Punicalagin

1084.72

1084.72

636592

Yellow powder

29389090

511

log Kow = -2.33 (est)

faint yellow to dark yellow

2.1±0.1 g/cm3

1.893

methanol: soluble5mg/mL, clear

2-8°C

3.47X10-61 mm Hg at 25 °C (est)

Henry's Law constant = 1.8X10-16 atm-cu m/mol at 25 °C (est)

NONH for all modes of transport

3

24/25

Stable under recommended storage conditions.

SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Air, light, and moisture sensitive.|Strong oxidizing agents, Acids

Not flammable or combustible.

Wear self contained breathing apparatus for fire fighting if necessary.|Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Sweep up and shovel. Keep in suitable, closed containers for disposal.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.|Provide appropriate exhaust ventilation at places where dust is formed.|If pregnant, nursing or taking any medications, consult your healthcare professional before taking this product. Keep out of reach of children.

In an effort to find botanicals containing polyphenolic compounds with the capacity to inhibit melanin biosynthesis, we identified a novel combination of Siberian larch (Larix sibirica) extract, standardized to 80% taxifolin, and pomegranate fruit (Punica granatum) extract, containing 20% punicalagins, that demonstrates a synergistic reduction of melanin biosynthesis in Melan-a cells. The combination of Siberian larch and pomegranate extracts (1:1) produced a 2-fold reduction in melanin content compared to Siberian larch or pomegranate extracts alone with no corresponding effect on cell viability. Siberian larch and pomegranate fruit extracts inhibited expression of melanocyte specific genes, tyrosinase (Tyr), microphthalmia transcription factor (Mitf), and melanosome structural proteins (Pmel17 and Mart1) but did not inhibit tyrosinase enzyme activity. These results suggest that the mechanism of inhibition of melanin biosynthesis by Siberian larch and pomegranate extracts, alone and in combination, is through downregulation of melanocyte specific genes and not due to inhibition of tyrosinase enzyme activity.|Terminalia catappa L. is a popular folk medicine for preventing hepatoma and treating hepatitis in Taiwan. In this paper, /the authors/ examined the protective effects of T. catappa leaf water extract (TCE) and its major tannin component, punicalagin, on bleomycin-induced genotoxicity in cultured Chinese hamster ovary cells. Pre-treatment with TCE or punicalagin prevented bleomycin-induced hgprt gene mutations and DNA strand breaks. TCE and punicalagin suppressed the generation of bleomycin-induced intracellular free radicals, identified as superoxides and hydrogen peroxides. The effectiveness of TCE and punicalagin against bleomycin-induced genotoxicity could be, at least in part, due to their antioxidative potentials.|/The authors/ investigated the effect of punicalagin (PC) on benzo[a]pyrene (BP)-induced DNA adducts in vitro and in vivo. Incubation of BP (1 uM) with rat liver microsomes, appropriate co-factors and DNA in the presence of vehicle or punicalagin (1-40 uM) showed dose-dependent inhibition of the resultant DNA adducts, with essentially complete (97%) inhibition at 40 uM. However, PC failed to inhibit anti-BPDE-induced DNA adducts when tested in an in vitro non-microsomal system, suggesting that the inhibition of the microsomal BP-DNA adducts occurred due to inhibition of P450 1A1 by PC. To determine its efficacy in vivo, female S/D rats were administered punicalagin via the diet (1500 ppm; approximately 19 mg/day/animal) or subcutaneous polymeric implants (two 2-cm, 200mg with 20% drug load; 40 mg PC/implant) and then treated with continuous low-dose of BP by a subcutaneous polymeric implant (2 cm, 200mg with 10% load; 20mg BP/implant) and euthanized after 10 days. Analysis of the lung DNA by (32)P-postlabeling showed significant (60%; p=0.029) inhibition of DNA adducts by PC administered via the implants; the dietary route showed modest (34%) but statistically insignificant inhibition. Furthermore, total PC administered by implants was approximately 38-fold lower compared with the dietary route. Analysis of the lung microsomes showed significant inhibition of cytochrome P450 1A1 activity and induction of glutathione. Release of PC from the implants was found to be biphasic starting with a burst release, followed by a gradual decline. Ultra performance liquid chromatography analysis showed no detectable PC in the plasma but its hydrolyzed product, ellagic acid was readily detected. The plasma concentration of ellagic acid was over two orders of magnitude higher (589 +/-78 ng/mL) in the implant group compared with diet (4.36 +/- 0.83 ng/mL). Together, our data show that delivery of PC by implants can reduce its effective dose substantially, and that the inhibition of DNA adducts in vivo occurred presumably due to the conversion of PC to ellagic acid|Punicalagin and punicalin, isolated from the leaves of Terminalia catappa L., are used to treat dermatitis and hepatitis. Both compounds have strong antioxidative activity. The antihepatotoxic activity of punicalagin and punicalin on carbon tetrachloride (CCl4)-induced toxicity in the rat liver was evaluated. Levels of serum glutamate-oxalate-transaminase and glutamate-pyruvate-trans-aminase were increased by administration of CCl4 and reduced by drug treatment. Histological changes around the liver central vein and oxidation damage induced by CCl4 also benefited from drug treatment. The results show that both punicalagin and punicalin have anti-hepatotoxic activity but that the larger dose of punicalin induced liver damage. Thus even if tannins have strong antioxidant activity at very small doses, treatment with a larger dose will induce cell damage.|For more Interactions (Complete) data for Punicalagin (6 total), please visit the HSDB record page.

