Ceriporic acid C, a hexadecenylitaconate produced by a lignin-degrading fungus, Ceriporiopsis subvermispora.
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.
Amirta
Rudianto
R
Laboratory of Biomass Conversion, Wood Research Institute, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan.
Fujimori
Kenya
K
Shirai
Nobuaki
N
Honda
Yoichi
Y
Watanabe
Takashi
T
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
D000080:Acetals; D003998:Dicarboxylic Acids; D006018:Glycols; D013386:Succinates; D014297:Trimethylsilyl Compounds; C488844:ceriporic acid C; D000096:Acetone; D008031:Lignin; C005229:itaconic acid