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| Targets |
Pinobanksin 3-acetate acts on multiple biological targets. It exhibits direct antibacterial activity by disrupting bacterial cell membranes and inhibiting essential enzymes (e.g., DNA gyrase). Its antifungal activity involves disruption of fungal cell wall integrity and inhibition of ergosterol biosynthesis. It shows antiviral effects, particularly against herpes viruses, by inhibiting viral replication. Pinobanksin 3-acetate also has anti-inflammatory properties, inhibiting the production of pro-inflammatory cytokines (e.g., TNF-alpha, IL-1beta, IL-6) and the activation of transcription factors such as NF-kappaB. The hydroxyl groups in its structure contribute to its antioxidant activity, allowing it to scavenge free radicals, chelate metal ions, and inhibit lipid peroxidation.
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| ln Vitro |
In vitro, Pinobanksin 3-acetate exhibits a wide range of biological activities. It has strong antibacterial activity against both Gram-positive bacteria (e.g., Staphylococcus aureus, including MRSA, with MIC 8-32 microg/mL) and Gram-negative bacteria (e.g., Escherichia coli, MIC 16-64 microg/mL), as well as antifungal activity against Candida albicans. The compound also demonstrates antioxidant activity (IC50 5-20 microg/mL) in DPPH, ABTS, and FRAP assays. It is non-toxic to normal cells at concentrations up to 100 microg/mL. Pinobanksin 3-acetate also shows anti-inflammatory activity in LPS-stimulated macrophages, reducing TNF-alpha and IL-6 production by 30-50% at 10-50 microM. It also inhibits alpha-glucosidase and pancreatic lipase, suggesting anti-diabetic and anti-obesity potential.
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| ln Vivo |
In vivo, the activities of Pinobanksin 3-acetate have been studied primarily as part of propolis extracts. In rodent models of carrageenan-induced paw edema, administration of propolis extract (containing Pinobanksin 3-acetate) reduces paw swelling, indicating anti-inflammatory activity. In a rat model of gastric ulcer, Pinobanksin 3-acetate (as part of propolis) promotes ulcer healing by increasing gastric mucus production and reducing oxidative stress. In a mouse model of skin wound healing, topical application of propolis extract containing this compound accelerates wound closure and improves tissue regeneration. Specific in vivo studies of isolated Pinobanksin 3-acetate are limited, and more research is needed.
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| Enzyme Assay |
A typical non-cellular (cell-free) protocol for evaluating the antioxidant activity of Pinobanksin 3-acetate uses the DPPH radical scavenging assay. A 0.1 mM DPPH solution is prepared in methanol. Pinobanksin 3-acetate is serially diluted in methanol to concentrations of 0.5-200 microg/mL. In a 96-well plate, 100 microL of DPPH solution is mixed with 100 microL of sample solution and incubated in the dark for 30 minutes at room temperature. Absorbance is measured at 517 nm. The percentage of scavenging is calculated as (Acontrol - Asample)/Acontrol × 100%. The IC50 is calculated by plotting the percentage scavenging versus log concentration. Ascorbic acid or Trolox is used as a positive control. For ABTS assay, ABTS radical cation (ABTS•+) is generated by reacting 7 mM ABTS with 2.45 mM potassium persulfate for 16 hours; the solution is diluted to an absorbance of 0.70+/-0.02 at 734 nm, mixed with sample, and incubated for 6 minutes before measuring absorbance.
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| Cell Assay |
An in vitro cellular protocol for evaluating the anti-inflammatory activity of Pinobanksin 3-acetate uses LPS-stimulated RAW 264.7 mouse macrophages. Cells are seeded in 24-well plates at 2×10⁵ cells/well in DMEM with 10% FBS and 1% penicillin/streptomycin, and cultured overnight. The cells are pre-incubated with various concentrations of Pinobanksin 3-acetate (5, 10, 25, 50 microM) for 1 hour, then stimulated with 1 microg/mL LPS for 24 hours. Culture supernatants are collected, and the levels of TNF-alpha, IL-1beta, IL-6, and NO (nitrite, using Griess reagent) are measured by ELISA or Griess assay. Cells are lysed for protein extraction, and the expression of iNOS, COX-2, and NF-kappaB p65 is assessed by Western blot. RNA is extracted for qRT-PCR of inflammatory genes. Pinobanksin 3-acetate should reduce cytokine production and NF-kappaB activation.
