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punicalagin

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CAS Number: 65995-63-3Picture of molecule3D/inchi
FDA UNII: Search
MDL:MFCD09838017
XlogP3-AA:1.50 (est)
Molecular Weight:1084.72716000
Formula:C48 H28 O30
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
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Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Flash Point: 32.00 °F. TCC ( 0.00 °C. ) (est)
logP (o/w): 1.442 (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Punicalagin 98%
BOC Sciences
For experimental / research use only.
Punicalagin >98%
Odor: characteristic
Use: Punicalagin is an ellagitannin, a type of phenolic compounds. It had a greater antifungal activity against T. rubrum. It has the potential to be developed as an alternative or supplemental agent for prevention of Salmonella infection.
Changsha Organic Herb
Pomegranate Extract Punicalagin A + B Ellagic Acid
Glentham Life Sciences
Punicalagin
Layn Natural ingredients
Pomegranate Bark Extract Punicalagin
Sigma-Aldrich: Sigma
For experimental / research use only.
Punicalagin ≥98% (HPLC), from pomegranate
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for punicalagin usage levels up to:
 not for fragrance use.
 
Recommendation for punicalagin flavor usage levels up to:
 not for flavor use.
 
Safety References:
ClinicalTrials.gov:search
Daily Med:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :16129719
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
Chemidplus:0065995633
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):16129719
Pubchem (sid):135029530
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB05795
FooDB:FDB016425
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 pomegranate bark
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 pomegranate fruit
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 pomegranate leaf
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 pomegranate pericarp
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 pomegranate root bark
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 pomegranate stem bark
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 terminalia catappa
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Synonyms:
 punicalagin
 

Articles:

PubMed:Effects of various protein- and polysaccharide-based clarification agents on antioxidative compounds and colour of pomegranate juice.
PubMed:Efficacy and safety of pomegranate medicinal products for cancer.
PubMed:Anti-atherogenic properties of date vs. pomegranate polyphenols: the benefits of the combination.
PubMed:Pomegranate juice polyphenols induce a phenotypic switch in macrophage polarization favoring a M2 anti-inflammatory state.
PubMed:The promiscuous and synergic molecular interaction of polyphenols in bactericidal activity: an opportunity to improve the performance of antibiotics?
PubMed:Nanoencapsulation of pomegranate bioactive compounds for breast cancer chemoprevention.
PubMed:Chemical fingerprint and quantitative analysis for quality control of polyphenols extracted from pomegranate peel by HPLC.
PubMed:Punicalagin attenuated cerebral ischemia-reperfusion insult via inhibition of proinflammatory cytokines, up-regulation of Bcl-2, down-regulation of Bax, and caspase-3.
PubMed:Pomegranate ellagitannins inhibit α-glucosidase activity in vitro and reduce starch digestibility under simulated gastro-intestinal conditions.
PubMed:Terminalia catappa L.: a medicinal plant from the Caribbean pharmacopeia with anti-Helicobacter pylori and antiulcer action in experimental rodent models.
PubMed:Mixed pro- and anti-oxidative effects of pomegranate polyphenols in cultured cells.
PubMed:Neuroprotective effect of punicalagin against cerebral ischemia reperfusion-induced oxidative brain injury in rats.
PubMed:An extract of pomegranate fruit and galangal rhizome increases the numbers of motile sperm: a prospective, randomised, controlled, double-blinded trial.
PubMed:Antifungal activity of pomegranate peel extract and isolated compound punicalagin against dermatophytes.
PubMed:Pomegranate phenolics inhibit formation of advanced glycation endproducts by scavenging reactive carbonyl species.
PubMed:Influence of the solvents on the extraction of major phenolic compounds (punicalagin, ellagic acid and gallic acid) and their antioxidant activities in pomegranate aril.
PubMed:Inhibitory effects of pomegranate extracts on recombinant human maltase-glucoamylase.
