Convenient Preparation and Quantification of 5,5'-Diferulic Acid.

5,5'-Diferulic acid (5,5'-DFA), which is one of the cross-linking residues in plant cell walls, was prepared by using a facile procedure. The phenol oxidation of vanillin with FeCl3 gave divanillin, which was further devoted to a Perkin reaction to give the desired product. It was found on (13)C-NMR that the chemical shift of C-5 of ferulic acid (FA) clearly shifted downfield, when this carbon is quaternarized by the oxidative dimerizaton to 5,5'-DFA, while those of other carbons of 5,5'-DFA are fundamentally same as those of FA. Also prepared was [9,9'-(13)C2]-5,5'-DFA, which was proved to be a good internal standard on GC-MS quantification of endogenous 5,5'-DFA from plant tissues.

[1]  J. Azuma,et al.  A NEW FERULOYLATED TRISACCHARIDE FROM BAGASSE , 1983 .

[2]  M. Peña,et al.  Changes in Dehydrodiferulic Acids and Peroxidase Activity against Ferulic Acid Associated with Cell Walls during Growth of Pinus pinaster Hypocotyl , 1996, Plant physiology.

[3]  C. Ohsumi,et al.  Involvement of Phenolic Esters in Cell Aggregation of Suspension-Cultured Rice Cells , 1994, Plant physiology.

[4]  T. Ishii,et al.  Linkage of phenolic acids to cell-wall polysaccharides of bamboo shoot. , 1990, Carbohydrate research.

[5]  I. Scott,et al.  Mass spectrometric quantification of salicylic acid in plant tissues , 1994 .

[6]  N. Shibuya.  Phenolic acids and their carbohydrate esters in rice endosperm cell walls , 1984 .

[7]  Y. Masuda,et al.  Correlation between cell wall extensibility and the content of diferulic and ferulic acids in cell walls of Oryza sativa coleoptiles grown under water and in air , 1991 .

[8]  Ronald D. Hatfield,et al.  Identification and synthesis of new ferulic acid dehydrodimers present in grass cell walls , 1994 .

[9]  Stephen C. Fry,et al.  Cross-Linking of Matrix Polymers in the Growing Cell Walls of Angiosperms , 1986 .

[10]  Tadashi Ishii,et al.  Structure and functions of feruloylated polysaccharides , 1997 .

[11]  H. Musso.  Über Phenol‐Oxydationen , 1963 .

[12]  S. Neill,et al.  Measurement of xanthoxin in higher plant tissues using 13c labelled internal standards , 1990 .

[13]  R. Helm,et al.  Lignin/Hydroxycinnamic Acid/Polysaccharide Complexes: Synthetic Models for Regiochemical Characterization , 1993 .

[14]  R. Hartley,et al.  GC/MS characterisation of cyclodimers from p‐coumaric and ferulic acids by photodimerisation—a possible factor influencing cell wall biodegradability , 1989 .

[15]  K. Freudenberg,et al.  Enzymatische Versuche zur Entstehung des Lignins , 1943 .

[16]  Keiko Takahashi,et al.  Diferulic and ferulic acid in the cell wall of Avena coleoptiles : their relationships to mechanical properties of the cell wall , 1990 .

[17]  T. Ishii,et al.  Isolation and characterization of a diferuloyl arabinoxylan hexasaccharide from bamboo shoot cell-walls. , 1991, Carbohydrate research.

[18]  R. Hartley,et al.  Diferulic acid as a component of cell walls of Lolium multiflorum , 1976 .

[19]  T. Ishii,et al.  Isolation and characterization of feruloylated arabinoxylan oligosaccharides from bamboo shoot cell-walls. , 1990, Carbohydrate research.

[20]  H. Richtzenhain.  Enzymatische Versuche zur Entstehung des Lignins, IV. Mitteil.: Dehydrierungen in der Guajacolreihe , 1949 .

[21]  T. Hoson,et al.  Abscisic Acid Suppresses the Increases in Cell Wall-Bound Ferulic and Diferulic Acid Levels in Dark-Grown Wheat (Triticum aestivum L.) Coleoptiles , 1997 .

[22]  Ronald D. Hatfield,et al.  Ferulate cross-linking in cell walls isolated from maize cell suspensions , 1995 .