Proanthocyanidin A2 (BioDeep_00000004330)

Main id: BioDeep_00000231015

Secondary id: BioDeep_00000017386, BioDeep_00000228386, BioDeep_00000621340

human metabolite PANOMIX_OTCML-2023 PANOMIX-Anthocyanidin natural product


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 (576.1268)
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) 100%

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

16 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; Proanthocyanidin A2



数据库引用编号

22 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)

108 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 12 AIMP2, APOE, BECN1, DCTN4, KEAP1, MAPK8, MAPK9, MARVELD1, MTOR, NFE2L2, SMAD2, SMAD3
Golgi apparatus, trans-Golgi network membrane 1 BECN1
Peripheral membrane protein 3 BECN1, GORASP1, MTOR
Endosome membrane 1 BECN1
Endoplasmic reticulum membrane 4 BECN1, CYP7A1, HMOX1, MTOR
Mitochondrion membrane 1 BECN1
Cytoplasmic vesicle, autophagosome 1 BECN1
Nucleus 14 AIMP2, APOE, BECN1, DCTN4, GABPA, HMOX1, KEAP1, MAPK8, MAPK9, MARVELD1, MTOR, NFE2L2, SMAD2, SMAD3
autophagosome 1 BECN1
cytosol 11 AIMP2, BECN1, DCTN4, HMOX1, KEAP1, MAPK8, MAPK9, MTOR, NFE2L2, SMAD2, SMAD3
dendrite 3 APOE, BECN1, MTOR
mitochondrial membrane 1 BECN1
nuclear body 1 BECN1
phagocytic vesicle 2 BECN1, MTOR
phosphatidylinositol 3-kinase complex, class III 1 BECN1
trans-Golgi network 1 BECN1
centrosome 2 DCTN4, NFE2L2
nucleoplasm 9 GABPA, HMOX1, KEAP1, MAPK8, MAPK9, MTOR, NFE2L2, SMAD2, SMAD3
RNA polymerase II transcription regulator complex 1 NFE2L2
Cell membrane 3 CLDN1, MARVELD1, TNF
Cytoplasmic side 3 GORASP1, HMOX1, MTOR
Multi-pass membrane protein 2 CLDN1, MARVELD1
Golgi apparatus membrane 2 GORASP1, MTOR
Synapse 1 MAPK8
cell cortex 1 DCTN4
cell surface 1 TNF
glutamatergic synapse 1 APOE
Golgi apparatus 3 APOE, GORASP1, NFE2L2
Golgi membrane 2 GORASP1, MTOR
lysosomal membrane 2 GAA, MTOR
neuronal cell body 2 APOE, TNF
Cytoplasm, cytosol 2 AIMP2, NFE2L2
Lysosome 2 GAA, MTOR
endosome 1 BECN1
plasma membrane 8 APOE, CLDN1, GAA, MAPK9, MARVELD1, NFE2L2, SMAD3, TNF
Membrane 8 AIMP2, APOE, CLDN1, GAA, HMOX1, MARVELD1, MTOR, SMAD2
apical plasma membrane 1 CLDN1
axon 1 MAPK8
basolateral plasma membrane 1 CLDN1
extracellular exosome 2 APOE, GAA
Lysosome membrane 2 GAA, MTOR
endoplasmic reticulum 4 APOE, BECN1, HMOX1, KEAP1
extracellular space 4 APOE, HMOX1, IL6, TNF
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 1 HMOX1
Schaffer collateral - CA1 synapse 1 MAPK9
Cell junction, tight junction 1 CLDN1
bicellular tight junction 1 CLDN1
mitochondrion 1 MAPK9
protein-containing complex 2 CLDN1, SMAD2
intracellular membrane-bounded organelle 2 CYP7A1, GAA
Microsome membrane 2 CYP7A1, MTOR
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Secreted 3 APOE, GAA, IL6
extracellular region 4 APOE, GAA, IL6, TNF
Mitochondrion outer membrane 1 MTOR
Single-pass membrane protein 1 CYP7A1
mitochondrial outer membrane 2 HMOX1, MTOR
transcription regulator complex 2 SMAD2, SMAD3
centriolar satellite 1 KEAP1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 DCTN4
external side of plasma membrane 1 TNF
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
midbody 1 KEAP1
Early endosome 1 APOE
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Membrane raft 1 TNF
Cytoplasm, cytoskeleton 2 DCTN4, MARVELD1
focal adhesion 1 DCTN4
cis-Golgi network 1 GORASP1
extracellular matrix 1 APOE
Nucleus, PML body 1 MTOR
PML body 1 MTOR
collagen-containing extracellular matrix 1 APOE
lateral plasma membrane 1 CLDN1
nuclear speck 1 MAPK9
nuclear inner membrane 1 SMAD3
Cytoplasm, myofibril, sarcomere 1 DCTN4
sarcomere 1 DCTN4
receptor complex 1 SMAD3
chromatin 4 GABPA, NFE2L2, SMAD2, SMAD3
mediator complex 1 NFE2L2
phagocytic cup 1 TNF
cytoskeleton 1 MARVELD1
Secreted, extracellular space 1 APOE
spindle pole 1 DCTN4
Cytoplasm, cell cortex 1 DCTN4
actin filament 1 KEAP1
blood microparticle 1 APOE
Basolateral cell membrane 1 CLDN1
Cul3-RING ubiquitin ligase complex 1 KEAP1
nuclear envelope 1 MTOR
Endomembrane system 1 MTOR
phagophore assembly site 1 BECN1
phosphatidylinositol 3-kinase complex, class III, type I 1 BECN1
phosphatidylinositol 3-kinase complex, class III, type II 1 BECN1
tertiary granule membrane 1 GAA
Melanosome 1 APOE
stress fiber 1 DCTN4
endoplasmic reticulum lumen 2 APOE, IL6
dynactin complex 1 DCTN4
kinetochore 1 DCTN4
azurophil granule membrane 1 GAA
tight junction 1 CLDN1
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GORASP1
cytoplasmic dynein complex 1 DCTN4
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
Single-pass type IV membrane protein 1 HMOX1
clathrin-coated endocytic vesicle membrane 1 APOE
Cytoplasm, cytoskeleton, stress fiber 1 DCTN4
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
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
Cytoplasmic vesicle, phagosome 1 MTOR
activin responsive factor complex 1 SMAD2
discoidal high-density lipoprotein particle 1 APOE
endocytic vesicle lumen 1 APOE
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
chylomicron remnant 1 APOE
intermediate-density lipoprotein particle 1 APOE
lipoprotein particle 1 APOE
multivesicular body, internal vesicle 1 APOE
inclusion body 1 KEAP1
interleukin-6 receptor complex 1 IL6
autolysosome lumen 1 GAA
cytoplasmic side of mitochondrial outer membrane 1 BECN1
[Beclin-1-C 35 kDa]: Mitochondrion 1 BECN1
[Beclin-1-C 37 kDa]: Mitochondrion 1 BECN1
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]
  • 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]
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  • 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]
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