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).
Infobox references

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

Penicillin Group of antibiotics derived from Penicillium fungi

Penicillins are a group of antibiotics originally obtained from Penicillium moulds, principally P. chrysogenum and P. rubens. Most penicillins in clinical use are chemically synthesised from naturally-produced penicillins. 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 members of the β-lactam antibiotics, which are some of the most powerful and successful achievements in modern science. They are still widely used today for different bacterial infections, though many types of bacteria have developed resistance following extensive use.

<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.

Mevastatin

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

History of penicillin

The history of penicillin follows a number of observations and discoveries of apparent evidence of antibiotic activity of the mould Penicillium. Following the identification of Penicillium rubens as the source of the compound in 1928 and with the production of pure compound in 1942, penicillin became the first naturally derived antibiotic. There are anecdotes about ancient societies using moulds to treat infections, and in the following centuries many people observed the inhibition of bacterial growth by various moulds. However, it is unknown if the species involved were Penicillium species or if the antimicrobial substances produced were penicillin.

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

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.

Brevianamide 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, but molecular phylogeny established that it is a distinct species and that P. notatum is P. rubens. 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.

Fungal isolates have been researched for decades. Because fungi often exist in thin mycelial monolayers, with no protective shell, immune system, and limited mobility, they have developed the ability to synthesize a variety of unusual compounds for survival. Researchers have discovered fungal isolates with anticancer, antimicrobial, immunomodulatory, and other bio-active properties. The first statins, β-Lactam antibiotics, as well as a few important antifungals, were discovered in fungi.

Medicinal fungi are fungi which contain metabolites or can be induced to produce metabolites through biotechnology to develop prescription drugs. Compounds successfully developed into drugs or are 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 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 herquei is an anamorph, filamentous species of the genus of Penicillium which produces citreorosein, emodin, hualyzin, herquline B, janthinone, citrinin and duclauxin,.

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

Penicillium striatisporum is an anamorph species of fungus in the genus Penicillium which was isolated from the rhizosphere of chilli peppers. Penicillium striatisporum has an selective antifungal activity against Candida albicans This species produces striatisporin A, striatisporolide A, versiol, calbistrin C, deformylcalbistrin A, citromycetin, citromycin, fulvic acid, (-)-2,3-dihydrocitromycetin and (+)-hexylitaconic acid

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

Phomoxanthone

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.