Isolation and evaluation of kaempferol glycosides from the fern Neocheiropteris palmatopedata |
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Authors: | Jian-Hong Yang Tamara P. Kondratyuk Laura E. Marler Xi Qiu Yongsoo Choi Hongmei Cao Rui Yu Megan Sturdy Scott Pegan Ying Liu Li-Qin Wang Andrew D. Mesecar Richard B. Van Breemen John M. Pezzuto Harry H.S. Fong Ye-Gao Chen Hong-Jie Zhang |
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Affiliation: | 1. Department of Chemistry, Yunnan Normal University, Kunming 650092, People’s Republic of China;2. College of Pharmacy, University of Hawaii at Hilo, 34 Rainbow Dr., Hilo, HI 96720, USA;3. Program for Collaborative Research in the Pharmaceutical Sciences, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood Street, Chicago, IL 60612, USA;4. Department of Medicinal Chemistry and Pharmacognosy and the Center for Pharmaceutical Biotechnology, University of Illinois at Chicago, 900 S. Ashland Ave., Chicago, IL 60607, USA;5. Department of Chemistry & Biochemistry, University of Denver, 2190 E.Iliff, Olin 202, Denver, CO 80208, USA |
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Abstract: | 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. |
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