Procyanidin C1 (BioDeep_00000000596)

 

Secondary id: BioDeep_00000398376

human metabolite PANOMIX_OTCML-2023 PANOMIX-Anthocyanidin natural product


代谢物信息卡片


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

化学式: C45H38O18 (866.2058)
中文名称: 原花青素 C1, 原花青素C1
谱图信息: 最多检出来源 Viridiplantae(plant) 27.62%

分子结构信息

SMILES: c12c([C@@H]([C@H]([C@H](O1)c1ccc(c(c1)O)O)O)c1c3c([C@H]([C@H]([C@H](O3)c3ccc(c(c3)O)O)O)c3c4c(C[C@H]([C@@H](O4)c4ccc(c(c4)O)O)O)c(cc3O)O)c(cc1O)O)c(cc(c2)O)O
InChI: InChI=1S/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37-,38+,39-,40-,41-,42-,43-/m1/s1

描述信息

Procyanidin C1 is a proanthocyanidin consisting of three (-)-epicatechin units joined by two successive (4beta->8)-linkages. It has a role as a metabolite, an anti-inflammatory agent, an antioxidant, a lipoxygenase inhibitor, an EC 1.17.3.2 (xanthine oxidase) inhibitor and an EC 3.2.1.20 (alpha-glucosidase) inhibitor. It is a hydroxyflavan, a proanthocyanidin and a polyphenol. It is functionally related to a (-)-epicatechin.
Procyanidin C1 is a natural product found in Campylotropis hirtella, Cinnamomum verum, and other organisms with data available.
See also: Maritime Pine (part of).
Procyanidin C1 is found in apple. Proanthocyanidin C1 is a B type proanthocyanidin. It is an epicatechin trimer found in grape (Vitis vinifera). (Wikipedia).
Proanthocyanidin C1 is a B type proanthocyanidin. It is an epicatechin trimer found in grape (Vitis vinifera). [Wikipedia]
A proanthocyanidin consisting of three (-)-epicatechin units joined by two successive (4beta->8)-linkages.
Procyanidin C1 (PCC1), a natural polyphenol with oral activity, causes DNA damage, cell cycle arrest and induces apoptosis. Procyanidin C1 decreases the level of Bcl-2, but enhances BAX, caspase 3 and 9 expression in cancer cells. Procyanidin C1 shows senotherapeutic activity and increases lifespan in mice[1][2].
Procyanidin C1 (PCC1), a natural polyphenol with oral activity, causes DNA damage, cell cycle arrest and induces apoptosis. Procyanidin C1 decreases the level of Bcl-2, but enhances BAX, caspase 3 and 9 expression in cancer cells. Procyanidin C1 shows senotherapeutic activity and increases lifespan in mice[1][2].

同义名列表

34 个代谢物同义名

(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol; (2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-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; (2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-8-yl]-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-4-yl]chromane-3,5,7-triol; (2R,3R,4R,2R,3R,4S,2R,3R)-2,2,2-Tris-(3,4-dihydroxy-phenyl)-3,4,3,4,3,4-hexahydro-2H,2H,2H-[4,8;4,8]terchromene-3,5,7,3,5,7,3,5,7-nonaol; (2r,2r,2r,3r,3r,3r,4r,4s)-2,2,2-tris(3,4-dihydroxyphenyl)-3,3,3,4,4,4-hexahydro-2h,2h,2h-4,8:4,8-terchromene-3,3,3,5,5,5,7,7,7-nonol; (4,8:4,8-Ter-2H-1-benzopyran)-3,3,3,5,5,5,7,7,7-nonol, 2,2,2-tris(3,4-dihydroxyphenyl)-3,3,3,4,4,4-hexahydro-, stereoisomer; (2R,2R,2R,3R,3R,3R,4R,4S)-2,2,2-Tris(3,4-dihydroxyphenyl)-[4,8:4,8-terchroman]-3,3,3,5,5,5,7,7,7-nonaol; EPICATECHIN-(4.BETA.->8)-EPICATECHIN-(4.BETA.->8)-EPICATECHIN; Epicatechin-(4.beta.-->8)epicatechin-(4.beta.-->8)epicatechin; Epicatechin-(4beta->8)-epicatechin-(4beta->8)-epicatechin; epicatechin-(4beta-8)-epicatechin-(4beta-8)-epicatechin; PROCYANIDIN C1 (CONSTITUENT OF MARITIME PINE) [DSC]; Epicatechin-(4b->8)-epicatechin-(4b->8)-epicatechin; Epicatechin-(4β->8)-epicatechin-(4β->8)-epicatechin; PROCYANIDIN C1 (CONSTITUENT OF MARITIME PINE); (Epicatechin-(4beta->8))2-epicatechin; [Epicatechin-(4beta->8)]2-epicatechin; [Epicatechin-(4b->8)]2-epicatechin; [Epicatechin-(4β->8)]2-epicatechin; (Epicatechin(4b->8))2-epicatechin; [Epicatechin(4b->8)]2-epicatechin; EC-(4b,8)-EC-(4b,8)-EC; procyanidin trimer C1; PROCYANIDIN C1, (+)-; [Epicatechin-(4beta-; Proanthocyanidin C1;; Proanthocyanidin C1; 8)]2-epicatechin; Procyanidin C-1; Cinnamtannin A1; Procyanidin C1; Procyanidol C1; PCC1; SCHEMBL1700872