LD50 Mice oral greater than 5000 mg/kg|LD50 Rats ip 217 mg/kg|LD50 Mice ip 187 mg/kg|LD50 Rats oral greater than 5000 mg/kg

Punicalagin is present in Punica granatum L., pomegranate(1).

Punicalagin's production and potential use as an inhibitor of cancer cell proliferation(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1X10+10(SRC), determined from a structure estimation method(2), indicates that punicalagin is expected to be immobile in soil(SRC). Volatilization of punicalagin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.8X10-16 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Punicalagin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5X10-61 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Biodegradation data in soil were not available(SRC,2013).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1X10+10(SRC), determined from a structure estimation method(2), indicates that punicalagin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.8X10-16 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of -2.33(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Punicalagin is expected to undergo hydrolysis in the environment due to the presence of functional groups that hydrolyze under environmental conditions(3). Biodegradation data in water were not available(SRC,2013).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), punicalagin, which has an estimated vapor pressure of 3.5X10-61 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase punicalagin may be removed from the air by wet or dry deposition(SRC). Punicalagin contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Punicalagin is expected to undergo hydrolysis in the environment due to the presence of functional groups that hydrolyze under environmental conditions(1). Punicalagin contains chromophores that absorb at wavelengths >290 nm(1) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3 was calculated in fish for punicalagin(SRC), using an estimated log Kow of -2.33(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of punicalagin can be estimated to be 1X10+10(SRC). According to a classification scheme(2), this estimated Koc value suggests that punicalagin is expected to be immobile in soil.

The Henry's Law constant for punicalagin is estimated as 1.8X10-16 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that punicalagin is expected to be essentially nonvolatile from moist soil and water surfaces(2). Punicalagin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5X10-61 mm Hg(SRC), determined from a fragment constant method(3).

Punicalagin is present in pomegranate (Punica granatum L.) fruit husk and during processing is extracted into the juice, reaching levels in excess of >2 g/L(1).

Occupational exposure to punicalagin may occur through dermal contact with this compound at workplaces where punicalagin is extracted or used. Use data indicate that the general population may be exposed to punicalagin via ingestion of pomegranate, pomegranate juices and dietary supplements containing pomegranate. (SRC)

