| Identification | Back Directory | [Name]
PROCYANIDIN C1 | [CAS]
37064-30-5 | [Synonyms]
procyanidolc1
PROCYANIDIN C1
Procyanidin ci
Cinnamtannin A1
PROCYANIDIN B2(P)
PROCYANIDIN C1 USP/EP/BP
(2R,2'R,2''R,3R,3'R,3''R,4R,4'S)
-2,2',2''-Tris(3,4-dihydroxyphenyl)
-[4,8':4',8''-terchroman]-3,3',3'',5,5',5'',7,7',7''-nonaol
4-dihydroxyphenyl)-3,3’,3’’,4,4’,4’’-hexahydro-is(stereoisomer
(4,8’:4’,8’’-ter-2h-1-benzopyran)-3,3’,3’’,5,5’,5’’,7,7’,7’’-nonol,2,2’,2’’-tr
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-, (2R,2R,2R,3R,3R,3R,4R,4S)-
(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,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 | [Molecular Formula]
C45H38O18 | [MDL Number]
MFCD01682743 | [MOL File]
37064-30-5.mol | [Molecular Weight]
866.77 |
| Chemical Properties | Back Directory | [density ]
1.747±0.06 g/cm3( 20 ºC : 760 Torr) | [storage temp. ]
-20°C | [solubility ]
Soluble in methan | [form ]
neat | [pka]
9.19±0.70(Predicted) | [color ]
Beige-brown | [Major Application]
food and beverages | [InChIKey]
MOJZMWJRUKIQGL-XILRTYJMSA-N | [SMILES]
O[C@@H]1Cc2c(O)cc(O)c([C@@H]3[C@@H](O)[C@H](Oc4c([C@@H]5[C@@H](O)[C@H](Oc6cc(O)cc(O)c56)c7ccc(O)c(O)c7)c(O)cc(O)c34)c8ccc(O)c(O)c8)c2O[C@@H]1c9ccc(O)c(O)c9 |
| Hazard Information | Back Directory | [Description]
Procyanidin C1 is a polyphenol flavonoid trimer of (–)-epicatechin (Item No. 11807) that has HIV-related and antioxidant activities.1,2 It activates latent HIV-1 provirus in JLR2 cells when used at concentrations ranging from 12.5 to 50 μM and increases NF-κB-dependent transcriptional activity in Jurkat T cells.1 Procyanidin C1 also scavenges 2,2’-diphenyl-1-picrylhydrazyl (DPPH) radicals (IC50 = 3.2 μg/ml) and inhibits the activity of α-glucosidase (IC50 = 3.8 μg/ml) and 15-lipoxygenase (15-LO; IC50 = 57.6 μg/ml).2 Procyanidin C1 (10 μg/ml) prevents phosphorylation of ERK1/2 and the production of reactive oxygen species (ROS) in THP-1 cells.3 | [Uses]
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]. | [Definition]
ChEBI: 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. | [in vivo]
Procyanidin C1 (20 mg/kg; i.p.; 2 weeks after the first MIT dose and then delivered biweekly) increases tumour regression[2]. Procyanidin C1 (20 mg/kg; i.p.; for 7 d) shows senolytic efficacy in mice with senescent mouse embryonic fibroblasts injection[2]. Procyanidin C1 (20 mg/kg; p.o.; for 3 d) increases the lifespan of old mice[2]. | Animal Model: | Non-obese diabetes and severe combined immunodficiency mice with PSC27 and PC3 cancer cells injection, and pre-treated with mitoxantrone (MIT)[2] | | Dosage: | 20 mg/kg | | Administration: | Intraperitoneal injection; 20 mg/kg; 2 weeks after the first MIT dose and then delivered biweekly | | Result: | Remarkably enhanced tumour regression (55.2% reduction in tumour size compared with
MIT alone; 74.9% reduction in tumour volume compared with the placebo treatment) and depleted the majority of senescent cells in chemotherapy treated animals.
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| Animal Model: | 24-27 months of age mice (both sexes)[2] | | Dosage: | 20 mg/kg | | Administration: | Oral gavage; 20 mg/kg; for three consecutive days | | Result: | Enhanced the median post-treatment lifespan with 64.2% and decreased the mortality hazard than the vehicle-treated group.
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| [References]
[1] Koteswari LL, et al. A comparative anticancer study on procyanidin C1 against receptor positive and receptor negative breast cancer. Nat Prod Res. 2019 Jan 8:1-8. DOI:10.1080/14786419.2018.1557173
[2] Xu Q, et al. The flavonoid procyanidin C1 has senotherapeutic activity and increases lifespan in mice. Nat Metab. 2021 Dec;3(12):1706-1726. DOI:10.1038/s42255-021-00491-8 |
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