title: Ceriporic acid C, a hexadecenylitaconate produced by a lignin-degrading fungus, Ceriporiopsis subvermispora.
abstract: A lignin-degrading basidiomycete, Ceriporiopsis subvermispora produces a series of alkyl- and alkenylitaconates (ceriporic acids). Previously, two alkylitaconic acids with tetradecyl and hexadecyl side chains were isolated and identified as 1-heptadecene-2,3-dicarboxylic acid (ceriporic acid A) and 1-nonadecene-2,3-dicarboxylic acid (ceriporic acid B). In the present study, one hexadecenylitaconate (ceriporic acid C) was isolated and its chemical structure was analyzed by glycolation and subsequent (1) trimethylsilation, or (2) acetalation with acetone and acetone-d6. Analyses of the isolated metabolite demonstrated that the hexadecenylitaconic acid was (Z)-1,10-nonadecadiene-2,3-dicarboxylic acid. The structure of the side chain in ceriporic acid C was the same as that of hexadecenylcitraconate, chaetomellic acid B. Thus, it was found that ceriporic acids share close structural similarity with alk(en)yl citraconate derivatives, chaetomellic acids and other lichen lactones, protolichesterinic, lichesterinic, and murolic acids.
authors: Laboratory of Biomass Conversion, Wood Research Institute, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan.
authors: Rudianto
authors: R
authors: Amirta
authors: Kenya
authors: K
authors: Fujimori
authors: Nobuaki
authors: N
authors: Shirai
authors: Yoichi
authors: Y
authors: Honda
authors: Takashi
authors: T
authors: Watanabe
mesh_terms: D000080:Acetals / Q000737:chemistry; D000096:Acetone / Q000737:chemistry; D001487:Basidiomycota / Q000737:chemistry* / Q000378:metabolism; D003998:Dicarboxylic Acids / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D006018:Glycols / Q000737:chemistry; D008031:Lignin / Q000378:metabolism; D013058:Mass Spectrometry / Q000379:methods; D008745:Methylation; D015394:Molecular Structure; D013237:Stereoisomerism; D013386:Succinates / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D014297:Trimethylsilyl Compounds / Q000737:chemistry
chemical_list: D000080:Acetals; D003998:Dicarboxylic Acids; D006018:Glycols; D013386:Succinates; D014297:Trimethylsilyl Compounds; C488844:ceriporic acid C; D000096:Acetone; D008031:Lignin; C005229:itaconic acid