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)

287 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 7 AIMP2, ANXA5, BCL2, CASP3, CASP9, MAPK8, NOS3
Peripheral membrane protein 1 ANXA5
Endoplasmic reticulum membrane 2 BCL2, HMOX1
Mitochondrion membrane 1 HIGD1A
Nucleus 8 AIMP2, BCL2, CASP3, CASP9, GABPA, HMOX1, MAPK8, NOS3
cytosol 8 AIMP2, ANXA5, BCL2, CASP3, CASP9, HMOX1, MAPK8, NOS3
nucleoplasm 6 CASP3, GABPA, HIGD1A, HMOX1, MAPK8, NOS3
Cell membrane 3 CD80, CD86, TNF
Cytoplasmic side 1 HMOX1
Multi-pass membrane protein 2 HIGD1A, KCNA3
Synapse 1 MAPK8
cell surface 3 CD80, CD86, TNF
glutamatergic synapse 2 CASP3, KCNA3
Golgi apparatus 1 NOS3
Golgi membrane 2 INS, NOS3
lysosomal membrane 1 GAA
mitochondrial inner membrane 1 HIGD1A
neuronal cell body 2 CASP3, TNF
presynaptic membrane 1 KCNA3
sarcolemma 1 ANXA5
Cytoplasm, cytosol 1 AIMP2
Lysosome 1 GAA
plasma membrane 8 CD80, CD86, GAA, IGHE, KCNA3, NOS3, PRSS27, TNF
Membrane 9 AIMP2, ANXA5, BCL2, CD80, CD86, GAA, HIGD1A, HMOX1, KCNA3
axon 2 KCNA3, MAPK8
caveola 1 NOS3
extracellular exosome 3 ANXA5, CD86, GAA
Lysosome membrane 1 GAA
endoplasmic reticulum 2 BCL2, HMOX1
extracellular space 6 HMOX1, IGHE, IL2, IL6, INS, TNF
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 3 HMOX1, KCNA3, NOS3
mitochondrion 3 BCL2, CASP9, HIGD1A
protein-containing complex 3 BCL2, CASP9, HIGD1A
intracellular membrane-bounded organelle 1 GAA
postsynaptic density 1 CASP3
Single-pass type I membrane protein 3 CD80, CD86, IGHE
Secreted 4 GAA, IL2, IL6, INS
extracellular region 8 ANXA5, GAA, IGHE, IL2, IL6, INS, PRSS27, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 2 BCL2, HMOX1
centriolar satellite 1 CD86
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 4 ANXA5, CD80, CD86, TNF
Cytoplasm, P-body 1 NOS3
P-body 1 NOS3
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 1 KCNA3
Mitochondrion inner membrane 1 HIGD1A
Membrane raft 2 KCNA3, TNF
pore complex 1 BCL2
focal adhesion 1 ANXA5
collagen-containing extracellular matrix 1 ANXA5
Zymogen granule membrane 1 ANXA5
chromatin 1 GABPA
IgE immunoglobulin complex 1 IGHE
phagocytic cup 1 TNF
cytoskeleton 1 NOS3
[Isoform 2]: Cell membrane 2 IGHE, KCNA3
endosome lumen 1 INS
tertiary granule membrane 1 GAA
Cytoplasm, Stress granule 1 NOS3
cytoplasmic stress granule 1 NOS3
myelin sheath 1 BCL2
voltage-gated potassium channel complex 1 KCNA3
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 IL6, INS
endocytic vesicle membrane 1 NOS3
transport vesicle 1 INS
azurophil granule membrane 1 GAA
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
Single-pass type IV membrane protein 1 HMOX1
apoptosome 1 CASP9
calyx of Held 1 KCNA3
vesicle membrane 1 ANXA5
ficolin-1-rich granule membrane 1 GAA
basal dendrite 1 MAPK8
death-inducing signaling complex 1 CASP3
[Isoform 1]: Cell membrane 1 KCNA3
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
[Isoform 3]: Cell membrane 1 IGHE
[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
interleukin-6 receptor complex 1 IL6
endothelial microparticle 1 ANXA5
autolysosome lumen 1 GAA
BAD-BCL-2 complex 1 BCL2
protein complex involved in cell adhesion 1 CD80
[Isoform 3]: Cytoplasm, perinuclear region 1 KCNA3
caspase complex 1 CASP9
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Tomas Heger, Marek Zatloukal, Martin Kubala, Miroslav Strnad, Jiri Gruz. Procyanidin C1 from Viola odorata L. inhibits Na+,K+-ATPase. Scientific reports. 2022 04; 12(1):7011. doi: 10.1038/s41598-022-11086-y. [PMID: 35487935]
  • Daniele C Cary, B Matija Peterlin. Procyanidin trimer C1 reactivates latent HIV as a triple combination therapy with kansui and JQ1. PloS one. 2018; 13(11):e0208055. doi: 10.1371/journal.pone.0208055. [PMID: 30475902]
  • 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]
  • 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]
  • Hyung-In Moon, Tae-im Kim, Hyun-Soo Cho, Eung Kweon Kim. Identification of potential and selective collagenase, gelatinase inhibitors from Crataegus pinnatifida. Bioorganic & medicinal chemistry letters. 2010 Feb; 20(3):991-3. doi: 10.1016/j.bmcl.2009.12.059. [PMID: 20053563]
  • 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]