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Polygodial (Poligodial; Tadeonal) 6754-20-7

Polygodial (Poligodial; Tadeonal) 6754-20-7

CAS No.: 6754-20-7

Polygodial (Poligodial) is an antifungal enhancer. Polygodial is a sesquiterpene with antihyperalgesic effects.
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Polygodial (Poligodial) is an antifungal enhancer. Polygodial is a sesquiterpene with antihyperalgesic effects.

Physicochemical Properties


Molecular Formula C15H22O2
Molecular Weight 234.33
Exact Mass 234.161
CAS # 6754-20-7
Related CAS # 6754-20-7
PubChem CID 72503
Appearance White to off-white solid powder
Density 1.1±0.1 g/cm3
Boiling Point 330.7±35.0 °C at 760 mmHg
Flash Point 124.0±22.9 °C
Vapour Pressure 0.0±0.7 mmHg at 25°C
Index of Refraction 1.570
LogP 3.84
Hydrogen Bond Donor Count 0
Hydrogen Bond Acceptor Count 2
Rotatable Bond Count 2
Heavy Atom Count 17
Complexity 367
Defined Atom Stereocenter Count 3
SMILES

C[C@]12CCCC([C@@H]1CC=C([C@@H]2C=O)C=O)(C)C

InChi Key AZJUJOFIHHNCSV-KCQAQPDRSA-N
InChi Code

InChI=1S/C15H22O2/c1-14(2)7-4-8-15(3)12(10-17)11(9-16)5-6-13(14)15/h5,9-10,12-13H,4,6-8H2,1-3H3/t12-,13-,15+/m0/s1
Chemical Name

(1R,4aS,8aS)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalene-1,2-dicarbaldehyde
HS Tariff Code 2934.99.9001
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)

Biological Activity


ln Vitro In standardized susceptibility testing (NCCLS), Polygodial demonstrates fungicidal effectiveness against Saccharomyces cerevisiae, Candida albicans, and other fungal infections. When Saccharomyces cerevisiae cells are treated with polygodial (12.5 μg/mL for 3 hours), they significantly shrink in comparison to controls when the minimum fungicidal concentration (MFC) is set for 106 CFU/mL in RPMI 1640 medium[3].
ln Vivo Polygodial is a sesquiterpene that was extracted from Drymis winteri's (Winteraceae) bark. Mice given Polygodial (0.5 to 10 mg/kg; 0.5 h; intraperitoneal method) significantly, dose-dependently, and nearly completely inhibits the constrictions in their abdomens caused by Acetic acid, Kaolin, and Zymosan. The estimated maximal inhibitions against acetic acid, kaolin, and zymosan are 90.0±3.0, 98.0±1.0, and 97.0±2.0 %, respectively, with mean ID50 values of 0.8, 2.1, and 2.6 mg/kg. At the ID50 level, polygodial has a potency that is roughly 14–27 times greater than hydroalcoholic extract (HE)[2].
Cell Assay Cell Viability Assay[3]
Cell Types: S. cerevisiae cells
Tested Concentrations: 12.5 μg/mL
Incubation Duration: 3 hrs (hours)
Experimental Results: Treated cells demonstrated significant shrinkage compared to controls, and the organization of subcellular organelles appeared either disrupted or compacted.
Animal Protocol Animal/Disease Models: Non-fasted male Swiss mice ( 20-30 g) or male Wistar rats (150-180 g)[2]
Doses: 0.1 to 10 mg/kg
Route of Administration: Injected ip 0.5 h before the injection of irritant substances
Experimental Results: Produced significant inhibition of Acetic acid, Kaolin and Zymosan -induced writhing in mice.
References

[1]. Polygodial, an antifungal potentiator. J Nat Prod. Jan-Feb 1988;51(1):22-9.

[2]. Anti-hyperalgesic properties of the extract and of the main sesquiterpene polygodial isolated from the barks of Drymis winteri (Winteraceae). Life Sci. 1998;63(5):369-81.

[3]. Effect of polygodial on the mitochondrial ATPase of Saccharomyces cerevisiae. Antimicrob Agents Chemother. 2000 Jul;44(7):1943-53.

Additional Infomation Polygodial is an aldehyde.
Polygodial has been reported in Apopellia endiviifolia, Dendrodoris tuberculosa, and other organisms with data available.

Solubility Data


Solubility (In Vitro) DMSO : ≥ 100 mg/mL (426.75 mM)
Solubility (In Vivo) Solubility in Formulation 1: ≥ 2.5 mg/mL (10.67 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 (10.67 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.

Solubility in Formulation 3: ≥ 2.5 mg/mL (10.67 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.2675 mL 21.3374 mL 42.6749 mL
5 mM 0.8535 mL 4.2675 mL 8.5350 mL
10 mM 0.4267 mL 2.1337 mL 4.2675 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.