Cereal Chem 65:452-456   |  VIEW ARTICLE

C-Glycosylflavones from Hard Red Spring Wheat Bran.

Y. Feng, C. E. McDonald, and B. A. Vick. Copyright 1988 by the American Association of Cereal Chemists, Inc. 

Two flavonoids were isolated from bran of hard red spring wheat (Len variety). They were identified as apigenin-6-C-arabinoside-8-C-hexoside, which is the major compound, and apigenin-6-C-hexoside-8-C- pentoside, which is the minor compound. The flavonoids were extracted from bran with dilute NaOH solution (pH 11). They were purified by chromatography on XAD-2 resin and Sephadex G-15 columns, followed by paper chromatography with three different solvents, and finally by thin-layer chromatography. Six ultraviolet spectra of the bran flavonoids in methanol and methanol plus five different shift additives indicated apigenin-type flavones. The 13C-NMR spectrum supported the same conclusion. Mass spectra showed two sugar molecules, a pentose and a hexose, bound to a flavone ring by carbon-carbon bonds. For the major flavonoid the pentose was at C-6 and hexose at C-8, and for the minor flavonoid the hexose was attached to C-6 and the pentose to C-8.