Chemical syntheses of caffeoyl and 5-OH coniferyl aldehydes and alcohols and determination of lignin O-methyltransferase activities in dicot and monocot species

被引：26

作者：

Chen, F ^{[1
]}

Kota, P ^{[1
]}

Blount, JW ^{[1
]}

Dixon, RA ^{[1
]}

机构：

[1] Samuel Roberts Noble Fdn Inc, Div Plant Biol, Ardmore, OK 73401 USA

来源：

PHYTOCHEMISTRY | 2001年 / 58卷 / 07期

关键词：

Medicago sativa; Medicago truncatula; Nicotiana tabacum; Triticum aestivum; Festuca arundinacea; Leguminosae; Solanaceae; Gramineae; syntheses; caffeoyl aldehyde; 5-hydroxyconiferaldehyde; O-methyltransferase; lignin;

D O I：

10.1016/S0031-9422(01)00391-0

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：

To investigate the substrate preferences of O-methyltransferases in the monolignol biosynthetic pathways, caffeoyl and 5-hydroxy coniferyl aldehydes were synthesized by a new procedure involving a Wittig reaction with the corresponding hydroxybenzaldehydes. The same procedure can also be used to synthesize caffeoyl and 5-hydroxyconiferyl alcohols. Relative O-methyltransferase activities against these substrates were determined using crude extracts and recombinant caffeic acid O-methyltransferase from alfalfa (Medicago sativa), and crude extracts from the model legume Medicago truncatula, tobacco, wheat and tall fescue. Extracts from all these species catalyzed methylation of the various monolignol aldehydes and alcohols more effectively than the corresponding hydroxycinnamic acids. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1035 / 1042

页数：8

共 23 条

[1] The Medicago Genome Initiative:: a model legume database
Bell, CJ
Dixon, RA
Farmer, AD
Flores, R
Inman, J
Gonzales, RA
Harrison, MJ
Paiva, NL
Scott, AD
Weller, JW
May, GD
[J]. NUCLEIC ACIDS RESEARCH, 2001, 29 (01) : 114 - 117
[2] BRADFORD MM, 1976, ANAL BIOCHEM, V72, P248, DOI 10.1016/0003-2697(76)90527-3
[3] Evidence for a novel biosynthetic pathway that regulates the ratio of syringyl to guaiacyl residues in lignin in the differentiating xylem of Magnolia kobus DC
Chen, F
Yasuda, S
Fukushima, K
[J]. PLANTA, 1999, 207 (04) : 597 - 603
[4] DAUBRESSE N, 1994, SYNTHESIS-STUTTGART, P369
[5] The biosynthesis of monolignols: a "metabolic grid", or independent pathways to guaiacyl and syringyl units?
Dixon, RA
Chen, F
Guo, DJ
Parvathi, K
[J]. PHYTOCHEMISTRY, 2001, 57 (07) : 1069 - 1084
[6] Molecular cloning and functional expression of O-methyltransferases common to isoquinoline alkaloid and phenylpropanoid biosynthesis
Frick, S
Kutchan, TM
[J]. PLANT JOURNAL, 1999, 17 (04) : 329 - 339
[7] Combinatorial biochemistry in plants:: the case of O-methyltransferases
Frick, S
Ounaroon, A
Kutchan, TM
[J]. PHYTOCHEMISTRY, 2001, 56 (01) : 1 - 4
[8] STRESS RESPONSES IN ALFALFA (MEDICAGO-SATIVA L) .10. MOLECULAR-CLONING AND EXPRESSION OF S-ADENOSYL-L-METHIONINE-CAFFEIC ACID 3-O-METHYLTRANSFERASE, A KEY ENZYME OF LIGNIN BIOSYNTHESIS
GOWRI, G
BUGOS, RC
CAMPBELL, WH
MAXWELL, CA
DIXON, RA
[J]. PLANT PHYSIOLOGY, 1991, 97 (01) : 7 - 14
[9] Downregulation of caffeic acid 3-O-methyltransferase and caffeoyl CoA 3-O-methyltransferase in transgenic alfalfa:: Impacts on lignin structure and implications for the biosynthesis of G and S lignin
Guo, DJ
Chen, F
Inoue, K
Blount, JW
Dixon, RA
[J]. PLANT CELL, 2001, 13 (01) : 73 - 88
[10] HIGUCHI T, 1996, BIOCH MOL BIOL WOOD, P156

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