Anti-Inflammatory and Cytotoxic Potential of New Phenanthrenoids from Luzula Sylvatica

Abstract

Phenanthrenoids have been widely described, in the Juncaceae family, for theirbiological properties such as antitumor, anxiolytic, anti-microbial, spasmolytic, and antiinflammatoryactivities. The Juncaceae family is known to contain a large variety ofphenanthrenoids possessing especially anti-inflammatory and cytotoxic properties. Luzulasylvatica, a Juncaceae species, is widely present in the Auvergne region of France, but has neverbeen studied neither for its phytochemical profile nor for its biological properties. We investigatedthe phytochemical profile and evaluated the potential anti-inflammatory activities of L. sylvaticaaerial parts extracts. A bioassay-guided fractionation was carried out to identify the most activefractions. Nine compounds were isolated, one coumarin 1 and eight phenanthrene derivatives (2-9), including four new compounds (4, 5, 8 and 9), from n-hexane and CH2Cl2, fractions. Theirstructures were established by HRESIMS, 1D and 2D NMR experiments. The biological properties,especially the anti-inflammatory/antioxidant activities (ROS production) and antiproliferativeactivity on THP-1, a monocytic leukemia cell line, of each compound, were evaluated. Threephenanthrene derivatives 4, 6, and 7 showed very promising antiproliferative activities.Phenanthrene derivatives.

Keywords: Luzula sylvatica; Phenanthrene derivatives; antiproliferative activities.

Figure 1

ROS production of blood leucocytes, incubated with the methanolic extract or fractions (10, 25 and 50 µg/mL) and stimulated with PMA (1 µM) for 1 h. Values are expressed as percentage of the control (cells incubated with PMA and without extract). Data are shown as means ± SEM (n = 3–6); * p < 0.05 compared with Control. All results are expressed as a percentage, with control (i.e., cells with PMA but without extract) normalized as 100%.

Figure 2

Isolated compounds from CH₂Cl₂ and n-hexane fractions.

Figure 3

Key COSY, HMBC and NOESY correlations for compounds 4, 5, 8 and 9.

Figure 4

ROS production of blood leucocytes, incubated with the compounds (2, 5, 10 and 20 µM for compounds 2–9 and 10, 25, 50 and 100 µM for compound 1) and stimulated with PMA (1 µM) for 1 h. Values are expressed as percentage of the control (cells incubated with PMA and without extract). Data are shown as means ± SEM (n = 3); * p < 0.05 compared with Control. All results are expressed as a percentage, with control (i.e., cells with PMA but without extract) normalized as 100%.