Phenanthrenes from Juncus effusus

Abstract

A chemical investigation of the EtOAc-soluble fraction from the ethanol extract of the medullae of Juncus effusus led to the isolation of three new 9,10-dihydrophenanthrenes, juncuenins E-G (1-3); two new phenanthrenes, dehydrojuncuenins D-E (4-5); one new feruloylated glycoside (6); and one known 9,10-dihydrophenanthrene (7). The structures of these compounds were determined by analyzing their spectroscopic data. Metabolites 1-4 and 7 were further evaluated for their in vitro cytotoxic activities against seven human cancer lines (A549, MCF-7, BEL-7402, HeLa, COLO205, BGC-823, and SK-OV-3). Among them, compound 1 exhibited weak cytotoxicity against MCF-7 and HeLa cell lines. Compound 7 showed moderate cytotoxicity against MCF-7 and HeLa cell lines, with IC50 values of 9.17 and 19.6 µM, respectively.

Family Juncaceae: promising source of biologically active natural phenanthrenes

“…The most frequently used solvents are MeOH and EtOH (Yang et al 2007), in some cases EtOAc (DellaGreca et al 2003) or even less polar solvents (light petrol) (DellaGreca et al 2002a) were used. The extracts are usually partitioned with solvents with increasing polarity, the most frequently used ones are CHCl 3 , EtOAc (Su et al 2013), and n-BuOH (Abdel-Razik et al 2009). In most of the cases, the next step is a column chromatographic separation using normal-or reversed-phase silica gel, the elution is performed in gradient conditions.…”

Bioactive secondary metabolites from Juncaceae species

“…Therefore, vinylated phenanthrenes can be considered as chemotaxonomic markers of Juncaceae species. [22][23][24][25][26][27][28][29][30][31] Most of the Juncaceae phenanthrenes are substituted with methyl groups. Methyl substitutions were generally found at C-1 or C-7.…”

“…Phenanthrenes isolated from different Juncaceae species exert many different activities, including antitumor, [28][29][30][31][32] anti-inflammatory, 23,27,29,31 antioxidant, 23 anxiolytic, 7,9 cell-protective, 11 sedative, 8,9 and spasmolytic 32 effects.…”

“…22 To date, almost one hundred novel phenanthrenes have been isolated from the family, but only from Juncus species. [23][24][25][26][27][28][29][30][31] Although many phenanthrenecontaining species have been used in folk medicine for hundreds of years in order to treat several diseases, however the chemical composition and the mechanism of action of many of these plants have not been studied thoroughly yet. Therefore, these plants and their secondary metabolites are worthy of future investigations.…”

“…antitumor, antibacterial, anti-inflammatory, antioxidant, anxiolytic, cell-protective, sedative, and spasmolytic activities) and their broad structural diversity. [7][8][9]11,23,[27][28][29][30][31][32][33][34][35] Probably, the most investigated naturally occurring phenanthrene derivate is denbinobin, which displays remarkable antitumour activity against several cancer cell lines. Moreover, its anti-HIV property is also very promising.…”