Phytochemical Analysis and Evaluation of Genotoxic, Antigenotoxic Effects in Bacterial Models, and Hypoglycemic Activity of Epilobium angustifolium L. with Bioguided Isolation of Active Compounds.

This study examined the effects of methanol extract and its sub-extracts from Epilobium angustifolium on α-glucosidase and α-amylase activity. Secondary metabolites and amino acids were quantified using LC-MS/MS. Dichloromethane sub-extract displayed the highest activity and was chosen for further investigation. Despite the widespread use of E. angustifolium, genotoxicity studies were conducted to assess its safety. Dichloromethane significantly inhibited α-glucosidase (IC50 =17.340 µg/mL), making it approximately 293 times more effective than acarbose. Six known compounds, including gallic acid (1), a mixture of quercetin-3-O-α-galactoside (2a) and quercetin-3-O-α-glucoside (2b), quercetin-3-O-α-glucuronic acid (3), quercetin-3-O-α-rhamnoside (4), and kaempferol-3-O-α-rhamnoside (5) were identified. Quercetin-3-O-α-rhamnoside exhibited the highest inhibition of α-glucosidase (IC50 =1735±85 µM), making it 3.70 times more effective than acarbose. Dichloromethane also showed significant antigenotoxic activity against mutagenesis induced by NaN3, 9-AA, 4-NPD, and MNNG. Gallic acid was found in the highest abundance (13253.6931 ng/mL) in the methanolic extract. Furthermore, L-Aspartic acid was the most concentrated amino acid (363.5620 nmol/mL) in the methanolic extract.

In vitro genotoxicity assessment of biosynthesized zinc oxide nanoparticles.

There are various studies on the toxicological potentials of conventionally synthesized zinc oxide (ZnO) nanoparticles, which are useful tools for many medical applications. However, knowledge about the biologically synthesized ones is still limited. In this study, the potential of producing ZnO nanoparticles via a green synthesis method, which enables safer, environmentally, economical and controlled production by using the Symphoricarpos albus L. plant, was investigated. For this purpose, aqueous extract was obtained from the fruits of the plant and reacted with zinc nitrate precursor. Characterization of the synthesized product was carried out by SEM and EDAX analyzes. In addition, the biosafety of the product was also investigated by using the Ames/Salmonella, E. coli WP2, Yeast DEL, seed germination, and RAPD test systems. The results obtained from SEM studies showed that spherical nanoparticles with an average diameter of 30 nm were synthesized as a result of the reaction. EDAX findings confirmed that these nanoparticles were composed of Zn and O elements. On the other hand, according to the findings of the biocompatibility tests, the synthesized nanoparticle did not show any toxic and genotoxic effects up to a concentration of 640 µg/ml in any of the test systems. Accordingly, considering the findings of our study, it was concluded that the aqueous extract of S. albus fruits can be used for the green synthesis of ZnO nanoparticles, the products obtained successfully passed the biocompatibility tests in our study, and additionally, more comprehensive biocompatibility tests should be performed before industrial scale production.

Two antigenotoxic chalcone glycosides from Mentha longifolia subsp. longifolia.

CONTEXT: Mentha L. (Labiatae) species (mint) with their flavoring properties have been used in food industries for centuries. Besides they have a great importance in drug development and medicinal applications due to various bioactive compounds of several members of the genus. OBJECTIVE: The aim of this study was to isolate bioactive compounds with antimutagenic potential by bio-guided fractionation and determine their structures by spectroscopic methods. MATERIALS AND METHODS: The structural elucidation of the isolated compounds was done based on spectroscopic methods, including MALDI-MS, UV, IR, and 2D NMR experiments, and the bio-guided fractionation process was done by using the Ames/Salmonella test system. Henceforth, solely genotoxic and antigenotoxic potential of the new compounds were also confirmed up to 2 µM/plate by using the same test system. RESULTS: Two new chalcone glycosides: (ßR)-ß,3,2',6'-tetrahydroxy-4-methoxy-4'-O-rutinosyldihydrochalcone and (ßR)-ß,4,2',6'-tetrahydroxy-4'-O-rutinosyldihydrochalcone, were isolated from Mentha longifolia (L.) Hudson subsp. longifolia, together with known six flavonoid glycosides and one phenolic acid: apigenin-7-O-glucoside, luteolin-7-O-glucoside, apigenin-7-O-rutinoside, luteolin-7-O-rutinoside, apigenin-7-O-glucuronide, luteolin-7-O-glucuronide, rosmarinic acid. According to the antimutagenicity results, both new test compounds significantly inhibited the mutagenic activity of 9-aminoacridine in a dose-dependent manner at the tested concentrations from 0.8 to 2 µM/plate. (ßR)-ß,4,2',6'-Tetrahydroxy-4'-O-rutinosyldihydrochalcone showed the maximum inhibition rate as 75.94% at 2 µM/plate concentration. CONCLUSIONS: This is the first report that two new chalcone glycosides were isolated from Mentha longifolia subsp. longifolia and their antimutagenic potentials by using mutant bacterial tester strains. In conclusion, the two new chalcone glycosides showed a significant antigenotoxic effect on 9-aminoacridine-induced mutagenesis at tested concentrations.

