Isolation and characterization of stelladerol, a new antioxidant naphthalene glycoside, and other antioxidant glycosides from edible daylily (hemerocallis) flowers.

Daylily (Hemerocallis spp.) flowers are utilized as an important ingredient in traditional Asian cuisine and are also valued for their reputed medicinal effects. In studies of the bioactive methanol and aqueous methanol extracts of lyophilized Hemerocallis cv. Stella de Oro flowers, kaempferol, quercetin, and isorhamnetin 3-O-glycosides (1-9), phenethyl beta-D-glucopyranoside (10), orcinol beta-D-glucopyranoside (11), phloretin 2'-O-beta-D-glucopyranoside (12), phloretin 2'-O-beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside (13), a new naphthalene glycoside, stelladerol (14), and an amino acid (longitubanine A) (15) have been isolated. All of these compounds were tested for their antioxidant and cyclooxygenase inhibitory activities. Stelladerol was found to possess strong antioxidant properties, inhibiting lipid oxidation by 94.6% +/- 1.4 at 10 microM in an in vitro assay. Several of the flavonol 3-O-glycoside isolates also demonstrated modest antioxidant activities at 10 microM. None of the isolates inhibited cyclooxygenase activity at 100 microM.