title: Screening of Luzula species native to the Carpathian Basin for anti-inflammatory activity and bioactivity-guided isolation of compounds from Luzula luzuloides (Lam.) Dandy & Wilmott.
abstract: The present study focused on the anti-inflammatory screening of Luzula species native to the Carpathian Basin and bioactivity-guided isolation of compounds of Luzula luzuloides (Lam.) Dandy & Wilmott. The anti-inflammatory properties of extracts with different polarity prepared from Luzula species were determined. Among them, the CH2Cl2-soluble fraction of L. luzuloides possessed strong inhibitory effects on superoxide anion generation (99.39±0.37%) and elastase release (114.22±3.13%) in fMLP/CB-induced human neutrophils at concentration of 10μg/mL. From this fraction, six compounds (1-6) were isolated by the combination of different chromatographic methods. The structures of the compounds were determined by means of MS, 1D and 2D NMR spectroscopy. The results allowed the identification of the new 1,6-dihydroxy-2-keto-1,7-dimethyl-8-vinyl-1,2-dihydrophenanthrene (1) from the plant, named luzulin A. Chiral HPLC and HPLC-ECD analysis revealed that 1 possesses low enantiomeric excess and TDDFT-ECD calculations afforded the configurational assignment of the separated enantiomers. Three known phenanthrenes [juncuenin B (2), dehydrojuncuenin B (3) and juncusol (4)] and two flavonoids [apigenin (5) and luteolin (6)] were also isolated. The anti-inflammatory activity of the isolated compounds was tested and IC50values were determined. This was the first time that phenanthrenes were detected in a Luzula species. The oxidative transformation of juncuenin B (3) led to the isolation of its possible biometabolites, namely luzulin A (1), dehydrojuncuenin B (4), and juncuenin D (7). The isolated compounds (1-4) confirm that besides flavonoids, phenanthrenes could also serve as chemotaxonomic markers for Luzula species and prove the close relationship of Juncus and Luzula genus.
authors.affiliation: Department of Pharmacognosy, University of Szeged, 6720 Szeged, Hungary.
authors.forename: Barbara
authors.initials: B
authors.lastname: Tóth
authors.affiliation: Graduate Institute of Natural Products, Kaohsiung Medical University, 807 Kaohsiung, Taiwan; Research Center for Environmental Medicine, Kaohsiung Medical University, 807 Kaohsiung, Taiwan; Department of Marine Biotechnology and Resources, National Sun Yat-sen University, 804 Kaohsiung, Taiwan.
authors.forename: Fang-Rong
authors.initials: FR
authors.lastname: Chang
authors.affiliation: Graduate Institute of Natural Products, Chang Gung University, 333 Taoyuan, Taiwan; Research Center for Industry of Human Ecology, Chang Gung University of Science and Technology, 333 Taoyuan, Taiwan; Department of Anesthesiology, Chang Gung Memorial Hospital, 333 Taoyuan, Taiwan; Research Center for Chinese Herbal Medicine, Chang Gung University of Science and Technology, 333 Taoyuan, Taiwan; Graduate Institute of Health Industry Technology, Chang Gung University of Science and Technology, 333 Taoyuan, Taiwan.
authors.forename: Tsong-Long
authors.initials: TL
authors.lastname: Hwang
authors.affiliation: Department of Organic Chemistry, University of Debrecen, 4032 Debrecen, Hungary.
authors.forename: Ádám
authors.initials: Á
authors.lastname: Szappanos
authors.affiliation: Department of Organic Chemistry, University of Debrecen, 4032 Debrecen, Hungary.
authors.forename: Attila
authors.initials: A
authors.lastname: Mándi
authors.affiliation: Department of Pharmacognosy, University of Szeged, 6720 Szeged, Hungary.
authors.forename: Attila
authors.initials: A
authors.lastname: Hunyadi
authors.affiliation: Department of Organic Chemistry, University of Debrecen, 4032 Debrecen, Hungary.
authors.forename: Tibor
authors.initials: T
authors.lastname: Kurtán
authors.affiliation: Institute of Environmental Sciences, Faculty of Water and Environmental Management, Szent István University, 5540 Szarvas, Hungary.
authors.forename: Gusztáv
authors.initials: G
authors.lastname: Jakab
authors.affiliation: Department of Pharmacognosy, University of Szeged, 6720 Szeged, Hungary; Interdisciplinary Centre of Natural Products, University of Szeged, 6720 Szeged, Hungary.
authors.forename: Judit
authors.initials: J
authors.lastname: Hohmann
authors.affiliation: Department of Pharmacognosy, University of Szeged, 6720 Szeged, Hungary. Electronic address: vasasa@pharmacognosy.hu.
authors.forename: Andrea
authors.initials: A
authors.lastname: Vasas
mesh_terms: D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification; D006801:Humans; D019272:Leukocyte Elastase / Q000378:metabolism; D019684:Magnoliopsida / Q000737:chemistry*; D015394:Molecular Structure; D009504:Neutrophils / Q000187:drug effects*; D010616:Phenanthrenes / Q000737:chemistry* / Q000302:isolation & purification; D010936:Plant Extracts / Q000737:chemistry; D013481:Superoxides / Q000378:metabolism
chemical_list: D000893:Anti-Inflammatory Agents; D005419:Flavonoids; D010616:Phenanthrenes; D010936:Plant Extracts; C000613492:luzulin A; D013481:Superoxides; D019272:Leukocyte Elastase
keywords: Anti-inflammatory activity; Electronic circular dichroism; Flavonoids; Juncaceae; Luzula luzuloides; Phenanthrenes