2-Benzyl-benzofurans from the tubers of Ophiopogon japonicus

Nguyen Hai Dang; Nguyen Dinh Chung; Ha Manh Tuan; Nguyen Thanh; Nguyen Tuan Hiep; Dongho Lee; Nguyen Tien Dat

doi:10.1186/s13065-017-0242-z

2-Benzyl-benzofurans from the tubers of Ophiopogon japonicus

Nguyen Hai Dang, Nguyen Dinh Chung, Ha Manh Tuan, Nguyen Thanh, Nguyen Tuan Hiep, Dongho Lee, Nguyen Tien Dat

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

Background: The overproduction of nitric oxide (NO) is known to involve in various inflammatory processes. A methanol extract of the tubers of Ophiopogon japonicus was found to strongly inhibit NO production. The present paper deals with the isolation, structural identification and NO inhibitory effect of five compounds isolated from the MeOH extract of O. japonicus tubers. Results: Three new compounds were elucidated to be (2R)-(4-methoxybenzyl)-5,7-dimethyl-6-hydroxyl-2,3-dihydrobenzofuran (1), 2-(2-hydroxyl-4-methoxy-benzyl)-5-methyl-6-methoxyl-2,3-dihydrobenzofuran (2), and 2-(4-hydroxy-benzyl)-5,6-dihydroxybenzofuran (3). In addition, two known compounds were isolated from a natural source for the first time including 2-(4-methoxy-benzyl)-6,7-dimethoxyl-2,3-dihydrobenzofuran (4), and 2-(4-methoxy-benzyl)-6,7-methylenedioxy-2,3-dihydrobenzofuran (5). The absolute configuration of compound 1 was determined by experimental and calculated circular dichroism spectra. The effects of the isolated compounds on LPS-induced NO production in RAW264.7 cells were evaluated. Compound 1 and 2 showed the inhibitory activity with IC₅₀ values of 11.4 and 29.1μM, respectively. Conclusions: The class of 2-benzyl-2,3-dihydrobenzofuran is uncommon in nature. In this work, three such compounds were isolated from O. japonicus. Two of them showed promising anti-inflammatory activity by inhibition of NO production.

Original language	English
Article number	15
Journal	Chemistry Central Journal
Volume	11
Issue number	1
DOIs	https://doi.org/10.1186/s13065-017-0242-z
Publication status	Published - 2017 Feb 6

Bibliographical note

Funding Information:
This work is supported by the National Foundation for Science and Technology Development (NAFOSTED 104.01-2014.05). We thank the Institute of Chemistry (VAST) for the NMR experiments.

Publisher Copyright:
© 2017 The Author(s).

Keywords

2-Benzyl-2,3-dihydroxybenzofuran
2-Benzyl-benzofuran
Dihydrobenzofuran
Inhibition of NO production
Ophiopogon japonicas

ASJC Scopus subject areas

General Chemistry

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10.1186/s13065-017-0242-z

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title = "2-Benzyl-benzofurans from the tubers of Ophiopogon japonicus",

abstract = "Background: The overproduction of nitric oxide (NO) is known to involve in various inflammatory processes. A methanol extract of the tubers of Ophiopogon japonicus was found to strongly inhibit NO production. The present paper deals with the isolation, structural identification and NO inhibitory effect of five compounds isolated from the MeOH extract of O. japonicus tubers. Results: Three new compounds were elucidated to be (2R)-(4-methoxybenzyl)-5,7-dimethyl-6-hydroxyl-2,3-dihydrobenzofuran (1), 2-(2-hydroxyl-4-methoxy-benzyl)-5-methyl-6-methoxyl-2,3-dihydrobenzofuran (2), and 2-(4-hydroxy-benzyl)-5,6-dihydroxybenzofuran (3). In addition, two known compounds were isolated from a natural source for the first time including 2-(4-methoxy-benzyl)-6,7-dimethoxyl-2,3-dihydrobenzofuran (4), and 2-(4-methoxy-benzyl)-6,7-methylenedioxy-2,3-dihydrobenzofuran (5). The absolute configuration of compound 1 was determined by experimental and calculated circular dichroism spectra. The effects of the isolated compounds on LPS-induced NO production in RAW264.7 cells were evaluated. Compound 1 and 2 showed the inhibitory activity with IC50 values of 11.4 and 29.1μM, respectively. Conclusions: The class of 2-benzyl-2,3-dihydrobenzofuran is uncommon in nature. In this work, three such compounds were isolated from O. japonicus. Two of them showed promising anti-inflammatory activity by inhibition of NO production.",

keywords = "2-Benzyl-2,3-dihydroxybenzofuran, 2-Benzyl-benzofuran, Dihydrobenzofuran, Inhibition of NO production, Ophiopogon japonicas",

author = "Dang, {Nguyen Hai} and Chung, {Nguyen Dinh} and Tuan, {Ha Manh} and Nguyen Thanh and Hiep, {Nguyen Tuan} and Dongho Lee and Dat, {Nguyen Tien}",

note = "Funding Information: This work is supported by the National Foundation for Science and Technology Development (NAFOSTED 104.01-2014.05). We thank the Institute of Chemistry (VAST) for the NMR experiments. Publisher Copyright: {\textcopyright} 2017 The Author(s).",

