Aristolochene

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Aristolochene
Aristolochene.png
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
  • InChI=1S/C15H24/c1-11(2)13-8-9-14-7-5-6-12(3)15(14,4)10-13/h9,12-13H,1,5-8,10H2,2-4H3/t12-,13-,15+/m0/s1 Yes check.svgY
    Key: YONHOSLUBQJXPR-KCQAQPDRSA-N Yes check.svgY
  • InChI=1/C15H24/c1-11(2)13-8-9-14-7-5-6-12(3)15(14,4)10-13/h9,12-13H,1,5-8,10H2,2-4H3/t12-,13-,15+/m0/s1
    Key: YONHOSLUBQJXPR-KCQAQPDRBL
  • C[C@H]1CCCC2=CC[C@@H](C[C@]12C)C(=C)C
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).
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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. [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 Research Articles

<i>Penicillium</i> Genus of fungi

Penicillium is a genus of ascomycetous fungi that is part of the mycobiome of many species and is of major importance in the natural environment, in food spoilage, and in food and drug production.

<span class="mw-page-title-main">Roquefort</span> French blue cheese

Roquefort is a sheep milk blue cheese from southern France. Though similar cheeses are produced elsewhere, EU law dictates that only those cheeses aged in the natural Combalou caves of Roquefort-sur-Soulzon may bear the name Roquefort, as it is a recognised geographical indication, and has a protected designation of origin.

A mycotoxin is a toxic secondary metabolite produced by fungi and is capable of causing disease and death in both humans and other animals. The term 'mycotoxin' is usually reserved for the toxic chemical products produced by fungi that readily colonize crops.

<span class="mw-page-title-main">Blue cheese</span> Cheese with blue veins of mold

Blue cheese is any of a wide range of cheeses made with the addition of cultures of edible molds, which create blue-green spots or veins through the cheese. Blue cheeses vary in taste from very mild to strong, and from slightly sweet to salty or sharp; in colour from pale to dark; and in consistency from liquid to hard. They may have a distinctive smell, either from the mold or from various specially cultivated bacteria such as Brevibacterium linens.

<i>Penicillium roqueforti</i> Species of fungus

Penicillium roqueforti is a common saprotrophic fungus in the genus Penicillium. Widespread in nature, it can be isolated from soil, decaying organic matter, and plants.

<i>Penicillium camemberti</i> Species of fungus

Penicillium camemberti is a species of fungus in the genus Penicillium. It is used in the production of Camembert, Brie, Langres, Coulommiers, and Cambozola cheeses, on which colonies of P. camemberti form a hard, white crust. It is responsible for giving these cheeses their distinctive flavors. An allergy to the antibiotic penicillin does not necessarily imply an allergy to cheeses made using P. camemberti.

<span class="mw-page-title-main">Cyclopiazonic acid</span> Chemical compound

Cyclopiazonic acid (α-CPA), a mycotoxin and a fungal neurotoxin, is made by the molds Aspergillus and Penicillium. It is an indole-tetramic acid that serves as a toxin due to its ability to inhibit calcium-dependent ATPases found in the endoplasmic and sarcoplasmic reticulum. This inhibition disrupts the muscle contraction-relaxation cycle and the calcium gradient that is maintained for proper cellular activity in cells.

Penicillium crustosum is a blue-green or blue-grey mold that can cause food spoilage, particularly of protein-rich foods such as meats and cheeses. It is identified by its complex biseriate conidiophores on which phialides produce asexual spores. It can grow at fairly low temperatures, and in low water activity environments.

The enzyme aristolochene synthase catalyzes the chemical reaction

The enzyme germacrene-A synthase (EC 4.2.3.23) catalyzes the chemical reaction

<span class="mw-page-title-main">Nodularin</span> Chemical compound

Nodularins are potent toxins produced by the cyanobacterium Nodularia spumigena, among others. This aquatic, photosynthetic cyanobacterium forms visible colonies that present as algal blooms in brackish water bodies throughout the world. The late summer blooms of Nodularia spumigena are among the largest cyanobacterial mass occurrences in the world. Cyanobacteria are composed of many toxic substances, most notably of microcystins and nodularins: the two are not easily differentiated. A significant homology of structure and function exists between the two, and microcystins have been studied in greater detail. Because of this, facts from microcystins are often extended to nodularins.

<span class="mw-page-title-main">Roquefortine C</span> Chemical compound

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 species commercially used as a source of proteolytic and lipolytic enzymes during maturation of the blue-veined cheeses, Roquefort, Danish Blue, Stilton and Gorgonzola.

Penicillopepsin is an enzyme. This enzyme catalyses the following chemical reaction

Deuterolysin is an enzyme. This enzyme catalyses the following chemical reaction

5-Epiaristolochene synthase is an enzyme with systematic name (2E,6E)-farnesyl-diphosphate diphosphate-lyase ( -5-epiaristolochene-forming). This enzyme catalyses the following chemical reaction

<span class="mw-page-title-main">Andrastin A</span> Chemical compound

Andrastin A is a farnesyltransferase inhibitor isolate of Penicillium species including Penicillium albocoremium and Penicillium roqueforti. It has been produced bio-synthetically by porting the relevant gene sequence into Aspergillus oryzae.

Penicillium carneum is a fungus species of the genus of Penicillium.Penicillium roqueforti var. carneum was reclassified to Penicillium carneum.P. carneum was isolated from spoiled meat products, silage, rye bread, water, beer, cheese, mouldy barkers yeast and cork. P. carneum produces patulin, penicillic acid, penitrem A, mycophenolic acid roquefortines.

Penicillium psychrosexualis is a filamentous fungus in the genus Penicillium. Described as new to science in 2010, the species was found growing on refrigerated moldy apples in the Netherlands. It is closely related to the blue cheese fungus P. roqueforti.

Penicillium nordicum is an anamorph species of fungus in the genus Penicillium which produces ochratoxin A. Penicillium nordicum contaminates protein rich foods and foods with high NaCl-konzentration. It is mostly found on dry-cured meat products and cheese products

<span class="mw-page-title-main">PR toxin</span> Chemical compound

Penicillin Roquefort toxin is a mycotoxin produced by the fungus Penicillium roqueforti. In 1973, PR toxin was first partially characterized by isolating moldy corn on which the fungi had grown. Although its lethal dose was determined shortly after the isolation of the chemical, details of its toxic effects were not fully clarified until 1982 in a study with mice, rats, anesthetized cats and preparations of isolated rat auricles.

References

  1. Terpene Biosynthesis Archived February 25, 2007, at the Wayback Machine , Chem 549, College of Pharmacy, University of Arizona
  2. 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.
  3. 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.