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65995-63-3,MFCD09838017
Catalog No.:AA00IKJ2

65995-63-3 | 2,3-(S)-Hexahydroxydiphenoyl-4,6-(S,S)-gallagyl-D-glucose

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1mg
≥95% mixture of anomers
in stock  
$36.00   $25.00
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5mg
≥95% mixture of anomers
in stock  
$135.00   $94.00
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1g
~40%(HPLC)
in stock  
$161.00   $113.00
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5g
~40%(HPLC)
in stock  
$548.00   $384.00
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00IKJ2
Chemical Name:
2,3-(S)-Hexahydroxydiphenoyl-4,6-(S,S)-gallagyl-D-glucose
CAS Number:
65995-63-3
Molecular Formula:
C48H28O30
Molecular Weight:
1084.7179
MDL Number:
MFCD09838017
SMILES:
O=CC1OC(=O)c2cc(O)c(c(c2c2c(C(=O)OC1C1OC(=O)c3cc(O)c(c(c3c3c(O)c(O)c4c5c3c(=O)oc3c5c(c(c5c(C(=O)OCC1O)cc(O)c(c5O)O)c(O)c3O)c(=O)o4)O)O)cc(c(c2O)O)O)O)O
Properties
Computed Properties
 
Complexity:
2380  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
78  
Hydrogen Bond Acceptor Count:
30  
Hydrogen Bond Donor Count:
17  
Undefined Atom Stereocenter Count:
1  
XLogP3:
1.7  

Literature

Title: Punicalagin, a polyphenol from pomegranate fruit, induces growth inhibition and apoptosis in human PC-3 and LNCaP cells.

Journal: Chemico-biological interactions 20170825

Title: Inhibitory effects of polyphenol punicalagin on type-II collagen degradation in vitro and inflammation in vivo.

Journal: Chemico-biological interactions 20130925

Title: Broad-spectrum antiviral activity of chebulagic acid and punicalagin against viruses that use glycosaminoglycans for entry.

Journal: BMC microbiology 20130101

Title: Inhibition of melanin production by a combination of Siberian larch and pomegranate fruit extracts.

Journal: Fitoterapia 20120901

Title: Anti-Helicobacter pylori activity of Terminalia macroptera root.

Journal: Fitoterapia 20120701

Title: Storage stability of sterilized liquid extracts from pomegranate peel.

Journal: Journal of food science 20120701

Title: Partial identification of antifungal compounds from Punica granatum peel extracts.

Journal: Journal of agricultural and food chemistry 20120516

Title: Pomegranate juice and punicalagin attenuate oxidative stress and apoptosis in human placenta and in human placental trophoblasts.

Journal: American journal of physiology. Endocrinology and metabolism 20120501

Title: Enhanced activity of punicalagin delivered via polymeric implants against benzo[a]pyrene-induced DNA adducts.

Journal: Mutation research 20120318

Title: Punicalagin and catechins contain polyphenolic substructures that influence cell viability and can be monitored by radical chemosensors sensitive to electron transfer.

Journal: Journal of agricultural and food chemistry 20120222

Title: Paraoxonase 1 (PON1) inhibits monocyte-to-macrophage differentiation.

Journal: Atherosclerosis 20111101

Title: Hydrolyzable tannins (chebulagic acid and punicalagin) target viral glycoprotein-glycosaminoglycan interactions to inhibit herpes simplex virus 1 entry and cell-to-cell spread.

Journal: Journal of virology 20110501

Title: Biological activities of phenolic compounds isolated from galls of Terminalia chebula Retz. (Combretaceae).

Journal: Natural product research 20101201

Title: Potent antifungal activity of extracts and pure compound isolated from pomegranate peels and synergism with fluconazole against Candida albicans.

Journal: Research in microbiology 20100901

Title: The influence of pomegranate by-product and punicalagins on selected groups of human intestinal microbiota.

Journal: International journal of food microbiology 20100615

Title: Paraoxonase 1 (PON1) expression in hepatocytes is upregulated by pomegranate polyphenols: a role for PPAR-gamma pathway.

Journal: Atherosclerosis 20100101

Title: Ellagitannins of the fruit rind of pomegranate (Punica granatum) antagonize in vitro the host inflammatory response mechanisms involved in the onset of malaria.

Journal: Malaria journal 20100101

Title: Pomegranate (Punica granatum) purified polyphenol extract inhibits influenza virus and has a synergistic effect with oseltamivir.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20091201

Title: Effects of pomegranate chemical constituents/intestinal microbial metabolites on CYP1B1 in 22Rv1 prostate cancer cells.