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doi = "10.1186/s13065-017-0242-z",

language = "English",

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T1 - 2-Benzyl-benzofurans from the tubers of Ophiopogon japonicus

AU - Dang, Nguyen Hai

AU - Chung, Nguyen Dinh

AU - Tuan, Ha Manh

AU - Thanh, Nguyen

AU - Hiep, Nguyen Tuan

AU - Lee, Dongho

AU - Dat, Nguyen Tien

N1 - Funding Information: This work is supported by the National Foundation for Science and Technology Development (NAFOSTED 104.01-2014.05). We thank the Institute of Chemistry (VAST) for the NMR experiments. Publisher Copyright: © 2017 The Author(s).

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Y1 - 2017/2/6

N2 - Background: The overproduction of nitric oxide (NO) is known to involve in various inflammatory processes. A methanol extract of the tubers of Ophiopogon japonicus was found to strongly inhibit NO production. The present paper deals with the isolation, structural identification and NO inhibitory effect of five compounds isolated from the MeOH extract of O. japonicus tubers. Results: Three new compounds were elucidated to be (2R)-(4-methoxybenzyl)-5,7-dimethyl-6-hydroxyl-2,3-dihydrobenzofuran (1), 2-(2-hydroxyl-4-methoxy-benzyl)-5-methyl-6-methoxyl-2,3-dihydrobenzofuran (2), and 2-(4-hydroxy-benzyl)-5,6-dihydroxybenzofuran (3). In addition, two known compounds were isolated from a natural source for the first time including 2-(4-methoxy-benzyl)-6,7-dimethoxyl-2,3-dihydrobenzofuran (4), and 2-(4-methoxy-benzyl)-6,7-methylenedioxy-2,3-dihydrobenzofuran (5). The absolute configuration of compound 1 was determined by experimental and calculated circular dichroism spectra. The effects of the isolated compounds on LPS-induced NO production in RAW264.7 cells were evaluated. Compound 1 and 2 showed the inhibitory activity with IC50 values of 11.4 and 29.1μM, respectively. Conclusions: The class of 2-benzyl-2,3-dihydrobenzofuran is uncommon in nature. In this work, three such compounds were isolated from O. japonicus. Two of them showed promising anti-inflammatory activity by inhibition of NO production.

AB - Background: The overproduction of nitric oxide (NO) is known to involve in various inflammatory processes. A methanol extract of the tubers of Ophiopogon japonicus was found to strongly inhibit NO production. The present paper deals with the isolation, structural identification and NO inhibitory effect of five compounds isolated from the MeOH extract of O. japonicus tubers. Results: Three new compounds were elucidated to be (2R)-(4-methoxybenzyl)-5,7-dimethyl-6-hydroxyl-2,3-dihydrobenzofuran (1), 2-(2-hydroxyl-4-methoxy-benzyl)-5-methyl-6-methoxyl-2,3-dihydrobenzofuran (2), and 2-(4-hydroxy-benzyl)-5,6-dihydroxybenzofuran (3). In addition, two known compounds were isolated from a natural source for the first time including 2-(4-methoxy-benzyl)-6,7-dimethoxyl-2,3-dihydrobenzofuran (4), and 2-(4-methoxy-benzyl)-6,7-methylenedioxy-2,3-dihydrobenzofuran (5). The absolute configuration of compound 1 was determined by experimental and calculated circular dichroism spectra. The effects of the isolated compounds on LPS-induced NO production in RAW264.7 cells were evaluated. Compound 1 and 2 showed the inhibitory activity with IC50 values of 11.4 and 29.1μM, respectively. Conclusions: The class of 2-benzyl-2,3-dihydrobenzofuran is uncommon in nature. In this work, three such compounds were isolated from O. japonicus. Two of them showed promising anti-inflammatory activity by inhibition of NO production.

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KW - Dihydrobenzofuran

KW - Inhibition of NO production

KW - Ophiopogon japonicas

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ER -

2-Benzyl-benzofurans from the tubers of Ophiopogon japonicus

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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