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 PUMID/DOI：DOI: 10.1016/j.fitote.2016.12.004 Fitoterapia. 2017 Jan;116:131-138. 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 +/- 037%) and elastase release (114.22 +/- 3.13%) in fMLP/CB-induced human neutrophils at concentration of 10 mu g/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-dimethy1-8-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 IC50 values 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. (C) 2016 Elsevier B.V. All rights reserved. Antibacterial screening of Juncaceae species native to the Carpathian Basin against resistant strains and LC-MS investigation of phenanthrenes responsible for the effect PUMID/DOI：DOI: 10.1016/j.fitote.2016.09.024 Fitoterapia. 2016 Dec;115:69-73. The main objective of this project was to investigate the antibacterial activity of 19 species (Junco acutus, J. alpinoarticulatus,J. articulatus,J. compressus,J. conglomeratus,J. effusus,J. filiformisd. gerardii,J.inilexus,J. maritimus, J. monanthos,J. squarrosus, J. tenuis, J. trifidus, Luzula campestris, L forsteri, L. luzuloides, L. sudetica and L sylvatica) belonging to the family Juncaceae against methicillin-resistant S. aureus (MRSA), extended-spectrum beta-lactamase (ESBL)-producing C. freundii, E. coli, E. cloacae, K. pneumoniae, and multiresistant A. baumannii and P. aeruginosa. Antibacterial susceptibilities were screened for inhibitory zones and MIC values determined by microdilution method. Among the tested extracts (n = 96) 16 extracts prepared from funcus species and 3 extracts from Luzula species showed mild to strong inhibitory activities against MRSA strains (inhibition zones = 6.7 mm-14.6 mm; MIC values 9.75-156 mu g/mL). It can be concluded that Juncus and Luzula species demonstrated promising anti-MRSA effect, and J. maritimus, J. tenuis and]. gerardii considered worthy of activity-guided phytochemical investigations. The main bioactive constituents of Juncaceae species are phenanthrenes. Four phenanthrenes [juncuenin D (1), juncusol (2), dehydrojuncuenin B (3), and jinflexin B (4)] isolated previously from J. inflexus with anti-MRSA activity were investigated by LC-MS in extracts proved to be active in antimicrobial test. (C) 2016 Elsevier B.V. All rights reserved. Phenanthrenoids from Juncus acutus L., new natural lipopolysaccharide-inducible nitric oxide synthase inhibitors PUMID/DOI：17666857 Chem Pharm Bull (Tokyo). 2007 Aug;55(8):1264-6. The novel natural product juncutol (1), 1,4,7-trimethyl-8,9-dihydro-4H-cyclopentaldeflphenanthrene-2,6-diol, along with the three related metabolites juncusol (2), dehydrojuncusol (3), and 6-hydroxymethyl-1-methyl-5vinyl-9,10-dihydrophenanthrene-2-ol (4), were isolated from the rhizomes of Juncus acutus L. (Juncaceae) growing in Egypt. The structural identity of 1 was determined on the basis of spectroscopic analyses, including 2D NMR spectroscopy. The inhibitory effect of these natural products on the expression of inducible nitric oxide synthase (iNOS) in lipopolysaccharide-stimulated RAW264.7 macrophage cells was determined for the first time. The unprecedented symmetrical compound juncutol (1) was found to be the most potent inhibitor against the induction of the proinflammatory iNOS protein. ANTIMICROBIAL AND ANTITUMOR PROPERTIES OF 9,10-DIHYDROPHENANTHRENES: STRUCTURE ACTIVITY STUDIES ON JUNCUSOL PUMID/DOI：4045930 J Med Chem. 1985 Oct;28(10):1543-7. The antimicrobial and cytotoxic properties of a series of 9,10-dihydrophenanthrenes structurally related to juncusol (1a), a postulated phytoalexin with confirmed cytotoxic properties, are detailed. Two simple 9,10-dihydrophenanthrenes, 2,7-dihydroxy-3,8-dimethyl-9,10-dihydrophenanthrene (2h, desvinyljuncusol) and 2-hydroxy-3-methyl-9,10-dihydrophenanthrene (3h), were found to possess in vitro antimicrobial activity comparable with that of the natural product. Two 9,10-dihydrophenanthrenes substituted with quaternary ammonium salts, 2d and 3d, each containing a reactive benzylic dimethyl[(phenylthio)methyl]ammonio group, were found to be 10-20 times more potent than juncusol (1a). Confirmed in vitro cytotoxic activity that parallels antimicrobial activity was found for juncusol (1a), desvinyljuncusol (2h), 2-hydroxy-3-methyl-9,10-dihydrophenanthrene (3h), and the quaternary dimethyl[(phenylthio)methyl]ammonium salts 2d and 3d in a human lymphoblastic leukemia cell culture (CCRF-CEM, IC50 = nt, 9.3, nt, 0.9 and 1.4 microgram/mL, respectively), B-16 mouse melanoma cell culture (IC50 = 12.5, 17.5, 27.7, 0.3, and 0.5 microgram/mL, respectively), and L-1210 mouse lymphocytic leukemia cell culture (IC50 = 13.8, 10.2, 24.5, 1.3, and 3.7 micrograms/mL, respectively). The comparable potency and spectrum of activity of juncusol (1a), desvinyljuncusol (2h), and 2-hydroxy-3-methyl-9,10-dihydrophenanthrene (3h) suggest that the agents are acting as simple phenols in exerting their antimicrobial and cytotoxic effects.
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Background: Phenanthrenes isolated from Juncus species possess different biological activities, including antiproliferative and antimigratory effects.
