Proanthocyanidin A2 (BioDeep_00000231015)

 

Secondary id: BioDeep_00000004330, BioDeep_00000230447

human metabolite PANOMIX_OTCML-2023 PANOMIX-Anthocyanidin natural product


代谢物信息卡片


8,14-Methano-2H,14H-1-benzopyrano[7,8-d][1,3]benzodioxocin-3,5,11,13,15-pentol, 2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-, [2R-(2.alpha,3.alpha.,8.beta.,14.beta.,15R*)]-

化学式: C30H24O12 (576.1268)
中文名称: 原花青素 A2, 原花青素A2, 原花色素 A2
谱图信息: 最多检出来源 Escherichia coli(otcml) 32.14%

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

Proanthocyanidin A2 is a proanthocyanidin obtained by the condensation of (-)-epicatechin units. It has a role as an antioxidant, an anti-HIV agent, a metabolite and an angiogenesis modulating agent. It is a hydroxyflavan and a proanthocyanidin. It is functionally related to a (-)-epicatechin.
Proanthocyanidin A2 is a natural product found in Cinnamomum iners, Cinnamomum aromaticum, and other organisms with data available.
See also: Litchi fruit (part of).
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).
A proanthocyanidin obtained by the condensation of (-)-epicatechin units.
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

32 个代谢物同义名

8,14-Methano-2H,14H-1-benzopyrano[7,8-d][1,3]benzodioxocin-3,5,11,13,15-pentol, 2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-, [2R-(2.alpha,3.alpha.,8.beta.,14.beta.,15R*)]-; (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; (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),9,15,17,19-hexaene-6,9,17,19,21-pentol; 8,14-Methano-2H,14H-1,7,9-trioxabenzo[6,7]cycloocta[1,2-a]naphthalene-3,5,11,13,15-pentol, 2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R,3R,8S,14R,15R)-; 8,14-Methano-2H,14H-1-benzopyrano[7,8-d][1,3]benzodioxocin-3,5,11,13,15-pentol, 2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R,3R,8S,14R,15R)-; 8,14-METHANO-2H,14H-1-BENZOPYRANO(7,8-D)(1,3)BENZODIOXOCIN-3,5,11,13,15-PENTOL, 2,8-BIS(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-, (2R,3R,8S,14R,15R)-; (2R,3R,8S,14R,15R)-2,8-Bis(3,4-dihydroxyphenyl)-3,4-dihydro-2H,14H-8,14-methanobenzo[7,8][1,3]dioxocino[4,5-h]chromene-3,5,11,13,15-pentaol; (2r,3r,8s,14r,15r)-2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-2h,14h-8,14-methanochromeno[7,8-d][1,3]benzodioxocine-3,5,11,13,15-pentol; 8,14-Methano-2H,8H,14H-1-benzopyrano(8,7-c)(1,5)benzodioxocin-3,5,9,11,15-pentol, 2,14-bis(3,4-dihydroxyphenyl)-3,4-dihydro-; 2,14-Bis(3,4-dihydroxyphenyl)-3,4-dihydro-8,14-methano-2H,8H,14H-1-benzopyrano(8,7-c)(1,5)benzodioxocin-3,5,9,11,15-pentol; PROANTHOCYANIDIN A2;PROCYANIDIN A2; PROCYANIDOEPICATECHIN; Epicatechin-(4.beta.-->8,2.beta.-->O-->7)epicatechin; (+)-Epicatechin-(4.beta.-8,2.beta.-O-7)-epicatechin; (+)-EPICATECHIN-(4beta-8,2beta-O-7)-EPICATECHIN; Epicatechin-(2beta->7,4beta->8)-epicatechin; Epicatechin-(2β->7,4β->8)-epicatechin; Epicatechin-(2b->7,4b->8)-epicatechin; Procyanidin A2, analytical standard; bis(3,4-dihydroxyphenyl)[?]pentol; (+)-Proanthocyanidin A-2; (+)-Proanthocyanidin A2; Procyanidoepicatechin; Procyanidin dimer A2; Proanthocyanidin A-2; proanthocyanidin A2; EC-(4b,8)(2b,7)-EC; Dimeric catechin; Procyanidin A2; Procyanidol A2; PROCYANIDINA2; Procyanidin; Proanthocyanidin A2



数据库引用编号

21 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)

