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Issue 31, 2012
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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

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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.

Graphical abstract: 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

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Publication details

The article was received on 25 Feb 2012, accepted on 22 May 2012 and first published on 06 Jun 2012


Article type: Paper
DOI: 10.1039/C2OB25415H
Org. Biomol. Chem., 2012,10, 6432-6442

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    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

    H. Nishimura, M. Sasaki, H. Seike, M. Nakamura and T. Watanabe, Org. Biomol. Chem., 2012, 10, 6432
    DOI: 10.1039/C2OB25415H

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