PubMed:Punicalagin inhibits Salmonella virulence factors and has anti-quorum-sensing potential.
PubMed:Punicalagin inhibits neuroinflammation in LPS-activated rat primary microglia.
PubMed:Punicalagin ameliorates lipopolysaccharide-induced acute respiratory distress syndrome in mice.
PubMed:Small molecule inhibitors of HCV replication from pomegranate.
PubMed:Punicalagin and ellagic acid demonstrate antimutagenic activity and inhibition of benzo[a]pyrene induced DNA adducts.
PubMed:Pomegranate juice and prostate cancer: importance of the characterisation of the active principle.
PubMed:Characterization and Quantification of Compounds in the Hydroalcoholic Extract of the Leaves from Terminalia catappa Linn. (Combretaceae) and Their Mutagenic Activity.
PubMed:Targeted metabolic profiling of pomegranate polyphenols and urolithins in plasma, urine and colon tissues from colorectal cancer patients.
PubMed:Antifungal activity of the ethanolic extracts of Punica granatum L. and evaluation of the morphological and structural modifications of its compounds upon the cells of Candida spp.
PubMed:Punicalagin inhibits inflammation in LPS-induced RAW264.7 macrophages via the suppression of TLR4-mediated MAPKs and NF-κB activation.
PubMed:Tannin-rich fraction from pomegranate rind damages membrane of Listeria monocytogenes.
PubMed:Ellagitannin oligomers and a neolignan from pomegranate arils and their inhibitory effects on the formation of advanced glycation end products.
PubMed:Inhibition of nonenzymatic protein glycation by pomegranate and other fruit juices.
PubMed:Inhibition of melanin content by Punicalagins in the super fruit pomegranate (Punica granatum).
PubMed:Mitochondrial dysfunction in obesity-associated nonalcoholic fatty liver disease: the protective effects of pomegranate with its active component punicalagin.
PubMed:[Addition of pomegranate juice to statin inhibits cholesterol accumulation in macrophages: protective role for the phytosterol beta-sitosterol and for the polyphenolic antioxidant punicalagin].
PubMed:The anti-inflammatory effect of a pomegranate husk extract on inflamed adipocytes and macrophages cultivated independently, but not on the inflammatory vicious cycle between adipocytes and macrophages.
PubMed:Chemical guide parameters for Punica granatum cv. 'Mollar' fruit juices processed at industrial scale.
PubMed:Punicalagin, a polyphenol in pomegranate juice, downregulates p53 and attenuates hypoxia-induced apoptosis in cultured human placental syncytiotrophoblasts.
PubMed:Punicalagin induces apoptotic and autophagic cell death in human U87MG glioma cells.
PubMed:Effects of certain polyphenols and extracts on furans and acrylamide formation in model system, and total furans during storage.
PubMed:HPLC Evaluation of Phenolic Profile, Nutritive Content, and Antioxidant Capacity of Extracts Obtained from Punica granatum Fruit Peel.
PubMed:Thermal stability of liquid antioxidative extracts from pomegranate peel.
PubMed:Broad-spectrum antiviral activity of chebulagic acid and punicalagin against viruses that use glycosaminoglycans for entry.
PubMed:Changes on indigenous microbiota, colour, bioactive compounds and antioxidant activity of pasteurised pomegranate juice.
PubMed:Inhibitory effects of polyphenol punicalagin on type-II collagen degradation in vitro and inflammation in vivo.
PubMed:Specific phenolic compounds and sensory properties of a new dealcoholized red wine with pomegranate (Punica granatum L.) extract.
PubMed:Oxidation of fatty acid may be enhanced by a combination of pomegranate fruit phytochemicals and acetic acid in HepG2 cells.
PubMed:The pomegranate: effects on bacteria and viruses that influence human health.
PubMed:Pomegranate and type 2 diabetes.
PubMed:NMR assignments and the acid-base characterization of the pomegranate ellagitannin punicalagin in the acidic pH-range.
