2011年11月
Epoxy ceriporic acid produced by selective lignin-degrading fungus Ceriporiopsis subvermispora
Chemistry and Physics of Lipids
- ,
- ,
- ,
- ,
- 巻
- 164
- 号
- 8
- 開始ページ
- 707
- 終了ページ
- 712
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1016/j.chemphyslip.2011.07.005
- 出版者・発行元
- ELSEVIER IRELAND LTD
Ceriporiopsis subvermispora is a selective white rot basidiomycete which degrades lignin in wood at a distance far from enzymes. Low molecular mass metabolites play a central role in the oxidative degradation of lignin. To understand the unique wood-decaying mechanism, we surveyed the oxidized derivatives of ceriporic acids (alk(en)ylitaconic acids) produced by C. subvermispora using high-resolution liquid chromatography multiple-stage mass spectrometry (HR-LC/MSn). The analysis of the precursor and product ions from the extract suggested that an epoxidized derivative of ceriporic acid is produced by the fungus. To identify the new metabolite, an authentic compound of ceriporic acid epoxide was synthesized in vitro by reacting (R)-3-[(Z)-hexadec-7-enyl]-itaconic acid (ceriporic acid C) with m-chloroperbenzoic acid. The precursor and product ions from the natural metabolite and authentic epoxide were identical and distinguishable from those of hydroxy and hydroperoxy derivatives after reduction with NaBD4. Feeding experiments with [U-C-13]-glucose, 99% and the subsequent analyses of the first and second generation product ions demonstrated that the oxidized ceriporic acid was (R)-3-(7,8-epoxy-hexadecyl)-itaconic acid. To our knowledge, this study is the first to report that natural alkylitaconic acid bears an epoxy group on its side chain. (C) 2011 Elsevier Ireland Ltd. All rights reserved.
- リンク情報
-
- DOI
- https://doi.org/10.1016/j.chemphyslip.2011.07.005
- J-GLOBAL
- https://jglobal.jst.go.jp/detail?JGLOBAL_ID=201202279319121546
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000297958000001&DestApp=WOS_CPL
- ID情報
-
- DOI : 10.1016/j.chemphyslip.2011.07.005
- ISSN : 0009-3084
- eISSN : 1873-2941
- J-Global ID : 201202279319121546
- Web of Science ID : WOS:000297958000001