title: Novel illudins from Coprinopsis episcopalis (syn. Coprinus episcopalis), and the distribution of illudin-like compounds among filamentous fungi.
abstract: The illudins are a family of fungal sesquiterpenes that have been studied as anti-tumor agents, and they also have antibacterial activity. Over a four-year period, 25 304 fungal isolates (approximately 97% ascomycetes and 3% basidiomycetes), were screened for antibacterial activity against methicillin-resistant Staphylococcus aureus. Illudin-like compounds with antibacterial and cytotoxic activity against tumor cell lines were observed in 10 basidiomycete strains. The isolates were recovered from different types of substrata using indirect methods and only formed sterile mycelia in pure culture. The isolates were genetically related but not identical, based on PCR-based fingerprinting techniques. DNA sequencing of the ITS1-5.8 S-ITS2 region of the strains revealed that nine had identical sequences, indicating that they were conspecific. The sequence of the remaining isolate was 96.34% similar, suggesting that it was a closely related species. The D1-D2 region of the 25 S rRNA gene of the two strain types was also sequenced. Both sequences were 99.39% similar, and Coprinopsis gonophylla (syn. Coprinus gonophyllus) was the closest match for both. Strains were grown in pure culture on a rice-based medium that allowed the development of basidiomata from one culture of the main strain type, which was identified as C. episcopalis, a close relative of C. gonophyllus. Both species (or strain types) produced different types of illudin-like compounds. Three novel illudins (I, I2 and J2) were found to be produced by the cultures identified as C. episcopalis, while only illudinic acid was produced by the other Coprinopsis sp. The taxonomical relationships of the Coprinops is species identified in this study with other illudin producers previously reported in the literature are discussed.
authors.affiliation: Centro de Investigación Básica, Merck Sharp & Dohme Research Laboratories, Josefa Valcárcel 38, E-28027 Madrid, Spain. ant_gonzalez@merck.com
authors.forename: Antonio
authors.initials: A
authors.lastname: Gonzalez del Val
authors.forename: Gonzalo
authors.initials: G
authors.lastname: Platas
authors.forename: Francisco
authors.initials: F
authors.lastname: Arenal
authors.forename: Juan Carlos
authors.initials: JC
authors.lastname: Orihuela
authors.forename: María
authors.initials: M
authors.lastname: Garcia
authors.forename: Pilar
authors.initials: P
authors.lastname: Hernández
authors.forename: Inmaculada
authors.initials: I
authors.lastname: Royo
authors.forename: Nuria
authors.initials: N
authors.lastname: De Pedro
authors.forename: Lynn L
authors.initials: LL
authors.lastname: Silver
authors.forename: Katherine
authors.initials: K
authors.lastname: Young
authors.forename: María Francisca
authors.initials: MF
authors.lastname: Vicente
authors.forename: Fernando
authors.initials: F
authors.lastname: Pelaez
mesh_terms: D000363:Agaricales / Q000235:genetics / Q000378:metabolism*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000378:metabolism; D001487:Basidiomycota / Q000235:genetics / Q000378:metabolism; D004271:DNA, Fungal / Q000235:genetics; D021903:DNA, Ribosomal Spacer / Q000235:genetics; D016106:Methicillin Resistance; D015394:Molecular Structure; D010802:Phylogeny; D012717:Sesquiterpenes / Q000737:chemistry / Q000378:metabolism*; D013211:Staphylococcus aureus / Q000187:drug effects
chemical_list: D000900:Anti-Bacterial Agents; D004271:DNA, Fungal; D021903:DNA, Ribosomal Spacer; D012717:Sesquiterpenes; C104806:illudinic acid