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ARS Home » Midwest Area » Madison, Wisconsin » U.S. Dairy Forage Research Center » Research » Publications at this Location » Publication #87739
Title: SIMPLE PREPARATION OF 8-5-COUPLED DIFERULATE

Author
item Ralph, John
item GARCIA-CONESA, MARIA - INST FOOD RES, NORWICH UK
item WILLIAMSON, GARY - INST FOOD RES, NORWICH UK

Submitted to: Journal of the Science of Food and Agriculture
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 5/19/1998
Publication Date: N/A
Citation: N/A

Interpretive Summary: Ferulic acid is a small molecule in the cell walls of plants that has important roles in wall architecture. It is found attached to certain of the polysaccharides as ferulates. Two ferulates can react with each other (to form ferulate dimers) and, in this way, the wall's polysaccharides become tied together or cross-linked. This adds strength and rigidity and various other crucial properties to the cell wall. The cross-linking is complex chemically because the ferulates can attach to each other at various sites giving at least 4 different structures (4 different ferulate dimers). Ferulates can also cross-link with another important wall polymer, lignin. Since our discovery of the range of ferulate dimers (only one was previously known), researchers around the world have needed the compounds for various studies ranging from natural antioxidants in foods to changing food qualities to how cross-linking affects plant digestibility by ruminants. Our lab developed the syntheses of these ferulate dimers and ha been a source for them, but most of the syntheses can only be carried out by accomplished synthetic chemists. Here we have developed a simple method to synthesize one of the most important ferulate dimers so that researchers can readily make their own material on a gram scale. This makes larger quantities available for the plethora of studies researchers wish to undertake, and frees our lab from the necessity of providing this compound. In our own labs, this material is used in research efforts ultimately aimed at improving agricultural sustainability and maximizing our plant resources.

Technical Abstract: Diferulates are important products of ferulate-mediated cross-linking of plant cell walls. Coupling of ferulates by radical mechanisms produces a range of diferulates. One of the major isomers, 8-5-coupled diferulate, can be synthesized by single-electron oxidants, but the yields are relatively low and purification is non-trivial. Significant quantities of this dimer are required for various analytical and reactivity studies. A simpler preparation utilizing the biomimetic peroxidase-H2O2 system, allows the production of gram-quantities of pure diethyl 8-5-diferulate.