Structure of Punicalagin
CAS No.: 65995-63-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Punicalagin, a natural product isolated and purified from the peel of Punica granatum L., is a potential alternative or supplemental agent for prevention of Salmonella infection, has a greater antifungal activity against T.
4.5
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CAS No. : | 65995-63-3 |
Formula : | C48H28O30 |
M.W : | 1084.72 |
SMILES Code : | OC(O1)[C@H](OC(C2=CC(O)=C(O)C(O)=C2C3=C(O)C(O)=C(O)C=C3C(O4)=O)=O)[C@@H]4[C@H](OC(C5=CC(O)=C(O)C(O)=C5C6=C(O)C(O)=C7C8=C6C(OC9=C(O)C(O)=C(C(C(O7)=O)=C89)C%10=C(O)C(O)=C(O)C=C%10%11)=O)=O)[C@H]1COC%11=O |
MDL No. : | MFCD09838017 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
In Vitro:
Cell Line
|
Concentration | Treated Time | Description | References |
THP-1 cells | 50 μM | 12 h | PUN upregulated AhR expression in THP-1 cells. | PMC11448010 |
Mouse peritoneal macrophages | 50 μM | 12 h | PUN alone or in combination with LPS upregulated AhR expression, with the combination being more potent. | PMC11448010 |
Bovine endometrial epithelial cells (bEECs) | 5, 10, 20 µg/ml | 2 h pretreatment followed by LPS stimulation for 12 h | To evaluate the inhibitory effect of punicalagin on LPS-induced pro-inflammatory cytokine expression. Results showed that punicalagin significantly reduced mRNA expression of IL-1β, IL-6, IL-8, and TNF-α. | PMC5482043 |
ARPE-19 cells | 10 µM | 24 hours | To evaluate the protective effect of PUN against UV-A radiation-induced oxidative damage. PUN pre-treatment significantly increased cell viability, reduced ROS levels, and activated the Nrf2/HO-1 signaling pathway. | PMC7346122 |
Lactic Acid Bacteria (LAB) | 30 μg/mL | 24 hours | To assess the ability of LAB to transform punicalagin into bioactive molecules such as ellagic acid. Results showed all tested LAB strains could convert punicalagin into ellagic acid, but no biosynthesis of urolithins was observed. | PMC9801417 |
RAW264.7 macrophages | 12.5, 25, 50 μM | 24 hours | To evaluate the anti-inflammatory effects of punicalagin on LPS-induced RAW264.7 macrophages. Results showed that punicalagin significantly inhibited LPS-induced release of NO and decreased pro-inflammatory cytokines TNF-α and IL-6 release at the highest concentration, and inhibited NF-κB and MAPK signaling pathways. | PMC6893462 |
Mouse chondrocytes | 50 μg/mL | 24 hours | To evaluate the effect of Punicalagin on chondrocyte viability, results showed that Punicalagin at 50 μg/mL had no significant cytotoxicity within 24 hours and reversed TBHP-induced decrease in cell viability | PMC7751323 |
Human U87MG glioma cells | 1-30 µg/mL | 24 or 48 hours | Punicalagin dose-dependently inhibited cell viability, associated with increased cyclin E levels and decreased cyclin B and A levels. | PMC4006469 |
CCD 841 (normal colon epithelial cells) | 0–100 µg/mL | 24, 48, 72 hours | To assess the toxicity of PU on normal cells. Results showed PU did not induce significant cytotoxicity on CCD 841 cells. | PMC7468705 |
VeroE6 cells | 0, 50, 100 μM | 30 minutes | Evaluate the inhibitory ability of Punicalagin on the binding of SARS-CoV-2 Spike protein to ACE2. Results showed Punicalagin exhibited the highest activity in inhibiting Spike-ACE2 interaction. | PMC10465125 |
NCI-H460 cells | 0, 50, 100 μM | 30 minutes | Evaluate the inhibitory ability of Punicalagin on the binding of SARS-CoV-2 Spike protein to ACE2. Results showed Punicalagin exhibited the highest activity in inhibiting Spike-ACE2 interaction. | PMC10465125 |
293T-ACE2 cells | 0, 50, 100 μM | 30 minutes | Evaluate the inhibitory ability of Punicalagin on the binding of SARS-CoV-2 Spike protein to ACE2. Results showed Punicalagin exhibited the highest activity in inhibiting Spike-ACE2 interaction. | PMC10465125 |
Human podocyte cell line | 1.5 μM | 30 minutes | Inhibited PAR2-mediated activation of ERK1/2 and NF-κB signaling pathways, reduced ICAM-1 and VCAM-1 expression | PMC7404282 |
In Vivo:
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
C57BL/6 mice | LPS-induced inflammation model | Intraperitoneal injection | 12.5 mg/kg | Single dose, lasting 12 hours | PUN increased the percentage of AhR-positive peritoneal macrophages in LPS-induced mice. | PMC11448010 |
Kunming mice | Hyperuricemia mice model | Oral gavage | 100, 200, 300 mg/kg | Once daily for two weeks | To evaluate the effect of PU on hyperuricemia and its mechanisms. PU significantly decreased serum uric acid levels in hyperuricemia mice and effectively alleviated kidney and intestinal damage caused by hyperuricemia. | PMC11954802 |
