Rugulosin

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Rugulosin
Rugulosin.svg
Names
IUPAC name
8,10,14,23,25,28-hexahydroxy-6,21-dimethyloctacyclo[14.11.1.02,11.02,15.04,9.013,17.017,26.019,24]octacosa-4(9),5,7,10,19(24),20,22,25-octaene-3,12,18,27-tetrone
Other names
NSC 160880
NSC 249990
Rugulosin A
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C30H22O10/c1-7-3-9-13(11(31)5-7)21(33)17-25(37)20-23(35)15-16-24(36)19(29(15,17)27(9)39)26(38)18-22(34)14-10(28(40)30(16,18)20)4-8(2)6-12(14)32/h3-6,15-16,19-20,23-24,31-36H,1-2H3
    Key: QFDPVUTXKUGISP-UHFFFAOYSA-N
  • CC1=CC2=C(C(=C1)O)C(=C3C(=O)C4C(C5C3(C2=O)C6C(C5C47C(=C(C8=C(C7=O)C=C(C=C8O)C)O)C6=O)O)O)O
  • natural:Cc1cc2c(c(c1)O)C(=O)C3=C([C@H]4[C@H]([C@H]5[C@]3(C2=O)[C@@H]6[C@H]([C@H]5[C@]47C(=O)c8cc(cc(c8C(=O)C7=C6O)O)C)O)O)O
Properties
C30H22O10
Molar mass 542.496 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Rugulosin is an anthraquinoid mycotoxin with the molecular formula C30H22O10 which is produced by Penicillium species. [1] [2] [3] Rugulosin is hepatotoxic and is cancerogenic. [4]

Related Research Articles

A mycotoxin is a toxic secondary metabolite produced by organisms of kingdom 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.

Trichothecene

Trichothecenes are a very large family of chemically related mycotoxins produced by various species of Fusarium, Myrothecium, Trichoderma, Trichothecium, Cephalosporium, Verticimonosporium, and Stachybotrys. Trichothecenes are a class of sesquiterpenes. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus, and the structure and position of the side-chain. They are produced on many different grains like wheat, oats or maize by various Fusarium species such as F. graminearum, F. sporotrichioides, F. poae and F. equiseti.

Citrinin Chemical compound

Citrinin is a mycotoxin which is often found in food. It is a secondary metabolite produced by fungi that contaminates long-stored food and it causes different toxic effects, like nephrotoxic, hepatotoxic and cytotoxic effects. Citrinin is mainly found in stored grains, but sometimes also in fruits and other plant products.

Mycotoxicology is the branch of mycology that focuses on analyzing and studying the toxins produced by fungi, known as mycotoxins. In the food industry it is important to adopt measures that keep mycotoxin levels as low as practicable, especially those that are heat-stable. These chemical compounds are the result of secondary metabolism initiated in response to specific developmental or environmental signals. This includes biological stress from the environment, such as lower nutrients or competition for those available. Under this secondary path the fungus produces a wide array of compounds in order to gain some level of advantage, such as incrementing the efficiency of metabolic processes to gain more energy from less food, or attacking other microorganisms and being able to use their remains as a food source.

Paxilline Chemical compound

Paxilline is a toxic, tremorgenic diterpene indole polycyclic alkaloid molecule produced by Penicillium paxilli which was first characterized in 1975. Paxilline is one of a class of tremorigenic mycotoxins, is a potassium channel blocker, and is potentially genotoxic.

Roquefortine C 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.

Penicillium brunneum is an anamorph fungus species of the genus of Penicillium which was isolated in imported rice an produces rugulosin a substance which is hepatocarcinogenic to mice and rats.

Penicillium isariiforme is an anamorph, phototropic species of the genus of Penicillium which produce secalonic acid D and F.

Penicillium islandicum is an anamorph species of the genus of Penicillium which produces luteoskyrin, simatoxin, cyclochlorotine, rugulosin, islanditoxin and chitosanase.