103 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
Cytoplasm 11 AIMP2, APOE, BCL2, CASP3, CASP9, MAPK8, NFE2L2, PPARG, RB1CC1, SMAD2, SMAD3
Peripheral membrane protein 1 GORASP1
Endoplasmic reticulum membrane 4 BCL2, CYP7A1, HMOX1, RB1CC1
Nucleus 12 AIMP2, APOE, BCL2, CASP3, CASP9, HMOX1, MAPK8, NFE2L2, PPARG, RB1CC1, SMAD2, SMAD3
cytosol 11 AIMP2, BCL2, CASP3, CASP9, HMOX1, MAPK8, NFE2L2, PPARG, RB1CC1, SMAD2, SMAD3
dendrite 1 APOE
centrosome 1 NFE2L2
nucleoplasm 7 CASP3, HMOX1, MAPK8, NFE2L2, PPARG, SMAD2, SMAD3
RNA polymerase II transcription regulator complex 2 NFE2L2, PPARG
Cell membrane 2 TNF, VCAM1
Cytoplasmic side 2 GORASP1, HMOX1
Golgi apparatus membrane 1 GORASP1
Synapse 1 MAPK8
cell surface 2 TNF, VCAM1
glutamatergic synapse 2 APOE, CASP3
Golgi apparatus 4 APOE, GORASP1, NFE2L2, VCAM1
Golgi membrane 2 GORASP1, INS
lysosomal membrane 1 GAA
neuronal cell body 3 APOE, CASP3, TNF
sarcolemma 1 VCAM1
Cytoplasm, cytosol 3 AIMP2, NFE2L2, RB1CC1
Lysosome 2 GAA, RB1CC1
plasma membrane 7 APOE, GAA, IGHE, NFE2L2, SMAD3, TNF, VCAM1
Membrane 7 AIMP2, APOE, BCL2, GAA, HMOX1, SMAD2, VCAM1
axon 1 MAPK8
extracellular exosome 3 APOE, GAA, VCAM1
Lysosome membrane 1 GAA
endoplasmic reticulum 4 APOE, BCL2, HMOX1, VCAM1
extracellular space 7 APOE, HMOX1, IGHE, IL6, INS, TNF, VCAM1
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 2 HMOX1, PPARG
mitochondrion 2 BCL2, CASP9
protein-containing complex 3 BCL2, CASP9, SMAD2
intracellular membrane-bounded organelle 3 CYP7A1, GAA, PPARG
Microsome membrane 1 CYP7A1
filopodium 1 VCAM1
postsynaptic density 1 CASP3
Single-pass type I membrane protein 2 IGHE, VCAM1
Secreted 4 APOE, GAA, IL6, INS
extracellular region 6 APOE, GAA, IGHE, IL6, INS, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 2 BCL2, CYP7A1
mitochondrial outer membrane 2 BCL2, HMOX1
transcription regulator complex 2 SMAD2, SMAD3
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 2 BCL2, RB1CC1
external side of plasma membrane 2 TNF, VCAM1
Endosome, multivesicular body 1 APOE
Extracellular vesicle 1 APOE
Secreted, extracellular space, extracellular matrix 1 APOE
chylomicron 1 APOE
high-density lipoprotein particle 1 APOE
low-density lipoprotein particle 1 APOE
multivesicular body 1 APOE
very-low-density lipoprotein particle 1 APOE
Early endosome 2 APOE, VCAM1
apical part of cell 1 VCAM1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Membrane raft 1 TNF
pore complex 1 BCL2
cis-Golgi network 1 GORASP1
extracellular matrix 1 APOE
collagen-containing extracellular matrix 1 APOE
nuclear inner membrane 1 SMAD3
receptor complex 2 PPARG, SMAD3
chromatin 4 NFE2L2, PPARG, SMAD2, SMAD3
mediator complex 1 NFE2L2
IgE immunoglobulin complex 1 IGHE
autophagosome membrane 1 RB1CC1
phagocytic cup 1 TNF
podosome 1 VCAM1
Secreted, extracellular space 1 APOE
blood microparticle 1 APOE
[Isoform 2]: Cell membrane 1 IGHE
endosome lumen 1 INS
microvillus 1 VCAM1
phagophore assembly site 1 RB1CC1
phagophore assembly site membrane 1 RB1CC1
tertiary granule membrane 1 GAA
Melanosome 1 APOE
myelin sheath 1 BCL2
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 APOE, IL6, INS
transport vesicle 1 INS
azurophil granule membrane 1 GAA
Endoplasmic reticulum-Golgi intermediate compartment membrane 2 GORASP1, INS
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
Single-pass type IV membrane protein 1 HMOX1
apoptosome 1 CASP9
clathrin-coated endocytic vesicle membrane 1 APOE
heteromeric SMAD protein complex 2 SMAD2, SMAD3
SMAD protein complex 2 SMAD2, SMAD3
synaptic cleft 1 APOE
protein-DNA complex 1 NFE2L2
ficolin-1-rich granule membrane 1 GAA
basal dendrite 1 MAPK8
death-inducing signaling complex 1 CASP3
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
Preautophagosomal structure 1 RB1CC1
Atg1/ULK1 kinase complex 1 RB1CC1
activin responsive factor complex 1 SMAD2
[Isoform 3]: Cell membrane 1 IGHE
discoidal high-density lipoprotein particle 1 APOE
endocytic vesicle lumen 1 APOE
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
[Isoform 1]: Secreted 1 IGHE
IgE B cell receptor complex 1 IGHE
immunoglobulin complex, circulating 1 IGHE
chylomicron remnant 1 APOE
intermediate-density lipoprotein particle 1 APOE
lipoprotein particle 1 APOE
multivesicular body, internal vesicle 1 APOE
interleukin-6 receptor complex 1 IL6
autolysosome lumen 1 GAA
BAD-BCL-2 complex 1 BCL2
[Vascular cell adhesion protein 1]: Cell membrane 1 VCAM1
[Soluble Vascular Cell Adhesion Molecule-1]: Secreted 1 VCAM1
alpha9-beta1 integrin-vascular cell adhesion molecule-1 complex 1 VCAM1
caspase complex 1 CASP9
homomeric SMAD protein complex 1 SMAD2
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


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]
  • 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]
  • 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]
  • 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]
  • 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]