Biosynthesis of the macrolide antibiotic patulolides by Penicillium urticae S11R59: identification of the origin of carbon atoms by 13C NMR spectroscopy.
Patulolides are 12-membered macrolides produced by Penicillium urticae S11R59, and they are the simplest macrolide antibiotics. All carbon signals, including six methylene signals of patulolides A (1), B (2), and C (3), were completely assigned by use of the 13C two-dimensional INADEQUATE. The biosynthesis of patulolides was investigated with 13C labeled acetate. Feeding of [1-13C]acetate to a culture of P. urticae S11R59 gave patulolides A (1), B (2), C (3), each of which showed enrichment at carbons 1, 3, 5, 7, 9, and 11; enrichment at carbons 2, 4, 6, 8, 10, and 12 was observed upon feeding of [2-13C]acetate. These results showed that patulolides A (1), B (2), and C (3) are pure acetogenic hexaketides derived from six acetate units coupled in head-to-tail fashion.
Rodphaya
D
D
Department of Fermentation Technology, Faculty of Engineering, Osaka University, Japan.
Nihira
T
T
Sakuda
S
S
Yamada
Y
Y
D000085:Acetates / Q000378:metabolism; D000900:Anti-Bacterial Agents / Q000096:biosynthesis*; D002244:Carbon / Q000378:metabolism; D007783:Lactones / Q000096:biosynthesis; D009682:Magnetic Resonance Spectroscopy; D010407:Penicillium / Q000378:metabolism*
D000085:Acetates; D000900:Anti-Bacterial Agents; D007783:Lactones; D002244:Carbon; C049725:patulolide A