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29106-49-8,MFCD01861513
Catalog No.:AA002X9S

29106-49-8 | Procyanidin B2

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1mg
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$81.00   $57.00
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5mg
≥90%
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25mg
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$457.00   $320.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA002X9S
Chemical Name:
Procyanidin B2
CAS Number:
29106-49-8
Molecular Formula:
C30H26O12
Molecular Weight:
578.5202
MDL Number:
MFCD01861513
SMILES:
Oc1cc(O)c2c(c1)O[C@@H]([C@@H]([C@H]2c1c(O)cc(c2c1O[C@@H]([C@@H](C2)O)c1ccc(c(c1)O)O)O)O)c1ccc(c(c1)O)O
Properties
Computed Properties
 
Complexity:
925  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Heavy Atom Count:
42  
Hydrogen Bond Acceptor Count:
12  
Hydrogen Bond Donor Count:
10  
Rotatable Bond Count:
3  
XLogP3:
2.4  

Downstream Synthesis Route

[1]JournaloftheChemicalSociety.PerkintransactionsI,1984,p.343-350

[2]Phytochemistry,1986,vol.25,p.1209-1216

[3]JournalofOrganicChemistry,2000,vol.65,p.5371-5381

[1]ChemistryofNaturalCompounds,1982,vol.18,p.282-287    KhimiyaPrirodnykhSoedinenii,1982,p.307-312

[2]ChemistryofNaturalCompounds,1982,vol.18,p.282-287    KhimiyaPrirodnykhSoedinenii,1982,p.307-312

[1]JournaloftheChemicalSociety.PerkintransactionsII,1985,p.1439-1444

[1]Tetrahedron,1990,vol.46,p.5733-5740

[2]Tetrahedron,1990,vol.46,p.5733-5740

[1]Chemicalandpharmaceuticalbulletin,1987,vol.35,p.4717-4729

Literature

Title: Procyanidin B2 ameliorates carrageenan-induced chronic nonbacterial prostatitis in rats via anti-inflammatory and activation of the Nrf2 pathway.

Journal: Biochemical and biophysical research communications 20171104

Title: Critical Role of FoxO1 in Granulosa Cell Apoptosis Caused by Oxidative Stress and Protective Effects of Grape Seed Procyanidin B2.

Journal: Oxidative medicine and cellular longevity 20160101

Title: Mechanisms of DNA methyltransferase-inhibitor interactions: Procyanidin B2 shows new promise for therapeutic intervention of cancer.

Journal: Chemico-biological interactions 20150525

Title: Effect of cinnamon and its procyanidin-B2 enriched fraction on diabetic nephropathy in rats.

Journal: Chemico-biological interactions 20141005

Title: Resveratrol and EGCG bind directly and distinctively to miR-33a and miR-122 and modulate divergently their levels in hepatic cells.

Journal: Nucleic acids research 20140101

Title: Bioactivity-guided fractionation of Phyllanthus orbicularis and identification of the principal anti HSV-2 compounds.

Journal: Phytotherapy research : PTR 20121001

Title: Comparison of isolated cranberry (Vaccinium macrocarpon Ait.) proanthocyanidins to catechin and procyanidins A2 and B2 for use as standards in the 4-(dimethylamino)cinnamaldehyde assay.

Journal: Journal of agricultural and food chemistry 20120509

Title: Glucuronidation and methylation of procyanidin dimers b2 and 3,3″-di-o-galloyl-b2 and corresponding monomers epicatechin and 3-o-galloyl-epicatechin in mouse liver.

Journal: Pharmaceutical research 20120301

Title: HPLC-DAD-ESI-MS analysis of flavonoid compounds in 5 seedless table grapes grown in Apulian Region.

Journal: Journal of food science 20120201

Title: Omega-3 docosahexaenoic acid and procyanidins inhibit cyclo-oxygenase activity and attenuate NF-κB activation through a p105/p50 regulatory mechanism in macrophage inflammation.

Journal: The Biochemical journal 20120115

Title: Procyanidin B2 and a cocoa polyphenolic extract inhibit acrylamide-induced apoptosis in human Caco-2 cells by preventing oxidative stress and activation of JNK pathway.

Journal: The Journal of nutritional biochemistry 20111201

Title: Dietary flavanols exert different effects on antioxidant defenses and apoptosis/proliferation in Caco-2 and SW480 colon cancer cells.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20111201

Title: Characterization of procyanidin B2 oxidation products in an apple juice model solution and confirmation of their presence in apple juice by high-performance liquid chromatography coupled to electrospray ion trap mass spectrometry.

