Procyanidin B3 (BioDeep_00000017387)

 

Secondary id: BioDeep_00000402764

human metabolite PANOMIX_OTCML-2023 PANOMIX-Anthocyanidin


代谢物信息卡片


(2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-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: 原花清素 B3, 原花青素 B3, 原花青素B3
谱图信息: 最多检出来源 Astragalus membranaceus(plant) 80%

分子结构信息

SMILES: C1(O)=CC2O[C@H](C3C=CC(O)=C(O)C=3)[C@@H](O)[C@H](C3=C(O)C=C(O)C4C[C@H](O)[C@@H](C5C=CC(O)=C(O)C=5)OC=43)C=2C(O)=C1
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 B3 is a proanthocyanidin consisting of two molecules of (+)-catechin joined by a bond between positions 4 and 8 in alpha-configuration. It can be found in red wine, in barley, in beer, in peach or in Jatropha macrantha, the Huanarpo Macho. It has a role as a metabolite, an antioxidant, an anti-inflammatory agent and an EC 2.3.1.48 (histone acetyltransferase) inhibitor. It is a hydroxyflavan, a proanthocyanidin, a biflavonoid and a polyphenol. It is functionally related to a (+)-catechin.
Procyanidin B3 is a natural product found in Quercus dentata, Quercus miyagii, and other organisms with data available.
Present in red wine. Occurs in Fragaria subspecies Procyanidin B3 is found in many foods, some of which are quince, strawberry, bilberry, and japanese persimmon.
Procyanidin B3 is found in alcoholic beverages. Procyanidin B3 is present in red wine. Procyanidin B3 occurs in Fragaria species.
Procyanidin B3 is a natural product, acts as a specific HAT inhibitor, binds to the other site of p300 instead of the active site, selectively inhibits p300-mediated androgen receptor acetylation. Procyanidin B3 has no effect on HDAC or HMT (histone methyltransferase)[1].
Procyanidin B3 is a natural product, acts as a specific HAT inhibitor, binds to the other site of p300 instead of the active site, selectively inhibits p300-mediated androgen receptor acetylation. Procyanidin B3 has no effect on HDAC or HMT (histone methyltransferase)[1].

同义名列表

28 个代谢物同义名

(2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-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,3S,4S)-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-(2alpha,3beta,4alpha(2R*,3S*)))-; (2R-(2alpha,3beta,4alpha(2R*,3S*)))-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,3S,4S)-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,3S,3S,4S)-; [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,3S,3S,4S)-; (2R,2R,3S,3S,4S)-2,2-bis(3,4-dihydroxyphenyl)-3,3,4,4-tetrahydro-2H,2H-4,8-bichromene-3,3,5,5,7,7-hexol; (2R,2R,3S,3S,4S)-2,2-Bis(3,4-dihydroxyphenyl)-[4,8-bichromane]-3,3,5,5,7,7-hexaol; Afzelechin-(4alpha->8)-afzelechin; Catechin-(4.alpha.-->8)catechin; catechin-(4alpha->8)-catechin; XFZJEEAOWLFHDH-AVFWISQGSA-N; 2,3-trans-proanthocyanidin; Catechin-(4a->8)-catechin; Catechin-(4α->8)-catechin; Catechin(4a->8)catechin; Proanthocyanidin B3; (-)-PROCYANIDIN B3; Catechin-(4alpha-; UNII-2TC1A0KEAQ; procyanidin B-3; PROCYANIDOL B3S; Procyanidin B3; PROCYANIDINB3; 8)-catechin; C-(4a,8)-C; 2TC1A0KEAQ



数据库引用编号

14 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)