Journal: Journal of agricultural and food chemistry 20091125

Title: The effect of pomegranate (Punica granatum L.) byproducts and ellagitannins on the growth of human gut bacteria.

Journal: Journal of agricultural and food chemistry 20090923

Title: Phytochemical and antifungal studies on Terminalia mollis and Terminalia brachystemma.

Journal: Fitoterapia 20090901

Title: International multidimensional authenticity specification (IMAS) algorithm for detection of commercial pomegranate juice adulteration.

Journal: Journal of agricultural and food chemistry 20090325

Title: Pomegranate juice inhibits sulfoconjugation in Caco-2 human colon carcinoma cells.

Journal: Journal of medicinal food 20081201

Title: Immune-suppressive activity of punicalagin via inhibition of NFAT activation.

Journal: Biochemical and biophysical research communications 20080711

Title: Macrophage paraoxonase 2 (PON2) expression is up-regulated by pomegranate juice phenolic anti-oxidants via PPAR gamma and AP-1 pathway activation.

Journal: Atherosclerosis 20071201

Title: In vitro studies on the binding, antioxidant, and cytotoxic actions of punicalagin.

Journal: Journal of agricultural and food chemistry 20070221

Title: Effects of a pomegranate fruit extract rich in punicalagin on oxidation-sensitive genes and eNOS activity at sites of perturbed shear stress and atherogenesis.

Journal: Cardiovascular research 20070115

Title: Absorption, metabolism, and antioxidant effects of pomegranate (Punica granatum l.) polyphenols after ingestion of a standardized extract in healthy human volunteers.

Journal: Journal of agricultural and food chemistry 20061115

Title: A new method of standartization of health-promoting pomegranate fruit (Punica granatum) extract.

Journal: Georgian medical news 20061101

Title: The dietary hydrolysable tannin punicalagin releases ellagic acid that induces apoptosis in human colon adenocarcinoma Caco-2 cells by using the mitochondrial pathway.

Journal: The Journal of nutritional biochemistry 20060901

Title: Pomegranate juice, total pomegranate ellagitannins, and punicalagin suppress inflammatory cell signaling in colon cancer cells.

Journal: Journal of agricultural and food chemistry 20060208

Title: beta-Secretase (BACE1) inhibitors from pomegranate (Punica granatum) husk.

Journal: Archives of pharmacal research 20051201

Title: In vitro antiproliferative, apoptotic and antioxidant activities of punicalagin, ellagic acid and a total pomegranate tannin extract are enhanced in combination with other polyphenols as found in pomegranate juice.

Journal: The Journal of nutritional biochemistry 20050601

Title: The potent in vitro antioxidant ellagitannins from pomegranate juice are metabolised into bioavailable but poor antioxidant hydroxy-6H-dibenzopyran-6-one derivatives by the colonic microflora of healthy humans.

Journal: European journal of nutrition 20040801

Title: Repeated oral administration of high doses of the pomegranate ellagitannin punicalagin to rats for 37 days is not toxic.

Journal: Journal of agricultural and food chemistry 20030521

Title: Evaluation of the bioavailability and metabolism in the rat of punicalagin, an antioxidant polyphenol from pomegranate juice.

Journal: European journal of nutrition 20030101

Title: In vitro anti-Neisseria gonorrhoeae activity of Terminalia macroptera leaves.

Journal: FEMS microbiology letters 20020604

Title: Antioxidant and hepatoprotective effects of punicalagin and punicalin on acetaminophen-induced liver damage in rats.

Journal: Phytotherapy research : PTR 20010501

Title: Seeram NP, et al. In vitro antiproliferative, apoptotic and antioxidant activities of punicalagin, ellagicacid and a total pomegranate tannin extract are enhanced in combination with otherpolyphenols as found in pomegranate juice. J Nutr Biochem. 2005 Jun;16(6):360-7.

Title: Lin CC, et al. Effects of punicalagin and punicalin on carrageenan-induced inflammation in rats. Am J Chin Med. 1999;27(3-4):371-6.

Title: Liu C, et al. Identification of hydrolyzable tannins (punicalagin, punicalin and geraniin) as novel inhibitors of hepatitis B virus covalently closed circular DNA. Antiviral Res. 2016 Oct;134:97-107.

Title: RuikunDu, et al. Discovery of Chebulagic Acid and Punicalagin as Novel Allosteric Inhibitors of SARS-CoV-2 3CLpro. Antivir Res. 2021, 105075.

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Tags:65995-63-3 Molecular Formula|65995-63-3 MDL|65995-63-3 SMILES|65995-63-3 2,3-(S)-Hexahydroxydiphenoyl-4,6-(S,S)-gallagyl-D-glucose