When Iris germanica, Hydrocotyle verticillata, Glyceria maxima and Jun
cus effusus plants were treated anoxically and subsequently returned t
o air, long-lived free radicals were rapidly generated in the plant ti
ssues and were detected by EPR spectroscopy. The free radicals in I. g
ermanica rhizomes were extracted into aqueous alkali; the EPR spectrum
of the aqueous solution showed fine structure which indicated the pre
sence of at least two oxygen-centred radicals. The EPR data, and the r
adical lifetimes, suggested that they were probably semiquinone radica
l anions. Product analysis of the alkaline extract indicated that the
main components were a set of flavonoids including quercetin, irisolon
e, selenone and derivatives of irigenin. The main flavonoids had more
reduced and/or more alkylated structures than those from I. germanica
grown under normal aerobic conditions. Semiquinone radical anions can
readily be generated from quercetin, and similar flavonoids with 1,2-d
ihydroxy- 1,4-dihydroxy- or trihydroxy-substitution patterns, by inter
action with superoxide. However, the EPR-detected radicals were probab
ly derived from flavonoids more heavily substituted than quercetin.