Aristolochene
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| Names | |
|---|---|
| IUPAC name 7α-Eremophila-9,11-diene | |
| Systematic IUPAC name (4S,4aR,6S)-4,4a-Dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene | |
| Other names (+)-Aristolochene | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider | |
PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
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| Properties | |
| C15H24 | |
| Molar mass | 204.357 g·mol−1 |
| Density | 0.894 g/mL |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Aristolochene is a bicyclic sesquiterpene produced by certain fungi including the cheese mold Penicillium roqueforti. It is biosynthesized from farnesyl pyrophosphate by aristolochene synthase and is the parent hydrocarbon of a large variety of fungal toxins.[1]
The substance was first isolated from Penicillium roqueforti, a fungus used to make blue cheeses like Roquefort, Danish Blue, Stilton cheese and gorgonzola.
Aristolochene is a precursor to PR toxin, a toxic chemical made in large amounts by Penicillium roqueforti.[2] PR toxin has been implicated in incidents of mycotoxicoses resulting from eating contaminated grains.[3]
Related Compounds
[edit]References
[edit]- ^ Terpene Biosynthesis Archived February 25, 2007, at the Wayback Machine, Chem 549, College of Pharmacy, University of Arizona
- ^ Proctor RH, Hohn TM (February 1993). "Aristolochene synthase. Isolation, characterization, and bacterial expression of a sesquiterpenoid biosynthetic gene (Ari1) from Penicillium roqueforti". J. Biol. Chem. 268 (6): 4543–8. doi:10.1016/S0021-9258(18)53644-9. PMID 8440737.
- ^ Chen FC, Chen CF, Wei RD (1982). "Acute toxicity of PR toxin, a mycotoxin from Penicillium roqueforti". Toxicon. 20 (2): 433–41. Bibcode:1982Txcn...20..433C. doi:10.1016/0041-0101(82)90006-X. PMID 7080052.