title: Acylated anthocyanins from sprouts of Raphanus sativus cv. Sango: isolation, structure elucidation and antioxidant activity.
abstract: Little is known on structure-activity relationships of antioxidant anthocyanins. Raphanus sativus cv Sango sprouts are among the richest sources (270 mg/100 g fresh weight). We isolated from sprouts' juice 9 acylated anthocyanins, including 4 new compounds. All comprise a cyanidin core bearing 3-4 glucose units, multiply acylated with malonic and phenolic acids (ferulic and sinapic). All compounds were equally effective in inhibiting the autoxidation of linoleic acid in aqueous micelles, with rate constant for trapping peroxyl radicals kinh=(3.8 ± 0.7) × 10(4)M(-1)s(-1) at 37 °C. In acetonitrile solution kinh varied with acylation: (0.9-2.1) × 10(5)M(-1)s(-1) at 30 °C. Each molecule trapped a number n of peroxyl radicals ranging from 4 to 7. Anthocyanins bearing sinapic acid were more effective than those bearing the ferulic moiety. Under identical settings, deacylated cyanin, ferulic and sinapic acids had kinh of 0.4 × 10(5), 0.3 × 10(5) and 1.6 × 10(5)M(-1)s(-1) respectively, with n ranging 2-3. Results show the major role of acylation on antioxidant performance.
authors: R&D Division, BeC S.r.l., Via C. Monteverdi 49, 47122 Forlì, Italy.
authors: Riccardo
authors: R
authors: Matera
authors: R&D Division, BeC S.r.l., Via C. Monteverdi 49, 47122 Forlì, Italy.
authors: Simone
authors: S
authors: Gabbanini
authors: Department of Chemistry "G. Ciamician", University of Bologna, Via S. Giacomo 11, 40126 Bologna, Italy.
authors: Serena
authors: S
authors: Berretti
authors: Department of Chemistry "G. Ciamician", University of Bologna, Via S. Giacomo 11, 40126 Bologna, Italy.
authors: Riccardo
authors: R
authors: Amorati
authors: Industrial Crop Research Centre, Agricultural Research Council, (CRA-CIN), Via di Corticella, 133, 40128 Bologna, Italy.
authors: Gina Rosalinda
authors: GR
authors: De Nicola
authors: Industrial Crop Research Centre, Agricultural Research Council, (CRA-CIN), Via di Corticella, 133, 40128 Bologna, Italy.
authors: Renato
authors: R
authors: Iori
authors: Department of Chemistry "G. Ciamician", University of Bologna, Via S. Giacomo 11, 40126 Bologna, Italy. Electronic address: luca.valgimigli@unibo.it.
authors: Luca
authors: L
authors: Valgimigli
mesh_terms: D000872:Anthocyanins / Q000737:chemistry*; D000975:Antioxidants / Q000737:chemistry*; D062385:Hydroxybenzoates / Q000737:chemistry*; D010084:Oxidation-Reduction; D031224:Raphanus / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000872:Anthocyanins; D000975:Antioxidants; D062385:Hydroxybenzoates; C017616:phenolic acid
keywords: Anthocyanins; Cyanidin CID 128861; Cyanin CID 441688; Ferulic acid CID 445858; Mass spectrometry; NMR; Peroxyl radicals; Phenolic acids; Radish sprouts; Sinapinic acid CID 637775