Purpose: In this study, nine phenanthrenes isolated from the roots of Juncus inflexus were investigated for their antiproliferative activity on several gynecological cancer cell lines, using non-cancerous cells as controls.
Methods: Antiproliferative activities of the compounds were determined by means of MTT assay. Flow cytometry was used for cell cycle analysis and determination of mitotic cells. Activities of caspase-3, -8, and -9 were detected by colorimetric kits. Tubulin polymerization was followed by kinetic absorbance determination. Action on tumor cell migration was described using wound healing assay. Western blot assays were used to determine apoptosis-related factors at protein level.
Results: Among the compounds tested, juncusol exhibited the most substantial antiproliferative effect against cervical cancer HeLa cells. It was also revealed that juncusol has a distinct growth inhibitory effect in cervical cancer cell lines of various HPV status: it was highly active in HPV type 18-positive HeLa cells, while it was inactive in HPV type 16-positive SiHa and CaSki cells. Cell cycle analysis showed an increase in G2/M and subG1 cell populations after juncusol treatment. Caspase-3, -8, and -9 were detected to be activated by juncusol in HeLa cells, indicating that juncusol induces apoptotic cell death. Moreover, juncusol inhibited tubulin polymerization, as well as EGFR activation, suggesting two possible additional mechanisms that may account for juncusol’s inducing a G2/M-phase cell cycle arrest and inhibiting cell migration.
Conclusion: These results suggest that juncusol is a potent antiproliferative agent against HPV-18 related cervical cancer and may be considered as a lead compound for the development of innovative anticancer agents.
Antiproliferative and antimigratory effects; Cell cycle arrest; Juncaceae; Juncus inflexus; Tubulin polymerization.
Investigation of natural phenanthrenes and the antiproliferative potential of juncusol in cervical cancer cell lines
Ching-Ying Kuo 1, Zsuzsanna Schelz 2, Barbara Toth 3, Andrea Vasas 3, Imre Ocsovszki 4, Fang-Rong Chang 5, Judit Hohmann 6, Istvan Zupko 7, Hui-Chun Wang 8
2019 May 21
Background: Juncunol is a phenanthrene isolated from the halophyte species Juncus acutus, with selective cytotoxic activity towards human hepatocarcinoma (HepG2) cells. However, its mechanism of action is unknown.
Methods: The in vitro cytotoxic mechanism of juncunol was evaluated on HepG2 cells through several methods to elucidate its potential to induce apoptotic features, decrease mitochondrial membrane potential, promote internal ROS production and influence cell cycle. We also report its haemolytic activity on human erythrocytes and in silico DNA-binding studies.
Results: Juncunol induced an increase in the number of apoptotic cells in a concentration-dependent manner, accompanied by a decrease in the mitochondrial membrane potential. No significant differences were observed in production of reactive oxygen species (ROS). Moreover, juncunol application at the IC50 value significantly induced cell cycle arrest in the G0/G1 phase comparatively to the control group. No significant haemolysis was detected. In silico studies indicate that juncunol seems to bind between GC base pairs.
Conclusion: Juncunol reduced HepG2 cells proliferation through the induction of apoptotic cellular death, in a concentration-dependent manner. Apoptosis induction seems to be related with a decrease of the mitochondrial membrane potential but not with ROS production. Juncunol had no haemolytic activity and may act as a DNA intercalator. Our data suggests juncunol as a suitable candidate for more detailed studies, including in vivo experiments, in order to completely characterize its mode of action.
Apoptosis; Cell cycle; DNA binding; Flow cytometry; Haemolysis; Mitochondrial membrane potential; Reactive oxygen species.
In vitro and in silico approaches to unveil the mechanisms underlying the cytotoxic effect of juncunol on human hepatocarcinoma cells
Maria João Rodrigues 1, Catarina Vizetto-Duarte 1, Katkam N Gangadhar 1, Gokhan Zengin 2, Adriano Mollica 3, João Varela 1, Luisa Barreira 1, Luisa Custodio 4
The present study has focused on an investigation of the antibacterial effects of Juncus inflexus and the isolation and identification of its active compounds. Eleven phenanthrenes were isolated from a methanolic extract of the roots. Four compounds (jinflexins A-D, 1-4) are new natural products, while seven phenanthrenes [juncuenins A (5), B (6), and D (8), juncusol (7), dehydrojuncuenins A (9) and B (11), and dehydrojuncusol (10)] were isolated for the first time from the plant. Jinflexin D (4) is a dimer with an unprecedented heptacyclic ring system. The absolute configurations of the new compounds were determined by TDDFT-ECD calculations, and their enantiomeric purity was checked by chiral HPLC analysis. Extracts of different polarity (n-hexane, dichloromethane, and ethyl acetate) were evaluated for their antimicrobial effects against methicillin-resistant Staphylococcus aureus, extended-spectrum β-lactamase (ESBL)-producing Citrobacter freundii, Escherichia coli, Enterobacter cloacae, Klebsiella pneumoniae, multiresistant Acinetobacter baumannii, and Pseudomonas aeruginosa. The MIC values of the isolated compounds were determined by a microdilution method. Jinflexin B (2), juncusol (7), juncuenin D (8), and dehydrojuncuenin B (11) showed significant activity (MIC value range 12.5-100 μg/mL) against MRSA strains.
Phenanthrenes from Juncus inflexus with Antimicrobial Activity against Methicillin-Resistant Staphylococcus aureus
Barbara Toth, Erika Liktor-Busa, Norbert Kúsz, adam Szappanos 1, Attila Mandi 1, Tibor Kurtan 1, Edit Urban 2, Judit Hohmann, Fang-Rong Chang 3, Andrea Vasas
2016 Nov 23