Tremorgenic mycotoxins from Penicillium crustosum: isolation of penitrems A–F and the structure elucidation and absolute configuration of penitrem A

Bioactive cyclobutane-containing alkaloids

“…Mycotoxins are produced by several Penicillium species: P. crustosum, P. brevicompactum, P. chrysogenum, P. expansum, P. roqueforti, P. spinulosum, P. viridicatum, P. commune, P. citrinum, and P. solitum, including mycophenolic acid, roquefortine C, penitrems A-F (53)(54)(55)(56)(57)(58) and thomitrems A and E (61 and 62) [99][100][101][102][103][104][105][106][107]. Penitrem G (59), a new alkaloid, has been isolated together with the already known mycotoxins penitrems A-D and F from the mycelium of P. crustosum [108].…”

Fungal Chemotaxonomy

“…Most often one of the extrolites is produced in a much higher amount than the others. In the case of the penitrem biosynthetic family, penitrem A is always the major product [77,80,81]. P. crustosum also produces the diketopiperazine roquefortine C as the major end product, whereas P. rubens and P. chrysogenum transform roquefortine C into meleagrin, as the major end product [96].…”

“…For example,Penicillium crustosum produces penitrem A-G [77,78] in addition to the accumulation of precursors and possible shunt metabolites, such as thomitrems A and E, PC-M5ʹ, PC-M6, paspaline, emindole SB, and secopenitrem D ( Table 7.1) [3,4,20,31,34,. This "molecular promiscuity" maybe an evolutionary advantage [109], but from a chemotaxonomic point of view the extra metabolites often give valuable information that can be used to classify and identify filamentous fungi.…”

A fungal prenyltransferase catalyzes the regular di-prenylation at positions 20 and 21 of paxilline

“…[1][2][3] In some cases, isoprenoids are attached to other moieties, such as a polyketide, 4) indole/tryptophan, 5) or (iso)flavonoid, 6) or to phenazine moieties. 7,8) Prenylated indole alkaloids such as paspalitrem A, 9) aflatrem, 10) janthitrems, 11,12) shearinines, 13,14) penitrem A, 15) lolilline, 16) and lolitrems, 17) all of which are produced by filamentous fungi, are examples of this. 18) These compounds are derived from polyprenyl diphosphates and tryptophan or its derivatives, and they show diverse chemical structures and biological activities.…”