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
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).
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
U2 - 10.1186/s13065-017-0242-z
DO - 10.1186/s13065-017-0242-z
M3 - Article
AN - SCOPUS:85011655237
SN - 1752-153X
VL - 11
JO - Chemistry Central Journal
JF - Chemistry Central Journal
IS - 1
M1 - 15
ER -