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Amelioration potential of synthetic oxime chemical cores against multiple sclerosis and Alzheimer's diseases: Evaluation in aspects of in silico and in vitro experiments
(Elsevier B.V., 2024) Yılmaz, Anıl; Koca, Murat; Ercan, Selami; Acar, Özden Özgün; Boğa, Mehmet; Şen, Alaattin; Kurt, Adnan
Alzheimer disease (AD) and multiple sclerosis (MS) are inflammatory neurological disorders. The main symptom of AD is dementia, and the main symptoms of MS are vertigo, sexual dysfunction, cognitive problems, and fatigue. Today, millions of people are affected by AD and MS, and the number is growing day by day. However, there are not any accurate remedies for both disorders. For this reason, discovering novel drug molecules against neurological disorders such as AD and MS is essential and precious. Oximes and benzofurans exhibit many pharmacological effects including anti-inflammatory and neurological activities. Thus, several novel compounds bearing oxime and benzofuran chemical cores were designed and synthesized, and their in vitro anticholinesterase activities were investigated in our previous study. A number of the synthesized molecules showed excellent anticholinesterase activity against both AChE and BChE enzymes. The mentioned study constituted a background for this study. In this study, we picked different chemical skeletons among all the synthesized molecules to conduct further in silico and in vitro experiments. In order to support our in vitro anticholinesterase findings, we also examined in silico anti-Alzheimer activity of the selected molecules. In addition, in silico and in vitro activities against MS disease of the synthesized molecules were investigated. Molecule 4 extraordinarily showed outstanding activity against AD disease both in silico and in vitro, as well as in silico activity against MS disease. This feature makes molecule 4 a possible drug lead molecule which is very limited in the market. On the other hand, molecule 1, a less substituted oxime skeleton, demonstrated the strongest in vitro activity against MS disease through in vitro anti-inflammatory effect. As an observation, molecule 4 was determined to be the most promising molecule to focus on in the further steps.
Anticholinesterase and antioxidant activities of novel heterocyclic Schiff base derivatives containing an aryl sulfonate moiety
(Wiley-V C H Verlag GMBH, 2022) Kamalı, Ayfer; Çakmak, Reşit; Boğa, Mehmet
In this research, nine novel heterocyclic Schiff base derivatives (10-18) bearing an aryl sulfonate moiety were designed, synthesized for the first time, and characterized. Then, their inhibitory effects on acetyl- and butyrylcholinesterase (AChE and BChE) were investigated in vitro conditions. Moreover, their antioxidant activities were examined by DPPH and ABTS methods. The results indicated that some of the tested molecules had varying enzyme inhibition and antioxidant activities. We determined that compounds 8, 9, 14, 17, and 18 indicated inhibitory effects with IC50 values ranging from 89.30 to 111.28 mu M against BChE, respectively compared to standard compound galanthamine (IC50 = 125.88 mu M). On the other hand, of the molecules tested, only compound 5 (IC50 = 36.64 mu M) displayed inhibitory activity higher than galanthamine against AChE. In DPPH assay, compounds 15 (IC50 = 161.93 mu M), 16 (IC50 = 191.76 mu M) and 17 (IC50 = 107.55 mu M) showed higher antioxidant activity than BHT (IC50 = 203.50 mu M). On the other hand, it was determined in ABTS assay that Schiff bases 10-17 (except for compound 18) indicated higher antioxidant activity than BHT.
Antioxidant and anticholinesterase potentials of novel 4,6-dimethoxyindole based unsymmetrical azines: Synthesis, molecular modeling, in silico ADME prediction and biological evaluations
(Taylor and Francis Ltd., 2023) Bingül, Murat; Ercan, Selami; Boğa, Mehmet; Bingül, Alev Arslantürk
Chemically and biologically important -C = N-N = C- diimine linkage was used to build unsymmetrical azine systems with indole heterocyclic backbone and substituted aromatic carbaldehydes. Ten novel compounds 7a-j were synthesized by the Schiff base reaction of 4,6-dimethoxyindole-7-hydrazone 5 and a range of substituted carbaldehydes 6a-j with high yields and purities. The biological study was directed to identify the antioxidant potentials due to the expected electronic delocalization capability of designated linkage which is important for possible hydrogen or electron donation. The three different assays, namely DPPH free radical scavenging, ABTS cationic radical decolarization and CUPRAC (cupric reducing antioxidant capacity) were employed to detect the antioxidant properties. The antioxidant potentials were found to be moderate for ABTS and CUPRAC assays and the compound 7j was the most potent candidate for all the antioxidant assays. More importantly, the anticholinesterase properties were investigated by acetylcholinesterase (ACh) and butyrylcholinesterase (BCh) enzyme inhibition assays. The molecular docking studies were also carried out to determine the possible poses of ligands 7a-j in binding sites of enzymes and ligand-residue interactions. The synthesized compounds were found to be more effective for the anticholinesterase activity with three promising candidates 7d, 7h and 7j in the case of BChE inhibitions. The compound 7h was determined as the best candidate with the comparable IC50 values for AChE and better inhibition potency for BChE with 7j. A range of hydrophobic and hydrophilic interactions were detected for the designated compound 7h and 7j through different amino acid residues and the computational results were found to be compatible with the biological counterparts.