The synthesis, characterization, antimicrobial and antimutagenic activities of hydroxyphenylimino ligands and their metal complexes of usnic acid isolated from Usnea longissima.

Novel multifunctional hydroxyphenylimino ligands (L1, L2 and L3) were synthesized by the condensation of 2-aminophenol, 3-aminophenol and 4-aminophenol with usnic acid, a lichen metabolite. The synthesized ligands and their Cu(II), Co(II), Ni(II) and Mn(II) complexes were characterized using FT-IR, UV-Vis, (1)H-NMR, (13)C-NMR, 1D- and 2D NMR (DEPT, COSY, HMQC and HMBC), LC-MS and TGA. In addition, the metal complexes of the novel ligands were prepared with high yields using Cu(II), Co(II), Ni(II) and Mn(II) salts and were characterized using the FT-MIR/FAR, UV-Vis, elemental analysis, ICP-OES and TG/DTA techniques. The ligands and their complexes were tested against ten important pathogen microorganisms using the disc diffusion method and the metal complexes of the ligands were more active against all of the microorganisms tested with a broad spectrum than the ligands exhibiting 11­32 mm inhibition zones. On the other hand, a broad spectrum of the strongest antimicrobial activity was determined for the Mn(II) and Cu(II) complexes of the hydroxyphenylimino ligand with usnic acid (L3). In addition, the antimutagenic activities of all of the ligands and their metal complexes were determined using the Ames-Salmonella and E. coli WP2 microbial assay systems and they showed varied and strong antimutagenic effects. In general, it has been found that the Co and Mn complexes of the ligands possess potent antimutagenic activity. In view of these results, it can be concluded that some metal complexes can be used as antimicrobial and anticancer agents.

Determination of genotoxic and antigenotoxic properties of essential oil from Ferula orientalis L. using Ames/Salmonella and E. coli WP2 bacterial test systems.

The essential oils having many application fields such as medicine, flavoring, cosmetics are natural products obtained from aromatic plants. As the natural products of Ferula species have a wide range of use in folk medicine, this study was planned to evaluate the mutagenic and antimutagenic activities of essential oils of leaves and flowers of Ferula orientalis grown in Erzurum, through the bacterial reverse mutation assay. Furthermore, the chemical compositions of essential oils isolated by the hyrodistillation method were analysed by gas chromatography (GC) and gas chromatography-mass spectroscopy (GC-MS), as their biological activities were connected to their contents. According to our results, any tested essential oil at any used concentration on Salmonella typhimurium TA1535 and TA1537 strains and in Escherichia coli WP2 uvrA strain showed no mutagenic activity. However, the tested materials at different concentrations showed antimutagenic activities against the used mutagens. The inhibition rates ranged against sodium azide (NaN3) on S. typhimurium TA1535 from 29% to 36%, against 9-aminoacridine (9-AA) on S. typhimurium TA1537 from 40% to 68% and against N-methyl-N'-nitro-N-nitrosoguanidine (MNNG) on E. coli WP2 uvrA from 23% to 52%, respectively. Also, it is revealed by GC and GC/MS analysis of the essential oils isolated from the leaves and flowers, respectively. The major compounds in these oils were determined as α-cadinol, δ-cadinene and germacrene D-4-ol. The results of this study indicate that as the essential oils of F. orientalis have many constituents, they show no mutagenic activity but significant antimutagenic activity, and these materials can be safely used in medicinal applications after further investigations.

