Aristolochene is a
bicyclic
In chemistry, a bicyclic molecule () is a molecule that features two joined rings. Bicyclic structures occur widely, for example in many biologically important molecules like α-thujene and camphor. A bicyclic compound can be carbocyclic (all ...
sesquiterpene
Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many unique combinations. Biochemical modificat ...
produced by certain
fungi
A fungus ( : fungi or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and molds, as well as the more familiar mushrooms. These organisms are classified as a kingdom, separately from ...
including the
cheese mold
A mold () or mould () is one of the structures certain fungi can form. The dust-like, colored appearance of molds is due to the formation of spores containing fungal secondary metabolites. The spores are the dispersal units of the fungi. Not ...
''
Penicillium roqueforti''. It is
biosynthesized
Biosynthesis is a multi-step, enzyme- catalyzed process where substrates are converted into more complex products in living organisms. In biosynthesis, simple compounds are modified, converted into other compounds, or joined to form macromolecules ...
from
farnesyl pyrophosphate by
aristolochene synthase and is the parent hydrocarbon of a large variety of
fungal toxins.
Terpene Biosynthesis
, Chem 549, College of Pharmacy, University of Arizona
The substance was first isolated from '' Penicillium roqueforti'', a fungus used to make blue cheeses like Roquefort
Roquefort is a sheep milk cheese from Southern France, and is one of the world's best known blue cheeses. Though similar cheeses are produced elsewhere, EU law dictates that only those cheeses aged in the natural Combalou caves of Roquefort-sur ...
, Danish Blue
Danablu, often marketed under the trademark Danish Blue Cheese within North America, is a strong, blue-veined cheese. This semi-soft creamery cheese is typically drum- or block-shaped and has a yellowish, slightly moist, edible rind. Made from f ...
, Stilton cheese and Gorgonzola
Gorgonzola (; ) is a veined blue cheese, originally from Italy, made from unskimmed cow's milk. It can be buttery or firm, crumbly and quite salty, with a "bite" from its blue veining.
History
Historically, gorgonzola has been produced for ...
.
Aristolochene is a precursor to the toxin known as PR toxin, made in large amounts by '' Penicillium roqueforti''.
Related Compounds
* Roquefortine C
Roquefortine C is a mycotoxin that belongs to a class of naturally occurring 2,5-diketopiperazines produced by various fungi, particularly species from the genus ''Penicillium''. It was first isolated from a strain of ''Penicillium roqueforti'', a ...
* Aflatoxin
Aflatoxins are various poisonous carcinogens and mutagens that are produced by certain molds, particularly ''Aspergillus'' species. The fungi grow in soil, decaying vegetation and various staple foodstuffs and commodities such as hay, sweetcorn ...
* Patulin
Patulin is an organic compound classified as a polyketide. It is a white powder soluble in acidic water and in organic solvents. It is a lactone that is heat-stable, so it is not destroyed by pasteurization or thermal denaturation.http://www.s ...
References
{{reflist
Sesquiterpenes
Mycotoxins