PubMed:Metabolite profiling of polyphenols in a Terminalia chebula Retzius ayurvedic decoction and evaluation of its chemopreventive activity.
PubMed:Anti-proliferative activity and protection against oxidative DNA damage by punicalagin isolated from pomegranate husk.
PubMed:Pomegranate polyphenols and extract inhibit nuclear factor of activated T-cell activity and microglial activation in vitro and in a transgenic mouse model of Alzheimer disease.
PubMed:Polyphenols are responsible for the proapoptotic properties of pomegranate juice on leukemia cell lines.
PubMed:Monocyte-macrophage membrane possesses free radicals scavenging activity: stimulation by polyphenols or by paraoxonase 1 (PON1).
PubMed:Purification, antioxidant activity and protein-precipitating capacity of punicalin from pomegranate husk.
PubMed:Sustained deficit irrigation affects the colour and phytochemical characteristics of pomegranate juice.
PubMed:Antiviral activity of punicalagin toward human enterovirus 71 in vitro and in vivo.
PubMed:Pomegranate phytosterol (β-sitosterol) and polyphenolic antioxidant (punicalagin) addition to statin, significantly protected against macrophage foam cells formation.
PubMed:Storage stability of sterilized liquid extracts from pomegranate peel.
PubMed:Anti-inflammatory effects of pomegranate (Punica granatum L.) husk ellagitannins in Caco-2 cells, an in vitro model of human intestine.
PubMed:Inhibition of melanin production by a combination of Siberian larch and pomegranate fruit extracts.
PubMed:Pomegranate materials inhibit flagellin gene expression and flagellar-propelled motility of uropathogenic Escherichia coli strain CFT073.
PubMed:Partial identification of antifungal compounds from Punica granatum peel extracts.
PubMed:Anti-Helicobacter pylori activity of Terminalia macroptera root.
PubMed:Pomegranate juice and punicalagin attenuate oxidative stress and apoptosis in human placenta and in human placental trophoblasts.
PubMed:Punicalagin and catechins contain polyphenolic substructures that influence cell viability and can be monitored by radical chemosensors sensitive to electron transfer.
PubMed:Enhanced activity of punicalagin delivered via polymeric implants against benzo[a]pyrene-induced DNA adducts.
PubMed:Simple solution for a complex problem: proanthocyanidins, galloyl glucoses and ellagitannins fit on a single calibration curve in high performance-gel permeation chromatography.
PubMed:The antioxidant HDL-associated paraoxonase-1 (PON1) attenuates diabetes development and stimulates β-cell insulin release.
PubMed:Paraoxonase 1 (PON1) inhibits monocyte-to-macrophage differentiation.
PubMed:Identification and quantification of phenolic compounds from pomegranate (Punica granatum L.) peel, mesocarp, aril and differently produced juices by HPLC-DAD-ESI/MS(n).
PubMed:Effects of mass ratio, pH, temperature, and reaction time on fabrication of partially purified pomegranate ellagitannin-gelatin nanoparticles.
PubMed:The swarming motility of Pseudomonas aeruginosa is blocked by cranberry proanthocyanidins and other tannin-containing materials.
PubMed:Fabrication of nanoparticles using partially purified pomegranate ellagitannins and gelatin and their apoptotic effects.
PubMed:Hydrolyzable tannins (chebulagic acid and punicalagin) target viral glycoprotein-glycosaminoglycan interactions to inhibit herpes simplex virus 1 entry and cell-to-cell spread.
PubMed:Pomegranate juice protects macrophages from triglyceride accumulation: inhibitory effect on DGAT1 activity and on triglyceride biosynthesis.
PubMed:Biological activities of phenolic compounds isolated from galls of Terminalia chebula Retz. (Combretaceae).
PubMed:Ellagitannins of the fruit rind of pomegranate (Punica granatum) antagonize in vitro the host inflammatory response mechanisms involved in the onset of malaria.