192 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

  • Nan Qin, Xin Lu, Yijun Liu, Yuting Qiao, Wei Qu, Feng Feng, Haopeng Sun. Recent research progress of Uncaria spp. based on alkaloids: phytochemistry, pharmacology and structural chemistry. European journal of medicinal chemistry. 2021 Jan; 210(?):112960. doi: 10.1016/j.ejmech.2020.112960. [PMID: 33148492]
  • Anwar E M Noreljaleel, Anke Wilhelm, Susan L Bonnet. Analysis of Commercial Proanthocyanidins. Part 6: Sulfitation of Flavan-3-Ols Catechin and Epicatechin, and Procyanidin B-3. Molecules (Basel, Switzerland). 2020 Oct; 25(21):. doi: 10.3390/molecules25214980. [PMID: 33126408]
  • Jae Sik Yu, Minji Park, Changhyun Pang, Luay Rashan, Won Hee Jung, Ki Hyun Kim. Antifungal Phenols from Woodfordia uniflora Collected in Oman. Journal of natural products. 2020 07; 83(7):2261-2268. doi: 10.1021/acs.jnatprod.0c00395. [PMID: 32639158]
  • 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]
  • Ermes Lo Piccolo, Ambra Viviani, Lucia Guidi, Damiano Remorini, Rossano Massai, Rodolfo Bernardi, Marco Landi. Discerning between Two Tuscany (Italy) Ancient Apple cultivars, 'Rotella' and 'Casciana', through Polyphenolic Fingerprint and Molecular Markers. Molecules (Basel, Switzerland). 2019 May; 24(9):. doi: 10.3390/molecules24091758. [PMID: 31067628]
  • Chen Yang, Zhengyan Hu, Meiling Lu, Pengliang Li, Junfeng Tan, Mei Chen, Haipeng Lv, Yin Zhu, Yue Zhang, Li Guo, Qunhua Peng, Weidong Dai, Zhi Lin. Application of metabolomics profiling in the analysis of metabolites and taste quality in different subtypes of white tea. Food research international (Ottawa, Ont.). 2018 04; 106(?):909-919. doi: 10.1016/j.foodres.2018.01.069. [PMID: 29580004]
  • Sylwia Cyboran-Mikołajczyk, Romuald Żyłka, Piotr Jurkiewicz, Hanna Pruchnik, Jan Oszmiański, Martin Hof, Halina Kleszczyńska. Interaction of procyanidin B3 with membrane lipids - Fluorescence, DSC and FTIR studies. Biochimica et biophysica acta. Biomembranes. 2017 Aug; 1859(8):1362-1371. doi: 10.1016/j.bbamem.2017.04.026. [PMID: 28472615]
  • Angela Wang, Daniel J Leong, Zhiyong He, Lin Xu, Lidi Liu, Sun Jin Kim, David M Hirsh, John A Hardin, Neil J Cobelli, Hui B Sun. Procyanidins Mitigate Osteoarthritis Pathogenesis by, at Least in Part, Suppressing Vascular Endothelial Growth Factor Signaling. International journal of molecular sciences. 2016 Dec; 17(12):. doi: 10.3390/ijms17122065. [PMID: 27941690]
  • Kátia Wolff Cordeiro, Josyelen Lousada Felipe, Kauê Franco Malange, Pâmela Rafaela do Prado, Patrícia de Oliveira Figueiredo, Fernanda Rodrigues Garcez, Karine de Cássia Freitas, Walmir Silva Garcez, Mônica Cristina Toffoli-Kadri. Anti-inflammatory and antinociceptive activities of Croton urucurana Baillon bark. Journal of ethnopharmacology. 2016 May; 183(?):128-135. doi: 10.1016/j.jep.2016.02.051. [PMID: 26944237]
  • Xiangrong Li, Mingjiang Geng. Probing the binding of procyanidin B3 to trypsin and pepsin: A multi-technique approach. International journal of biological macromolecules. 2016 Apr; 85(?):168-78. doi: 10.1016/j.ijbiomac.2015.12.075. [PMID: 26740464]
  • Izabela Fecka, Alicja Zofia Kucharska, Adam Kowalczyk. Quantification of tannins and related polyphenols in commercial products of tormentil (Potentilla tormentilla). Phytochemical analysis : PCA. 2015 Sep; 26(5):353-66. doi: 10.1002/pca.2570. [PMID: 26047031]