Journal: Journal of mass spectrometry : JMS 20111101

Title: Intestinal transit and systemic metabolism of apple polyphenols.

Journal: European journal of nutrition 20111001

Title: Comparative effects of dietary flavanols on antioxidant defences and their response to oxidant-induced stress on Caco2 cells.

Journal: European journal of nutrition 20110801

Title: Grape seed procyanidin B2 inhibits advanced glycation end product-induced endothelial cell apoptosis through regulating GSK3β phosphorylation.

Journal: Cell biology international 20110701

Title: Induction of lactadherin mediates the apoptosis of endothelial cells in response to advanced glycation end products and protective effects of grape seed procyanidin B2 and resveratrol.

Journal: Apoptosis : an international journal on programmed cell death 20110701

Title: Oligomeric proanthocyanidins from Rumex acetosa L. inhibit the attachment of herpes simplex virus type-1.

Journal: Antiviral research 20110101

Title: Grape seed procyanidin b2 inhibits human aortic smooth muscle cell proliferation and migration induced by advanced glycation end products.

Journal: Bioscience, biotechnology, and biochemistry 20110101

Title: Procyanidin B2 catabolism by human fecal microflora: partial characterization of 'dimeric' intermediates.

Journal: Archives of biochemistry and biophysics 20100901

Title: A comparison of the in vitro biotransformation of (-)-epicatechin and procyanidin B2 by human faecal microbiota.

Journal: Molecular nutrition & food research 20100601

Title: Influence of gallate esterification on the activity of procyanidin B2 in androgen-dependent human prostate carcinoma LNCaP cells.

Journal: Pharmaceutical research 20100401

Title: In vivo bioavailability, absorption, excretion, and pharmacokinetics of [14C]procyanidin B2 in male rats.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20100201

Title: Reliability of bond dissociation enthalpy calculated by the PM6 method and experimental TEAC values in antiradical QSAR of flavonoids.

Journal: Bioorganic & medicinal chemistry 20100101

Title: Influence of apple polyphenols on inflammatory gene expression.

Journal: Molecular nutrition & food research 20091001

Title: Proanthocyanidin from blueberry leaves suppresses expression of subgenomic hepatitis C virus RNA.

Journal: The Journal of biological chemistry 20090807

Title: Cinchonain Ib isolated from Eriobotrya japonica induces insulin secretion in vitro and in vivo.

Journal: Journal of ethnopharmacology 20090715

Title: Cocoa procyanidins attenuate 4-hydroxynonenal-induced apoptosis of PC12 cells by directly inhibiting mitogen-activated protein kinase kinase 4 activity.

Journal: Free radical biology & medicine 20090515

Title: Cocoa procyanidins suppress transformation by inhibiting mitogen-activated protein kinase kinase.

Journal: The Journal of biological chemistry 20080725

Title: Cocoa procyanidins inhibit expression and activation of MMP-2 in vascular smooth muscle cells by direct inhibition of MEK and MT1-MMP activities.

Journal: Cardiovascular research 20080701

Title: Analysis of CYP3A inhibitory components of star fruit (Averrhoa carambola L.) using liquid chromatography-mass spectrometry.

Journal: Journal of natural medicines 20080701

Title: Cocoa procyanidins protect PC12 cells from hydrogen-peroxide-induced apoptosis by inhibiting activation of p38 MAPK and JNK.

Journal: Mutation research 20080402

Title: Dimeric procyanidin B2 inhibits constitutively active NF-kappaB in Hodgkin's lymphoma cells independently of the presence of IkappaB mutations.

Journal: Biochemical pharmacology 20080401

Title: Rapid preparation of procyanidins B2 and C1 from Granny Smith apples by using low pressure column chromatography and identification of their oligomeric procyanidins.

Journal: Journal of agricultural and food chemistry 20080326

Title: [Phenols from the rhizomes of Arachniodes exilis].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20080201

Title: [Studies on chemical constituents from roots of Craibiodendron henryi].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20070401

Title: Degradation of procyanidins by Aspergillus fumigatus: identification of a novel aromatic ring cleavage product.

Journal: Biochimie 20061201

Title: Inhibitory effects of procyanidin B(2) dimer on lipid-laden macrophage formation.

Journal: Journal of cardiovascular pharmacology 20060801

Title: Procyanidin dimer B2 [epicatechin-(4beta-8)-epicatechin] suppresses the expression of cyclooxygenase-2 in endotoxin-treated monocytic cells.

Journal: Biochemical and biophysical research communications 20060623

Title: Catalytic inhibition of human DNA topoisomerase II by interactions of grape cell culture polyphenols.

