Evidence for the biosynthetic pathway from sinapic acid to syringyl lignin using labeled sinapic acid with stable isotope at both methoxy groups in Robinia pseudoacacia and Nerium indicum

被引:20
作者
Yamauchi, K [1 ]
Yasuda, S [1 ]
Fukushima, K [1 ]
机构
[1] Nagoya Univ, Grad Sch Bioagr Sci, Nagoya, Aichi 4648601, Japan
关键词
lignin biosynthesis; heptadeutero sinapic acid-[8-D, 3,5-OCD3; tracer experiments; sinapyl alcohol; robinia; oleander; 4-coumarate-CoA ligase (4CL);
D O I
10.1021/jf011565x
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
A tracer experiment using synthesized labeled lignin precursors was designed to confirm the actual biosynthetic pathway for syringyl lignin. Tetradeuteroferulic acid-[8-D, 3-OCD3] and heptadeuterosinapic acid-[8-D, 3,5-OCD3] were synthesized and fed to shoots of robinia (Robinia pseudoacacia) and oleander (Nerium indicum) trees. The incorporation of each labeled precursor into lignin was traced by gas chromatography-mass spectrometry. The synthesized sinapic acid, in which both methoxy groups were labeled, was useful in monitoring the conversion of sinapic acid into syringyl lignin. When heptadeuterosinapic acid was fed, syringyl units containing seven deuterium labels were detected. The results of this study support the traditionally accepted pathway that sinapic acid is converted to sinapyl alcohol via sinapoyl-CoA in robinia and oleander.
引用
收藏
页码:3222 / 3227
页数:6
相关论文
共 17 条
[1]  
ALLEN CFH, 1951, ORG SYNTH, V31, P92
[2]   4-coumarate:coenzyme A ligase in hybrid poplar -: Properties of native enzymes, cDNA cloning, and analysis of recombinant enzymes [J].
Allina, SM ;
Pri-Hadash, A ;
Theilmann, DA ;
Ellis, BE ;
Douglas, CJ .
PLANT PHYSIOLOGY, 1998, 116 (02) :743-754
[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 [J].
Chen, F ;
Yasuda, S ;
Fukushima, K .
PLANTA, 1999, 207 (04) :597-603
[4]   Three 4-coumarate:coenzyme A ligases in Arabidopsis thaliana represent two evolutionarily divergent classes in angiosperms [J].
Ehlting, J ;
Büttner, D ;
Wang, Q ;
Douglas, CJ ;
Somssich, IE ;
Kombrink, E .
PLANT JOURNAL, 1999, 19 (01) :9-20
[5]  
Fukushima K, 1997, MOKUZAI GAKKAISHI, V43, P254
[6]  
HIGUCHI T, 1990, WOOD SCI TECHNOL, V24, P23, DOI 10.1007/BF00225306
[7]   Compartmentalized expression of two structurally and functionally distinct 4-coumarate:CoA ligase genes in aspen (Populus tremuloides) [J].
Hu, WJ ;
Kawaoka, A ;
Tsai, CJ ;
Lung, JH ;
Osakabe, K ;
Ebinuma, H ;
Chiang, VL .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (09) :5407-5412
[8]  
ISHIHARA T, 1974, Mokuzai Gakkaishi, V20, P39
[9]   The last step of syringyl monolignol biosynthesis in angiosperms is regulated by a novel gene encoding sinapyl alcohol dehydrogenase [J].
Li, LG ;
Cheng, XF ;
Leshkevich, J ;
Umezawa, T ;
Harding, SA ;
Chiang, VL .
PLANT CELL, 2001, 13 (07) :1567-1585
[10]   5-Hydroxyconiferyl aldehyde modulates enzymatic methylation for syringyl monolignol formation, a new view of monolignol biosynthesis in angiosperms [J].
Li, LG ;
Popko, JL ;
Umezawa, T ;
Chiang, VL .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2000, 275 (09) :6537-6545