Stability to light, heat, and hydrogen peroxide at different pH values and DPPH radical scavenging activity of acylated anthocyanins from red radish extract.
The stability of red radish extract to light, heat, and hydrogen peroxide at different pH values (3, 5, and 7) was examined, in which major anthocyanins were pelargonidin glycosides acylated with a combination of p-coumaric, ferulic, or caffeic acids. The light irradiation (fluorescence light, 5000 lx; at 25 degrees C) indicated that the red radish extract was more stable at lower pH than at higher pH. The HPLC analyses revealed that diacylated anthocyanins in the extract were more stable to light at pH 3 than monoacylated anthocyanins. No significant difference in degradation rates of acylated anthocyanins at pH 5 was observed, whereas anthocyanins acylated with p-coumaric or ferulic acids were more stable at pH 7 than ones with caffeic acids. The stability to heat (at 90-95 degrees C) showed a tendency similar to that for light. The number of intramolecular acyl units contributes to stability to light and heat at lower pH, whereas the characteristics of intramolecular acyl units influence the stability at higher pH. The degradation behavior of red radish extract to H2O2 were almost the same to those of light and heat, depending on the pH. However, HPLC analyses revealed that the stability of individual acylated anthocyanins were independent of the pH. These data suggest that the characteristics, the number, and the binding site of intramolecular acyl units affect the stability of anthocyanin to H2O2. DPPH radical scavenging activity of all acylated anthocyanins was higher than those of pelargonidin and perlargonidin-3-glucoside. The activity of acylated anthocyanins mostly depended on the activity of intramolecular acyl units (caffeic acid > ferulic acid > p-coumaric acid). However, the activity was highly affected by the binding site of intramolecular acyl units even if anthocyanins have common acyl units.
Matsufuji
Hiroshi
H
College of Bioresource Sciences, Nihon University, 1866 Kameino, Fujisawa, Kanagawa 252-8510, Japan. hmatsufu@brs.nihon-u.ac.jp
Kido
Hirotsugu
H
Misawa
Hisashi
H
Yaguchi
Junichi
J
Otsuki
Takashi
T
Chino
Makoto
M
Takeda
Mitsuharu
M
Yamagata
Kazuo
K
D000215:Acylation; D000872:Anthocyanins / Q000737:chemistry*; D001713:Biphenyl Compounds; D004355:Drug Stability; D016166:Free Radical Scavengers / Q000737:chemistry*; D006358:Hot Temperature; D006861:Hydrogen Peroxide / Q000494:pharmacology*; D006863:Hydrogen-Ion Concentration; D008027:Light; D010851:Picrates; D010936:Plant Extracts / Q000737:chemistry; D031224:Raphanus / Q000737:chemistry*
D000872:Anthocyanins; D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D010851:Picrates; D010936:Plant Extracts; D006861:Hydrogen Peroxide; C004931:1,1-diphenyl-2-picrylhydrazyl