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| The substance was first isolated from ''Penicillium roqueforti'', a fungus used to make blue cheeses like ], ], ] and ]. | The substance was first isolated from ''Penicillium roqueforti'', a fungus used to make blue cheeses like ], ], ] and ]. | ||
| Aristolochene is a precursor to ], a toxic chemical made in large amounts by ''Penicillium roqueforti''.<ref name="pmid8440737">{{cite journal|vauthors=Proctor RH, Hohn TM |title=Aristolochene synthase. Isolation, characterization, and bacterial expression of a sesquiterpenoid biosynthetic gene (Ari1) from ''Penicillium roqueforti'' |journal=J. Biol. Chem. |volume=268 |issue=6 |pages=4543–8 |date=February 1993 |doi=10.1016/S0021-9258(18)53644-9 |pmid=8440737 |url=http://www.jbc.org/cgi/pmidlookup?view=long&pmid=8440737|doi-access=free }}</ref> PR toxin has been implicated in incidents of ] resulting from eating contaminated grains.<ref name="pmid7080052">{{cite journal |vauthors=Chen FC, Chen CF, Wei RD |title=Acute toxicity of PR toxin, a mycotoxin from ''Penicillium roqueforti'' |journal=Toxicon |volume=20 |issue=2 |pages=433–41 |year=1982 |pmid=7080052 |doi= 10.1016/0041-0101(82)90006-X}}</ref> | Aristolochene is a precursor to ], a toxic chemical made in large amounts by ''Penicillium roqueforti''.<ref name="pmid8440737">{{cite journal|vauthors=Proctor RH, Hohn TM |title=Aristolochene synthase. Isolation, characterization, and bacterial expression of a sesquiterpenoid biosynthetic gene (Ari1) from ''Penicillium roqueforti'' |journal=J. Biol. Chem. |volume=268 |issue=6 |pages=4543–8 |date=February 1993 |doi=10.1016/S0021-9258(18)53644-9 |pmid=8440737 |url=http://www.jbc.org/cgi/pmidlookup?view=long&pmid=8440737|doi-access=free }}</ref> PR toxin has been implicated in incidents of ] resulting from eating contaminated grains.<ref name="pmid7080052">{{cite journal |vauthors=Chen FC, Chen CF, Wei RD |title=Acute toxicity of PR toxin, a mycotoxin from ''Penicillium roqueforti'' |journal=Toxicon |volume=20 |issue=2 |pages=433–41 |year=1982 |pmid=7080052 |doi= 10.1016/0041-0101(82)90006-X|bibcode=1982Txcn...20..433C }}</ref> | ||
| == Related Compounds == | == Related Compounds == | ||
Latest revision as of 00:51, 26 October 2024
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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 | |
| CAS Number | |
| 3D model (JSmol) | |
| ChEBI | |
| ChemSpider | |
| PubChem CID | |
| UNII | |
| CompTox Dashboard (EPA) | |
InChI
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SMILES
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| Properties | |
| Chemical formula | C15H24 |
| Molar mass | 204.357 g·mol |
| Density | 0.894 g/mL |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 N verify (what is ?)
Infobox references
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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.
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. PR toxin has been implicated in incidents of mycotoxicoses resulting from eating contaminated grains.
Related Compounds
References
- 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.