Protective effects of methanol extracts from Cladonia rangiformis and Umbilicaria vellea against known mutagens sodium azide and 9-aminoacridine.

Lichens and their various extracts have been occasionally used in the treatment of many diseases. Cladonia rangiformis and Umbilicaria vellea are two important species of these lichens and they have several biological activities. In the present study, methanol extracts of these lichens, which are grown in the Eastern Anatolia Region of Turkey, were isolated, and their mutagenic and antimutagenic properties were investigated by using AMES-Salmonella and Zea mays Root Tip Mitotic Index mutagenicity and antimutagenicity assay systems. Known mutagens sodium azide (NaN(3)) and 9-Aminoacridine (9-AA) were used to determine antimutagenic properties of methanol extracts. The results showed that all methanol extracts, investigated in the present study, can be considered genotoxically safe because they do not have mutagenic activity at the tested concentrations. Besides, all of them have antimutagenic activity against 9-AA known as a model intercalator agent in the AMES-Salmonella test system. The inhibition rates obtained from the antimutagenicity assays ranged from 37.07% (C. rangiformis-5 µg/plate) to 54.39% (C. rangiformis-5 µg/plate). Furthermore, all the methanol extracts have significant antimutagenic activity against NaN(3) mutagenicity in Z. mays Root Tip Mitotic Index assay system. These activities are valuable towards an extension of the employ of these drugs as new phytotherapeutic or preservative ingredients.

Isolation of 3 flavonoids from Mentha longifolia (L.) Hudson subsp. longifolia and determination of their genotoxic potentials by using the E. coli WP2 test system.

UNLABELLED: Flavonoids, abundant in most of plant species, are widely used in medicine and development studies on phytotherapeutic drugs due to their various biological activities. In the present study, 3 flavonoids, apigenin-7-O-glucoside, apigenin-7-O-rutinoside, and apigenin-7-O-glucuronide, were isolated from Mentha longifolia (L.) Hudson subsp. longifolia by using E. coli WP2 genotoxicity assay guided fractionation procedures. Later, the mutagenic and antimutagenic properties of each flavonoid were evaluated by using the same genotoxicity assay. The results showed that all the test compounds have significant antimutagenic activity at tested concentrations with or without S9 activation. The inhibition rates were between 25.3% (apigenin-7-O-glucoside with S9-2.0 µM/plate) and 59.0% (apigenin-7-O-rutinoside without S9-2.0 µM/plate). In conclusion, the results revealed that the 3 flavonoids from Mentha longifolia (L.) Hudson subsp. longifolia have significant antimutagenic activity, and the findings of the present study are valuable for further investigations, focus on the phytotherapeutic drug discovery. PRACTICAL APPLICATION: Apigenin derivatives can be thought as genetically safe at tested concentrations because they did not show mutagenic activity. Furthermore, they have also significant antimutagenic activity. These are valuable for further research focus on phytotherapeutic drug discovery and development.

Mutagenic and antimutagenic effects of hexane extract of some Astragalus species grown in the eastern Anatolia region of Turkey.

Medical plants and their various extracts have been occasionally used in the treatment of many diseases. Astragalus is one of those medical plants and it has several biological activities. In the present study, the hexane extracts of six Astragalus species, which are grown in the eastern Anatolia region of Turkey, were isolated, and their mutagenic and antimutagenic properties were investigated by using Salmonella typhimurium TA1535, TA1537 and Escherichia coli WP2uvrA tester strains at 0.05, 0.5 and 5 microg/plate concentrations. Known mutagens sodium azide (NaN(3)), 9-Aminoacridine (9-AA) and N-Methyl-N'-nitro-N-nitrosoguanidine (MNNG) were used to determine antimutagenic properties of hexane extracts. The results showed that all hexane extracts, investigated in the present study, can be considered genotoxically safe because they do not have mutagenic activity at the tested concentrations. But, a great many of them have antimutagenic activity against 9-Aminoacridine known as a model intercalator agent. The inhibition rates obtained from the antimutagenicity assays ranged from 27.51% (A. macrocephalus--0.05 microg/plate) to 54.39% (A. galegiformis--5 microg/plate). These activities are valuable toward an extension of the employ of these drugs as new phytotherapeutic or preservative ingredients.