Biosynthesis of the hemi- and monoterpene moieties of isoprenyl phenyl ethers from the liverwort Trichocolea tomentella

被引:18
作者
Barlow, AJ
Becker, H
Adam, KP
机构
[1] Univ Otago, Dept Chem, New Zealand Inst Crop & Food Res Ltd, Plant Extracts Res Unit, Dunedin, New Zealand
[2] Univ Saarland, D-66041 Saarbrucken, Germany
关键词
Trichocolea tomentella; isopentenyl diphosphate; mevalonic acid pathway; methylerythritol phosphate pathway; isoprenoids; hemiterpene; monoterpcne; phytol; stigmasterol; C-13-labelling; liverwort; quantitative C-13 NMR spectroscopy;
D O I
10.1016/S0031-9422(01)00002-4
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The incorporation of C-13 labelled glucose into trichocolein, deoxytomentellin, trans-phytol and stigmasterol has been studied in axenic cultures of the liverwort Trichocolea tomentella. Quantitative C-13 NMR spectroscopic analysis of the resulting labelling patterns showed that the isoprene units of the hemi- and monoterpenoid moieties and the diterpene phytol are derived from the methylerythritol phosphate pathway, whereas the isoprene units of stigmasterol are built up via the mevalonic acid pathway. These results indicate the involvement of both IPP biosynthetic pathways in different cellular compartments. A new, hydroperoxy geranyl phenyl ether derivative is also described. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7 / 14
页数:8
相关论文
共 39 条
[1]   Partial purification and characterization of a monoterpene cyclase, limonene synthase, from the liverwort Ricciocarpos natans [J].
Adam, KP ;
Crock, J ;
Croteau, R .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1996, 332 (02) :352-356
[2]   Monoterpene biosynthesis in the liverwort Conocephalum conicum:: Demonstration of sabinene synthase and bornyl diphosphate synthase [J].
Adam, KP ;
Croteau, R .
PHYTOCHEMISTRY, 1998, 49 (02) :475-480
[3]   Involvement of the mevalonic acid pathway and the glyceraldehyde-pyruvate pathway in terpenoid biosynthesis of the liverworts Ricciocarpos natans and Conocephalum conicum [J].
Adam, KP ;
Thiel, R ;
Zapp, J ;
Becker, H .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1998, 354 (01) :181-187
[4]   Biosynthesis of the isoprene units of chamomile sesquiterpenes [J].
Adam, KP ;
Zapp, J .
PHYTOCHEMISTRY, 1998, 48 (06) :953-959
[5]   Incorporation of 1-[1-13C]deoxy-D-xylulose in chamomile sesquiterpenes [J].
Adam, KP ;
Thiel, R ;
Zapp, J .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1999, 369 (01) :127-132
[6]   Terpenoid biosynthesis from 1-deoxy-D-xylulose in higher plants by intramolecular skeletal rearrangement [J].
Arigoni, D ;
Sagner, S ;
Latzel, C ;
Eisenreich, W ;
Bacher, A ;
Zenk, MH .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1997, 94 (20) :10600-10605
[7]   Biosynthesis of the dimethylallyl moiety of glabrol in Glycyrrhiza glabra hairy root cultures via a non-mevalonate pathway [J].
Asada, Y ;
Li, W ;
Yoshikawa, T .
PHYTOCHEMISTRY, 2000, 55 (04) :323-326
[8]  
Becker H., 1994, J HATTORI BOT LAB, V76, P283, DOI [10.18968/jhbl.76.0_283, DOI 10.18968/JHBL.76.0_283]
[9]   NATURALLY-OCCURRING TERPENE DERIVATIVES .462. SESQUITERPENE LACTONES AND OTHER CONSTITUENTS FROM SCHISTOSTEPHIUM-SPECIES [J].
BOHLMANN, F ;
JAKUPOVIC, J ;
AHMED, M ;
SCHUSTER, A .
PHYTOCHEMISTRY, 1983, 22 (07) :1623-1636
[10]  
BRAUN S, 1996, 100 MORE BASIC EXPT