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In vitro conversion of chanoclavine-I aldehyde to the stereoisomers festuclavine and pyroclavine controlled by the second reduction step

“…at C-8 differs from that of fumigaclavines from A. fumigatus. [15][16][17][18]20 To confirm the configuration of fumigaclavine A from P. commune NRRL2033, the fungus was cultivated on wheat medium and extracted with ethyl acetate (see Experimental Section{). HPLC analysis of the extract showed the presence of one predominant peak at 19.4 min (Fig.…”

“…Coexistence of 3, 4 and fumigaclavine A and B was reported for P. commune VKM F-3088 (= NRRL2033). 15 Unfortunately, no structures and therefore no information on the stereochemistry for C-8 were given for fumigaclavines in that work. 15 As confirmed in this study, only (8R,9S)-fumigaclavine A accumulated in P. commune NRRL2033.…”

“…11,12 The end products of the biosynthetic pathways in A. fumigatus and P. commune were found to be fumigaclavine C and fumigaclavine A, respectively. [13][14][15] The structural difference of these ergot alkaloids in the two fungi is perfectly reflected by the presence of an additional prenyltransferase gene fgaPT1 in A. fumigatus. 14 An additional difference between the structures of fumigaclavine A from Penicillium, and fumigaclavines from Aspergillus is the stereochemistry at C-8 (Fig.…”

Reverse Prenyltransferase in the Biosynthesis of Fumigaclavine C in Aspergillus fumigatus: Gene Expression, Purification, and Characterization of Fumigaclavine C Synthase FGAPT1

“…Penicillium commune NRRL 2033 was kindly provided by the ARS Culture Collection (Peoria, Illinois) and was maintained on Czapek Dox Agar. For production of fumigaclavine A, the fungus was cultivated in modified Czapek Dox liquid medium49 (6 L) containing (g L −1 ) sucrose (30), yeast extract (5.1), NaNO 3 (2.0), KH 2 PO 4 (1.0), MgSO 4 ⋅ 7 H 2 O (0.3) and FeSO 4 ⋅ 7 H 2 O (0.01) in surface culture at 24 °C for 14 days 50…”

Identification of a Hybrid PKS/NRPS Required for Pseurotin A Biosynthesis in the Human Pathogen Aspergillus fumigatus

“…[17,18,19] It is possible that the two genes, Afu8g00620 and Afu8g00540, could also contribute to the biosynthesis of a prenylated metabolite derived from amino acid and malonate, such as b-cyclopiazonic acid. b-Cyclopiazonic acid has also been isolated from A. fumigatus [20] and is derived from diA C H T U N G T R E N N U N G meth-A C H T U N G T R E N N U N G ylallyl diphosphate, l-tryptophan and two molecules of malonate. [21] We have determined an unidentified peak observed in A. fumigatus culture extracts by HPLC [6] to be pseurotin A (this work).…”