2-2--azino-di-(3-ethylbenzothiazoline)-6-sulfonic-acid and artocarpin-lectin

A new dihydrochalcone, 2',4'-dihydroxy-3,4-(2″,2″-dimethylchromeno)-3'-prenyldihydrochalcone (1) together with 4-hydroxyonchocarpin (2), isobavachalcone (3), 4',5-dihydroxy-6,7-(2,2-dimethylpyrano)-2'-methoxy-8-γ,γ-dimethylallyflavone (4), artocarpin (5) and cycloheterophyllin (6) were successfully isolated from the leaves and heartwoods of Artocarpus lowii King (Moraceae). The structures of these compounds were fully characterised using spectroscopic methods and by direct comparison with published data. These compounds were tested for their antioxidant and tyrosinase inhibitory activities. Compound (1) displayed moderate antioxidant activity towards DPPH and tyrosinase inhibitory activities with SC

Topics: Antioxidants; Artocarpus; Benzothiazoles; Biphenyl Compounds; Chalcones; Chromatography, Thin Layer; Enzyme Inhibitors; Flavonoids; Free Radical Scavengers; Magnetic Resonance Spectroscopy; Mannose-Binding Lectins; Monophenol Monooxygenase; Picrates; Plant Extracts; Plant Leaves; Plant Lectins; Spectrophotometry, Ultraviolet; Sulfonic Acids; Wood

The interaction of antiperoxidative flavonoids artocarpin (AR), cycloartocarpin (CAR), dalspinin (DP), dalspinosin (DPO), and dalspinin-7-O-galactoside (DPG) with 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS(.+)) and O2(-.) was studied in phosphate buffer (pH 7.4). The ability of these compounds to inhibit lipid peroxidation and DNA scission was also investigated. The radical scavenging efficiency of flavonoids is demonstrated by the reduction of nitrogen-centered radical cation (ABTS(.+)). The reduction of ABTS(.+) follows the order quercetin > morin > Trolox > AR > DPO > CAR > DP. Inhibition of lipid peroxidation was studied by following Mb(IV) reduction, induced by lipid, arachidonic acid. These results are compared with those obtained for well-known antioxidants such as quercetin, morin, and Trolox. The structure-activity relationships between chemical structures of the flavonoids and their radical scavenging activities are anlayzed. The scavenging of O2(-.), inhibition of lipid peroxidation, and DNA damage depend on the oxidation potential of the flavonoids. The possible mechanism for radical scavenging activities of flavonoids in relation to their structure is also outlined.

Topics: Antioxidants; Benzothiazoles; DNA Damage; Flavonoids; Free Radical Scavengers; Lipid Peroxidation; Mannose-Binding Lectins; Plant Lectins; Structure-Activity Relationship; Sulfonic Acids; Superoxides