Abstract
S-adenosyl-L-methionine (SAM)-dependent O-methyltransferases (OMTs) catalyze the methylation of hydroxycinnamic acid derivatives for the synthesis of methylated plant polyphenolics, including lignin. The distinction in the extent of methylation of lignins in angiosperms and gymnosperms, mediated by substrate-specific OMTs, represents one of the fundamental differences in lignin biosynthesis between these two classes of plants. In angiosperms, two types of structurally and functionally distinct lignin pathway OMTs, caffeic acid 3-O-methyltransferases (CAOMTs) and caffeoyl CoA 3-O-methyltransferases (CCoAOMTs), have been reported and extensively studied. However, little is known about lignin pathway OMTs in gymnosperms. We report here the first cloning of a loblolly pine (Pinus taeda) xylem cDNA encoding a multifunctional enzyme, SAM:hydroxycinnamic Acids/hydroxycinnamoyl CoA Esters OMT (AEOMT). The deduced protein sequence of AEOMT is partially similar to, but clearly distinguishable from, that of CAOMTs and does not exhibit any significant similarity with CCoAOMT protein sequences. However, functionally, yeast-expressed AEOMT enzyme catalyzed the methylation of CAOMT substrates, caffeic and 5-hydroxyferulic acids, as well as CCoAOMT substrates, caffeoyl CoA and 5-hydroxyferuloyl CoA esters, with similar specific activities and was completely inactive with substrates associated with flavonoid synthesis. The lignin-related substrates were also efficiently methylated in crude extracts of loblolly pine secondary xylem. Our results support the notion that, in the context of amino acid sequence and biochemical function, AEOMT represents a novel SAM-dependent OMT, with both CAOMT and CCoAOMT activities and thus the potential to mediate a dual methylation pathway in lignin biosynthesis in loblolly pine xylem.
MeSH Terms
Amino Acid Sequence
Base Sequence
Cloning, Molecular
Consensus Sequence
Conserved Sequence
Escherichia coli
Genes, Plant
Lignin/biosynthesis
Methylation
Molecular Sequence Data
Pinus taeda
Protein O-Methyltransferase/biosynthesis,chemistry,metabolism
Recombinant Proteins/biosynthesis,chemistry,metabolism
Sequence Homology, Amino Acid
Substrate Specificity
Chemicals
Recombinant Proteins
Lignin
Protein O-Methyltransferase
Authors & Affiliations
7 authors, click to expand affiliations / ORCID
Li L
Plant Biotechnology Research Center, School of Forestry and Wood Products, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931, USA.
Popko J L
Zhang X H
Osakabe K
Tsai C J
Joshi C P
Chiang V L
References (20)
20 references, click to expand
-
Preparation of caffeic and dihydrocaffeic acids by methods suitable for introduction of C14 into the beta-position.
Can J Biochem Physiol. 1959 Dec;37:1431-8
PMID: 14426410
-
Characterization of bispecific caffeic acid/5-hydroxyferulic acid O-methyltransferase from aspen.
Phytochemistry. 1992 May;31(5):1495-8
PMID: 1368360
-
Differential expression of two O-methyltransferases in lignin biosynthesis in Zinnia elegans.
Plant Physiol. 1995 Jun;108(2):459-67
PMID: 7610157
-
Putative polyadenylation signals in nuclear genes of higher plants: a compilation and analysis.
Nucleic Acids Res. 1987 Dec 10;15(23):9627-40
PMID: 3697078
-
Molecular cloning, induction and taxonomic distribution of caffeoyl-CoA 3-O-methyltransferase, an enzyme involved in disease resistance.
J Biol Chem. 1991 Sep 15;266(26):17416-23
PMID: 1894629
-
Modification of lignin biosynthesis in transgenic Nicotiana through expression of an antisense O-methyltransferase gene from Populus.
Plant Mol Biol. 1994 Oct;26(1):61-71
PMID: 7948906
-
Crystal structure of catechol O-methyltransferase.
Nature. 1994 Mar 24;368(6469):354-8
PMID: 8127373
-
Chemical syntheses and properties of hydroxycinnamoyl-coenzyme A derivatives.
Z Naturforsch C. 1975 May-Jun;30(3):352-8
PMID: 126581
-
Arabidopsis thaliana defense-related protein ELI3 is an aromatic alcohol:NADP+ oxidoreductase.
Proc Natl Acad Sci U S A. 1996 Nov 26;93(24):14199-203
PMID: 11038530
-
S-adenosyl-L-methionine:trans-caffeoyl-coenzyme A 3-O-methyltransferase from elicitor-treated parsley cell suspension cultures.
Arch Biochem Biophys. 1989 Jun;271(2):488-94
PMID: 2499260
-
cDNA cloning, sequence analysis and seasonal expression of lignin-bispecific caffeic acid/5-hydroxyferulic acid O-methyltransferase of aspen.
Plant Mol Biol. 1991 Dec;17(6):1203-15
PMID: 1932694
-
Lignin Biosynthesis.
Plant Cell. 1995 Jul;7(7):1001-1013
PMID: 12242395
-
An analysis of vertebrate mRNA sequences: intimations of translational control.
J Cell Biol. 1991 Nov;115(4):887-903
PMID: 1955461
-
Molecular cloning and expression of a Eucalyptus gunnii cDNA clone encoding cinnamyl alcohol dehydrogenase.
Plant Mol Biol. 1993 Mar;21(6):1085-95
PMID: 8490129
-
An inspection of the domain between putative TATA box and translation start site in 79 plant genes.
Nucleic Acids Res. 1987 Aug 25;15(16):6643-53
PMID: 3628002
-
Molecular cloning of 4-coumarate:coenzyme A ligase in loblolly pine and the roles of this enzyme in the biosynthesis of lignin in compression wood.
Plant Physiol. 1997 Jan;113(1):65-74
PMID: 9008388
-
A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding.
Anal Biochem. 1976 May 7;72:248-54
PMID: 942051
-
Sequence analysis of a mannitol dehydrogenase cDNA from plants reveals a function for the pathogenesis-related protein ELI3.
Proc Natl Acad Sci U S A. 1995 Aug 1;92(16):7148-52
PMID: 7638158
-
Nucleotide sequence of a cDNA clone encoding caffeoyl-coenzyme A 3-O-methyltransferase of Stellaria longipes (Caryophyllaceae).
Plant Physiol. 1995 May;108(1):429-30
PMID: 7784517
-
An alternative methylation pathway in lignin biosynthesis in Zinnia.
Plant Cell. 1994 Oct;6(10):1427-39
PMID: 7994176