Different polyketide folding modes converge to an identical molecular architecture.
Metabolic diversity is being studied intensively by evolutionary biologists, but so far there has been no comparison of biosynthetic pathways leading to a particular secondary metabolite in both prokaryotes and eukaryotes. We have detected the bioactive anthraquinone chrysophanol, which serves as a chemical defense in diverse eukaryotic organisms, in a bacterial Nocardia strain, thereby permitting the first comparative biosynthetic study. Two basic modes of folding a polyketide chain to fused-ring aromatic structures have so far been described: mode F (referring to fungi) and mode S (from Streptomyces). We have demonstrated that in eukaryotes (fungi, higher plants and insects), chrysophanol is formed via folding mode F. In actinomycetes, by contrast, the cyclization follows mode S. Thus, chrysophanol is the first polyketide synthase product that is built up by more than one polyketide folding mode.
Bringmann
Gerhard
G
Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany. bringman@chemie.uni-wuerzburg.de
Noll
Torsten F
TF
Gulder
Tobias A M
TA
Grüne
Matthias
M
Dreyer
Michael
M
Wilde
Christopher
C
Pankewitz
Florian
F
Hilker
Monika
M
Payne
Gail D
GD
Jones
Amanda L
AL
Goodfellow
Michael
M
Fiedler
Hans-Peter
HP
D000818:Animals; D000880:Anthraquinones / Q000737:chemistry / Q000378:metabolism*; D003500:Cyclization; D005057:Eukaryotic Cells / Q000737:chemistry / Q000378:metabolism; D005658:Fungi / Q000737:chemistry / Q000378:metabolism*; D007313:Insecta; D007814:Larva; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D015394:Molecular Structure; D009615:Nocardia / Q000235:genetics / Q000378:metabolism; D048630:Polyketide Synthases / Q000737:chemistry; D012015:Reference Standards; D013302:Streptomyces / Q000737:chemistry / Q000378:metabolism*
D000880:Anthraquinones; D048630:Polyketide Synthases; C027113:chrysophanic acid