Hydrolyzable Tannins|EXPL THER Human enterovirus 71 is one of the major causative agents of hand, foot and mouth disease in children and has caused mortalities in large-scale outbreaks in the Asia-Pacific region in recent years. No vaccine or antiviral therapy is available currently in the clinic. ...this work... investigated the antiviral effect of punicalagin on enterovirus 71 both in vitro and in vivo. The results showed that punicalagin reduced the viral cytopathic effect on rhabdomyosarcoma cells with an IC50 value of 15 ug/mL. Moreover, punicalagin treatment of mice challenged with a lethal dose of enterovirus 71 resulted in a reduction of mortality and relieved clinical symptoms by inhibiting viral replication. /This/ work suggested that punicalagin have the potential for further development as antiviral agents against enterovirus 71.|EXPL THER Since T cell activation is central to the development of autoimmune diseases, /the authors/ screened a natural product library comprising 1400 samples of medicinal herbal extracts, to identify compounds that suppress T cell activity. Punicalagin (PCG) isolated from the fruit of Punica granatum was identified as a potent immune suppressant, based on its inhibitory action on the activation of the nuclear factor of activated T cells (NFAT). PCG downregulated the mRNA and soluble protein expression of interleukin-2 from anti-CD3/anti-CD28-stimulated murine splenic CD4+ T cells and suppressed mixed leukocytes reaction (MLR) without exhibiting cytotoxicity to the cells. In vivo, the PCG treatment inhibited phorbol 12-myristate 13-acetate (PMA)-induced chronic ear edema in mice and decreased CD3+ T cell infiltration of the inflamed tissue. These results suggest that PCG could be a potential candidate for the therapeutics of various immune pathologies.

... The present study evaluated the possible toxic effect of punicalagin in Sprague-Dawley rats upon repeated oral administration of a 6% punicalagin-containing diet for 37 days. Punicalagin and related metabolites were identified by HPLC-DAD-MS-MS in plasma, liver, and kidney. Five punicalagin-related metabolites were detected in liver and kidney, that is, two ellagic acid derivatives, gallagic acid, 3,8-dihydroxy-6H-dibenzo[b,d]pyran-6-one glucuronide, and 3,8,10-trihydroxy-6H-dibenzo[b,d]pyran-6-one.

Pomegranate, a fruit native to the Middle East, has gained widespread popularity as a functional food and nutraceutical source. The health effects of the whole fruit, as well as its juices and extracts, have been studied in relation to a variety of chronic diseases. Promising results against cardiovascular disease, diabetes, and prostate cancer have been reported from human clinical trials. The in vitro antioxidant activity of pomegranate has been attributed to its high polyphenolic content, specifically punicalagins, punicalins, gallagic acid, and ellagic acid. These compounds are metabolized during digestion to ellagic acid and urolithins, suggesting that the bioactive compounds that provide in vivo antioxidant activity may not be the same as those present in the whole food...|Pomegranates have been shown to contain 124 different phytochemicals, and some of them act in concert to exert antioxidant and anti-inflammatory effects on cancer cells. Ellagitannins are bioactive polyphenols present in pomegranate. Pomegranate juice obtained by squeezing the whole fruit has the highest concentration of ellagitannins than any commonly consumed juice and contains the unique ellagitannin, punicalagin. Punicalagin is the known largest molecular weight polyphenol. Pomegranate ellagitannins are not absorbed intact into the blood stream but are hydrolyzed to ellagic acid over several hours in the intestine. Ellagitannins are also metabolized into urolithins by gut flora, which are conjugated in the liver and excreted in the urine. These urolithins are also bioactive and inhibit prostate cancer cell growth...