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 journalArticle

3 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 languageEnglish
Article number15
JournalChemistry Central Journal
Volume11
Issue number1
DOIs
Publication statusPublished - 2017 Feb 6

Fingerprint

Benzofurans
Nitric Oxide
Hydroxyl Radical
Methanol
Anti-Inflammatory Agents
coumaran

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Dang, N. H., Chung, N. D., Tuan, H. M., Thanh, N., Hiep, N. T., Lee, D., & Dat, N. T. (2017). 2-Benzyl-benzofurans from the tubers of Ophiopogon japonicus. Chemistry Central Journal, 11(1), [15]. https://doi.org/10.1186/s13065-017-0242-z

2-Benzyl-benzofurans from the tubers of Ophiopogon japonicus. / Dang, Nguyen Hai; Chung, Nguyen Dinh; Tuan, Ha Manh; Thanh, Nguyen; Hiep, Nguyen Tuan; Lee, Dongho; Dat, Nguyen Tien.

In: Chemistry Central Journal, Vol. 11, No. 1, 15, 06.02.2017.

Research output: Contribution to journalArticle

Dang, NH, Chung, ND, Tuan, HM, Thanh, N, Hiep, NT, Lee, D & Dat, NT 2017, '2-Benzyl-benzofurans from the tubers of Ophiopogon japonicus', Chemistry Central Journal, vol. 11, no. 1, 15. https://doi.org/10.1186/s13065-017-0242-z
Dang, Nguyen Hai ; Chung, Nguyen Dinh ; Tuan, Ha Manh ; Thanh, Nguyen ; Hiep, Nguyen Tuan ; Lee, Dongho ; Dat, Nguyen Tien. / 2-Benzyl-benzofurans from the tubers of Ophiopogon japonicus. In: Chemistry Central Journal. 2017 ; Vol. 11, No. 1.
@article{88e04abcff9a4946a2ff40884cc8b32f,
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}",
year = "2017",
month = "2",
day = "6",
doi = "10.1186/s13065-017-0242-z",
language = "English",
volume = "11",
journal = "Chemistry Central Journal",
issn = "1752-153X",
publisher = "Chemistry Central",
number = "1",

}

TY - JOUR

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

PY - 2017/2/6

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.

KW - 2-Benzyl-2,3-dihydroxybenzofuran

KW - 2-Benzyl-benzofuran

KW - Dihydrobenzofuran

KW - Inhibition of NO production

KW - Ophiopogon japonicas

UR - http://www.scopus.com/inward/record.url?scp=85011655237&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85011655237&partnerID=8YFLogxK

U2 - 10.1186/s13065-017-0242-z

DO - 10.1186/s13065-017-0242-z

M3 - Article

AN - SCOPUS:85011655237

VL - 11

JO - Chemistry Central Journal

JF - Chemistry Central Journal

SN - 1752-153X

IS - 1

M1 - 15

ER -