Chemical and Biological Perspectives of Monoterpene Indole Alkaloids From Rauwolfia species
(Elsevier, 2018) Boğa, Mehmet; Bingül, Murat; Özkan, Esra Eroğlu; Şahin, Hasan
The biosynthesis of monoterpene indole alkaloids (MIAs) starts with a geraniol for the terpenoid portion. Secologanin, a secoiridoid glycoside, is derived from 10-hydroxygeraniol, produced in the presence of geraniol 10-hydroxylase. The indole portion of MIAs contain tryptamine, produced by the decarboxylation of tryptophan. Conjugation of secologanin with tryptamine is achieved with strictosidine synthase to produce strictosidine. Over 2500 known MIAs found in many plants from several families, such as Apocynaceae, Loganiaceae, Rubiaceae, and Nyssaceae, are produced by modification of strictosidine. A number of pharmacologically active compounds, namely, reserpine, ajmalicine, ajmaline, serpentine, and yohimbine, isolated from different Rauwolfia species, are examples of MIAs
Chemical constituents, cytotoxic, antioxidant and cholinesterases inhibitory activities of Silene Compacta (fischer) extracts
(Marmara University, 2017) Boğa, Mehmet
In Turkey, Silene species have been used as infusion in urinary bladder and biliary tract diseases in traditional medicine. Silene species have been also consumed as food in Anatolia and Europe. In this study, the phenolic, fatty acid and essential oil profiles and the cytotoxic, antioxidant and cholinesterases inhibitory activities, and total phenolic-flavonoid content of Silene compacta Fischer (SC) were studied. The essential oil and fatty acid compositions of S. compacta were determined by using GC/MS in the current study. The chemical composition of the methanol extract was determined using LC-MS/MS for quantitative and qualitative purposes. The major components of the essential oil and fatty acid were identified as α-selinene (12.4%) and palmitic acid (26.3%), respectively. The methanol extract (SCM: S. compacta methanol extract) which possessed the best activity in four tested antioxidant methods among the tested extracts exhibited very strong cholinesterases inhibitory activities. Additionaly, this extract indicated the highest cytotoxic effect against A549 cells. In the SCM extract, hesperidin and rutin, quinic and malic acids were quantified by LC-MS/MS as major contituents.
Chemical fingerprints and bioactivities of 12 Anatolian Achillea L. species by LC-MS/ MS with chemometric approach: novel phytonutrients, natural food preservatives and chlorogenic acid sources
(Turkiye Klinikleri, 2022) Yılmaz, Mustafa Abdullah; Ertaş, Abdulselam; Yener, İsmail; Türkmenoğlu, Fatma Pınar; Ölmez, Özge Tokul; Öztürk, Mehmet; Altun, Muhammed; Çakır, Oğuz; Tarhan, Abbas; Boğa, Mehmet
The objective of this study was to evaluate the biological activities and chemical fingerprint profiles of the extracts obtained from twelve Achillea L. species (A. lycaonica, A. biebersteinii (syn: A. arabica), A. kotschyi subsp. kotschyi, A. schischkinii, A. millefolium subsp. millefolium, A. sintenisii, A. setacea, A. teretifolia, A. wilhelmsii subsp. wilhelmsii (syn: A. santolinoides subsp. wilhelmsii), A. nobilis, A. goniocephala, A. spinulifolia). The antioxidant, enzyme inhibitory and cytotoxic effects were evaluated to investigate their bioactivity profiles. Furthermore, the total flavonoid and phenolic contents were determined and LC-MS/MS analysis was performed to reveal the phytochemical profile of the investigated extracts. A. kotschyi and A. nobilis species were detected to have very high antioxidant potential as well as high total phenolic content (260.00 ± 3.38 and 282.97 ± 3.14 μg of PEs mg extract–1, respectively). According to the LC-MS/ MS results, A. kotschyi and A. nobilis species were found to contain very high concentrations of chlorogenic acid (55812.20 and 46407 μg analyte g extract–1). Besides, the bioactivities and phenolic composition of these species were chemometrically analyzed using principal component analysis (PCA) and hierarchical clustering analysis (HCA) techniques. It has also been determined that Achillea species generally exhibit quite high cytotoxic activity against the HeLa cell line. The studied species showed high urease enzyme activities.