|Intraperitoneal and oral administration of synthesized urolithin A led to uptake of urolithin A and its conjugates in prostate tissue, and levels were higher in prostate, colon, and intestinal tissues relative to other organs. It is unclear why pomegranate ellagitannins metabolites localize at higher levels in the prostate, colon, and intestinal tissues relative to the other organs studied. Importantly, the predilection of bioactive pomegranate ellagitannins metabolites to localize in prostate tissue, combined with clinical data demonstrating the anticancer effects of pomegranate juice, suggests the potential for pomegranate products to play a role in prostate cancer chemoprevention. Whether uro-lithins in human prostate tissue can be used as a biomarker following the long-term administration of pomegranate juice or pomegranate extract remains to be determined. /pomegranate extract/|... The present study evaluated the possible toxic effect of punicalagin in Sprague-Dawley rats upon repeated oral administration of a 6% punicalagin-containing diet for 37 days. Punicalagin and related metabolites were identified by HPLC-DAD-MS-MS in plasma, liver, and kidney. Five punicalagin-related metabolites were detected in liver and kidney, that is, two ellagic acid derivatives, gallagic acid, 3,8-dihydroxy-6H-dibenzo[b,d]pyran-6-one glucuronide, and 3,8,10-trihydroxy-6H-dibenzo[b,d]pyran-6-one.|Several fruit juices have been reported to cause food-drug interactions, mainly affecting cytochrome P450 activity; however, little is known about the effects of fruit juices on conjugation reactions. Among several fruit juices tested (apple, peach, orange, pineapple, grapefruit, and pomegranate), pomegranate juice potently inhibited the sulfoconjugation of 1-naphthol in Caco-2 cells. This inhibition was both dose- and culture time-dependent, with a 50% inhibitory concentration (IC(50)) value calculated at 2.7% (vol/vol). In contrast, no obvious inhibition of glucuronidation of 1-naphthol in Caco-2 cells was observed by any of the juices examined. Punicalagin, the most abundant antioxidant polyphenol in pomegranate juice, was also found to strongly inhibit sulfoconjugation in Caco-2 cells with an IC(50) of 45 uM, which is consistent with that of pomegranate juice. These data suggest that punicalagin is mainly responsible for the inhibition of sulfoconjugation by pomegranate juice. /The authors/ additionally demonstrated that pomegranate juice and punicalagin both inhibit phenol sulfotransferase activity in Caco-2 cells in vitro, at concentrations that are almost equivalent to those used in the Caco-2 cells. Pomegranate juice, however, shows no effects on the expression of the sulfotransferase SULT1A family of genes (SULT1A1 and SULT1A3) in Caco-2 cells. These results indicate that the inhibition of sulfotransferase activity by punicalagin in Caco-2 cells is responsible for the reductions seen in 1-naphthyl sulfate accumulation. /The/ data also suggest that constituents of pomegranate juice, most probably punicalagin, impair the enteric functions of sulfoconjugation and that this might have effects upon the bioavailability of drugs and other compounds present in food and in the environment. These effects might be related to the anticarcinogenic properties of pomegranate juice.

