Biosynthesis of scorpinone, a 2-azaanthraquinone from Amorosia littoralis, a fungus from marine sediment.
The biogenetic origin of the carbon atoms in the 2-azaanthraquinone scorpinone ( 1), produced by the rare fungus Amorosia littoralis isolated from marine sediment, was explored through isotopic enrichment studies utilizing [2- (13)C]-acetate and [1,2- (13)C]-acetate. The labeling results reveal a heptaketide precursor is involved in the biosynthesis of 1, as has been found for the structurally related naphthoquinone dihydrofusarubin. The previously identified naphthoquinone herbarin ( 2) was also isolated and appears to bear the same biogenetic relationship to 1 as the fusarubins do to the fungal 2-azaanthraquinone bostrycoidins.
Van Wagoner
Ryan M
RM
University of North Carolina, Wilmington, North Carolina 28409, USA.
Mantle
Peter G
PG
Wright
Jeffrey L C
JL
D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry; D001203:Ascomycota / Q000737:chemistry*; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001444:Bahamas; D019015:Geologic Sediments / Q000382:microbiology*; D015394:Molecular Structure
D000880:Anthraquinones; D001372:Aza Compounds; C438633:scorpinone