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MedKoo Cat#: 564535 | Name: Procyanidin B1
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Procyanidin B1 is a natural anti-inflammatory agent via interaction with the TLR4-MD-2 heterodimer and p38 MAPK and NF-κB signaling -- Procyanidin B1 displays potential anticancer effects.

Chemical Structure

Procyanidin B1
CAS#20315-25-7

Theoretical Analysis

MedKoo Cat#: 564535

Name: Procyanidin B1

CAS#: 20315-25-7

Chemical Formula: C30H26O12

Exact Mass: 578.1424

Molecular Weight: 578.53

Elemental Analysis: C, 62.28; H, 4.53; O, 33.19

Price and Availability

Size Price Availability Quantity
1mg USD 375.00
5mg USD 625.00
10mg USD 950.00
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Synonym
Proanthocyanidin B1; Epicatechin-(4beta->8)-ent-epicatechin; Procyanidin B1
IUPAC/Chemical Name
(2R,3S)-2-(3,4-Dihydroxyphenyl)-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
InChi Key
XFZJEEAOWLFHDH-UKWJTHFESA-N
InChi Code
InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26+,27+,28+,29+/m0/s1
SMILES Code
O[C@@H]1[C@@H](C2=CC=C(O)C(O)=C2)OC3=C(C(O)=CC(O)=C3[C@@H]4[C@@H](O)[C@@H](C5=CC=C(O)C(O)=C5)OC6=C4C(O)=CC(O)=C6)C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Procyanidin B1 is a polyphenolic flavonoid isolated from commonly eaten fruits, binds to TLR4/MD-2 complex, and has anti-inflammatory activity.
In vitro activity:
The production of TNF-α was significantly decreased by procyanidin B1 in LPS-treated THP1 cells (p < 0.05). Procyanidin B1 also significantly suppressed levels of phosphorylated p38 MAPK and NF-κB protein, as well as mRNA levels of MD-2, TRAF-6, and NF-κB (all p < 0.05). Procyanidin B1 can compete with LPS for binding to the TLR4-MD-2 heterodimer and suppress downstream activation of p38 MAPK and NF-κB signaling pathways. Reference: Mol Cell Biochem. 2015 Sep;407(1-2):89-95. https://pubmed.ncbi.nlm.nih.gov/26037075/
In vivo activity:
Flavangenol suppressed intrahepatic fat accumulation in Western diet-loaded Tsumura Suzuki Obese Diabetes (TSOD) mice, which develop various metabolic diseases. Procyanidin B1, one of the major components of Flavangenol, also suppressed fat accumulation and induced mRNA expression of the fatty acid oxidative enzymes. As mentioned above, Flavangenol showed a significant suppressive effect in the NAFLD model, and it was suggested that the molecular mechanism is induction of fatty acid oxidation, with the effect mainly attributed to procyanidin B1. Reference: Eur J Pharmacol. 2012 Feb 29;677(1-3):147-53. https://pubmed.ncbi.nlm.nih.gov/22227333/
Solvent mg/mL mM comments
Solubility
DMF 30.0 51.86
DMSO 51.7 89.31
Ethanol 30.0 51.86
PBS (pH 7.2) 10.0 17.29
