DPPH Radical Scavengers from Dried Leaves of Oregano (Origanum vulgare)

• Published in: Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2003-11, Vol.67 (11), p.2311-2316
• Main Authors: MATSUURA, Hideyuki, CHIJI, Hideyuki, ASAKAWA, Chikako, AMANO, Midori, YOSHIHARA, Teruhiko, MIZUTANI, Junya
• Format: Article
• Language: English
• Subjects: 1,1-dipehnyl-2-picrylhydrazyl (DPPH) radical scavenger; Achillea; Biological and medical sciences; Biphenyl Compounds; Comfrey; Free Radical Scavengers - analysis; Free Radical Scavengers - isolation & purification; Fundamental and applied biological sciences. Psychology; herb; Hydrazines; Ocimum; oregano; Origanum - chemistry; Origanum vulgare; Petroselinum; Picrates; Plant Extracts - chemistry; Plant Leaves - chemistry; Species Specificity; Spectrophotometry, Infrared
• ISSN: 0916-8451; 1347-6947
• DOI: 10.1271/bbb.67.2311

1,1-Dipehnyl-2-picrylhydrazyl (DPPH) radical scavenging activities were found in the extract of dried leaves of oregano (Origanum vulgare). The water-soluble active ingredients were isolated, and their structures were determined to be 4′-O-β-D-glucopyranosyl-3′,4′-dihydroxybenzyl protocatechuate and 4′-O-β-D-glucopyranosyl-3′,4′-dihydroxybenzyl 4-O-methylprotocatechuate by 1 H-, 13 C-NMR, DEPT, HMQC, and HMBC spectral analyses, and by NOE experiments. The DPPH radical scavenging activities of these compounds were compared with those of rutin, quercetin and rosmarinic acid at a concentration of 2×10 -5 M. The scavenging activity of 4′-O-β-D-glucopyranosyl-3′,4′-dihydroxybenzyl protocatechuate was almost the same as that of quercetin and rosmarinic acid, but that of 4′-O-β-D-glucopyranosyl-3′,4′-dihydroxybennzyl 4-O-methylprotocatechuate was less than that of quercetin, rosmarinic acid and 4′-O-β-D-glucopyranosyl-3′,4′-dihydroxybenzyl protocatechuate. The amount of 4′-O-β-D-glucopyranosyl-3′,4′-dihydroxybenzyl protocatechuate was estimated to be 3.8 mg/1 g of dried leaves by an HPLC analysis.