Penicillium persicinum is a species of fungus in the genus Penicillium which was isolated from soil from the Qinghai Province in China. Penicillium persicinum produces griseofulvin, lichexanthone, roquefortine C, roquefortine D, patulin and chrysogine

Penicillium radicum is an anamorph species of the genus of Penicillium which was isolated from rhizosphere of Australian wheat. This species has the ability to solubilise inorganic phosphates, this can promote plant growth Penicillium radicum produces rugulosin

Penicillium resedanum is an anamorph species of fungus in the genus Penicillium which produces monorden.

Penicillium rubrum is a species of fungus in the genus Penicillium which produces kojic acid, mitorubrin, mitorubrinol, rubratoxin A, rubratoxin B rubralactone, rubramin and occurs in grain corn and soybeans. Penicillium rubrum is similar to the species Penicillium chrysogenum.

Penicillium rugulosum is an anamorph species of fungus in the genus Penicillium which produces inulinase, luteoskyrin and (+) rugulosin.

Penicillium tulipae is a species of fungus in the genus Penicillium which produces penicillic acid, roquefortine C, roquefortine D, terrestric acid, glandicoline A, glandicoline B, meleagrin, oxaline, penitrem A and epineoxaline.

Penicillium viridicatum is a psychrophilic species of fungus in the genus, penicillic acid and citrinin. Penicillium viridicatum can spoil grapes and melons.

Lolitrem B Chemical compound

Lolitrem B is one of many toxins produced by a fungus called Epichloë festucae var. lolii), which grows in Lolium perenne. The fungus is symbiotic with the ryegrass; it doesn't harm the plant, and the toxins it produces kill insects that feed on ryegrass. Lolitrem B is one of these toxins, but it is also harmful to mammals. The shoots and flowers of infected ryegrass have especially high concentrations of lolitrem B, and when livestock eat too much of them, they get perennial ryegrass staggers. At low doses the animals have tremors, and at higher doses they stagger, and at higher yet doses the animals become paralyzed and die. The blood pressure of the animals also goes up. The effect of the lolitrem B comes on slowly and fades out slowly, as it is stored in fat after the ryegrass is eaten. The condition is especially common in New Zealand and Australia, and plant breeders there have been trying to develop strains of fungus that produce toxins only harmful to pests, and not to mammals.

PR toxin Chemical compound

Penicillin Roquefort Toxin is a mycotoxin produced by the fungi 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 auricle.

Luteoskyrin Chemical compound

Luteoskyrin is a carcinogenic mycotoxin with the molecular formula C30H22O12 which is produced by the mold Penicillium islandicum. Luteoskyrin has strong cytotoxic effects. Luteoskyrin can cause the yellow rice disease.

Gregatin B Chemical compound

Gregatin B is a metabolite of the fungi Cephalosporium gregatum and Aspergillus panamensis with the molecular formula C14H18O4 Gregatin B is a weak antibiotic. Gregatin B was discovered on 1982.

References

  1. "Rugulosin". Pubchem.
  2. Ueno, Yoshio; Sato, Norio; Ito, Teruo; Ueno, Ikuko; Enomoto, Makoto; Tsunoda, Hiroshi (1980). "Chronic Toxicity and Hepatocarcinogenicity of (+) Rugulosin, an Anthraquinoid Mycotoxin from Penicillium Species: Preliminary Surveys in Mice". The Journal of Toxicological Sciences. 5 (4): 295–302. doi: 10.2131/jts.5.295 . PMID   7218376.
  3. Ueno, Y; Ueno, I; Sato, N; Iitoi, Y; Saito, M (June 1971). "Toxicological approach to (+) rugulosin, an anthraquinoid mycotoxin of Penicillium rugulosum Thom". The Japanese Journal of Experimental Medicine. 41 (3): 177–188. PMID   5314585.
  4. Eisenbrand, Gerhard; Schreier, Peter (28 May 2014). RÖMPP Lexikon Lebensmittelchemie, 2. Auflage, 2006 (in German). Georg Thieme Verlag. ISBN   978-3-13-179532-8.

Further reading