Polyphenol-rich dietary foodstuffs have attracted attention due to their cancer chemopreventive and chemotherapeutic properties. Ellagitannins (ETs) belong to the so-called hydrolysable tannins found in strawberries, raspberries, walnuts, pomegranate, oak-aged red wine, etc. Both ETs and their hydrolysis product, ellagic acid (EA), have been reported to induce apoptosis in tumour cells. Ellagitannins are not absorbed in vivo but reach the colon and release EA that is metabolised by the human microflora. Our aim was to investigate the effect of a dietary ET [pomegranate punicalagin (PUNI)] and EA on human colon cancer Caco-2 and colon normal CCD-112CoN cells. Both PUNI and EA provoked the same effects on Caco-2 cells: down-regulation of cyclins A and B1 and upregulation of cyclin E, cell-cycle arrest in S phase, induction of apoptosis via intrinsic pathway (FAS-independent, caspase 8-independent) through bcl-XL down-regulation with mitochondrial release of cytochrome c into the cytosol, activation of initiator caspase 9 and effector caspase 3. Neither EA nor PUNI induced apoptosis in normal colon CCD-112CoN cells (no chromatin condensation and no activation of caspases 3 and 9 were detected). In the case of Caco-2 cells, no specific effect can be attributed to PUNI since it was hydrolysed in the medium to yield EA, which entered into the cells and was metabolised to produce dimethyl-EA derivatives. Our study suggests that the anticarcinogenic effect of dietary ETs could be mainly due to their hydrolysis product, EA, which induced apoptosis via mitochondrial pathway in colon cancer Caco-2 cells but not in normal colon cells.|Terminalia catappa and its major tannin component, punicalagin, have been characterized to possess antioxidative and anti-genotoxic activities. However, their effects on reactive oxygen species (ROS) mediated carcinogenesis are still unclear. In the present study, H-ras-transformed NIH3T3 cells were used to evaluate the chemopreventive effect of T. catappa water extract (TCE) and punicalagin. In the cell proliferation assay, TCE and punicalagin suppressed the proliferation of H-ras-transformed NIH3T3 cells with a dose-dependent manner but only partially affected non-transformed NIH3T3 cells proliferation. The differential cytotoxicity of TCE/punicalagin on the H-ras-transformed and non-transformed NIH3T3 cells indicated the selectivity of TCE/punicalagin against H-ras induced transformation. TCE or punicalagin treatment reduced anchorage-independent growth that could be due to a cell cycle arrest at G0/G1 phase. The intracellular superoxide level, known to modulate downstream signaling of Ras protein, was decreased by punicalagin treatments. The levels of phosphorylated JNK-1 and p38 were also decreased with punicalagin treatments. Thus, the chemopreventive effect of punicalagin against H-ras induced transformation could result from inhibition of the intracellular redox status and JNK-1/p38 activation.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/HUMAN EXPOSURE STUDIES/ The human placenta is key to pregnancy outcome, and the elevated oxidative stress present in many complicated pregnancies contributes to placental dysfunction and suboptimal pregnancy outcomes. /The authors/ tested the hypothesis that pomegranate juice, which is rich in polyphenolic antioxidants, limits placental trophoblast injury in vivo and in vitro. Pregnant women with singleton pregnancies were randomized at 35 /to/ 38 wk gestation to 8 oz/day of pomegranate juice or apple juice (placebo) until the time of delivery. Placental tissues from 12 patients (4 in the pomegranate group and 8 in the control group) were collected for analysis of oxidative stress. The preliminary in vivo results were extended to oxidative stress and cell death assays in vitro. Placental explants and cultured primary human trophoblasts were exposed to pomegranate juice or glucose (control) under defined oxygen tensions and chemical stimuli. /The authors/ found decreased oxidative stress in term human placentas from women who labored after prenatal ingestion of pomegranate juice compared with apple juice as control. Moreover, pomegranate juice reduced in vitro oxidative stress, apoptosis, and global cell death in term villous explants and primary trophoblast cultures exposed to hypoxia, the hypoxia mimetic cobalt chloride, and the kinase inhibitor staurosporine. Punicalagin, but not ellagic acid, both prominent polyphenols in pomegranate juice, reduced oxidative stress and stimulus-induced apoptosis in cultured syncytiotrophoblasts. /The authors/ conclude that pomegranate juice reduces placental oxidative stress in vivo and in vitro while limiting stimulus-induced death of human trophoblasts in culture. The polyphenol punicalagin mimics this protective effect. /The authors/ speculate that antenatal intake of pomegranate may limit placental injury and thereby may confer protection to the exposed fetus.