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-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.
Yang
Jian-Hong
JH
Department of Chemistry, Yunnan Normal University, Kunming, People's Republic of China.
Kondratyuk
Tamara P
TP
Marler
Laura E
LE
Qiu
Xi
X
Choi
Yongsoo
Y
Cao
Hongmei
H
Yu
Rui
R
Sturdy
Megan
M
Pegan
Scott
S
Liu
Ying
Y
Wang
Li-Qin
LQ
Mesecar
Andrew D
AD
Van Breemen
Richard B
RB
Pezzuto
John M
JM
Fong
Harry H S
HH
Chen
Ye-Gao
YG
Zhang
Hong-Jie
HJ
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
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)