C-Methylated Flavonoids from Cleistocalyx operculatus and Their Inhibitory Effects on Novel Influenza A (H1N1) Neuraminidase

Trong-Tuan Dao; Bui-Thanh Tung; Phi-Hung Nguyen; Phuong-Thien Thuong; Sung-Sik Yoo; Eun-Hee Kim; Sang-Kyum Kim; Won-Keun Oh

doi:10.1021/np1002753

C-Methylated Flavonoids from Cleistocalyx operculatus and Their Inhibitory Effects on Novel Influenza A (H1N1) Neuraminidase

Trong-Tuan Dao, Bui-Thanh Tung, Phi-Hung Nguyen, Phuong-Thien Thuong, Sung-Sik Yoo, Eun-Hee Kim, Sang-Kyum Kim, Won-Keun Oh

77 Citationer (Scopus)

Abstract

As part of an ongoing study focused on the discovery of anti-influenza agents from plants, four new (1-4) and 10 known (5-14) C-methylated flavonoids were isolated from a methanol extract of Cleistocalyx operculatus buds using an influenza H1N1 neuraminidase inhibition assay. Compounds 4, 7, 8, and 14, with a chalcone skeleton, showed significant inhibitory effects on the viral neuraminidases from two influenza viral strains, H1N1 and H9N2. Compound 4 showed the strongest inhibitory activity against the neuraminidases from novel influenza H1N1 (WT) and oseltamivir-resistant novel H1N1 (H274Y mutant) expressed in 293T cells with IC50 values of 8.15 ± 1.05 and 3.31 ± 1.34 μM, respectively. Compounds 4, 7, 8, and 14 behaved as noncompetitive inhibitors in the kinetic studies. These results indicate that C-methylated flavonoids from C. operculatus have the potential to be developed as neuraminidase inhibitors for novel influenza H1N1.

Originalsprog	Engelsk
Tidsskrift	Journal of Natural Products
Vol/bind	73
Udgave nummer	10
Sider (fra-til)	1636-42
Antal sider	7
ISSN	0163-3864
DOI	https://doi.org/10.1021/np1002753
Status	Udgivet - 22 okt. 2010

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10.1021/np1002753

Citationsformater

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title = "C-Methylated Flavonoids from Cleistocalyx operculatus and Their Inhibitory Effects on Novel Influenza A (H1N1) Neuraminidase",

abstract = "As part of an ongoing study focused on the discovery of anti-influenza agents from plants, four new (1-4) and 10 known (5-14) C-methylated flavonoids were isolated from a methanol extract of Cleistocalyx operculatus buds using an influenza H1N1 neuraminidase inhibition assay. Compounds 4, 7, 8, and 14, with a chalcone skeleton, showed significant inhibitory effects on the viral neuraminidases from two influenza viral strains, H1N1 and H9N2. Compound 4 showed the strongest inhibitory activity against the neuraminidases from novel influenza H1N1 (WT) and oseltamivir-resistant novel H1N1 (H274Y mutant) expressed in 293T cells with IC50 values of 8.15 ± 1.05 and 3.31 ± 1.34 μM, respectively. Compounds 4, 7, 8, and 14 behaved as noncompetitive inhibitors in the kinetic studies. These results indicate that C-methylated flavonoids from C. operculatus have the potential to be developed as neuraminidase inhibitors for novel influenza H1N1.",

keywords = "Antiviral Agents, Flavonoids, HEK293 Cells, Humans, Influenza A Virus, H1N1 Subtype, Influenza A Virus, H9N2 Subtype, Influenza, Human, Inhibitory Concentration 50, Kinetics, Molecular Structure, Myrtaceae, Neuraminidase, Oseltamivir, Journal Article",

author = "Trong-Tuan Dao and Bui-Thanh Tung and Phi-Hung Nguyen and Phuong-Thien Thuong and Sung-Sik Yoo and Eun-Hee Kim and Sang-Kyum Kim and Won-Keun Oh",

year = "2010",

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doi = "10.1021/np1002753",

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AU - Dao, Trong-Tuan

AU - Tung, Bui-Thanh

AU - Nguyen, Phi-Hung

AU - Thuong, Phuong-Thien

AU - Yoo, Sung-Sik

AU - Kim, Eun-Hee

AU - Kim, Sang-Kyum

AU - Oh, Won-Keun

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N2 - As part of an ongoing study focused on the discovery of anti-influenza agents from plants, four new (1-4) and 10 known (5-14) C-methylated flavonoids were isolated from a methanol extract of Cleistocalyx operculatus buds using an influenza H1N1 neuraminidase inhibition assay. Compounds 4, 7, 8, and 14, with a chalcone skeleton, showed significant inhibitory effects on the viral neuraminidases from two influenza viral strains, H1N1 and H9N2. Compound 4 showed the strongest inhibitory activity against the neuraminidases from novel influenza H1N1 (WT) and oseltamivir-resistant novel H1N1 (H274Y mutant) expressed in 293T cells with IC50 values of 8.15 ± 1.05 and 3.31 ± 1.34 μM, respectively. Compounds 4, 7, 8, and 14 behaved as noncompetitive inhibitors in the kinetic studies. These results indicate that C-methylated flavonoids from C. operculatus have the potential to be developed as neuraminidase inhibitors for novel influenza H1N1.

AB - As part of an ongoing study focused on the discovery of anti-influenza agents from plants, four new (1-4) and 10 known (5-14) C-methylated flavonoids were isolated from a methanol extract of Cleistocalyx operculatus buds using an influenza H1N1 neuraminidase inhibition assay. Compounds 4, 7, 8, and 14, with a chalcone skeleton, showed significant inhibitory effects on the viral neuraminidases from two influenza viral strains, H1N1 and H9N2. Compound 4 showed the strongest inhibitory activity against the neuraminidases from novel influenza H1N1 (WT) and oseltamivir-resistant novel H1N1 (H274Y mutant) expressed in 293T cells with IC50 values of 8.15 ± 1.05 and 3.31 ± 1.34 μM, respectively. Compounds 4, 7, 8, and 14 behaved as noncompetitive inhibitors in the kinetic studies. These results indicate that C-methylated flavonoids from C. operculatus have the potential to be developed as neuraminidase inhibitors for novel influenza H1N1.

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KW - Humans

KW - Influenza A Virus, H1N1 Subtype

KW - Influenza A Virus, H9N2 Subtype

KW - Influenza, Human

KW - Inhibitory Concentration 50

KW - Kinetics

KW - Molecular Structure

KW - Myrtaceae

KW - Neuraminidase

KW - Oseltamivir

KW - Journal Article

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C-Methylated Flavonoids from Cleistocalyx operculatus and Their Inhibitory Effects on Novel Influenza A (H1N1) Neuraminidase

Abstract

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