Comparative analysis of antioxidant, anticholinesterase, and antibacterial activity of microbial chondroitin sulfate and commercial chondroitin sulfate
(Wiley-V C H Verlag Gmbh, 2023) Ünver, Tuba; Erenler, Ayşe Şebnem; Bingül, Murat; Boğa, Mehmet; 0000-0002-8655-2716; 0000-0002-1786-5022; 0000-0002-3909-0694; 0000-0003-4163-9962
Chondroitin synthesis was performed using the recombinant Escherichia coli(C2987) strain created by transforming the plasmid pETM6-PACF-vgb, which carries the genes responsible for chondroitin synthesis, kfoA, kfoC, kfoF, and the Vitreoscilla hemoglobin gene (vgb). Then, Microbial chondroitin sulfate (MCS)'s antioxidant, anticholinesterase, and antibacterial activity were compared with commercial chondroitin sulfate (CCS). The antioxidant studies revealed that the MCS and CCS samples could be potential targets for scavenging radicals and cupric ion reduction. MCS demonstrated better antioxidant properties in the ABTS assay with the IC50 value of 0.66 mg than CCS. MCS showed 2.5-fold for DPPH and almost 5-fold for ABTS *+ (with a value of 3.85 mg/mL) better activity than the CCS. However, the compounds were not active for cholinesterase enzyme inhibitions. In the antibacterial assay, the Minimum inhibitory concentration (MIC) values of MCS against S. aureus, E. aerogenes, E. coli, P. aeruginosa, and K. pneumoniae (0.12, 0.18, 0.12, 0.18, and 0.18 g/mL, respectively) were found to be greater than that of CCS (0.42, 0.48, 0.36, 0.36, and 0.36 g/mL, respectively). This study demonstrates that MCS is a potent pharmacological agent due to its physicochemical properties, and its usability as a therapeutic-preventive agent will shed light on future studies.
Comparative phytochemical and bioactivity studies on two related Scorzonera L. species: A chemotaxonomic contribution
(Elsevier, 2023) Şahin, Hasan; Demir, Serhat; Boğa, Mehmet; Sarı, Aynur; Makbul, Serdar; Gültepe, Mutlu
Scorzonera L. (Asteraceae) is considered a taxonomically difficult genus with its more than 160 species. Scorzonera bella (SB) and S. veratrifolia (SV) species have been treated as synonyms since 1975. Recent botanical studies suggested the separation of the two taxa based on phenetic dissimilarities. Isolation, LC-MS/MS (including 53 phytochemicals as standard), and GC-MS (followed by library search) analyzes were conducted on the aerial parts of the plants to compare their phytochemical compositions and contribute to the classification of the two taxa. While flavonoid profile of SB was dominated by flavones, the majority of SV consisted of flavonols, among the analyzed standards. Nicotiflorin, the most abundant compound of SV, was the most notable difference which was not determined in SB. Kaempferol glycosides might be chemotaxonomic markers for the classification at subgenus levels. Caffeoylquinic acid esters were in common and similar amounts according to profiling and isolation results. Phytochemical compositions of nonpolar fractions of the plants differed significantly in phthalic acid esters, ursane, and hopane type triterpenoids which were only determined in SV. Phytochemical findings supported the separation of the two taxa. Antioxidant, anti-diabetic, anti-Alzheimer, and anti-hyperpigmentation potentials of the plants were evaluated in-vitro.
Comprehensive analysis of an uninvestigated wild edible medicinal garlic species from Turkey: Allium macrochaetum Boiss. & Hausskn.