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 578.53 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Xing J, Li R, Li N, Zhang J, Li Y, Gong P, Gao D, Liu H, Zhang Y. Anti-inflammatory effect of procyanidin B1 on LPS-treated THP1 cells via interaction with the TLR4-MD-2 heterodimer and p38 MAPK and NF-κB signaling. Mol Cell Biochem. 2015 Sep;407(1-2):89-95. doi: 10.1007/s11010-015-2457-4. Epub 2015 Jun 3. PMID: 26037075. 2. Kanno H, Kawakami Z, Tabuchi M, Mizoguchi K, Ikarashi Y, Kase Y. Protective effects of glycycoumarin and procyanidin B1, active components of traditional Japanese medicine yokukansan, on amyloid β oligomer-induced neuronal death. J Ethnopharmacol. 2015 Jan 15;159:122-8. doi: 10.1016/j.jep.2014.10.058. Epub 2014 Nov 4. PMID: 25446602. 3. Gao W, Yu T, Li G, Shu W, Jin Y, Zhang M, Yu X. Antioxidant Activity and Anti-Apoptotic Effect of the Small Molecule Procyanidin B1 in Early Mouse Embryonic Development Produced by Somatic Cell Nuclear Transfer. Molecules. 2021 Oct 12;26(20):6150. doi: 10.3390/molecules26206150. PMID: 34684730; PMCID: PMC8540974. 4. Shimada T, Tokuhara D, Tsubata M, Kamiya T, Kamiya-Sameshima M, Nagamine R, Takagaki K, Sai Y, Miyamoto K, Aburada M. Flavangenol (pine bark extract) and its major component procyanidin B1 enhance fatty acid oxidation in fat-loaded models. Eur J Pharmacol. 2012 Feb 29;677(1-3):147-53. doi: 10.1016/j.ejphar.2011.12.034. Epub 2011 Dec 29. PMID: 22227333.
In vitro protocol:
1. Xing J, Li R, Li N, Zhang J, Li Y, Gong P, Gao D, Liu H, Zhang Y. Anti-inflammatory effect of procyanidin B1 on LPS-treated THP1 cells via interaction with the TLR4-MD-2 heterodimer and p38 MAPK and NF-κB signaling. Mol Cell Biochem. 2015 Sep;407(1-2):89-95. doi: 10.1007/s11010-015-2457-4. Epub 2015 Jun 3. PMID: 26037075. 2. Kanno H, Kawakami Z, Tabuchi M, Mizoguchi K, Ikarashi Y, Kase Y. Protective effects of glycycoumarin and procyanidin B1, active components of traditional Japanese medicine yokukansan, on amyloid β oligomer-induced neuronal death. J Ethnopharmacol. 2015 Jan 15;159:122-8. doi: 10.1016/j.jep.2014.10.058. Epub 2014 Nov 4. PMID: 25446602.
In vivo protocol:
1. Gao W, Yu T, Li G, Shu W, Jin Y, Zhang M, Yu X. Antioxidant Activity and Anti-Apoptotic Effect of the Small Molecule Procyanidin B1 in Early Mouse Embryonic Development Produced by Somatic Cell Nuclear Transfer. Molecules. 2021 Oct 12;26(20):6150. doi: 10.3390/molecules26206150. PMID: 34684730; PMCID: PMC8540974. 2. Shimada T, Tokuhara D, Tsubata M, Kamiya T, Kamiya-Sameshima M, Nagamine R, Takagaki K, Sai Y, Miyamoto K, Aburada M. Flavangenol (pine bark extract) and its major component procyanidin B1 enhance fatty acid oxidation in fat-loaded models. Eur J Pharmacol. 2012 Feb 29;677(1-3):147-53. doi: 10.1016/j.ejphar.2011.12.034. Epub 2011 Dec 29. PMID: 22227333.
1: Hou JH, Kong FY, Mu LT, Gao JS, Sun SY, Zhang Y, Sun CH. A recoverable hydrophilic deep eutectic solvent for efficient extraction of polyphenolic compounds from raspberry root. J Food Sci. 2024 Aug 21. doi: 10.1111/1750-3841.17318. Epub ahead of print. PMID: 39169544. 2: Liu Z, Yang Y, Xu Y, Zhang Z, Tang R, Liu J, Jiang H, Zhao R. Procyanidin B1 and p-coumaric acid from whole highland barley ameliorated HFD-induced impaired glucose tolerance via small intestinal barrier and hepatic glucose metabolism. Food Funct. 2024 Aug 20. doi: 10.1039/d4fo02805h. Epub ahead of print. PMID: 39162187. 