Prenylated benzoylphloroglucinols and xanthones from the leaves of garcinia oblongifolia with antienteroviral activity

Hong Zhang; Ling Tao; Wen Wei Fu; Shuang Liang; Yi Fu Yang; Qing Hong Yuan; Da Jian Yang; Aiping LYU; Hong Xi Xu

doi:10.1021/np500124e

Prenylated benzoylphloroglucinols and xanthones from the leaves of garcinia oblongifolia with antienteroviral activity

Hong Zhang, Ling Tao, Wen Wei Fu, Shuang Liang, Yi Fu Yang, Qing Hong Yuan, Da Jian Yang, Aiping LYU^*, Hong Xi Xu

^*Corresponding author for this work

School of Chinese Medicine

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

51 Citations (Scopus)

Abstract

An acetone extract of the leaves of Garcinia oblongifolia showed antiviral activity against enterovirus 71 (EV71) using a cytopathic effect inhibition assay. Bioassay-guided fractionation yielded 12 new prenylated benzoylphloroglucinols, oblongifolins J-U (1-12), and five known compounds. The structures of 1-12 were elucidated by spectroscopic analysis including 1D- and 2D-NMR and mass spectrometry methods. The absolute configurations were determined by a combination of a Mosher ester procedure carried out in NMR tubes and ECD calculations. Compared to ribavirin (IC₅₀ 253.1 μM), compounds 1, 4, and 13 exhibited significant anti-EV71 activity in vitro, with IC₅₀ values of 31.1, 16.1, and 12.2 μM, respectively. In addition, the selectivity indices of these compounds were 1.5, 2.4, and 3.0 in African green monkey kidney (Vero) cells, respectively.

Original language	English
Pages (from-to)	1037-1046
Number of pages	10
Journal	Journal of Natural Products
Volume	77
Issue number	4
DOIs	https://doi.org/10.1021/np500124e
Publication status	Published - 25 Apr 2014

Scopus Subject Areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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10.1021/np500124e

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@article{ce497bbe8fd3483b9ab44a9ba931143f,

title = "Prenylated benzoylphloroglucinols and xanthones from the leaves of garcinia oblongifolia with antienteroviral activity",

abstract = "An acetone extract of the leaves of Garcinia oblongifolia showed antiviral activity against enterovirus 71 (EV71) using a cytopathic effect inhibition assay. Bioassay-guided fractionation yielded 12 new prenylated benzoylphloroglucinols, oblongifolins J-U (1-12), and five known compounds. The structures of 1-12 were elucidated by spectroscopic analysis including 1D- and 2D-NMR and mass spectrometry methods. The absolute configurations were determined by a combination of a Mosher ester procedure carried out in NMR tubes and ECD calculations. Compared to ribavirin (IC50 253.1 μM), compounds 1, 4, and 13 exhibited significant anti-EV71 activity in vitro, with IC50 values of 31.1, 16.1, and 12.2 μM, respectively. In addition, the selectivity indices of these compounds were 1.5, 2.4, and 3.0 in African green monkey kidney (Vero) cells, respectively.",

author = "Hong Zhang and Ling Tao and Fu, {Wen Wei} and Shuang Liang and Yang, {Yi Fu} and Yuan, {Qing Hong} and Yang, {Da Jian} and Aiping LYU and Xu, {Hong Xi}",

note = "This research was supported by the National Natural Science Foundation of China (No. 81273403), National Specific Program on TCM (No. 200907001), and the Innovation Ability Construction Project for Chongqing Scientific Research Institutes of Chongqing (Grant No. cstc2012 pt-kyys10001). ",

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doi = "10.1021/np500124e",

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T1 - Prenylated benzoylphloroglucinols and xanthones from the leaves of garcinia oblongifolia with antienteroviral activity

AU - Zhang, Hong

AU - Tao, Ling

AU - Fu, Wen Wei

AU - Liang, Shuang

AU - Yang, Yi Fu

AU - Yuan, Qing Hong

AU - Yang, Da Jian

AU - LYU, Aiping

AU - Xu, Hong Xi

N1 - This research was supported by the National Natural Science Foundation of China (No. 81273403), National Specific Program on TCM (No. 200907001), and the Innovation Ability Construction Project for Chongqing Scientific Research Institutes of Chongqing (Grant No. cstc2012 pt-kyys10001).

PY - 2014/4/25

Y1 - 2014/4/25

N2 - An acetone extract of the leaves of Garcinia oblongifolia showed antiviral activity against enterovirus 71 (EV71) using a cytopathic effect inhibition assay. Bioassay-guided fractionation yielded 12 new prenylated benzoylphloroglucinols, oblongifolins J-U (1-12), and five known compounds. The structures of 1-12 were elucidated by spectroscopic analysis including 1D- and 2D-NMR and mass spectrometry methods. The absolute configurations were determined by a combination of a Mosher ester procedure carried out in NMR tubes and ECD calculations. Compared to ribavirin (IC50 253.1 μM), compounds 1, 4, and 13 exhibited significant anti-EV71 activity in vitro, with IC50 values of 31.1, 16.1, and 12.2 μM, respectively. In addition, the selectivity indices of these compounds were 1.5, 2.4, and 3.0 in African green monkey kidney (Vero) cells, respectively.

AB - An acetone extract of the leaves of Garcinia oblongifolia showed antiviral activity against enterovirus 71 (EV71) using a cytopathic effect inhibition assay. Bioassay-guided fractionation yielded 12 new prenylated benzoylphloroglucinols, oblongifolins J-U (1-12), and five known compounds. The structures of 1-12 were elucidated by spectroscopic analysis including 1D- and 2D-NMR and mass spectrometry methods. The absolute configurations were determined by a combination of a Mosher ester procedure carried out in NMR tubes and ECD calculations. Compared to ribavirin (IC50 253.1 μM), compounds 1, 4, and 13 exhibited significant anti-EV71 activity in vitro, with IC50 values of 31.1, 16.1, and 12.2 μM, respectively. In addition, the selectivity indices of these compounds were 1.5, 2.4, and 3.0 in African green monkey kidney (Vero) cells, respectively.

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Prenylated benzoylphloroglucinols and xanthones from the leaves of garcinia oblongifolia with antienteroviral activity

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