燈心草類植物活性二次代謝物

The family Juncaceae is an abundant source of bioactive phenanthrenes. The objectives of the present work were the evaluation of the antibacterial and anti-inflammatory effects of Juncaceae species native to the Carpathian Basin, and isolation and structure determination of biologically active compounds from the most promising species. Extracts with different polarity were prepared from 19 Juncaceae species and screened in vitro for their antimicrobial effects against ten resistant bacterial strains by disc-diffusion and microdilution methods. According to the results Juncus inflexus was chosen for further studies. Luzula species were assayed for their anti-inflammatory properties. The CH2Cl2-soluble fraction of Luzula luzuloides inhibited significantly the superoxide anion generation and the elastase release on fMLP/CB-induced human neutrophils. Isolation of the compounds was carried out by multistep separation procedures, including OCC, VLC, MPLC, PLC, GF and RP-HPLC. The structures of the isolated compounds were elucidated by means of spectroscopic methods (HRMS, MS and NMR). The absolute configuration of the chiral compounds was determined by HPLC-ECD analyses and ECD calculations. Four new natural phenanthrenes [jinflexin A (1), jinflexin B (2), jinflexin C (3) and jinflexin D (4)], four dihydrophenanthrenes [juncuenin A (5), juncuenin B (6), juncusol (7), juncuenin D (8)], three known phenanthrenes [dehydrojuncuenin A (9), dehydrojuncusol (10), dehydrojuncuenin B (11)], and the flavonoid chrysoeriol (12) were isolated from the root parts of J. inflexus. Juncusol (7) and juncuenin D (8) displayed significant anti MRSA-activity, while marked activity was recorded for jinflexin B (2) and dehydrojuncuenin B (11). The HPLC-MS investigation of the chemical composition of other active Juncaceae extracts revealed the presence of juncusol (7) in all the investigated extracts, and the presence of jinflexin B (2) in some cases. J. gerardii, J. maritimus and J. tenuis are promising candidates for further investigations in the search for new active antibacterial natural compounds. The apolar extract of L. luzuloides exerted noteworthy anti-inflammatory activity in vitro. A new phenanthrenequinone, luzulin A (13), three known phenanthrene derivatives [juncuenin B (6), juncusol (7) and dehydrojuncuenin B (11)] and two flavonoids [apigenin (14) and luteolin (15)] were isolated from the plant. Noteworthy anti-inflammatory activities were recorded for juncuenin B (6), juncusol (7), dehydrojuncuenin B (11), apigenin (14) and luteolin (15). The oxidative semi-synthetic transformation of juncuenin B (6) led to the isolation of its possible biometabolites: juncuenin D (8), dehydrojuncuenin B (11) and luzulin A (13). All of the isolated compounds were detected for the first time from the investigated plants. The chemical constituents of J. inflexus and L. luzuloides have not been investigated previously. This was the first time that phenanthrenes were detected from a Luzula species.

關鍵字

燈心草

並列摘要

並列關鍵字

Juncaceae

參考文獻

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