title: Alkadienyl and alkenyl itaconic acids (ceriporic acids G and H) from the selective white-rot fungus Ceriporiopsis subvermispora: a new class of metabolites initiating ligninolytic lipid peroxidation.
abstract: New ceriporic acids-alkadienyl and alkenyl itaconic acids having a bis-allyl (3-[(Z,Z)-hexadec-7,10-dienyl]-itaconic acid; ceriporic acid G) and a monoene (3-[(Z)-octadec-9-enyl]-itaconic acid; ceriporic acid H) structure in their side chains-were isolated from the cultures of the selective lignin-degrading fungus Ceriporiopsis subvermispora. The new metabolites ceriporic acid G and H were synthesized by a cross-aldol condensation and a Grignard substitution reaction, respectively. Ceriporic acid G triggered the manganese peroxidase (MnP)-catalyzed lipid peroxidation and decomposed a recalcitrant non-phenolic lignin substructure model compound. Except for simple fatty acids, this is the first report of a fungal metabolite that induced ligninolytic lipid peroxidation.
authors: Research Institute for Sustainable Humanosphere, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan.
authors: Hiroshi
authors: H
authors: Nishimura
authors: Midori
authors: M
authors: Sasaki
authors: Hirofumi
authors: H
authors: Seike
authors: Masaharu
authors: M
authors: Nakamura
authors: Takashi
authors: T
authors: Watanabe
mesh_terms: D000475:Alkenes / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D055453:Coriolaceae / Q000737:chemistry / Q000201:enzymology / Q000378:metabolism*; D003998:Dicarboxylic Acids / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D019281:Dimerization; D008031:Lignin / Q000378:metabolism*; D015227:Lipid Peroxidation; D010544:Peroxidases / Q000378:metabolism
chemical_list: D000475:Alkenes; D003998:Dicarboxylic Acids; C576341:ceriporic acid G; C576342:ceriporic acid H; D008031:Lignin; D010544:Peroxidases; C051129:manganese peroxidase