Journal: Journal of agricultural and food chemistry 20060322

Title: Procyanidin oligomers counteract TGF-beta1- and TGF-beta2-induced apoptosis in hair epithelial cells: an insight into their mechanisms.

Journal: Skin pharmacology and physiology 20060101

Title: Procyanidin B2 has anti- and pro-oxidant effects on metal-mediated DNA damage.

Journal: Free radical biology & medicine 20051015

Title: Systematic synthesis of galloyl-substituted procyanidin B1 and B2, and their ability of DPPH radical scavenging activity and inhibitory activity of DNA polymerases.

Journal: Bioorganic & medicinal chemistry 20050415

Title: Improved HPLC determination of phenolic compounds in cv. golden delicious apples using a monolithic column.

Journal: Journal of agricultural and food chemistry 20040114

Title: Chemoprevention of colorectal cancer by grape seed proanthocyanidin is accompanied by a decrease in proliferation and increase in apoptosis.

Journal: Nutrition and cancer 20040101

Title: Hawthorn extracts inhibit LDL oxidation.

Journal: Die Pharmazie 20030801

Title: Hyperforin a constituent of St John's wort (Hypericum perforatum L.) extract induces apoptosis by triggering activation of caspases and with hypericin synergistically exerts cytotoxicity towards human malignant cell lines.

Journal: European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20030701

Title: Isolation and structural elucidation of some procyanidins from apple by low-temperature nuclear magnetic resonance.

Journal: Journal of agricultural and food chemistry 20030618

Title: Phenolic constituents and antioxidant capacities of Crataegus monogyna (Hawthorn) callus extracts.

Journal: Die Nahrung 20030601

Title: Plasma levels of hypericin in presence of procyanidin B2 and hyperoside: a pharmacokinetic study in rats.

Journal: Planta medica 20030301

Title: Identification and biochemical characterization of mutants in the proanthocyanidin pathway in Arabidopsis.

Journal: Plant physiology 20021001

Title: Bioactive constituents from Iryanthera megistophylla.

Journal: Journal of natural products 20021001

Title: Varietal differences among the polyphenol profiles of seven table grape cultivars studied by LC-DAD-MS-MS.

Journal: Journal of agricultural and food chemistry 20020925

Title: Absorption and urinary excretion of procyanidin B2 [epicatechin-(4beta-8)-epicatechin] in rats.

Journal: Free radical biology & medicine 20020701

Title: Identification and in vitro biological activities of hop proanthocyanidins: inhibition of nNOS activity and scavenging of reactive nitrogen species.

Journal: Journal of agricultural and food chemistry 20020605

Title: Antiviral and antioxidant activity of flavonoids and proanthocyanidins from Crataegus sinaica.

Journal: Planta medica 20020601

Title: Influence of procyanidins on the color stability of oenin solutions.

Journal: Journal of agricultural and food chemistry 20020522

Title: Immunomodulatory proanthocyanidins from Ecdysanthera utilis.

Journal: Journal of natural products 20020401

Title: Catechins and their oligomers linked by C4 --> C8 bonds are major cacao polyphenols and protect low-density lipoprotein from oxidation in vitro.

Journal: Experimental biology and medicine (Maywood, N.J.) 20020101

Title: Quantification of procyanidins in oral herbal medicinal products containing extracts of Crataegus species.

Journal: Arzneimittel-Forschung 20020101

Title: Pharmacological and endocrine effects of Hypericum perforatum and hypericin after repeated treatment.

Journal: Pharmacopsychiatry 20010701

Title: Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures.

Journal: Nutrition and cancer 20010101

Title: Biological evaluation of proanthocyanidin dimers and related polyphenols.

Journal: Journal of natural products 19990701

Title: Inhibitory effects of Sudanese plant extracts on HIV-1 replication and HIV-1 protease.

Journal: Phytotherapy research : PTR 19990201

Title: Avelar MM, et al. Procyanidin b2 cytotoxicity to mcf-7 human breast adenocarcinoma cells. Indian J Pharm Sci. 2012 Jul;74(4):351-5.

Title: Yang H, et al. Procyanidin B2 inhibits NLRP3 inflammasome activation in human vascular endothelial cells. Biochem Pharmacol. 2014 Dec 15;92(4):599-606.

Title: Wu S, et al. Procyanidin B2 attenuates neurological deficits and blood-brain barrier disruption in a rat model of cerebral ischemia. Mol Nutr Food Res. 2015 Oct;59(10):1930-41.

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Tags:29106-49-8 Molecular Formula|29106-49-8 MDL|29106-49-8 SMILES|29106-49-8 Procyanidin B2