(Blackwell Publishing Ltd., 2019) Kayıran, Serpil Demirci; Özkan, Esra Eroğlu; Kara, Emel Mataracı; Yılmaz, Mustafa Abdullah; Zengin, Gökhan; Boğa, Mehmet
The study was aimed to investigate the phenolic compounds of Allium macrochaetum by LC-MS/MS, as well as the antioxidant, antialzheimer, and antimicrobial activities of the extracts, and determination of the essential oil and fatty acid compositions by GC-MS. The results indicate that malic acid and t-caffeic acid are the major compounds in the bulbs. The main components of fatty acids were found to be linolenic (40.72%), oleic (19.79%), and palmitic (18.45%) acids. The allyl disulfide (66.97%) was found as major compound in the essential oil. The ethanol extract of the bulbs exhibited stronger ABTS cation (IC50: 55.90 ± 1.08 µg/ml) and DPPH free (IC50: 204.43 ± 2.17 µg/ml) radical scavenging activities than the other extracts. The extract also showed moderate cupric reducing activity with 1.52 absorbance at 100 µg/ml concentration. Only the ethanol extract of the bulbs showed weak inhibition (23.34 ± 0.11%) against butrylcholinesterase enzyme at 200 µg/ml. Practical applications: Allium macrochaetum is a wild and edible garlic species which grown in Turkey, Iran, Iraqi, and Syria. A. macrochaetum has been used by local people in Turkish folk medicine as an antibiotic, and for the treatment of alopecia. The health benefits and nutritional values of A. macrochaetum were clarified in the first time. Phenolic compounds of A. macrochaetum were detected by LC-MS/MS. The essential oil and fatty acid compositions of A. macrochaetum were identified by GC-MS. Antioxidant, antialzheimer, and antimicrobial activities potential of A. macrochaetum were determined.
A Comprehensive study on a medicinal and edible plant scorzonera incisa DC., discussing the natural limits of phytochemical profiling
(Wiley, 2023) Şahin, Hasan; Demir, Serhat; Boğa, Mehmet; Sarı, Aynur; Makbul, Serdar; Coşkunçelebi, Kamil
Leaves of Scorzonera incisa DC. (Asteraceae) are eaten raw against diabetes and headache. Evaluation of medicinal, edible plants using profiling methods has become a common phenomenon. Petroleum ether (PE), ethyl acetate (EA), and nbutanol (BU) fractions were prepared from ethanol extract of the aerial parts of the plant. Isolation by HPLC and phenolic profiling by validated LC-MS/MS method with 53 compounds were conducted on the EA fraction. GC-MS method was used to profile the PE fraction. In-vitro inhibitory activities of all fractions against α-amylase, α-glucosidase, AChE, BChE, tyrosinase and urease enzymes were measured. Isoorientin, vitexin, cynaroside and chlorogenic acid were isolated and characterized from the EA fraction as major compounds. LC-MS/MS analysis quantified 36 compounds in the EA fraction. 20 compounds were tentatively determined in the PE fraction. Compounds with the same molecular and fragment ions, a low percentage of identified compounds, and very close polarities were revealed to be some limits of the nature for LC-MS/MS profiling. Particularly, the presence and amount of substances other than the standard compounds used in the profiling methods and possible misdetections should not be neglected in evaluating medicinal plants and establishing a correlation between compounds and bioactivity.
