Citromycin

Last updated
Citromycin
Citromycin Structure.svg
Names
Preferred IUPAC name
8,9-Dihydroxy-2-methyl-4H,5H-pyrano[3,2-c][1]benzopyran-4-one
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C13H10O5/c1-6-2-9(14)8-5-17-12-4-11(16)10(15)3-7(12)13(8)18-6/h2-4,15-16H,5H2,1H3
    Key: QZZUHPUWIRSQPB-UHFFFAOYSA-N
  • InChI=1/C13H10O5/c1-6-2-9(14)8-5-17-12-4-11(16)10(15)3-7(12)13(8)18-6/h2-4,15-16H,5H2,1H3
    Key: QZZUHPUWIRSQPB-UHFFFAOYAO
  • CC1=CC(=O)C2=C(O1)C3=CC(=C(C=C3OC2)O)O
Properties
C13H10O5
Molar mass 246.218 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Citromycin is a chemical compound produced by Penicillium . [1] It was first discovered in 1969 and was found to have weak antibiotic activity. [2]

Related Research Articles

<span class="mw-page-title-main">Penicillin</span> Group of antibiotics derived from Penicillium fungi

Penicillins are a group of β-lactam antibiotics originally obtained from Penicillium moulds, principally P. chrysogenum and P. rubens. Most penicillins in clinical use are synthesised by P. chrysogenum using deep tank fermentation and then purified. A number of natural penicillins have been discovered, but only two purified compounds are in clinical use: penicillin G and penicillin V. Penicillins were among the first medications to be effective against many bacterial infections caused by staphylococci and streptococci. They are still widely used today for various bacterial infections, though many types of bacteria have developed resistance following extensive use.

β-Lactam antibiotic Class of broad-spectrum antibiotics

β-Lactam antibiotics are antibiotics that contain a β-lactam ring in their chemical structure. This includes penicillin derivatives (penams), cephalosporins and cephamycins (cephems), monobactams, carbapenems and carbacephems. Most β-lactam antibiotics work by inhibiting cell wall biosynthesis in the bacterial organism and are the most widely used group of antibiotics. Until 2003, when measured by sales, more than half of all commercially available antibiotics in use were β-lactam compounds. The first β-lactam antibiotic discovered, penicillin, was isolated from a strain of Penicillium rubens.

<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.

<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.

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

Mevastatin is a hypolipidemic agent that belongs to the statins class.

Penicillium aurantiogriseum is a plant pathogen infecting asparagus and strawberry. Chemical compounds isolated from Penicillium aurantiogriseum include anicequol and auranthine.

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

Brevianamides are indole alkaloids that belong to a class of naturally occurring 2,5-diketopiperazines produced as secondary metabolites of fungi in the genus Penicillium and Aspergillus. Structurally similar to paraherquamides, they are a small class compounds that contain a bicyclo[2.2.2]diazoctane ring system. One of the major secondary metabolites in Penicillium spores, they are responsible for inflammatory response in lung cells.

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

Penicillium chrysogenum is a species of fungus in the genus Penicillium. It is common in temperate and subtropical regions and can be found on salted food products, but it is mostly found in indoor environments, especially in damp or water-damaged buildings. It has been recognised as a species complex that includes P. notatum, P. meleagrinum, and P. cyaneofulvum. Molecular phylogeny has established that Alexander Fleming's first discovered penicillin producing strain is of a distinct species, P. rubens, and not of P. notatum. It has rarely been reported as a cause of human disease. It is the source of several β-lactam antibiotics, most significantly penicillin. Other secondary metabolites of P. chrysogenum include roquefortine C, meleagrin, chrysogine, 6-MSA YWA1/melanin, andrastatin A, fungisporin, secalonic acids, sorbicillin, and PR-toxin.