3: Chen M, Ye S, Deng M, Zhang L, Yu S. Enzyme-esterified grape seed proanthocyanidin derivatives as novel lipid-lowering agents. Food Res Int. 2024 Oct;193:114860. doi: 10.1016/j.foodres.2024.114860. Epub 2024 Jul 31. PMID: 39160055. 4: Belenichev I, Ryzhenko V, Popazova O, Bukhtiyarova N, Gorchakova N, Oksenych V, Kamyshnyi O. Optimization of the Search for Neuroprotectors among Bioflavonoids. Pharmaceuticals (Basel). 2024 Jul 3;17(7):877. doi: 10.3390/ph17070877. PMID: 39065728; PMCID: PMC11279701. 5: Salih E, Mgbeahuruike EE, Prévost-Monteiro S, Sipari N, Väre H, Novak B, Julkunen-Tiitto R, Fyhrqvist P. Polyphenols and Phenolic Glucosides in Antibacterial Twig Extracts of Naturally Occurring Salix myrsinifolia (Salisb.), S. phylicifolia (L.) and S. starkeana (Willd.) and the Cultivated Hybrid S. x pendulina (Wender.). Pharmaceutics. 2024 Jul 9;16(7):916. doi: 10.3390/pharmaceutics16070916. PMID: 39065613; PMCID: PMC11280161. 6: Fernandes FG, da Costa WKA, Dos Santos Lima M, de Lima Costa IH, Magnani M, da Silva Campelo Borges G. A new plant-based probiotic from juá: Source of phenolics, fibers and antioxidant properties. Food Chem. 2024 Nov 15;458:140162. doi: 10.1016/j.foodchem.2024.140162. Epub 2024 Jun 19. PMID: 38943964. 7: Ningsih SS, Fadilah F, Jusman SWA, Syaidah R, Yashiro T. Profibrotic Inflammatory Cytokines and Growth Factors Are Predicted as the Key Targets of Uncaria gambir (Hunter) Roxb. in Keloids: An Epistatic and Molecular Simulation Approach. Pharmaceuticals (Basel). 2024 May 21;17(6):662. doi: 10.3390/ph17060662. PMID: 38931330; PMCID: PMC11206663. 8: Liu Z, Liu J, Tang R, Zhang Z, Tian S. Procyanidin B1 and Coumaric Acid from Highland Barley Alleviated High-Fat-Diet-Induced Hyperlipidemia by Regulating PPARα-Mediated Hepatic Lipid Metabolism and Gut Microbiota in Diabetic C57BL/6J Mice. Foods. 2024 Jun 12;13(12):1843. doi: 10.3390/foods13121843. PMID: 38928784; PMCID: PMC11202444. 9: Li P, Wang C, Chen G, Han Y, Lu H, Li N, Lv Y, Chu C, Peng X. Molecular mechanisms of Tetrastigma hemsleyanum Diels&Gilg against lung squamous cell carcinoma: From computational biology and experimental validation. J Ethnopharmacol. 2024 Sep 15;331:118326. doi: 10.1016/j.jep.2024.118326. Epub 2024 May 17. PMID: 38750988. 10: Athaillah ZA, Wang SC. Physical and chemical characteristics of walnut (Juglans regia L.) kernels with different skin lightness. J Food Sci. 2024 May;89(5):2730-2746. doi: 10.1111/1750-3841.17042. Epub 2024 Mar 27. PMID: 38534189. 11: Francisco AP, Sganzerla WG, Nochi Castro LE, Cruz Tabosa Barroso TL, da Silva APG, da Rosa CG, Nunes MR, Forster-Carneiro T, Rostagno MA. Pressurized liquid extraction of bioactive compounds from grape peel and application in pH- sensing carboxymethyl cellulose films: A promising material to monitor the freshness of pork and milk. Food Res Int. 2024 Mar;179:114017. doi: 10.1016/j.foodres.2024.114017. Epub 2024 Jan 12. PMID: 38342539. 12: Tan MJ, Li Y, Zhao SQ, Yue FH, Cai DJ, Wu JT, Zeng XA, Li J, Han Z. Synergistic ultrasound pulsed electric field extraction of litchi peel polyphenols and determination of their properties. Int J Biol Macromol. 