Hydroxylated 2-amino-3H-phenoxazin-3-one derivatives as products of 2-hydroxy-1,4-benzoxazin-3-one (HBOA) biotransformation by Chaetosphaeria sp., an endophytic fungus from Aphelandra tetragona.
The biotransformation of the phytoanticipin HBOA and its major degradation metabolites 2-hydroxy-N-(2-hydroxyphenyl)acetamide (7) and N-(2-hydroxyphenyl)acetamide (8) by Chaetosphaeria sp., an endophytic fungus isolated from Aphelandra tetragona, was studied. Three new metabolites could be identified as 2-amino-7-hydroxy-3H-phenoxazin-3-one (12), 2-acetylamino-7-hydroxy-3H-phenoxazin-3-one (13) and 7-hydroxy-2-(2-hydroxyacetyl)-amino-3H-phenoxazin-3-one (14). Structure elucidation of 12 and 13 was performed by MS, 1H, 13C NMR and 2D NMR techniques and confirmed by chemical transformation.
Zikmundová
Martina
M
Organisch-chemisches Institut der Universität Zürich, Switzerland.
Drandarov
Konstantin
K
Hesse
Manfred
M
Werner
Christa
C
D027901:Acanthaceae / Q000382:microbiology*; D019659:Asteraceae / Q000382:microbiology*; D048588:Benzoxazines; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D006900:Hydroxylation; D006999:Hypocreales / Q000254:growth & development / Q000302:isolation & purification / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D010078:Oxazines / Q000737:chemistry / Q000378:metabolism*
C436752:2-hydroxy-1,4-benzoxazin-3-one; D048588:Benzoxazines; D010078:Oxazines