Isolation and evaluation of kaempferol glycosides from the fern Neocheiropteris palmatopedata

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; Hongjie Zhang

doi:10.1016/j.phytochem.2010.01.002

Isolation and evaluation of kaempferol glycosides from the fern Neocheiropteris palmatopedata

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^*, Hongjie Zhang

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › peer-review

37 Citations (Scopus)

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.

Original language	English
Pages (from-to)	641-647
Number of pages	7
Journal	Phytochemistry
Volume	71
Issue number	5-6
DOIs	https://doi.org/10.1016/j.phytochem.2010.01.002
Publication status	Published - Apr 2010

Scopus Subject Areas

Biochemistry
Molecular Biology
Plant Science
Horticulture

User-Defined Keywords

Aromatase
Cancer chemoprevention
COX-1
COX-2
Flavone
Kaempferol glycosides
Neocheiropteris palmatopedata
NF-κB
NO
Palmatosides
Polypodiaceae
QR2

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.phytochem.2010.01.002

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Yang, J. H., Kondratyuk, T. P., Marler, L. E., Qiu, X., Choi, Y., Cao, H., Yu, R., Sturdy, M., Pegan, S., Liu, Y., Wang, L. Q., Mesecar, A. D., Breemen, R. B. V., Pezzuto, J. M., Fong, H. H. S., Chen, Y. G., & Zhang, H. (2010). Isolation and evaluation of kaempferol glycosides from the fern Neocheiropteris palmatopedata. Phytochemistry, 71(5-6), 641-647. https://doi.org/10.1016/j.phytochem.2010.01.002

@article{7c48d40c2d9c400b816d65fe1b2726fd,

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-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.",

keywords = "Aromatase, Cancer chemoprevention, COX-1, COX-2, Flavone, Kaempferol glycosides, Neocheiropteris palmatopedata, NF-κB, NO, Palmatosides, Polypodiaceae, QR2",

author = "Yang, {Jian Hong} and Kondratyuk, {Tamara P.} and Marler, {Laura E.} and Xi Qiu and Yongsoo Choi and Hongmei Cao and Rui Yu and Megan Sturdy and Scott Pegan and Ying Liu and Wang, {Li Qin} and Mesecar, {Andrew D.} and Breemen, {Richard B.Van} and Pezzuto, {John M.} and Fong, {Harry H.S.} and Chen, {Ye Gao} and Hongjie Zhang",

year = "2010",

month = apr,

doi = "10.1016/j.phytochem.2010.01.002",

language = "English",

volume = "71",

pages = "641--647",

journal = "Phytochemistry",

issn = "0031-9422",

publisher = "Elsevier Ltd.",

number = "5-6",

}

Yang, JH, Kondratyuk, TP, Marler, LE, Qiu, X, Choi, Y, Cao, H, Yu, R, Sturdy, M, Pegan, S, Liu, Y, Wang, LQ, Mesecar, AD, Breemen, RBV, Pezzuto, JM, Fong, HHS, Chen, YG & Zhang, H 2010, 'Isolation and evaluation of kaempferol glycosides from the fern Neocheiropteris palmatopedata', Phytochemistry, vol. 71, no. 5-6, pp. 641-647. https://doi.org/10.1016/j.phytochem.2010.01.002

TY - JOUR

T1 - Isolation and evaluation of kaempferol glycosides from the fern Neocheiropteris palmatopedata

AU - Yang, Jian Hong

AU - Kondratyuk, Tamara P.

AU - Marler, Laura E.

AU - Qiu, Xi

AU - Choi, Yongsoo

AU - Cao, Hongmei

AU - Yu, Rui

AU - Sturdy, Megan

AU - Pegan, Scott

AU - Liu, Ying

AU - Wang, Li Qin

AU - Mesecar, Andrew D.

AU - Breemen, Richard B.Van

AU - Pezzuto, John M.

AU - Fong, Harry H.S.

AU - Chen, Ye Gao

AU - Zhang, Hongjie

PY - 2010/4

Y1 - 2010/4

N2 - 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.

AB - 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.

KW - Aromatase

KW - Cancer chemoprevention

KW - COX-1

KW - COX-2

KW - Flavone

KW - Kaempferol glycosides

KW - Neocheiropteris palmatopedata

KW - NF-κB

KW - NO

KW - Palmatosides

KW - Polypodiaceae

KW - QR2

UR - http://www.scopus.com/inward/record.url?scp=77949875111&partnerID=8YFLogxK

U2 - 10.1016/j.phytochem.2010.01.002

DO - 10.1016/j.phytochem.2010.01.002

M3 - Journal article

C2 - 20100622

AN - SCOPUS:77949875111

SN - 0031-9422

VL - 71

SP - 641

EP - 647

JO - Phytochemistry

JF - Phytochemistry

IS - 5-6

ER -

Isolation and evaluation of kaempferol glycosides from the fern Neocheiropteris palmatopedata

Abstract

Scopus Subject Areas

User-Defined Keywords

UN SDGs

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