CAS 6754-20-7|(-)-Polygodial
| Common Name | (-)-Polygodial | ||
|---|---|---|---|
| CAS Number | 6754-20-7 | Molecular Weight | 234.334 |
| Density | 1.1±0.1 g/cm3 | Boiling Point | 330.7±35.0 °C at 760 mmHg |
| Molecular Formula | C15H22O2 | Melting Point | / |
| MSDS | ChineseUSA | Flash Point | 124.0±22.9 °C |
Names
| Name | polygodial |
|---|---|
| Synonym | More Synonyms |
(-)-Polygodial BiologicalActivity
| Description | Polygodial (Poligodial) is an antifungal potentiator[1]. Polygodial is a sesquiterpene with anti-hyperalgesic properties[2]. |
|---|---|
| Related Catalog | Research Areas >>InfectionSignaling Pathways >>Anti-infection >>FungalResearch 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 |
| InChIKey | AZJUJOFIHHNCSV-KCQAQPDRSA-N |
| SMILES | CC1(C)CCCC2(C)C(C=O)C(C=O)=CCC12 |
| Storage condition | 20°C |
Safety Information
| Hazard Codes | Xn |
|---|---|
| Risk Phrases | 52/53 |
| RIDADR | NONH for all modes of transport |
| RTECS | QJ2850000 |
Articles25
More 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... |
Synonyms
| (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 |
