title: Isolation and evaluation of kaempferol glycosides from the fern Neocheiropteris palmatopedata.
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-alpha)-induced NF-kappaB 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-kappaB activity with IC(50) values of 15.7 and 24.1 microM, respectively; multiflorin A (4) inhibited aromatase enzyme with an IC(50) value of 15.5 microM; afzelin (6) showed 68.3% inhibition against QR2 at a concentration of 11.5 microg/ml; palmatoside A (1) showed 52% inhibition against COX-1 enzyme at a concentration of 10 microg/ml; and multiflorin B (5) showed 52% inhibition against nitric oxide production at a concentration of 20 microg/ml. In addition, compounds 3-6 were shown to bind QR2 enzyme using LC-MS ultrafiltration binding assay.
authors.affiliation: Department of Chemistry, Yunnan Normal University, Kunming, People's Republic of China.
authors.forename: Jian-Hong
authors.initials: JH
authors.lastname: Yang
authors.forename: Tamara P
authors.initials: TP
authors.lastname: Kondratyuk
authors.forename: Laura E
authors.initials: LE
authors.lastname: Marler
authors.forename: Xi
authors.initials: X
authors.lastname: Qiu
authors.forename: Yongsoo
authors.initials: Y
authors.lastname: Choi
authors.forename: Hongmei
authors.initials: H
authors.lastname: Cao
authors.forename: Rui
authors.initials: R
authors.lastname: Yu
authors.forename: Megan
authors.initials: M
authors.lastname: Sturdy
authors.forename: Scott
authors.initials: S
authors.lastname: Pegan
authors.forename: Ying
authors.initials: Y
authors.lastname: Liu
authors.forename: Li-Qin
authors.initials: LQ
authors.lastname: Wang
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Mesecar
authors.forename: Richard B
authors.initials: RB
authors.lastname: Van Breemen
authors.forename: John M
authors.initials: JM
authors.lastname: Pezzuto
authors.forename: Harry H S
authors.initials: HH
authors.lastname: Fong
authors.forename: Ye-Gao
authors.initials: YG
authors.lastname: Chen
authors.forename: Hong-Jie
authors.initials: HJ
authors.lastname: Zhang
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification / Q000494:pharmacology*; D047072:Aromatase Inhibitors / Q000302:isolation & purification / Q000494:pharmacology*; D002460:Cell Line; D045744:Cell Line, Tumor; D016861:Cyclooxygenase Inhibitors / Q000302:isolation & purification / Q000494:pharmacology*; D006027:Glycosides / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D020128:Inhibitory Concentration 50; D044949:Kaempferols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000037:antagonists & inhibitors; D016328:NF-kappa B / Q000037:antagonists & inhibitors; D009569:Nitric Oxide / Q000037:antagonists & inhibitors; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D018517:Plant Roots; D029621:Polypodiaceae / Q000737:chemistry*; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D047072:Aromatase Inhibitors; D016861:Cyclooxygenase Inhibitors; D006027:Glycosides; D044949:Kaempferols; D016328:NF-kappa B; D010936:Plant Extracts; D014409:Tumor Necrosis Factor-alpha; C552277:palmatoside A; C552276:palmatoside B; C552275:palmatoside C; D009569:Nitric Oxide; D016660:NAD(P)H Dehydrogenase (Quinone)