Proanthocyanidin A2 (BioDeep_00000004330)

Main id: BioDeep_00000231015

Secondary id: BioDeep_00000017386, BioDeep_00000228386, BioDeep_00000621340

human metabolite PANOMIX_OTCML-2023 PANOMIX-Anthocyanidin


代谢物信息卡片


(1R,5R,6R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol

化学式: C30H24O12 (576.1267703999999)
中文名称: 原花青素A2, 原花青素A1
谱图信息: 最多检出来源 Astragalus membranaceus(otcml) 66.67%

分子结构信息

SMILES: c1(cc(c2c(c1)O[C@@]1([C@@H]([C@H]2c2c3c(c(cc2O1)O)C[C@H]([C@H](O3)c1cc(c(cc1)O)O)O)O)c1cc(c(cc1)O)O)O)O
InChI: InChI=1S/C31H26O12/c1-11-4-13(6-20(37)27(11)39)31-30(40)26(24-19(36)7-14(32)8-22(24)42-31)25-23(43-31)10-17(34)15-9-21(38)28(41-29(15)25)12-2-3-16(33)18(35)5-12/h2-8,10,21,26,28,30,32-40H,9H2,1H3/t21-,26-,28-,30-,31+/m1/s1

描述信息

Isolated from cassia bark (Cinnamomum aromaticum). Proanthocyanidin A2 is found in many foods, some of which are herbs and spices, cinnamon, avocado, and lingonberry.
Proanthocyanidin A2 is found in apple. Proanthocyanidin A2 is isolated from cassia bark (Cinnamomum aromaticum).
Procyanidin A1 (Proanthocyanidin A1) is a procyanidin dimer, which inhibits degranulation downstream of protein kinase C activation or Ca2+ influx from an internal store in RBL-213 cells. Procyanidin A1 has antiallergic effects[1].
Procyanidin A1 (Proanthocyanidin A1) is a procyanidin dimer, which inhibits degranulation downstream of protein kinase C activation or Ca2+ influx from an internal store in RBL-213 cells. Procyanidin A1 has antiallergic effects[1].
Procyanidin A2 is a flavonoid found in grapes, with anti-cancer, antioxidant, antimicrobial and anti-inflammation activity[1][2].
Procyanidin A2 is a flavonoid found in grapes, with anti-cancer, antioxidant, antimicrobial and anti-inflammation activity[1][2].

同义名列表

15 个代谢物同义名

(1R,5R,6R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol; Epicatechin-(2beta->7,4beta->8)-epicatechin; Epicatechin-(2β->7,4β->8)-epicatechin; Epicatechin-(2b->7,4b->8)-epicatechin; (+)-Proanthocyanidin A-2; (+)-Proanthocyanidin A2; Procyanidoepicatechin; Procyanidin dimer A2; Proanthocyanidin A-2; proanthocyanidin A2; EC-(4b,8)(2b,7)-EC; Procyanidin A1; Procyanidin A2; Procyanidol A2; Proanthocyanidin A1



数据库引用编号

20 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)

