Aristolochene
From Wikipedia, the free encyclopedia
 | |
| 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) |
|
| |
| |
| 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, most notably the cheese mold Penicillium roqueforti. It is biosynthesized from farnesyl pyrophosphate by the enzyme aristolochene synthase and serves as the parent hydrocarbon for a variety of fungal toxins.[1]
Aristolochene was first isolated and structurally characterized in 1969 from the roots of Aristolochia indica by Govindachari, Mohamed, and Parthasarathy.[2] However, this discovery involved the (−)-enantiomeric form, not the bioactive (+)-enantiomer characteristic of fungal biosynthetic pathways. The (+)-enantiomer was later identified and experimentally confirmed in Penicillium roqueforti through studies centered around aristolochene synthase activity and the ari1 locus which encodes the enzyme.[3][4]
_&_(−)_Aristolochene_Enantiomers.png)
Applications
Aristolochene is primarily recognized as the precursor to PR toxin, a mycotoxin produced in large quantities by Penicillium roqueforti. PR toxin has been implicated in incidents of mycotoxicoses resulting from consumption of contaminated grains;[5] moreover, strains of Penicillium roqueforti are frequently used in commercial blue cheese production. Common blue cheese products include, Roquefort, Danish Blue, Stilton cheese, and Gorgonzola.
In addition to PR toxin, aristolochene is a biosynthetic precursor to eremofortins (A-C), a group of metabolites that function as canonical upstream intermediates in the PR toxin biosynthetic pathway.[6][7][8][9] Variation in their expression can influence host-organism metabolism and modulate interactions with the surrounding environment.[10]
The influence of aristolochene on fungal metabolic regulation is an evolving area of research. Its role as an upstream precursor has relevance towards food safety, natural product chemistry, and pharmaceutical development.