|/ALTERNATIVE and IN VITRO TESTS/ Nanoparticles possess unique chemical and biological properties compared to bulk materials. Bioactive food components encapsulated in nanoparticles may have increased bioavailability and bioactivities. Self-assembled nanoparticles made of partially purified pomegranate ellagitannins (PPE) and gelatin were fabricated using three PPE-to-gelatin mass ratios (1:5, 5:5, and 7:5). The PPE contained 16.6% (w/w) of punicalagin A, 32.5% (w/w) of punicalagin B, and a small amount of ellagic acid-hexoside and ellagic acid (1%, w/w). Nanoparticles fabricated using the ratio 5:5 had a particle size of 149.3 +/-1.8 nm, positive zeta-potential of 17.8 +/-0.9 mV, production efficiency 53.0 +/-4.2%, and spherical morphology under scanning electron microscopy. Loading efficiency of punicalagin A and punicalagin B in these particles were 94.2 +/-0.4% and 83.8 +/-0.5 %, respectively. Loading capacity was 14.8 +/-1.5% and 25.7 +/-2.2%, respectively. Only punicalagin anomers were able to bind with gelatin to form nanoparticles, whereas ellagic acid-hexoside or ellagic acid could not. Fourier transform infrared spectroscopy suggested that the interactions between ellagitannins and gelatin were hydrogen bonding and hydrophobic interactions. PPE-gelatin nanoparticle suspension was less effective than PPE in inducing the early stage of apoptosis on human promyelocytic leukemia cells HL-60. But they had similar effects in inducing late stage of apoptosis and necrosis. Pomegranate ellagitannins bind with gelatin to form self-assembled nanoparticles. Ellagitannins encapsulated in nanoparticles had decreased apoptotic effects on leukemia cells HL-60.|/ALTERNATIVE and IN VITRO TESTS/ The protective bioactivity of punicalagin, a high molecular weight polyphenol isolated from pomegranate fruit pith and carpellary membrane, against oxidative damages to lipids, amino acids constituting the proteins, and guanosine as a model for DNA has been investigated. The ABTS*-, guanosine, and tryptophan radical generated pulse radiolytically were repaired by punicalagin, k = (0.9-15) x 10+7 cu dm mol-1 s-1. The results are rationalized on the basis of the scavenging activity of punicalagin against various one-electron oxidizing radicals, namely, /hydroxyl radical, azide radical, and nitrogen dioxide/. The formation of the transient species in these reactions and the rate constants of the scavenging reactions have been probed using a time-resolved kinetic spectrophotometric technique. The antioxidant action of punicalagin is expressed not only through its scavenging reactions but also by its ability to form metal chelates. Binding of punicalagin with bovine serum albumin and metal ions such as iron and copper revealed different binding affinities, whereas its binding with DNA was very weak and nonspecific. In vitro cytotoxic studies against three cell lines, namely, Vero (normal African green monkey kidney cell line), Hep-2 (human larynx epithelial cancer cell line), and A-549 (human small cell lung carcinoma cell line) showed that this polyphenol is toxic only at higher concentration.|/ALTERNATIVE and IN VITRO TESTS/ The Punica granatum L. (pomegranate) by-product POMx was partitioned between water, EtOAc and n-BuOH, and the EtOAc and n-BuOH extracts were purified by XAD-16 and Sephadex LH-20 column chromatography to afford ellagic acid (1), gallagic acid (2), punicalins (3), and punicalagins (4). Compounds 1 - 4 and the mixture of tannin fractions (XAD-16 eluates) were evaluated for antioxidant, antiplasmodial, and antimicrobial activities in cell-based assays. The mixture of tannins (TPT), XAD-EtOAc, XAD-H2O, XAD-PJ and XAD-BuOH, exhibited IC50 values against reactive oxygen species (ROS) generation at 0.8 - 19 ug/mL. Compounds 1 - 4 showed IC50 values of 1.1, 3.2, 2.3 and 1.4 uM, respectively, against ROS generation and no toxicity up to 31.25 ug/mL against HL-60 cells. Gallagic acid (2) and punicalagins (4) exhibited antiplasmodial activity against Plasmodium falciparum D6 and W2 clones with IC50 values of 10.9, 10.6, 7.5 and 8.8 uM, respectively. Fractions XAD-EtOAc, XAD-BuOH, XAD-H2O and XAD-PJ compounds 1 - 4 revealed antimicrobial activity when assayed against Escherichia coli, Pseudomonas aeruginosa, Candida albicans, Cryptococcus neoformans, methicillin-resistant Staphylococcus aureus (MRSA), Aspergillus fumigatus and Mycobacterium intracellulare. Compounds 2 and 4 showed activity against P. aeruginosa, C. neoformans, and MRSA...|For more Human Toxicity Excerpts (Complete) data for Punicalagin (6 total), please visit the HSDB record page.