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| Animal Protocol |
An in vivo animal protocol for evaluating the anti-inflammatory activity of Pinobanksin 3-acetate uses the carrageenan-induced paw edema model. Male Sprague-Dawley rats (150-200 g) are divided into groups (n=6 per group). Pinobanksin 3-acetate is suspended in 0.5% carboxymethylcellulose (CMC) and administered orally at doses of 10, 25, and 50 mg/kg, 1 hour before carrageenan injection. The control group receives vehicle (0.5% CMC), and the positive control group receives indomethacin (10 mg/kg). After 1 hour, 0.1 mL of 1% carrageenan in saline is injected into the subplantar region of the right hind paw. Paw volume is measured using a plethysmometer at 0, 1, 2, 3, 4, 5, and 6 hours after carrageenan injection. The percentage of edema inhibition is calculated as (Vcontrol - Vtreated)/Vcontrol × 100%. At the end of the study (6 hours), rats are euthanized, and paw tissue is collected for myeloperoxidase (MPO) activity measurement and histology (H&E).
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of Pinobanksin 3-acetate have not been fully characterized. As a flavonoid compound, its oral bioavailability is likely low due to poor solubility, extensive first-pass metabolism, and efflux by transporters (e.g., P-glycoprotein). The compound is likely metabolized by phase II enzymes (glucuronidation, sulfation) and possibly by gut microbiota. The peak plasma concentration (Cmax) after oral administration would likely be reached within 1-3 hours (Tmax). The elimination half-life (t½) is likely short (2-4 hours). Better absorption and bioavailability may be achieved by co-administration with absorption enhancers or by formulation in lipid-based delivery systems. Further studies are needed.
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| Toxicity/Toxicokinetics |
Pinobanksin 3-acetate is a natural flavonoid and, when consumed as part of propolis, is generally recognized as safe (GRAS). However, purified compound toxicity data are limited. In cell culture, it shows low toxicity to normal cells (e.g., fibroblasts, hepatocytes) at concentrations up to 100 microg/mL. In acute oral toxicity studies in rodents, propolis extracts containing this compound have not shown significant toxicity at doses up to 2000 mg/kg. High doses may cause mild gastrointestinal discomfort. Standard laboratory safety precautions are sufficient when handling the compound. Pinobanksin 3-acetate is for research use only and is not intended for human therapeutic use without regulatory approval. It should be stored at -20degC, protected from light and moisture.
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| References | |
| Additional Infomation |
Pinobanksin 3-O-acetate is a dihydroflavonol compound. It has been reported that 3-O-acetylPinobanksin is found in bees, Yunnan poplar, and other organisms with relevant data.
Pinobanksin 3-acetate is a flavonoid natural product found in propolis (bee glue) and contributes significantly to its biological activities. Its molecular formula is C17H14O6, and its molecular weight is 314.29. Pinobanksin 3-acetate exhibits a range of beneficial activities, including antibacterial, antifungal, antiviral, anti-inflammatory, antioxidant, anti-diabetic (alpha-glucosidase inhibition), anti-obesity (pancreatic lipase inhibition), and hepatoprotective effects. It has applications in natural product research, antimicrobial drug discovery, and the development of functional foods and nutraceuticals. As of 2026, Pinobanksin 3-acetate is not an FDA-approved drug and remains an investigational natural product. It is intended for research use only. |
| Molecular Formula |
C17H14O6
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|---|---|
| Molecular Weight |
314.29
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| Exact Mass |
314.079
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| CAS # |
52117-69-8
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| PubChem CID |
148556
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| Appearance |
White to off-white solid
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
547.6±50.0 °C at 760 mmHg
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| Flash Point |
205.1±23.6 °C
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| Vapour Pressure |
0.0±1.5 mmHg at 25°C
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| Index of Refraction |
1.661
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| LogP |
3.85
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
23
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| Complexity |
458
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| Defined Atom Stereocenter Count |
2
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| SMILES |
CC(=O)OC1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=CC=C3
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| InChi Key |
BJYHZSNSMVEQEH-SJORKVTESA-N
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| InChi Code |
InChI=1S/C17H14O6/c1-9(18)22-17-15(21)14-12(20)7-11(19)8-13(14)23-16(17)10-5-3-2-4-6-10/h2-8,16-17,19-20H,1H3/t16-,17+/m1/s1
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| Chemical Name |
[(2R,3R)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydrochromen-3-yl] acetate
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| Synonyms |
Pinobanksin 3-acetate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: 100 mg/mL (318.18 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.95 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.95 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (7.95 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.1818 mL | 15.9089 mL | 31.8177 mL | |
| 5 mM | 0.6364 mL | 3.1818 mL | 6.3635 mL | |
| 10 mM | 0.3182 mL | 1.5909 mL | 3.1818 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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