Medicinal fungi are fungi that contain metabolites or can be induced to produce metabolites through biotechnology to develop prescription drugs. Compounds successfully developed into drugs or under research include antibiotics, anti-cancer drugs, cholesterol and ergosterol synthesis inhibitors, psychotropic drugs, immunosuppressants and fungicides.

Penicillium brefeldianum is an anamorph fungus species of the genus of Penicillium which produces brefeldin A a fungal metabolite.

Penicillium chermesinum is an anamorph fungus species of the genus of Penicillium which was isolated from soil from Nova Scotia in Canada.Penicillium chermesinum produces plastatin, luteosporin, xanthomegnin, azaphilones, p-terphenyls and costaclavine.

Penicillium citrinum is an anamorph, mesophilic fungus species of the genus of Penicillium which produces tanzawaic acid A-D, ACC, Mevastatin, Quinocitrinine A, Quinocitrinine B, and nephrotoxic citrinin. Penicillium citrinum is often found on moldy citrus fruits and occasionally it occurs in tropical spices and cereals. This Penicillium species also causes mortality for the mosquito Culex quinquefasciatus. Because of its mesophilic character, Penicillium citrinum occurs worldwide. The first statin (Mevastatin) was 1970 isolated from this species.

Penicillium coralligerum is a species of the genus of Penicillium. It is a marine species sometimes referred to as a deep-sea fungus and in some languages named the equivalent of "deep-sea mold".

Penicillium cyaneum is a species of the genus of Penicillium which was isolated from an oil-field. Penicillium cyaneum produces fatty acid, Brefeldin A and the antibiotic Cyanein

Penicillium decumbens is an anamorph species of the genus of Penicillium which occurs widespread in nature, mainly in subtropical and tropical soil but it also occur in food. Analysis have shown that Penicillium decumbens has antibiotic activity Penicillium decumbens produces the cyclopentenone cyclopenicillone

Penicillium herquei is an anamorph, filamentous species of the genus of Penicillium which produces citreorosein, emodin, hualyzin, herquline B, janthinone, citrinin and duclauxin,.

Penicillium janczewskii is an anamorph and filamentous species of the genus of Penicillium which was isolated from the rhizosphere of Vernonia herbacea. Penicillium janczewskii produces griseofulvin

Penicillium minioluteum is an anamorph species of the genus Penicillium which produces dextranase, miniolin A, miniolin B and miniolin C.

Penicillium waksmanii is an anamorph species of the genus of Penicillium which was isolated from the alga Sargassum ringgoldianum. Penicillium waksmanii produces pyrenocine A, pyrenocine C, pyrenocine D and pyrenocine E

<span class="mw-page-title-main">Phomoxanthone</span> Class of chemical compounds

The phomoxanthones are a loosely defined class of natural products. The two founding members of this class are phomoxanthone A and phomoxanthone B. Other compounds were later also classified as phomoxanthones, although a unifying nomenclature has not yet been established. The structure of all phomoxanthones is derived from a dimer of two covalently linked tetrahydroxanthones, and they differ mainly in the position of this link as well as in the acetylation status of their hydroxy groups. The phomoxanthones are structurally closely related to other tetrahydroxanthone dimers such as the secalonic acids and the eumitrins. While most phomoxanthones were discovered in fungi of the genus Phomopsis, most notably in the species Phomopsis longicolla, some have also been found in Penicillium sp.

References

  1. Capon, RJ; Stewart, M; Ratnayake, R; Lacey, E; Gill, JH (2007). "Citromycetins and bilains A-C: New aromatic polyketides and diketopiperazines from Australian marine-derived and terrestrial Penicillium spp". Journal of Natural Products. 70 (11): 1746–52. doi:10.1021/np0702483. PMID   17958395.
  2. Kusakabe, Y; Yamauchi, Y; Nagatsu, C; Abe, H; Akasaki, K (1969). "Citromycin, a new antibiotic. I. Isolation and characterization". The Journal of Antibiotics. 22 (3): 112–8. doi: 10.7164/antibiotics.22.112 . PMID   4978096.