A comprehensive study on chemical and biological profiles of Algerian Azadirachta indica (A. Juss)
(Elsevier Ltd, 2024) Boukeloua, Ahmed; Leila, Soudani; Bendif, Hamdi; Elkadeem, Ahmed Mustafa; Boğa, Mehmet; Serralheiro, Maria Luísa; Yılmaz, Mustafa Abdullah; Yener, İsmail
The study aimed to analyse the chemical and biological composition of Azadirachta indica (A. Juss) (A. indica) leaves. Minerals were quantified using inductively coupled plasma-mass spectrometry (ICP-MS). Phenolic compounds and water-soluble vitamins were identified via LC-MS/MS. Antioxidant activity was assessed using ABTS cation radicals and cupric reducing antioxidant capacity (CUPRAC), while anticholinesterase effect was tested against butyrylcholinesterase (BChE) and Acetylcholinesterase (AChE). Results revealed significant levels of major elements (e.g., Zn, Cu) making it a promising source. Predominant phenolic acids included tannic and salicylic acid, with major flavonoids being hyperoside, kaempferol, and quercetin. Main water-soluble vitamins were nicotinic acid, nicotinamide, and pantothenic acid, followed by pyridoxine, thiamine, and riboflavin. Ethanol extract exhibited moderate antioxidant activity (30.02 % inhibition of ABTS radicals; IC50 0.918 ?g/mL for CUPRAC and low inhibition of BChE and AChE (2.29 % and 3.17 % respectively). These findings highlight A. indica as a valuable natural source of nutritionally significant compounds and antioxidants. © 2024 Phytochemical Society of Europe
Cytotoxic and apoptotic effects of Hypericum androsaemum on prostate adenocarcinoma (PC-3) and hepatocellular carcinoma (Hep G2) cell lines with identification of secondary metabolites by LC-HRMS
(Scientific Technical Research Council Turkey-TUBITAK, 2021) Bektaş, Nurdan Yazıcı; Ersoy, Ezgi; Boğa, Mehmet; Boran, Tuğçe; Çınar, Ercan; Özhan, Gül; Gören, Ahmet Ceyhan; Özkan, Esra Eroğlu
The study aims to determine the secondary metabolites of Hypericum androsaemum L. extracts by liquid chromatography-high resolution mass spectrometry (LC-HRMS), and investigate the antioxidant and cytotoxic activities of the plant. Cytotoxic activity was evaluated by MTT assay, and apoptosis induction abilities on human prostate adenocarcinoma (PC-3), and hepatocellular carcinoma (Hep G2) cell lines. Accordingly, major secondary metabolites were found as hederagenin (762 +/- 70.10 mu g/g) in the leaves dichloromethane (LD), herniarin (167 +/- 1.50 mu g/g) in fruit dichloromethane (FD), (-)-epicatechin (6538 +/- 235.36 mu g/g) in the leaves methanol (LM), (-)-epigallocatechin gallate (758 +/- 20.46 mu g/g) in the fruit methanol (FM), and caffeic acid (370 +/- 8.88 mu g/g) in the fruit water (FW), and (3313 +/- 79.51 mu g/g) in the leaves water (LW) extracts. LM exerted strong antioxidant activity in DPPH free (IC50 10.94 +/- 0.08 mu g/mL), and ABTS cation radicals scavenging (IC50 9.09 +/- 0.05 mu g/mL) activities. FM exhibited cytotoxic activity with IC50 values of 73.23 +/- 3.06 mu g/mL and 31.64 +/- 2.75 mu g/mL on PC-3 and Hep G2 cell lines, respectively. Being the richest extract in terms of quillaic acid (630 +/- 18.9 mu g/g), which is a well-known cytotoxic triterpenoid with proven apoptosis induction ability on different cells, FM extract showed apoptosis induction activity with 64.75% on PC-3 cells at 50 mu g/mL concentration. The study provides promising results about the potential of Hypericum androsaemum on cancer prevention.
Design, synthesis and biological evaluation of 1,3-diaryltriazene-substituted sulfonamides as antioxidant, acetylcholinesterase and butyrylcholinesterase inhibitors
(Turkish Chemical Society, 2019) Akocak, Süleyman; Boğa, Mehmet; Lolak, Nabih; Tuneğ, Muhammed; Sanku, Rajesh Kishore Kumar
1,3-diaryltriazenes are one of the most useful and important linkers for many pharmaceutical applications. Therefore, in the current work, a series of 1,3-diaryltriazene sulfonamides 4(a-k) were synthesized by reacting diazonium salt of sulfanilamide and substituted aromatic amine derivatives 3(a-k). The obtained compounds were investigated for antioxidant properties by using different methods such as a DPPH radical scavenging assay, ABTS radical decolarization, cupric reducing antioxidant capacity (CUPRAC) and metal chelating methods. The cholinesterase inhibition activities (acetylcholinesterase and butyrylcholinesterase) of synthesized compounds were also tested. In general, compounds showed weak antioxidant activity, except compounds 4d (IC50 =114.89 for DPPH activity), 4i (IC50 =25.31 for ABTS activity), 4a (IC50 = 86.33 for metal chelating activity), and 4k (absorbance value 1.229 µM for CUPRAC). Some of the compounds showed great % inhibition against both acetylcholinesterase and butyrylcholinesterase with % inhibition values ranging from 11.54 to 93.67 and 62.24 to 98.47, respectively.