PubMed:Potent antifungal activity of extracts and pure compound isolated from pomegranate peels and synergism with fluconazole against Candida albicans.
PubMed:The influence of pomegranate by-product and punicalagins on selected groups of human intestinal microbiota.
PubMed:Effects of pomegranate chemical constituents/intestinal microbial metabolites on CYP1B1 in 22Rv1 prostate cancer cells.
PubMed:Paraoxonase 1 (PON1) expression in hepatocytes is upregulated by pomegranate polyphenols: a role for PPAR-gamma pathway.
PubMed:Pomegranate juice polyphenols increase recombinant paraoxonase-1 binding to high-density lipoprotein: studies in vitro and in diabetic patients.
PubMed:Environmental conditions affect the color, taste, and antioxidant capacity of 11 pomegranate accessions' fruits.
PubMed:The effect of pomegranate (Punica granatum L.) byproducts and ellagitannins on the growth of human gut bacteria.
PubMed:Pomegranate (Punica granatum) purified polyphenol extract inhibits influenza virus and has a synergistic effect with oseltamivir.
PubMed:Ellagitannins from Terminalia calamansanai induced apoptosis in HL-60 cells.
PubMed:Phytochemical and antifungal studies on Terminalia mollis and Terminalia brachystemma.
PubMed:International multidimensional authenticity specification (IMAS) algorithm for detection of commercial pomegranate juice adulteration.
PubMed:Pomegranate juice inhibits sulfoconjugation in Caco-2 human colon carcinoma cells.
PubMed:Multitargeted therapy of cancer by ellagitannins.
PubMed:Immune-suppressive activity of punicalagin via inhibition of NFAT activation.
PubMed:Tannin 1-alpha-O-galloylpunicalagin induces the calcium-dependent activation of endothelial nitric-oxide synthase via the phosphatidylinositol 3-kinase/Akt pathway in endothelial cells.
PubMed:The use of microfluorometric method for activity-guided isolation of antiplasmodial compound from plant extracts.
PubMed:Pomegranate phenolics from the peels, arils, and flowers are antiatherogenic: studies in vivo in atherosclerotic apolipoprotein e-deficient (E 0) mice and in vitro in cultured macrophages and lipoproteins.
PubMed:Antioxidant activity, polyphenol content, and related compounds in different fruit juices and homogenates prepared from 29 different pomegranate accessions.
PubMed:Preparative separation of punicalagin from pomegranate husk by high-speed countercurrent chromatography.
PubMed:Cytoprotective effect of preparations from various parts of Punica granatum L. fruits in oxidatively injured mammalian cells in comparison with their antioxidant capacity in cell free systems.
PubMed:Macrophage paraoxonase 2 (PON2) expression is up-regulated by pomegranate juice phenolic anti-oxidants via PPAR gamma and AP-1 pathway activation.
PubMed:In vitro studies on the binding, antioxidant, and cytotoxic actions of punicalagin.
PubMed:A new method of standartization of health-promoting pomegranate fruit (Punica granatum) extract.
PubMed:Morphology and biochemistry of non-glandular trichomes in Cistus salvifolius L. leaves growing in extreme habitats of the Mediterranean basin.
PubMed:Absorption, metabolism, and antioxidant effects of pomegranate (Punica granatum l.) polyphenols after ingestion of a standardized extract in healthy human volunteers.
PubMed:Effects of a pomegranate fruit extract rich in punicalagin on oxidation-sensitive genes and eNOS activity at sites of perturbed shear stress and atherogenesis.
PubMed:Pomegranate juice, total pomegranate ellagitannins, and punicalagin suppress inflammatory cell signaling in colon cancer cells.
PubMed:The dietary hydrolysable tannin punicalagin releases ellagic acid that induces apoptosis in human colon adenocarcinoma Caco-2 cells by using the mitochondrial pathway.
