Constituents of Amomum tsao-ko and their radical scavenging and antioxidant activities

Constituents of the fruit of Amomum tsao-ko were investigated following a preliminary screening of the antioxidant activity of several extracts of the fruit of this plant that showed that the dichloromethane extract and the ethyl acetatesoluble and water-soluble fractions of the 70% aqueous acetone extract had higher activity than α-tocopherol and butylated hydroxytoluene (BHT). Eleven compounds were isolated from the ethyl acetate-soluble fraction, and their structures were elucidated as (+)-hannokinol (1), meso-hannokinol (2), (+)-epicatechin (3), (−)-catechin (4), β-sitosterol (5), β-sitosterol 3-O-glucoside (6), 2,6-dimethoxyphenol (7), protocatechualdehyde (8), protocatechuic acid (9), vanillic acid (10), and p-hydroxybenzoic acid (11) based on mass and various nuclear magnetic resonance (NMR) spectroscopic techniques. This is the first isolation of epicatechin and catechin from the genus Amomum. The radical scavenging activity of the isolated compounds was evaluated using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and colorimetric and electron spin resonance (ESR) analyses. The antioxidant activity of the compounds was also determined based on the oxidative stability index (OSI). The catechins and catechol derivatives showed strong activities in both the DPPH radical scavenging activity and antioxidant activity assays.