A new microbial degradation pathway of steroid alkaloids.
In the degradation pathway of the steroid alkaloid tomatidine by Gymnoascus reesii the A-ring of tomatidine is opened with the formation of the 4-hydroxy-3,4-secotomatidine-3-oic acid, which was identified in the form of N-acetyl-3,4-tomatidine-carbolactone by mass, IR and 1H NMR spectra. Cleavage of the A-ring in the starting reaction indicates that an alternative pathway must be operating, instead of the general oxidative one.
D000470:Alkaloids / Q000378:metabolism*; D001203:Ascomycota / Q000378:metabolism*; D001711:Biotransformation; D055598:Chemical Phenomena; D002621:Chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013053:Spectrophotometry / Q000379:methods; D014053:Tomatine / Q000031:analogs & derivatives / Q000378:metabolism*
D000470:Alkaloids; C003677:tomatidine; D014053:Tomatine