(-)-Polygodial

Names

[ Name ]:
(-)-Polygodial

[Synonym ]:
(1R,4aS,8aS)-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalene-1,2-dicarbaldehyde
UNII:A00RAV0W57
Podofilox
Wartec
Condylox
Podophyllotoxin 7
1,2-Naphthalenedicarboxaldehyde, 1,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethyl-, (1R,4aS,8aS)-
Condyline
[1R-(1a,4ab,8aa)]-1,4,4a,5,6,7,8,8a-Octahydro-5,5,8a-trimethyl-1,2-naphthalenedicarboxaldehyde
S-Isopropylisothiourea hydrobromide
Polygodial
Warticon
(1R,4aS,8aS)-5,5,8a-Trimethyl-1,4,4a,5,6,7,8,8a-octahydro-1,2-naphthalenedicarbaldehyde
Podophyllinic acid lactone

Biological Activity

[Description]:

Polygodial (Poligodial) is an antifungal potentiator[1]. Polygodial is a sesquiterpene with anti-hyperalgesic properties[2].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

Research Areas >> Inflammation/Immunology

[In Vitro]

Polygodial exhibits fungicidal activity against Saccharomyces cerevisiae, Candida albicans, and other fungal pathogens in standardized susceptibility tests (NCCLS). Polygodial (12.5 μg/mL, 3 hours) induces significant shrinkage compared to controls in Saccharomyces cerevisiae cells with the minimum fungicidal concentration (MFC) for 106 CFU/mL in RPMI 1640 medium[3]. Cell Viability Assay[3] Cell Line: S. cerevisiae cells Concentration: 12.5 μg/mL Incubation Time: 3 hours Result: Treated cells exhibited significant shrinkage compared to controls, and the organization of subcellular organelles appears either disrupted or compacted.

[In Vivo]

Polygodial is a sesquiterpene isolated from the barks of Drymis winteri (Winteraceae). Polygodial (0.5 to 10 mg/kg; 0.5 h; given by i.p. route to mice) induces significant, dose-related and almost complete inhibition of Acetic acid, Kaolin and Zymosan-induced abdominal constrictions. The calculated mean ID50 values are 0.8, 2.1 and 2.6 mg/kg and maximal inhibitions of 90.0±3.0, 98.0±1.0 and 97.0±2.0 %, against Acetic acid, Kaolin and Zymosan, respectively. Polygodial is about 14- to 27-fold more potent than the hydroalcoholic extract (HE) at the ID50 level[2]. Animal Model: Non-fasted male Swiss mice (20-30 g) or male Wistar rats (150-180 g)[2] Dosage: 0.1 to 10 mg/kg Administration: Injected i.p. 0.5 h before the injection of irritant substances Result: Produced significant inhibition of Acetic acid, Kaolin and Zymosan-induced writhing in mice.

[References]

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

[2]. G L Mendes, et al. 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]. C S Lunde, et al. Effect of polygodial on the mitochondrial ATPase of Saccharomyces cerevisiae. Antimicrob Agents Chemother. 2000 Jul;44(7):1943-53.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
330.7±35.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₅H₂₂O₂

[ Molecular Weight ]:
234.334

[ Flash Point ]:
124.0±22.9 °C

[ Exact Mass ]:
234.161987

[ PSA ]:
34.14000

[ LogP ]:
3.84

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.570

[ Storage condition ]:
20°C

Safety Information

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
52/53

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
QJ2850000

Articles

Screening for negative effects of candidate ascidian antifoulant compounds on a target aquaculture species, Perna canaliculus Gmelin.

Biofouling 29(1) , 29-37, (2013)

The natural chemical compounds radicicol, polygodial and ubiquinone-10 (Q10) have previously been identified as inhibitors of metamorphosis in ascidian larvae. Accordingly, they have potential as a sp...

Preventing ascidian fouling in aquaculture: screening selected allelochemicals for anti-metamorphic properties in ascidian larvae.

Biofouling 28(1) , 39-49, (2012)

Fouling by ascidians causes major stock losses and disrupts production in marine aquaculture, especially bivalve aquaculture. Currently, no cost effective solution exists despite the testing of many p...

Inhibition of the mitochondrial ATP synthesis by polygodial, a naturally occurring dialdehyde unsaturated sesquiterpene.

Biochem. Pharmacol. 70(1) , 82-9, (2005)

Polygodial is a naturally occurring sesquiterpene dialdehyde that exhibits several pharmacologically interesting activities. Among them, its antifungal properties have been more thoroughly studied. Th...