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Isolation and evaluation of kaempferol glycosides from the fern Neocheiropteris palmatopedata

Yang, Jian-Hong, Marler, Laura E., Qiu, Xi, Choi, Yongsoo, Cao, Hongmei, Yu, Rui, Sturdy, Megan, Pegan, Scott, Liu, Ying, Wang, Li-Qin, Mesecar, Andrew D., Van Breemen, Richard B., Pezzuto, John M., Fong, Harry H.S., Chen, Ye-Gao
Phytochemistry 2010 v.71 no.5-6 pp. 641-647
human diseases, glycosidic linkages, kaempferol, nitric oxide, cytotoxicity, human health, tumor necrosis factor-alpha, ferns and fern allies, Polypodiaceae, glycosides, anticarcinogenic activity
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-α)-induced NF-κB activity, nitric oxide (NO) production, aromatase, quinone reductase 2 (QR2) and COX-1/-2 activities. Palmatosides B (2) and C (3) inhibited TNF-α-induced NF-κB activity with IC50 values of 15.7 and 24.1 μM, respectively; multiflorin A (4) inhibited aromatase enzyme with an IC50 value of 15.5 μM; afzelin (6) showed 68.3% inhibition against QR2 at a concentration of 11.5 μg/ml; palmatoside A (1) showed 52% inhibition against COX-1 enzyme at a concentration of 10 μg/ml; and multiflorin B (5) showed 52% inhibition against nitric oxide production at a concentration of 20 μg/ml. In addition, compounds 3–6 were shown to bind QR2 enzyme using LC–MS ultrafiltration binding assay.