Determination of anticholinesterase and antioxidant activities of methanol and water extracts of leaves and fruits of Chamaerops humilis L.
(Applied and Natural Science Foundation, 2019) Bouhafsoun, Aicha; Boğa, Mehmet; Boukeloua, Ahmed; Temel, Hamdi; Kaid-Harche, Meriem
The present study was carried out to investigate the antioxidant activity of the water and methanol extracts of leaves and fruits extracts of Chamaerops humilis L. by using ABTS cation radicals and cupric reducing antioxidant capacity (CUPRAC). Anticholinesterase effect of the extracts was tested against both AChE and BChE using a microplate-reader assay based on the Ellman method. The methanol extracts of C. humilis leaves contained relatively higher content of flavonoids and total phenolics than those of fruits. All the extracts were found to have different levels of antioxidant activity in the systems tested. The leave extract showed the highest value of antioxidant activity, based on ABTS radical-scavenging activity, while the fruit water extract showed the highest value (0.53±0.50 µg/ mL) of cupric reducing antioxidant activity. Our data indicates that both methanol and water fruit extract were active for BChE inhibition (31.65 ± 0.37 and 30.19 ± 0.56%) respectively, whereas, all leave extracts did not show any activity against BChE. The present study demonstrated that the methanol and water extracts fractions of C. humilis have different responses with different antioxidant methods. Our results suggest that the C. humilis could be used as a source of antioxidant agents and may be beneficial in the AD treatment.
Determination of cytotoxic, anticholinesterase, antioxidant and antimicrobial activities of some wild mushroom species
(Informa Healthcare, 2016) Dündar, Abdurrahman; Okumuş, Veysi; Özdemir, Sadin; Çelik, Kadir Serdar; Boğa, Mehmet; Özçağlı, Eren; 0000-0002-5505-2700
In the performed study of methanol extraction of wild edible mushroom species; Agaricus arvensis, Agaricus campestris, Armillaria mellea, Fomes fomentarius, Coprinus micaceus, Coriolus versicolor and Lactarius deliciosus were examined for screening their cytotoxic, anticholinesterase, antioxidant and antimicrobial capacity. Phenolic acid composition of mushrooms was also analysed. L. deliciosus and F. fomentarius were generally showed the highest activities at antioxidant test systems (metal chelating, superoxide anion radical scavenging, total antioxidant, 2,2-diphenyl-1-picrylhydrazyl radical scavenging and reducing power activity tests). The highest activities at antimicrobial activity displayed by A. arvensis and as 18 ± 0.8 against to Staphylococcus aureus. The best IC50 values of mushroom methanol extracts at anticancer activities on HeLa and NRK-52E were 7.09 and 18.23 mg/mL exhibited by C. micaceus and A. campestris, respectively. The highest butyrylcholinesterase activity exhibited by L. deliciosus. Total amount of phenolic acids were found as 1,224.70 mg/kg at L. deliciosus.
Determination of phytochemical contents and antioxidant capacities of Turkish and Ceylon black teas
(Harran Üniversitesi, 2024) Efe, Ahmet; Yılmaz, Hayrullah; Boğa, Mehmet
In this study, 5 Ceylon and 5 Turkish commercial black teas (Camellia sinensis) were obtained from supermarkets in Diyarbakır province. Black teas were analyzed both dry and by brewing for different times (5, 10, 15, 30, 45, 60 min). Dry black teas were extracted in ethanol for antioxidant activities (DPPH and ABTS), while total phenolic and flavonoid content, phenolic acids (quinic acid, gallic acid, salicic acid, chlorogenic acid, 4-OH-benzoic acid), catechins (catechin, epicatechin gallate, epigallocatechin and epigallocatechin gallate), hesperidin, alkaloids (theophylline, caffeine and theobromine) were extracted in methanol. In addition, the above-mentioned analyses and theaflavin (TF) and thearubigin (TR) analyses were performed on black teas brewed for 5, 10, 15, 30, 45, and 60 minutes. Antioxidant activities, total phenolic and flavonoid content, theaflavin (TF) and thearubigin (TR) contents were determined by spectrophotometric method, while phenolic acids, catechins, hesperidin and alkaloids were analyzed by LC/MS-MS device. As a result of the analysis, the antioxidant activities, total phenolic and flavonoid substance amounts, phenolic acids, catechins, hesperidin and alkaloid amounts of Ceylon black tea extracts were determined to be higher compared to Turkish black tea samples. When the results of the analyses performed on the infusions of both Ceylon and Turkish black teas brewed for different durations are examined, it is observed that antioxidant activities (ABTS and DPPH), total flavonoid and phenolic substance amounts increase in direct proportion to the duration. The highest TF and TR levels were determined in the infusions at the end of 60 minutes of brewing. The highest values of phenolic acids, catechins, hesperidin and alkaloids (theophylline, caffeine and theobromine) that pass into the tea vary according to the tea type and brewing times. While the amounts of local Turkish teas were determined to be higher in some brewing times, the amounts of imported Ceylon teas were determined to be higher in some brewing times.