31 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

  • Pooja M, Gangavaram Jyothi Reddy, Kanipakam Hema, Sujatha Dodoala, Bharathi Koganti. Unravelling high-affinity binding compounds towards transmembrane protease serine 2 enzyme in treating SARS-CoV-2 infection using molecular modelling and docking studies. European journal of pharmacology. 2021 Jan; 890(?):173688. doi: 10.1016/j.ejphar.2020.173688. [PMID: 33130280]
  • Shan Han, Hongwei Gao, Shaoru Chen, Qinqin Wang, Xinxing Li, Li-Jun Du, Jun Li, Ying-Ying Luo, Jun-Xiu Li, Li-Chun Zhao, Jianfang Feng, Shilin Yang. Procyanidin A1 Alleviates Inflammatory Response induced by LPS through NF-κB, MAPK, and Nrf2/HO-1 Pathways in RAW264.7 cells. Scientific reports. 2019 10; 9(1):15087. doi: 10.1038/s41598-019-51614-x. [PMID: 31636354]
  • Jau-Tien Lin, Yuan-Yen Chang, Yi-Chen Chen, Po-Lin Liao, Deng-Jye Yang. Litchi (Litchi chinensis Sonn.) flower proanthocyanidin fraction exhibited protective efficacy to suppress nickel-induced expression for vascular endothelial growth factor in HepG2 cells. Journal of food biochemistry. 2019 07; 43(7):e12882. doi: 10.1111/jfbc.12882. [PMID: 31353727]
  • Dayanne da S Freitas, José A Morgado-Díaz, Adriana S Gehren, Flávia C B Vidal, Raquel Maria T Fernandes, Wanderson Romão, Lilian V Tose, Fabiola N S Frazão, Maria Célia P Costa, Dulcelena F Silva, Maria do Desterro S B Nascimento. Cytotoxic analysis and chemical characterization of fractions of the hydroalcoholic extract of the Euterpe oleracea Mart. seed in the MCF-7 cell line. The Journal of pharmacy and pharmacology. 2017 Jun; 69(6):714-721. doi: 10.1111/jphp.12679. [PMID: 28211563]
  • Jana Gau, Martine Prévost, Pierre Van Antwerpen, Menyhárt-Botond Sarosi, Steffen Rodewald, Jürgen Arnhold, Jörg Flemmig. Tannins and Tannin-Related Derivatives Enhance the (Pseudo-)Halogenating Activity of Lactoperoxidase. Journal of natural products. 2017 05; 80(5):1328-1338. doi: 10.1021/acs.jnatprod.6b00915. [PMID: 28368593]
  • Yong Sui, Yan Zheng, Xiaopeng Li, Shuyi Li, Bijun Xie, Zhida Sun. Characterization and preparation of oligomeric procyanidins from Litchi chinensis pericarp. Fitoterapia. 2016 Jul; 112(?):168-74. doi: 10.1016/j.fitote.2016.06.001. [PMID: 27282208]
  • Tatiane L C Oldoni, Priscilla S Melo, Adna P Massarioli, Ivani A M Moreno, Rosângela M N Bezerra, Pedro L Rosalen, Gil V J da Silva, Andréa M Nascimento, Severino M Alencar. Bioassay-guided isolation of proanthocyanidins with antioxidant activity from peanut (Arachis hypogaea) skin by combination of chromatography techniques. Food chemistry. 2016 Feb; 192(?):306-12. doi: 10.1016/j.foodchem.2015.07.004. [PMID: 26304352]
  • Jason M Walsh, Xiaobai Ren, Carly Zampariello, Daniel A Polasky, Diane L McKay, Jeffrey B Blumberg, C-Y Oliver Chen. Liquid chromatography with tandem mass spectrometry quantification of urinary proanthocyanin A2 dimer and its potential use as a biomarker of cranberry intake. Journal of separation science. 2016 Jan; 39(2):342-9. doi: 10.1002/jssc.201500922. [PMID: 26573891]
  • Zhi Siang Toh, Hongyu Wang, Yew Mun Yip, Yuyun Lu, Benedict Jeffrey Ang Lim, Daiwei Zhang, Dejian Huang. Phenolic group on A-ring is key for dracoflavan B as a selective noncompetitive inhibitor of α-amylase. Bioorganic & medicinal chemistry. 2015 Dec; 23(24):7641-9. doi: 10.1016/j.bmc.2015.11.008. [PMID: 26631440]
  • Silvia C Heredia-Vieira, Ana M Simonet, Wagner Vilegas, Francisco A Macías. Unusual C,O-Fused Glycosylapigenins from Serjania marginata Leaves. Journal of natural products. 2015 Jan; 78(1):77-84. doi: 10.1021/np500715x. [PMID: 25517504]
  • 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]
