2-Benzyl-benzofurans from the tubers of Ophiopogon japonicus

Abstract

BackgroundThe 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.ResultsThree 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 29.1 μM, respectively.ConclusionsThe 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.Electronic supplementary materialThe online version of this article (doi:10.1186/s13065-017-0242-z) contains supplementary material, which is available to authorized users.

Virtual screening and network pharmacology-based synergistic mechanism identification of multiple components contained in Guanxin V against coronary artery disease

“…ShenMai injection, prepared from Panax ginseng and Ophiopogon japonicus, is used as an add-on therapy for CAD [72,73]. The main components of Ophiopogon japonicus exhibit various pharmacological activities, such as cardiovascular protection [74][75][76][77], anti-inflammation [74,76,[78][79][80], antioxidation [74][75][76]81], mitochondrial function preservation [81], apoptosis inhibition [75,81], and immunomodulation [74,77]. The extract of Ophiopogon japonicus decreased ICAM-1 and VCAM-1 to play an endothelial protective role from oxidative damage and dysfunction [82].…”

Withanolides from the whole plant of Physalis angulata and their anti‐inflammatory activities

“…The effects of isolated compounds on the NO production in LPS-stimulated RAW264.7 macrophages were evaluated as previous description in Ref. [15]. The cells were sowed in a 96-well plate at a density of 2.5×105 cells/well and incubated for 12 h. The plate was pretreated with isolated compounds in various concentrations (from 1 to 100 µM) for 30 min and then incubated for another 24 h with or without 1 μg/ml LPS.…”

Anti‐inflammatory and cytotoxic activities of constituents from Wedelia trilobata (L.) Hitchc.

“…This was conducted according to published protocols with modifications, as detailed in a previous paper. [12]…”

“…The activity is comparable to that of the positive control, cardamonin (IC50 = 2.8 µM). [12] Compounds 1-5 were also evaluated for their cytotoxic effect against A549 (lung), MCF-7 (breast carcinoma), Hep3B (hepatoma), and PC3 (prostate) human cancer cell lines using 3-(4,5dimethylthiazolyl-2)-2,5-diphenyltetrazoliumbromide (MTT) assays for 48h (at concentrations of 10, 30, 50, and 100 µM). [13] Among the tested compounds, moderate effects were observed with compounds 1 and 3 on Hep3B and PC3 cells with IC50 values of 49.3, 55.6 µM and 34.6, 61.0 µM, respectively (at the highest concentration tested 100 μM).…”