Verrucosidin

Last updated
Verrucosidin
Verrucosidin Structure.svg
Names
Preferred IUPAC name
4-Methoxy-3,5-dimethyl-6-[(2R,3S)-2-methyl-3-{(2E,4E)-4-methyl-5-[(1S,2S,4R,5R)-2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl]penta-2,4-dien-2-yl}oxiran-2-yl]-2H-pyran-2-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C24H32O6/c1-12(11-22(6)21-23(7,30-21)16(5)28-22)10-13(2)18-24(8,29-18)19-14(3)17(26-9)15(4)20(25)27-19/h10-11,16,18,21H,1-9H3/b12-11+,13-10+/t16-,18+,21+,22+,23-,24-/m1/s1
    Key: JSVLNARHSWZARV-FOOXNAEUSA-N
  • C[C@@H]1[C@@]2([C@@H](O2)[C@](O1)(C)/C=C(\C)/C=C(\C)/[C@H]3[C@](O3)(C)C4=C(C(=C(C(=O)O4)C)OC)C)C
Properties
C24H32O6
Molar mass 416.514 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Verrucosidin is a toxic pyrone-type polyketide produced by Penicillium aurantiogriseum , Penicillium melanoconidium , and Penicillium polonicum . [1]

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<span class="mw-page-title-main">Mold</span> Wooly, dust-like fungal structure or substance

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<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.

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

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<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.

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<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.

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<span class="mw-page-title-main">Charles Thom</span> American icrobiologist and mycologist (1872–1956)

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

Penicillium rubens is a species of fungus in the genus Penicillium and was the first species known to produce the antibiotic penicillin. It was first described by Philibert Melchior Joseph Ehi Biourge in 1923. For the discovery of penicillin from this species Alexander Fleming shared the Nobel Prize in Physiology or Medicine in 1945. The original penicillin-producing type has been variously identified as Penicillium rubrum, P. notatum, and P. chrysogenum among others, but genomic comparison and phylogenetic analysis in 2011 resolved that it is P. rubens. It is the best source of penicillins and produces benzylpenicillin (G), phenoxymethylpenicillin (V) and octanoylpenicillin (K). It also produces other important bioactive compounds such as andrastin, chrysogine, fungisporin, roquefortine, and sorbicillins.

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

Penicillium commune is an indoor fungus belonging to the genus Penicillium. It is known as one of the most common fungi spoilage moulds on cheese. It also grows on and spoils other foods such as meat products and fat-containing products like nuts and margarine. Cyclopiazonic acid and regulovasine A and B are the most important mycotoxins produced by P. commune. The fungus is the only known species to be able to produce both penitrem A and roquefortine. Although this species does not produce penicillin, it has shown to have anti-pathogenic activity. There are no known plant, animal or human diseases caused by P. commune.

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

Penicillium spinulosum is a non-branched, fast-growing fungus with a swelling at the terminal of the stipe (vesiculate) in the genus Penicillium. P. spinulosum is able to grow and reproduce in environment with low temperature and low water availability, and is known to be acidotolerant. P. spinulosum is ubiquitously distributed, and can often be isolated from soil. Each individual strain of P. spinulosum differs from others in their colony morphology, including colony texture, amount of sporulation and roughness of conidia and conidiophores.

References

  1. Frisvad, JC; Smedgaard, J; Larsen, TO; Samson, RA (2004). "Mycotoxins, drugs, and other extrolites produced by species in Penicillium subgenus Penicillium". Studies in Mycology. 49: 201–241. ISSN   0166-0616.