NZB/W F1 mice | Lupus nephritis model | Intraperitoneal injection | 0.3, 1, 3 mg/kg | 3 times per week for 7 weeks | PCG significantly improved kidney injury and splenomegaly, reduced proteinuria and renal ICAM-1 and VCAM-1 expression | PMC7404282 |
Sprague-Dawley rats | Parkinson's disease model (induced by MnCl2) and social isolation model | Oral | 30 mg/kg | Once daily for 5 weeks | To evaluate the neuroprotective effects of Punicalagin against Parkinson's disease and social isolation. Punicalagin significantly improved behavioral, biochemical, and histopathological changes by modulating multiple pathways (e.g., HMGB1/RAGE/TLR4/NF-κB/NLRP3/Caspase-1, JAK-2/STAT-3, PI3K/AKT/GSK-3β/CREB, AMPK/SIRT-1, Nrf2/HO-1, and PERK/CHOP/Bcl-2) to mitigate oxidative stress, neuroinflammation, and neuronal apoptosis. | PMC10610313 |
Wistar albino rats | DENA-induced hepatocarcinogenesis model | Oral | 18.5 mg/kg bw | Daily administration for 11 weeks | To investigate the chemoprevention effects of Punicalagin against DENA-induced hepatocarcinogenesis. Results showed that Punicalagin induced some modulation in DENA-treated rats but did not show potent chemoprevention activity and induced some side effects. | PMC9628031 |
Swiss albino mice | Methotrexate-induced hepatotoxicity model | Oral | 25 and 50 mg/kg | Once daily for 10 days | Punicalagin protects against the development of methotrexate-induced hepatotoxicity in mice via activating Nrf2 signaling and decreasing oxidative stress, inflammation, and cell death. | PMC9604463 |
C57BL/6J mice | High-fat diet/streptozotocin-induced diabetic mice model | Intragastric administration | 20 mg/kg | Once a day for 8 weeks | Punicalagin ameliorates diabetic nephropathy by inhibiting pyroptosis via the TXNIP/NLRP3 pathway. Results showed that punicalagin significantly decreased blood urea nitrogen, serum creatinine, and urine albumin to creatinine ratio in diabetic mice, and alleviated symptoms of glomerular interstitial hyperplasia and glomerular hypertrophy. | PMC7284711 |
C57BL/6 mice | Destabilization of the medial meniscus (DMM) model | Oral gavage | 20 mg/kg | Once daily for 8 weeks | To evaluate the therapeutic effect of Punicalagin on osteoarthritis in DMM model mice, results showed that Punicalagin treatment significantly alleviated cartilage degeneration and synovitis | PMC7751323 |
Bio Calculators | ||||
Preparing Stock Solutions | ![]() |
1mg | 5mg | 10mg |
1 mM 5 mM 10 mM |
0.92mL 0.18mL 0.09mL |
4.61mL 0.92mL 0.46mL |
9.22mL 1.84mL 0.92mL |
Tags: Punicalagin | SARS-CoV | HBV | SARS coronavirus | Hepatitis B virus | Antioxidant | polyphenol | ingredient | Pomegranate | antioxidant | anti-inflammatory | anticancer | 3CLpro inhibitor | SARS-CoV-2 replication | HBV treatment | 65995-63-3
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P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
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P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
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P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
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P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
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P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
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P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
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P321 | |
P322 | |
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P337 | If eye irritation persists: |
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P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
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P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
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P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
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P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
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P420 | Store away from other materials. |
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P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
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H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
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H228 | Flammable solid |
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H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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