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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H22O2
Molecular Weight 234.334
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of POLYGODIAL

SMILES

[H][C@@]12CC=C(C=O)[C@H](C=O)[C@@]1(C)CCCC2(C)C

InChI

InChIKey=AZJUJOFIHHNCSV-KCQAQPDRSA-N
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

HIDE SMILES / InChI

Description

Polygodial is a sesquiterpene dialdehyde isolated from the leaves of certain peppers and related plants, that exhibits anti-inflammatory, antiallergic, antinociceptive, anticancer, antifungal and antimicrobial activities. Polygodial’s primary antifungal action is as a nonionic surfactant, disrupting the lipid-protein interface of integral proteins nonspecifically, denaturing their functional conformation. It is also likely that Polygodial permeates by passive diffusion across the plasma membrane, and once inside the cells may react with a variety of intracellular compounds. Polygodial is a component of the “hot taste” in peppery spices of traditional Japanese cuisine.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
59.0 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
tablet twice a day of a K-712 (10 mg of oleoresin from Pseudowintera colorata at 30 percent concentration in Polygodial) for 4 weeks and then for the first 2 weeks of each month for a total of 6 months.
Route of Administration: Oral
In Vitro Use Guide
Mice beta-pancreatic insulinoma INS 1E cell line were used for activity evaluation. INS 1E cells (2 x 10^5/well) were seeded in 24-well plate and incubated in the same conditions of regular cell culture. Different polygodial concentrations (30, 300, 3000 nM, diluted in EtOH) stimulus were assessed for 1 h and 24 h of incubation in order to evaluate the acute and chronic effect of the compound, respectively. After growth and treatment with polygodial, cells were detached with trypsin and 1 mL of the PBS suspension and centrifuged. The cellular pellet was resuspended in 300 mkL of a 50 mkg/mL propidium iodide 0.1% hypotonic solution with sodium citrate 0.1% and Triton X-100 0.1%. Afterwards, samples were incubated for 30 min at 4 C and analyzed by flow cytometry in a FACScalibur system (BD Bioscience, San Jose, CA, USA).