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Details

Stereochemistry RACEMIC
Molecular Formula C15H22O2
Molecular Weight 234.334
Optical Activity ( + / - )
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
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/16457780 | https://www.ncbi.nlm.nih.gov/pubmed/26360047 | https://www.ncbi.nlm.nih.gov/pubmed/20356305 | https://www.ncbi.nlm.nih.gov/pubmed/27645309

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

Sources: Nippon Kagaku Zasshi (1962), 83, 757-60

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Anti-hyperalgesic properties of the extract and of the main sesquiterpene polygodial isolated from the barks of Drymis winteri (Winteraceae).
1998
In vitro antifungal susceptibilities of Candida albicans and other fungal pathogens to polygodial, a sesquiterpene dialdehyde.
1999 Apr
Assessment of mechanisms involved in antinociception caused by sesquiterpene polygodial.
2000 Jan
Patents

Sample Use Guides

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
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).
Name Type Language
POLYGODIAL, (±)-
Common Name English
(±)-POLYGODIAL
Common Name English
1,2-NAPHTHALENEDICARBOXALDEHYDE, 1,4,4A,5,6,7,8,8A-OCTAHYDRO-5,5,8A-TRIMETHYL-, (1R,4AS,8AS)-REL-
Systematic Name English
POLYGODIAL (±)-FORM [MI]
Common Name English
Code System Code Type Description
WIKIPEDIA
Polygodial
Created by admin on Sat Dec 16 09:34:24 GMT 2023 , Edited by admin on Sat Dec 16 09:34:24 GMT 2023
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FDA UNII
A00RAV0W57
Created by admin on Sat Dec 16 09:34:24 GMT 2023 , Edited by admin on Sat Dec 16 09:34:24 GMT 2023
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CAS
33118-34-2
Created by admin on Sat Dec 16 09:34:24 GMT 2023 , Edited by admin on Sat Dec 16 09:34:24 GMT 2023
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MERCK INDEX
m8960
Created by admin on Sat Dec 16 09:34:24 GMT 2023 , Edited by admin on Sat Dec 16 09:34:24 GMT 2023
PRIMARY Merck Index
PUBCHEM
72503
Created by admin on Sat Dec 16 09:34:24 GMT 2023 , Edited by admin on Sat Dec 16 09:34:24 GMT 2023
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EPA CompTox
DTXSID50954741
Created by admin on Sat Dec 16 09:34:24 GMT 2023 , Edited by admin on Sat Dec 16 09:34:24 GMT 2023
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