Isolation and evaluation of kaempferol glycosides from the fern Neocheiropteris palmatopedata

Kaempferol glycosides, named palmatosides A (1), B (2) and C(3), together with three known kaempferol glycosides, multiflorins A (4) and B (5), and afzelin (6), were isolated from the roots of the fern Neocheiropteris palmatopedata. Palmatosides A (1) and B (2) each possessed an unusual sugar moiety containing a 4,4-dimethyl-3-oxo-butoxy substituent group. The isolated compounds were evaluated for their cancer chemopreventive potential based on their ability to inhibit tumor necrosis factor alpha (TNF-alpha)-induced NF-kappa B activity, nitric oxide (NO) production, aromatase, quinone reductase 2 (QR2) and COX-1/-2 activities. Palmatosides B (2) and C (3) inhibited TNF-alpha-induced NF-kappa B activity with IC(50) values of 15.7 and 24.1 mu M, respectively; multiflorin A (4) inhibited aromatase enzyme with an IC(50) value of 15.5 mu M; afzelin (6) showed 68.3% inhibition against QR2 at a concentration of 11.5 mu g/ml; palmatoside A (1) showed 52% inhibition against COX-1 enzyme at a concentration of 10 mu g/ml; and multiflorin B (5) showed 52% inhibition against nitric oxide production at a concentration of 20 mu g/ml. In addition, compounds 3-6 were shown to bind QR2 enzyme using LC-MS ultrafiltration binding assay. (C) 2010 Elsevier Ltd. All rights reserved,