Di-, and triterpenoids isolation and LC-MS analysis of salvia marashica extracts with bioactivity studies
(ACG Publications, 2021) Aydın, Sibel Kıran; Ertaş, Abdulselam; Boğa, Mehmet; Erol, Ebru; Toraman, Gülbahar O. Alim; Saygı, Tuba Kusman; Halfon, Belkıs; Topçu, Gülaçtı
Abstract: In this study, dichloromethane, acetone, and methanol extracts of the aerial parts of the Salvia marashica plant which is an endemic species to Anatolia, were investigated. The total phenolic amounts of these extracts were determined as pyrocatechol equivalent and total flavonoids as quercetin equivalent. Antioxidant activity was determined by four complementary methods including inhibition of lipid peroxidation (by βcarotene color expression), DPPH free radical scavenging activity, ABTS cation radical scavenging activity and CUPRAC methods. Anticholinesterase activity of the extracts was investigated by the Ellman method against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. Viability and cytotoxic activity tests were carried out on the fibroblast L929 cells and cytotoxic A549 lung cancer cells, respectively. The triterpenoids and diterpenoids constitute the major secondary metabolites of the S. marashica acetone and methanol extracts isolated by chromatographic methods. Their structures were determined based on spectroscopic methods, namely NMR and mass analyses. Ten terpenoids were obtained from either acetone or methanol extracts of the S. marashica. Seven of them were triterpenoids, elucidated as lupeol, lupeol-3-acetate, lup-12, 20(29)-diene, lup-20(29)-ene, α-amyrin-tetracosanoate, oleanolic acid and ursolic acid besides a steroid β-sitosterol. Two abietane diterpenes, abieta-8,11,13-triene (1) and 18-acetoxymethylene-abieta-8,11,13-triene (2), were obtained from the acetone extract which were isolated from a Salvia species for the first time in the present study. The methanol extract was found to be very rich in rosmarinic acid determined by LC-MS/MS analysis.
Evaluation of acetyl-and butyrylcholinesterase enzyme inhibitory activities and cytotoxic activities of anthraquinone derivatives
(Turkish Chemical Society, 2022) Özkök, Funda; Boğa, Mehmet; Tuneğ, Muhammed; Atalay, Vildan Enisoğlu; Onul, Nihal Yılmaz; Asgarova, Kamala
In this study, the enzyme activity of anthraquinone compounds which were synthesized beforehand by our research group was investigated. Molecular docking studies were performed for compounds 1-(4-aminophenylthio)anthracene-9,10-dione (3) and 1-(4-chlorophenylthio)anthracene9,10-dione (5). Compound 3 was synthesized from the reaction of 1-chloroanthraquinone (1) and 4aminothiophenol (2). Compound 5 was synthesized (1) from the reaction of 1-chloroanthraquinone (1) and 4-chlorothiophenol (4). Anthraquinone analogs (3, 5) were synthesized with a new reaction method made by our research group (2). Inhibitory effects of compounds 3 and 5 were investigated against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) enzymes which are related to Alzheimer’s Disease (AD). Compounds 3 and 5 exhibited strong anti-acetyl-and butyryl-cholinesterase inhibition activities than galanthamine used as standard compound (92.11±1.08 and 80.95±1.77 %, respectively). The EHOMO-ELUMO values, molecular descriptors, and the calculated UV-Vis spectra of anthraquinone derivatives were computed by B3LYP/6-31+G(d,p) levels in the CHCl3 phase. Based on the fluorescence property of the anthraquinone skeleton, the fluorescence activity of the bioactive anthraquinone analogue (5) was investigated. MTT test was performed to determine the cytotoxic effects of thioanthraquinone molecules 3 and 5. In MTT analyses, 3 compounds showed the highest effect against Ishikawa cells at a dose of 10 µg/mL, while compound 5 showed the highest effect at a dose of 50 µg/mL. The cell viability for compound 3 was 84.18% for 10 µg/mL and the cell viability for compound 5 was 75.02% for 50 µg/mL.
