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Phenylpropane
n Lignin
is the second abundant and important
organic substance in the plant world.
n Theincorporation of lignin into the cell walls of
plants gave them the chance to conquer the Earth’s
land surface.
n Ligninincreased the mechanical strength properties
to such an extent that huge plants such as trees
with heights of even more than 100 m can remain
upright.
Outline of the
Biosynthetic
Pathway of
Phenylpropanoids
Phenylpropanoid pathway
phenylpropanoid pathway.
(C6-C3-C6)n
Shikimate Cinnamate
pathway pathway
C6-C1 C6-C3 (C6-C3)2
(C6-C3)n
L-Phenylalanine Cinnamic acid
Gallic acid
1. Shikimate pathway
phosphoenol pyruvic acid
3-dehydroquinic acid
3-deoxy-D-arabino-heptulosonic
D-erythrose 4-phosphate acid 7-phosphate
NADP-linked shikimate
dehydrogenase
3-dehydroshikimic acid
phosphochorismic acid shikimic acid
(1)
phosphorylated
phenylpyruvic acid
苯丙胺酸
arogenic acid
prephenic acid
chorismic acid
n Localization of enzymes
n Occurrence of isozymes
Biosynthesis of Lignin
n The hydroxylation and methylation reactions that ultimately
determine the monomeric composition of lignin (because the
three monolignols differ only in their degree of methoxylation)
have long been considered to occur at the level of the cinnamic
acids.
n Several experiments have demonstrated that the methylation
steps can also take place at the hydroxycinnamoyl-CoA level,
mediated by either caffeic acid/5-hydroxyferulic acid O-
methyltransferase (COMT) or caffeoyl- CoA O-methyltransferase
(CCoAOMT).
Biosynthesis of Lignin
n Recent work based on radiotracer and in vitro enzyme assays
has shown that the hydroxylation and methylation reactions
occur preferentially at the cinnamaldehyde and cinnamyl
alcohol level in reactions catalyzed by ferulic acid 5-
hydroxylase (F5H; also named coniferaldehyde 5-hydroxylase
or Cald5H) and COMT (alternatively called 5-
hydroxyconiferaldehyde O-methyltransferase or AldOMT).
n COMT preferentially methylates caffeyl aldehyde, 5-
hydroxyconiferaldehyde, and 5-hydroxyconiferyl alcohol,
although differences exist between the COMTs of different
Biosynthesis of Lignin
Phenylalanine Ammonia-Lyase
脢,一為單核酸黃素(Flavine Mononucleotide--
FMN)及雙核酸腺嘌呤黃素(Flavine-adenine
dinucleotide--FAD)。此兩種輔脢可形成許多不同脢
系統的不足處,故有彌補群脢之稱。此群脢亦叫做
黃素蛋白(Flavoprotein),主要涉及氫離子的傳輸,
亦即是電子傳輸的作用。D-胺基酸的氧化脢為
FAD,而L-胺基酸的氧化脢為FMN,但較特別的甘
胺酸的去氫脢為FAD。
Cinnamate 4-Hydroxylase (C4H)
4-Coumarate:Coenzyme A Ligase
(4CL)
n Generally,
trans forms of cinnamates are preferable as
substrates.
n 4-coumarate and CoA as substrates, and AMP as
product inhibit the enzyme reaction depending on their
concentrations.
n 4CL
is distributed in various higher plants, especially in
young stems.
n Isozymes
Lignin Synthesis - Lignin Precursors and Aromatic
Constituents
n Softwood lignin is an
aromatic polymer in which
the monomeric
guaiacylpropane units are
the major components
(>90%) and are connected
by both ether and carbon-
carbon linkage
Lignin Synthesis – Softwood Lignin
Formation of Monolignols
Hydroxylation of 4-coumarate
derivatives
n Phenoloxidases activate
molecular oxygen and hydroxylate
4-coumaric acid to caffiec acid.
Methylation of Caffeate derivatives
types of OMTs.
enzymes.
OMT
OMT
Dehydrogenative Polymerization of
Monolignols of Lignins
coniferyl alcohol.
Dehydrogenative Polymerization of
Monolignols of Lignins
carbons.
Dehydrogenative Polymerization of
Monolignols of Lignins
n The origin of H2O2 required for the peroxidase reaction was investigated
using horseradish cell walls and cell walls isolate from Forsythia xylem.
林木基因體學
vs.
蛋白體學