-ols: a randomized cross-over study in humans. Molecular nutrition & food research. 2015 Apr; 59(4):610-21. doi: 10.1002/mnfr.201400422. [PMID: 25546356]
  • Hitomi Kanno, Zenji Kawakami, Masahiro Tabuchi, Kazushige Mizoguchi, Yasushi Ikarashi, Yoshio Kase. Protective effects of glycycoumarin and procyanidin B1, active components of traditional Japanese medicine yokukansan, on amyloid β oligomer-induced neuronal death. Journal of ethnopharmacology. 2015 Jan; 159(?):122-8. doi: 10.1016/j.jep.2014.10.058. [PMID: 25446602]
  • Ji Hee Jeong, Hyeon Ju Kim, Seon Kyeong Park, Dong Eun Jin, O-Jun Kwon, Hyun-Jin Kim, Ho Jin Heo. An investigation into the ameliorating effect of black soybean extract on learning and memory impairment with assessment of neuroprotective effects. BMC complementary and alternative medicine. 2014 Dec; 14(?):482. doi: 10.1186/1472-6882-14-482. [PMID: 25496367]
  • Lindsey L Kimble, Bridget D Mathison, Kerrie L Kaspar, Christina Khoo, Boon P Chew. Development of a fluorometric microplate antiadhesion assay using uropathogenic Escherichia coli and human uroepithelial cells. Journal of natural products. 2014 May; 77(5):1102-10. doi: 10.1021/np400781y. [PMID: 24749980]
  • Haiyan Xie, Jing-Rong Wang, Lee-Fong Yau, Yong Liu, Liang Liu, Quan-Bin Han, Zhongzhen Zhao, Zhi-Hong Jiang. Catechins and procyanidins of Ginkgo biloba show potent activities towards the inhibition of β-amyloid peptide aggregation and destabilization of preformed fibrils. Molecules (Basel, Switzerland). 2014 Apr; 19(4):5119-34. doi: 10.3390/molecules19045119. [PMID: 24759072]
  • Angel L Alvarez, Kevin P Dalton, Inés Nicieza, Yolanda Diñeiro, Anna Picinelli, Santiago Melón, Annele Roque, Belén Suárez, Francisco Parra. Bioactivity-guided fractionation of Phyllanthus orbicularis and identification of the principal anti HSV-2 compounds. Phytotherapy research : PTR. 2012 Oct; 26(10):1513-20. doi: 10.1002/ptr.4608. [PMID: 22318977]
  • Tsutomu Shimada, Daisuke Tokuhara, Masahito Tsubata, Tomoyasu Kamiya, Mayu Kamiya-Sameshima, Rika Nagamine, Kinya Takagaki, Yoshimichi Sai, Ken-Ichi Miyamoto, Masaki Aburada. Flavangenol (pine bark extract) and its major component procyanidin B1 enhance fatty acid oxidation in fat-loaded models. European journal of pharmacology. 2012 Feb; 677(1-3):147-53. doi: 10.1016/j.ejphar.2011.12.034. [PMID: 22227333]
  • Changwei Ao, Tatsunori Higa, Hui Ming, Yu-ting Ding, Shinkichi Tawata. Isolation and identification of antioxidant and hyaluronidase inhibitory compounds from Ficus microcarpa L. fil. bark. Journal of enzyme inhibition and medicinal chemistry. 2010 Jun; 25(3):406-13. doi: 10.3109/14756360903213473. [PMID: 20233084]
  • Mathias Jung, Sven Triebel, Timm Anke, Elke Richling, Gerhard Erkel. Influence of apple polyphenols on inflammatory gene expression. Molecular nutrition & food research. 2009 Oct; 53(10):1263-80. doi: 10.1002/mnfr.200800575. [PMID: 19764067]
  • Shinzo Hosoi, Eri Shimizu, Kazuhiko Arimori, Manabu Okumura, Muneaki Hidaka, Mitsuko Yamada, Akiyo Sakushima. Analysis of CYP3A inhibitory components of star fruit (Averrhoa carambola L.) using liquid chromatography-mass spectrometry. Journal of natural medicines. 2008 Jul; 62(3):345-8. doi: 10.1007/s11418-008-0239-y. [PMID: 18404300]
  • Shoko Taniguchi, Kayo Kuroda, Kou-ichi Doi, Masahiro Tanabe, Takashi Shibata, Takashi Yoshida, Tsutomu Hatano. Revised structures of gambiriins A1, A2, B1, and B2, chalcane-flavan dimers from gambir (Uncaria gambir extract). Chemical & pharmaceutical bulletin. 2007 Feb; 55(2):268-72. doi: 10.1248/cpb.55.268. [PMID: 17268100]
  • Atsushi Sano, Jun Yamakoshi, Shoichi Tokutake, Koichiro Tobe, Yoshiro Kubota, Mamoru Kikuchi. Procyanidin B1 is detected in human serum after intake of proanthocyanidin-rich grape seed extract. Bioscience, biotechnology, and biochemistry. 2003 May; 67(5):1140-3. doi: 10.1271/bbb.67.1140. [PMID: 12834296]
  • Emma Cantos, Juan Carlos Espín, Francisco A Tomás-Barberán. Varietal differences among the polyphenol profiles of seven table grape cultivars studied by LC-DAD-MS-MS. Journal of agricultural and food chemistry. 2002 Sep; 50(20):5691-6. doi: 10.1021/jf0204102. [PMID: 12236700]