  • Maria S Pesca, Fabrizio Dal Piaz, Rokia Sanogo, Antonio Vassallo, Maryan Bruzual de Abreu, Antonio Rapisarda, Maria P Germanò, Giovanna Certo, Sandro De Falco, Nunziatina De Tommasi, Alessandra Braca. Bioassay-guided isolation of proanthocyanidins with antiangiogenic activities. Journal of natural products. 2013 Jan; 76(1):29-35. doi: 10.1021/np300614u. [PMID: 23268742]
  • M Artini, R Papa, G Barbato, G L Scoarughi, A Cellini, P Morazzoni, E Bombardelli, L Selan. Bacterial biofilm formation inhibitory activity revealed for plant derived natural compounds. Bioorganic & medicinal chemistry. 2012 Jan; 20(2):920-6. doi: 10.1016/j.bmc.2011.11.052. [PMID: 22182580]
  • Keisuke Tomochika, Akiko Shimizu-Ibuka, Tomoko Tamura, Kiyoshi Mura, Naoki Abe, Jun-Ichi Onose, Soichi Arai. Effects of peanut-skin procyanidin A1 on degranulation of RBL-2H3 cells. Bioscience, biotechnology, and biochemistry. 2011; 75(9):1644-8. doi: 10.1271/bbb.110085. [PMID: 21897038]
  • Jian Sun, Weiqiang Su, Hongxiang Peng, Jianhua Zhu, Liangxiong Xu, Nuria Martí Bruñá. Two endogenous substrates for polyphenoloxidase in pericarp tissues of postharvest rambutan fruit. Journal of food science. 2010 Aug; 75(6):C473-7. doi: 10.1111/j.1750-3841.2010.01660.x. [PMID: 20722899]
  • H Koo, S Duarte, R M Murata, K Scott-Anne, S Gregoire, G E Watson, A P Singh, N Vorsa. Influence of cranberry proanthocyanidins on formation of biofilms by Streptococcus mutans on saliva-coated apatitic surface and on dental caries development in vivo. Caries research. 2010; 44(2):116-26. doi: 10.1159/000296306. [PMID: 20234135]
  • Xiuhai Gan, Xin Zhou, Huaguo Chen, Xiaojian Gong, Chao Zhao. [Chemical constituents of Periploca forrestii]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 Dec; 34(24):3225-8. doi: . [PMID: 20353006]
  • Jayma L Koerner, Victor L Hsu, Jungmin Lee, James A Kennedy. Determination of proanthocyanidin A2 content in phenolic polymer isolates by reversed-phase high-performance liquid chromatography. Journal of chromatography. A. 2009 Feb; 1216(9):1403-9. doi: 10.1016/j.chroma.2008.12.086. [PMID: 19168185]
  • Meng-Chieh Hsieh, Yi-Jane Shen, Yueh-Hsiung Kuo, Lucy Sun Hwang. Antioxidative activity and active components of longan (Dimocarpus longan Lour.) flower extracts. Journal of agricultural and food chemistry. 2008 Aug; 56(16):7010-6. doi: 10.1021/jf801155j. [PMID: 18662011]
  • Fumihide Takano, Takanobu Takata, Akio Yoshihara, Yuka Nakamura, Yukiko Arima, Tomihisa Ohta. Aqueous extract of peanut skin and its main constituent procyanidin A1 suppress serum IgE and IgG1 levels in mice-immunized with ovalbumin. Biological & pharmaceutical bulletin. 2007 May; 30(5):922-7. doi: 10.1248/bpb.30.922. [PMID: 17473436]
  • Xiang-Zhong Huang, Yue Liu, Shi-Shan Yu, You-Cai Hu, Jing Qu. [Studies on chemical constituents from roots of Craibiodendron henryi]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 Apr; 32(7):599-603. doi: . [PMID: 17583200]
  • Abdelaaty A Shahat, Paul Cos, Tess De Bruyne, Sandra Apers, Fayza M Hammouda, Shams I Ismail, Safa Azzam, Magda Claeys, Etienne Goovaerts, Luc Pieters, Dirk Vanden Berghe, Arnold J Vlietinck. Antiviral and antioxidant activity of flavonoids and proanthocyanidins from Crataegus sinaica. Planta medica. 2002 Jun; 68(6):539-41. doi: 10.1055/s-2002-32547. [PMID: 12094299]
  • Lie-Chwen Lin, Yuh-Chi Kuo, Cheng-Jen Chou. Immunomodulatory proanthocyanidins from Ecdysanthera utilis. Journal of natural products. 2002 Apr; 65(4):505-8. doi: 10.1021/np010414l. [PMID: 11975489]
  • C Ma, N Nakamura, M Hattori, H Kakuda, J Qiao, H Yu. Inhibitory effects on HIV-1 protease of constituents from the wood of Xanthoceras sorbifolia. Journal of natural products. 2000 Feb; 63(2):238-42. doi: 10.1021/np9902441. [PMID: 10691716]