Formation of substituted truxillic and truxinic acids in plant cell walls

a rationale

A B Hanley, Wendy Roslyn Russell, Andrew Chesson

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

The formation of phenolic cyclobutane dicarboxylic acids (truxillic and truxinic acids) in plant cell wall materials was investigated using model compounds. Two possible mechanisms were considered—cyclodimerization initiated by light or by a free radical process. Diesters formed by reaction of cinnamic acid with a series of diols had a range of distances separating the double bonds and, upon irradiation with ultraviolet light, gave dimerization products. Dimerization did not occur when peroxidase was added to the diesters to mimic phenolic coupling reactions leading to the formation of lignin in vivo. A minimum separation of two cinnamyl moieties and an optimal relative orientation was observed which can be used to predict substitution patterns for unsaturated phenolic residues on the sugar backbone in plant cell walls.

Original languageEnglish
Pages (from-to)957-960
Number of pages4
JournalPhytochemistry
Volume33
Issue number5
DOIs
Publication statusPublished - 23 Jul 1993

Fingerprint

dimerization
Dimerization
Plant Cells
Cell Wall
cell walls
Cyclobutanes
dicarboxylic acids
Dicarboxylic Acids
glycols
Lignin
cinnamic acid
acids
Ultraviolet Rays
Sugars
Peroxidase
Free Radicals
ultraviolet radiation
lignin
peroxidase
Substitution reactions

Keywords

  • Gramineae
  • truxillic acid
  • truxinic acid
  • photodimerization

Cite this

Formation of substituted truxillic and truxinic acids in plant cell walls : a rationale. / Hanley, A B; Russell, Wendy Roslyn; Chesson, Andrew.

In: Phytochemistry, Vol. 33, No. 5, 23.07.1993, p. 957-960.

Research output: Contribution to journalArticle

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AB - The formation of phenolic cyclobutane dicarboxylic acids (truxillic and truxinic acids) in plant cell wall materials was investigated using model compounds. Two possible mechanisms were considered—cyclodimerization initiated by light or by a free radical process. Diesters formed by reaction of cinnamic acid with a series of diols had a range of distances separating the double bonds and, upon irradiation with ultraviolet light, gave dimerization products. Dimerization did not occur when peroxidase was added to the diesters to mimic phenolic coupling reactions leading to the formation of lignin in vivo. A minimum separation of two cinnamyl moieties and an optimal relative orientation was observed which can be used to predict substitution patterns for unsaturated phenolic residues on the sugar backbone in plant cell walls.

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