PubMed:beta-Secretase (BACE1) inhibitors from pomegranate (Punica granatum) husk.
PubMed:Chemopreventive effect of punicalagin, a novel tannin component isolated from Terminalia catappa, on H-ras-transformed NIH3T3 cells.
PubMed:Chemical identification of the sources of commercial Fructus Chebulae.
PubMed:Identification of urolithin a as a metabolite produced by human colon microflora from ellagic acid and related compounds.
PubMed:MALDI-TOF mass spectrometry of oligomeric food polyphenols.
PubMed: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.
PubMed:Antimicrobial activity of 10 different plant polyphenols against bacteria causing food-borne disease.
PubMed:Pomegranate fruit extract modulates UV-B-mediated phosphorylation of mitogen-activated protein kinases and activation of nuclear factor kappa B in normal human epidermal keratinocytes paragraph sign.
PubMed:Determination of hydrolyzable tannins in the fruit of Terminalia chebula Retz. by high-performance liquid chromatography and capillary electrophoresis.
PubMed: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.
PubMed:Repeated oral administration of high doses of the pomegranate ellagitannin punicalagin to rats for 37 days is not toxic.
PubMed:Evaluation of the bioavailability and metabolism in the rat of punicalagin, an antioxidant polyphenol from pomegranate juice.
PubMed:Two ellagitannins from Punica granatum heartwood.
PubMed:Pharmacologically active ellagitannins from Terminalia myriocarpa.
PubMed:In vitro anti-Neisseria gonorrhoeae activity of Terminalia macroptera leaves.
PubMed:In vitro antiprotozoal activity of extract and compounds from the stem bark of Combretum molle.
PubMed:Investigations on antimycobacterial activity of some Ethiopian medicinal plants.
PubMed:Antioxidant and hepatoprotective effects of punicalagin and punicalin on acetaminophen-induced liver damage in rats.
PubMed:Antioxidant and free radical scavenging effects of the tannins of Terminalia catappa L.
PubMed:Application of high performance liquid chromatography coupled with ultraviolet spectroscopy and electrospray mass spectrometry to the characterisation of ellagitannins from Terminalia macroptera roots.
PubMed:Antioxidant activity of pomegranate juice and its relationship with phenolic composition and processing.
PubMed:Folk medicine Terminalia catappa and its major tannin component, punicalagin, are effective against bleomycin-induced genotoxicity in Chinese hamster ovary cells.
PubMed:Effects of punicalagin and punicalin on carrageenan-induced inflammation in rats.
PubMed:Antioxidant and hepatoprotective activity of punicalagin and punicalin on carbon tetrachloride-induced liver damage in rats.
PubMed:Antitumorigenic and antipromoting activities of ellagic acid, ellagitannins and oligomeric anthocyanin and procyanidin.
PubMed:Antimicrobial activity of tannins from Terminalia citrina.
PubMed:Isolation and structure determination of terminalin A toxic condensed tannin from Terminalia oblongata.
PubMed:Carbonic anhydrase inhibitors from the pericarps of Punica granatum L.
PubMed:Hepatotoxic and nephrotoxic principles in Terminalia oblongata.
PubMed:Anti-AIDS agents, 2: Inhibitory effects of tannins on HIV reverse transcriptase and HIV replication in H9 lymphocyte cells.
 
Notes:
hepatoprotective agent isolated from terminalia catappa. Constit. of Punica granatum (pomegranate) Punicalagin is the major tannin component of Terminalia catappa and have been characterized to possess antioxidative and anti-genotoxic activities. ; T. catappa has been a popular folk medicine for preventing hepatoma and treating hepatitis in Taiwan; the leaves contain many hydrolyzable tannins. Although the leaves of T. catappa have been claimed to be effective in preventing hepatoma, the mechanism of its chemopreventive effect remains to be elucidated, and their effects on reactive oxygen species (ROS) mediated carcinogenesis are still unclear. (PMID: 16242868)
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