  • Akinori Kakumu, Masayuki Ninomiya, Mai Efdi, Morina Adfa, Masahiro Hayashi, Kaori Tanaka, Mamoru Koketsu. Phytochemical analysis and antileukemic activity of polyphenolic constituents of Toona sinensis. Bioorganic & medicinal chemistry letters. 2014 Sep; 24(17):4286-90. doi: 10.1016/j.bmcl.2014.07.022. [PMID: 25074815]
  • 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]
  • Nguyen Phuong Thao, Bui Thi Thuy Luyen, Bui Huu Tai, Seo Young Yang, Sung Hoo Jo, Nguyen Xuan Cuong, Nguyen Hoai Nam, Young In Kwon, Chau Van Minh, Young Ho Kim. Rat intestinal sucrase inhibition of constituents from the roots of Rosa rugosa Thunb. Bioorganic & medicinal chemistry letters. 2014 Feb; 24(4):1192-6. doi: 10.1016/j.bmcl.2013.12.098. [PMID: 24461297]
  • Victor Pallarès, Damien Calay, Lídia Cedó, Anna Castell-Auví, Martine Raes, Montserrat Pinent, Anna Ardévol, Lluís Arola, Mayte Blay. Additive, antagonistic, and synergistic effects of procyanidins and polyunsaturated fatty acids over inflammation in RAW 264.7 macrophages activated by lipopolysaccharide. Nutrition (Burbank, Los Angeles County, Calif.). 2012 Apr; 28(4):447-57. doi: 10.1016/j.nut.2011.07.027. [PMID: 22169119]
  • Rui Gonçalves, Nuno Mateus, Victor De Freitas. Influence of carbohydrates on the interaction of procyanidin B3 with trypsin. Journal of agricultural and food chemistry. 2011 Nov; 59(21):11794-802. doi: 10.1021/jf203060s. [PMID: 21950419]
  • Kwan Hee Park, Sun Eun Choi, Young Wook Choi, Do Ik Lee, Seong Soo Joo, Mi Sook Jeong, Hyoweon Bang, Chung Soo Lee, Mi-Kyung Lee, Seong Jun Seo, Min Won Lee. Topical application of two condensed tannins from the root of Rosa multiflora Thunberg for the treatment of atopic dermatitis (AD) in NC/Nga mice. Phytotherapy research : PTR. 2011 Oct; 25(10):1564-9. doi: 10.1002/ptr.3578. [PMID: 21717518]
  • Sun Eun Choi, Kwan Hee Park, Byeong Hoon Han, Mi Sook Jeong, Seong Jun Seo, Do Ik Lee, Seong Soo Joo, Min Won Lee. Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 expression by phenolic compounds from roots of Rhododendron mucronulatum. Phytotherapy research : PTR. 2011 Sep; 25(9):1301-5. doi: 10.1002/ptr.3376. [PMID: 21312305]
  • 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]
  • 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]
  • Ying-Yu Cui, Heng Xie, Kang-Biao Qi, Yan-Ming He, Jin-Fa Wang. Effects of Pinus massoniana bark extract on cell proliferation and apoptosis of human hepatoma BEL-7402 cells. World journal of gastroenterology. 2005 Sep; 11(34):5277-82. doi: 10.3748/wjg.v11.i34.5277. [PMID: 16149132]
  • Tsutomu Hatano, Mami Hori, Richard W Hemingway, Takashi Yoshida. Size exclusion chromatographic analysis of polyphenol-serum albumin complexes. Phytochemistry. 2003 Aug; 63(7):817-23. doi: 10.1016/s0031-9422(03)00340-6. [PMID: 12877923]
  • Jan F Stevens, Cristobal L Miranda, Kirsten R Wolthers, Michael Schimerlik, Max L Deinzer, Donald R Buhler. Identification and in vitro biological activities of hop proanthocyanidins: inhibition of nNOS activity and scavenging of reactive nitrogen species. Journal of agricultural and food chemistry. 2002 Jun; 50(12):3435-43. doi: 10.1021/jf0116202. [PMID: 12033808]
  • Q Guo, B Zhao, L Packer. Electron spin resonance study of free radicals formed from a procyanidin-rich pine (Pinus maritima) bark extract, pycnogenol. Free radical biology & medicine. 1999 Dec; 27(11-12):1308-12. doi: 10.1016/s0891-5849(99)00168-9. [PMID: 10641725]