2024 Mar;260(Pt 2):129613. doi: 10.1016/j.ijbiomac.2024.129613. Epub 2024 Jan 20. PMID: 38246440. 13: Bie S, Zhao S, Cai S, Yi J, Zhou L. The profiles of free, esterified and insoluble-bound phenolics in peach juice after high pressure homogenization and evaluation of their antioxidant capacities, cytoprotective effect, and inhibitory effects on α-glucosidase and dipeptidyl peptidase-Ⅳ. Food Chem X. 2023 Dec 25;21:101092. doi: 10.1016/j.fochx.2023.101092. PMID: 38223527; PMCID: PMC10784678. 14: Chen X, Song H, Zhou S, Yuan C, Li J. Exploring separation patterns and mechanisms of proanthocyanidins in grape seeds and pomace with diverse molecular weights, compositions, and structures. Food Chem X. 2023 Nov 14;20:101008. doi: 10.1016/j.fochx.2023.101008. PMID: 38144768; PMCID: PMC10740050. 15: Galaz Torres C, Ricci A, Parpinello GP, Gambuti A, Rinaldi A, Moio L, Rolle L, Paissoni MA, Mattivi F, Perenzoni D, Arapitsas P, Marangon M, Mayr Marangon C, Slaghenaufi D, Ugliano M, Versari A. Multivariate prediction of Saliva Precipitation Index for relating selected chemical parameters of red wines to the sensory perception of astringency. Curr Res Food Sci. 2023 Oct 26;7:100626. doi: 10.1016/j.crfs.2023.100626. PMID: 38021261; PMCID: PMC10651451. 16: Piccolo V, Maisto M, Schiano E, Iannuzzo F, Keivani N, Manuela Rigano M, Santini A, Novellino E, Carlo Tenore G, Summa V. Phytochemical investigation and antioxidant properties of unripe tomato cultivars (Solanum lycopersicum L.). Food Chem. 2024 Apr 16;438:137863. doi: 10.1016/j.foodchem.2023.137863. Epub 2023 Nov 10. PMID: 37980871. 17: Gandhi Y, Rawat H, Singh Dhanjal D, Kumar V, Charde V, Soni H, Mishra SK, Singh G, Singh S, Sharma P, Shakya SK, Narsimhaji CV, Meena AK, Singh A, Singh R, Srikanth N, Acharya R. A Comparative Analysis of Phytochemicals, Metal Ions, Volatile Metabolites in Heart Wood, Stem Bark and Leaves of Salix alba L. along with in Vitro Antioxidant, Antacid, Antimicrobial Activities for Sake of Environment Conservation by Substitution of Stem Bark With Leaf. Chem Biodivers. 2023 Dec;20(12):e202301234. doi: 10.1002/cbdv.202301234. Epub 2023 Nov 27. PMID: 37867394. 18: Xu Y, Wang J, Wu Z, Huang J, Li Z, Xu J, Long D, Ye T, Wang G, Yin J, Luo Z, Xu Y. The role of glutathione in stabilizing aromatic volatile organic compounds in Rougui Oolong tea: A comprehensive study from content to mechanisms. Food Chem. 2024 Mar 30;437(Pt 1):137802. doi: 10.1016/j.foodchem.2023.137802. Epub 2023 Oct 19. PMID: 37866345. 19: Lv H, Guo S. Comparative analysis of flavonoid metabolites from different parts of Hemerocallis citrina. BMC Plant Biol. 2023 Oct 13;23(1):491. doi: 10.1186/s12870-023-04510-6. PMID: 37828495; PMCID: PMC10571393. 20: Lei Y, Deng X, Zhang Z, Chen J. Natural product procyanidin B1 as an antitumor drug for effective therapy of colon cancer. Exp Ther Med. 2023 Sep 14;26(5):506. doi: 10.3892/etm.2023.12205. PMID: 37822589; PMCID: PMC10562962.

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