Evaluation of the medicinal potential of a traditionally important plant from Turkey: Cerinthe minor L.
(Istanbul University Press, 2022) Ersoy, Ezgi; Karahan, Selim; Boğa, Mehmet; Çınar, Ercan; İzgi, Sevcan; Kara, Emel Mataracı
Background and Aims: Cerinthe minor L. has been used for both culinary and medicinal purposes in Turkey. Since the plant has remained uninvestigated pharmacognostically, this study aims to provide data on the phytochemical profile and in vitro biological activities of the ethanol extract prepared from the aerial and root parts of Cerinthe minor L. Methods: The phytochemical profile of the extract was determined by LC-MS/MS. Total phenolic and total flavonoid contents of Cerinthe minor ethanol extract were determined as pyrocatechol, and quercetin equivalents, respectively. Antioxidant activity of the extract was investigated by DPPH, and ABTS cation radical scavenging activity, and CUPRAC activity assays. Enzyme inhibitory activity assays were used to investigate anticholinesterase, antityrosinase, and antiurease activities. Cytotoxic potential of the plant was clarified by using the XTT method, and antimicrobial activity of the extract was established by the microbroth dilution technique. Results: According to the LC-MS/MS results, 11 different constituents were present in the extract, and the major com-pounds were, malic acid (5392.18 +/- 60.93 mu g/g extract), fumaric acid (4730.99 +/- 58.66 mu g/g extract), and rosmarinic acid (2470.07 +/- 176.12 mu g/g extract). Total phenolic and flavonoid contents were found as 10.39 +/- 0.73 mu g PEs/mg extract, and 0.75 +/- 0.07 mu g QEs/mg extract, respectively. The extract demonstrated moderate antioxidant activity, whereas no enzyme inhibitory activity was exerted against the tested enzymes. No cytotoxic activity was observed on human renal (A498, UO-31) or human colon (COLO205, KM12) cancer cell lines. The extract was shown to possess low-moderate antimicrobial activity against C. tropicalis with a MIC value of 78.12 mu g/mL. Conclusion: Having several pharmacologically valuable compounds, and not causing any toxicity on studied cell lines, Cerin-the minor is a plant that requires attention with its medicinal potential
Heterocyclic Schiff base derivatives containing pyrazolone moiety: Synthesis, characterization, and in vitro biological studies
(Wiley, 2021) Çınar, Ercan; Başaran, Eyüp; Erdoğan, Ömer; Çakmak, Reşit; Boğa, Mehmet; Çevik, Özge
In this study, some pyrazolone-based Schiff base derivatives 2a-e (except 2a)were synthesized for the first time and structurally illuminated by some spec-troscopic techniques (1H,13C NMR, FT-IR) and elemental analysis. Allsynthesized molecules were screened for their anticancer and antioxidantactivities, as well as AChE, BChE, and tyrosinase inhibitory properties.The obtained results exhibited that compounds 1b (IC50= 9.497 Μ) and 2a(IC50= 30.49 Μ) significantly decreased the proliferation of HeLa cells. Onthe other hand, the apoptotic effects of these two compounds were investigatedwith acridine orange/propidium iodide double staining. The apoptotic cellratios of the molecules treated with these two compounds were determined as60 and 64%. Compound 2b (IC50= 17.95 ± 0.47 Μ ) was determined to be avery active substance in the ABTS assay. Compound 2e (A0.5= 43.75± 0.62 M) indicated the closest antioxidant activity to the standard compoundα-TOC (A0.5= 50.58 ± 0.39 M) in the cupric reducing antioxidant capacity(CUPRAC) assay. In inhibition studies of enzymes, it was determined thatcompound 2c had a very active molecule in AChE, BChE, and tyrosinaseinhibitory activities with 82.79 ± 1.03, 91.39 ± 1.06, and 92.60 ± 1.80% inhibi-tion, respectively. It was determined that the target molecules 2a-e showedbetter antioxidant and enzyme inhibitory activities than those of ester deriva-tives 1a-e.

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