punicalagin

... Self-assembled nanoparticles made of partially purified pomegranate ellagitannins (PPE) and gelatin were fabricated using three PPE-to-gelatin mass ratios (1:5, 5:5, and 7:5). The PPE contained 16.6% (w/w) of punicalagin A, 32.5% (w/w) of punicalagin B, and a small amount of ellagic acid-hexoside and ellagic acid (1%, w/w). ...|Proprietary Blend consisting of Pomegranate(Punica granatum) (fruit, rind & seed) extract standardized to contain 30% punicalagin & 25% ellagic acid and a proprietary blend of other ellagitannin complexes. Pomegranate (punica granatum) Seed Extract

An ellagitannin implicated as the bioactive constituent responsible for >50% of pomegranate juice's antioxidant activity|Application in traditional Chinese medicine|Compounds: Pomegranate fruit peel: Tannins (25 to 28%; gallo tannins): including punicalin (granatine D), punicalagin (granatine C), granatine A, granatine B.|The pomegranate fruit ( Punica granatum ) has become an international high-value crop for the production of commercial pomegranate juice (PJ). The perceived consumer value of PJ is due in large part to its potential health benefits based on a significant body of medical research conducted with authentic PJ. To establish criteria for authenticating PJ, a new International Multidimensional Authenticity Specifications (IMAS) algorithm was developed through consideration of existing databases and comprehensive chemical characterization of 45 commercial juice samples from 23 different manufacturers in the United States. In addition to analysis of commercial juice samples obtained in the United States, data from other analyses of pomegranate juice and fruits including samples from Iran, Turkey, Azerbaijan, Syria, India, and China were considered in developing this protocol. There is universal agreement that the presence of a highly constant group of six anthocyanins together with punicalagins characterizes polyphenols in PJ. At a total sugar concentration of 16 degrees Brix, PJ contains characteristic sugars including mannitol at >0.3 g/100 mL. Ratios of glucose to mannitol of 4-15 and of glucose to fructose of 0.8-1.0 are also characteristic of PJ. In addition, no sucrose should be present because of isomerase activity during commercial processing. Stable isotope ratio mass spectrometry as > -25 per thousand assures that there is no added corn or cane sugar added to PJ. Sorbitol was present at <0.025 g/100 mL; maltose and tartaric acid were not detected. The presence of the amino acid proline at >25 mg/L is indicative of added grape products. Malic acid at >0.1 g/100 mL indicates adulteration with apple, pear, grape, cherry, plum, or aronia juice. Other adulteration methods include the addition of highly concentrated aronia, blueberry, or blackberry juices or natural grape pigments to poor-quality juices to imitate the color of pomegranate juice, which results in abnormal anthocyanin profiles. To adjust the astringent taste of poor-quality juice or peel extract, addition of nonpomegranate sugars is a commonly detected adulteration method. The profile generated from these analyses combined with information from existing databases and published literature has been integrated into a validated IMAS for PJ, which can be utilized to detect PJ adulteration. In this survey of commercial pomegranate juices, only 6 of 23 strictly met all of the IMAS criteria.

Punicalagin, the main ingredient of pomegranate (Punica granatum L.) husk, is a high molecular weight polyphenolic compound. It has shown remarkable pharmacological activities attributed in the presence of dissociable OH groups. To isolate punicalagin, previous methods included labor intensive and expensive solid phase extractions by column chromatography (C-18, polyamides, dellulose, Sephadex Lipophilic LH-20, Diaion HP20). High-speed countercurrent chromatography (HSCCC) was used for isolation and purification of punicalagin from pomegranate husk. Using preparative HSCCC about a 350 mg amount of the crude extract was separated, yielding 105 mg of punicalagin at a high-purity of over 92%. Eighty milligrams of gallic acid was simultaneously separated as another product, at a purity of 75%.|In vitro antiplasmodial activity of methanolic extracts of 16 medicinal plants was evaluated by fluorometric assay using PicoGreen. The IC50s, as determined by parasite DNA concentration, ranged from <11 to >200 and <13 to >200 ug/mL for Plasmodium falciparum 3D7 and K1, respectively; and the most active extracts were those from Anogeissus leiocarpus and Terminalia avicennoides (<11- > or =14 ug/mL). Aqueous, butanolic, ethyl acetate, and methanolic fractions of these two extracts revealed butanolic fraction to have a relatively better activity (IC50, 10-12 ug/mL). Activity-guided chromatographic separation of the butanolic fraction on Sephadex LH-20 followed by nuclear magnetic resonance and correlation high-performance liquid chromatography revealed the presence of known hydrolysable tannins and some related compounds-castalagin, ellagic acid, flavogallonic acid, punicalagin, terchebulin, and two other fractions. ...|This paper describes the isolation and structure elucidation of two toxic tannins, named alpha- and beta-punicalagin, from Terminalia oblongata, an Australian tree. Techniques used in the structure determination included Fast Atom Bombardment (FAB) mass spectrometry, and one- and two-dimensional NMR, UV, and IR spectroscopy. A number of microscale derivatisations were performed, followed by FAB analysis