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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-beta-D-glucopyranosyl-3',4'-dihydroxybenzyl protocatechuate and 4'-O-beta-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 x 10(-5) M. The scavenging activity of 4'-O-beta-D-glucopyranosyl-3',4'-dihydroxybenzyl protocatechuate was almost the same as that of quercetin and rosmarinic acid, but that of 4'-O-beta-D-glucopyranosyl-3',4'-dihydroxybennzyl 4-O-methylprotocatechuate was less than that of quercetin, rosmarinic acid and 4'-O-beta-D-glucopyranosyl-3',4'-dihydroxybenzyl protocatechuate. The amount of 4'-O-beta-D-glucopyranosyl-3',4'-dihydroxybenzyl protocatechuate was estimated to be 3.8 mg/1 g of dried leaves by an HPLC analysis.

Verbesina encelioides (Cav.) Benth. & Hook. F. ex. A. Gray (Asteraceae) is a perennial weed that interferes with the growth and establishment of crop species in semiarid regions of India. The present research was designed to understand the probable involvement of allelopathy in its interference mechanism. We studied the effect of soils amended with different dilutions of V. encelioides root leachate (full strength and 1:2 and 1:4 (v/v) ratios of root leachate to water) on the growth of radish seedlings (Raphanus sativus L.). Soils that were not amended were used as controls. We also investigated the influence of different levels of N fertilization (1, 5, and 10 mM) on the modification of the allelopathic potential of amended soils, in terms of their effect on soil total phenolics and radish seedling growth. The addition of both full strength and 1:2 dilution of V. encelioides root leachate resulted in significant (P < 0.05) suppression of root (-25.7 and -17.2%, respectively) and shoot (-21.3 and -13.8%, respectively) growth of radish seedlings. The total level of phenolics in soil amended with full-strength (8.53 ± 0.55 µg/g), 1:2 dilution (5.43 ± 0.4 µg/g), and 1:4 dilution (4.17 ± 0.36 µg/g) was significantly (P < 0.05) higher compared with that of control (2.98 ± 0.47 µg/g) soil. Although the different amounts of N fertilization in soil amended with V. encelioides root leachate could not counteract the probable allelopathic interference, we observed an increase in root growth of radish seedlings in soil amended with 10 mM N fertilization plus either a 1:2 dilution (+21.2%) or a 1:4 dilution (+36.5%) of root leachate. No significant differences in NO3- and NH4+ concentration were observed between control soil and soil amended with different amounts of root leachate and N fertlization. Since allelopathic activities include both inhibitory and stimulatory growth responses, the radish seedling growth responses to V. encelioides root leachate can be explained by allelopathy. High performance liquid chromatography data indicate qualitative and quantitative differences in phenolic peaks of both control and amended soil. Our research demonstrates the allelopathic potential of V. encelioides roots and the probable involvement of allelopathy in its interference success.

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