De novo synthesis of (Z)- and (E)-7-hexadecenylitaconic acids by a selective lignin-degrading fungus, Ceriporiopsis subvermispora.
Ceriporic acids are a class of alk(en)ylitaconic acids produced by a selective lignin-degrading fungus, Ceriporiopsis subvermispora. Their structural units have similarity with biologically important lichen acids, such as chaetomellic and protolichesterinic acids. The unique function of alkylitaconic acid is the redox silencing of the Fenton reaction system by inhibiting reduction of Fe(3+). As estimated by the catalytic function of Delta9-desaturases, 7-hexadecenyl derivatives bearing a trans configuration have not been reported in the family of alk(en)ylitaconic acids, i.e. the structurally similar lichen acids-alk(en)ylcitraconic and paraconic acids. In this paper, we discuss the isolation of an itaconic acid derivative with an (E)-7-hexadecenyl chain from cultures of C. subvermispora. To identify the natural metabolite, (E)- and (Z)-7-hexadecenylitaconic acids were chemically synthesised. The isolated metabolite was identical to the synthetic (E)-hexadecenylitaconic acid and was designated as ceriporic acid D. Administration of (13)C-[U]-glucose demonstrated that ceriporic acid C and trans-7-hexadecenylitaconic acid (ceriporic acid D) were biosynthesised de novo by C. subvermispora.
Laboratory of Biomass Conversion, Research Institute for Sustainable Humanosphere, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan.
Hiroshi
H
Nishimura
Saeko
S
Tsuda
Hitoe
H
Shimizu
Yasunori
Y
Ohashi
Takahito
T
Watanabe
Yoichi
Y
Honda
Takashi
T
Watanabe
D000475:Alkenes / Q000138:chemical synthesis / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D055453:Coriolaceae / Q000378:metabolism*; D003998:Dicarboxylic Acids / Q000138:chemical synthesis / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D015394:Molecular Structure; D013386:Succinates / Q000138:chemical synthesis / Q000378:metabolism*
D000475:Alkenes; D003998:Dicarboxylic Acids; D013386:Succinates; C488844:ceriporic acid C; C534201:ceriporic acid D; C005229:itaconic acid