Xanosporic acid, an intermediate in bacterial degradation of the fungal phototoxin cercosporin.
The red fungal perylenequinone phototoxin cercosporin is oxidized by Xanthomonas campestris pv zinniae to a non-toxic, unstable green metabolite xanosporic acid, identified via its lactone as 1,12-bis(2'R-hydroxypropyl)-4,9-dihydroxy-6,7-methylenedioxy-11-methoxy-3-oxaperylen-10H-10-one-2-carboxylic acid. Xanosporolactone was isolated in approximately 2:1 ratio of M:P atropisomers.
Mitchell
Thomas K
TK
Department of Plant Pathology, North Carolina State University, Raleigh, NC 27695, USA.
Alejos-Gonzalez
Fatima
F
Gracz
Hanna S
HS
Danehower
David A
DA
Daub
Margaret E
ME
Chilton
William Scott
WS
D001551:Benz(a)Anthracenes / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D001673:Biodegradation, Environmental; D002264:Carboxylic Acids / Q000737:chemistry / Q000378:metabolism*; D002942:Circular Dichroism; D005658:Fungi / Q000737:chemistry; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D010569:Perylene / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism; D016959:Xanthomonas campestris / Q000378:metabolism*
D001551:Benz(a)Anthracenes; D002264:Carboxylic Acids; D007783:Lactones; C466301:xanosporic acid; C466302:xanosporolactone; D010569:Perylene; C026363:cercosporin