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Öğe Chemical and Biological Perspectives of Monoterpene Indole Alkaloids From Rauwolfia species(Elsevier, 2018) Boğa, Mehmet; Bingül, Murat; Özkan, Esra Eroğlu; Şahin, HasanThe 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 MIAsÖğe 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, MehmetThe 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.Öğe 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 EroğluThe 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.Öğe Micromeria myrtifolia Boiss. & Hohen. Bitkisinin Farmakolojik Potansiyelinin Araştırılması: Fenolik İçeriğinin ve Biyolojik Aktivitelerinin Belirlenmesi(ABADER (Adıyaman Bilimsel Araştırmalar Derneği), 2024) Ersoy, Ezgi; Yıldızhan, Rümeysa Batal; Yılmaz, Mustafa Abdullah; Yeşil, Yeter; Şahin, Hasan; Özkan, Esra Eroğlu; Boğa, MehmetMicromeria myrtifolia Boiss. & Hohen., Türkiye'nin önemli tıbbi bitkilerindendir ve ülke genelinde farklı tıbbi amaçlarla oldukça yaygın olarak kullanılmaktadır. Bu çalışmada, M. myrtifolia örnekleri Muğla, Türkiye'den toplanmış hem topraküstü kısımlarından hem de köklerden ayrı ayrı etanol ekstreleri hazırlanmıştır. Ekstrelerin fitokimyasal içeriklerini belirlemek için detaylı bir LC-MS/MS analizi yapılmıştır. Analiz sonuçlarına göre her iki ekstrenin de fenolik bileşikler açısından oldukça zengin olduğu belirlenmiştir. Her iki ekstrede de ana bileşen olarak nikotiflorin öne çıkmış ve topraküstü kısımlarından hazırlanan ekstrede 12878.31±355.44 µg/g, kök ekstresinde ise 47512.4±1311.34 µg/g nikotiflorin tespit edilmiştir. Ayrıca ekstrelerde rozmarinik asit ve kafeik asit gibi önemli fenolik asitler ile hesperidin gibi flavonoitlerin varlığı da belirlenmiştir. Ekstrelerin antioksidan aktiviteleri DPPH serbest radikal giderici, ABTS katyon radikali giderici ve CUPRAC aktivitesi metotları ile değerlendirilmiş, buna göre her iki ekstre de sentetik antioksidan bileşiklere kıyasla anlamlı antioksidan aktiviteler sergilemiştir. Bunun yanı sıra ekstreler enzim inhibisyon aktiviteleri açısından değerlendirildiğinde, ekstrelerin 2 mg/mL konsantrasyonda %73.03±0.16 (topraküstü) ve %47.06±0.41 (kök) oranında anti-glukozidaz aktivite gösterdiği tespit edilmiştir. Kök ekstresi ayrıca orta düzeyde butirilkolinesteraz inhibe edici aktivite de göstermiştir. Bu çalışma, M. myrtifolia bitkisinin kimyasal içeriği ve biyolojik aktiviteleri konusunda mevcut literatüre önemli katkılarda bulunmakla birlikte, bitkinin geleneksel ve modern tıp uygulamalarındaki yeni ve potansiyel kullanım alanlarını keşfetmeye yönelik gelecek araştırmalara da zemin hazırlamaktadır.Öğe Phytochemical analysis of essential oils and the extracts of an ethnomedicinal plant, Teucrium multicaule collected from two different locations with focus on their important biological activities(Elsevier, 2023) Ersoy, Ezgi; Tanaman, Irmak; Özkan, Esra Eroğlu; Karahan, Selim; Şahin, Hasan; Çınar, Ercan; Cantürk, Yeter Yeşil; Kara, Emel Mataracı; Zengin, Gökhan; Boğa, MehmetTeucrium species have been among the most commonly used traditional medicinal plants and they are known to have extensive therapeutic applications. The main focus of this study, Teucrium multicaule is also renowned for being an important medicinal and aromatic plant in Turkiye. Volatile profiling of the essential oils was conducted by GC MS, phytochemical profiling of the ethanol extracts was carried out by LC HRMS, antioxidant, anticholinesterase, antityrosinase, antiurease, antidiabetic, anticancer, and antimicrobial activities were revealed by different assays. Germacrene D was the most abundant compound in the essential oils from Diyarbakir (TmuD) with 45.4%, and Batman (TmuB) with 54.7%. All extracts were found to be quite rich in phytochemicals by LC HRMS, and herniarin, caffeic acid, naringenin, luteolin, scutellarein, hispidulin, rhamnocitrin, penduletin, eupatilin, (-)-epigallocatechin gallate, hederagenin, and verbascoside were found to be present in all extracts. T. multicaule roots extract from Diyarbakir (TmuRD) demonstrated the highest radical scavenging, a-amylase inhibitory (59.82§0.36%), and antibutyrylcholinesterase activity (61.96§ 1.72%), whereas T. multicaule aerial parts extract from Batman (TmuHB) exhibited the strongest antityrosinase (66.17§0.92%), antiurease (67.85§0.69%), and cytotoxic (54.76 § 1.57 mg/mL) activities. TmuRD also showed significant antimicrobial activity against S. epidermidis with 156.2 mg/mL MIC value. As revealed by this first detailed report on T. multicaule, the plant demonstrates various important biological activities attributed to its rich phytochemicals, which also justifies its use in ethnomedicine.Öğe The Therapeutic potential of ethnomedicinally important Anatolian thyme species: A Phytochemical and biological assessment(Frontiers, 09.06.2022) Özkan, Esra Eroğlu; Ersoy, Ezgi; Cantürk, Yeter Yeşil; Kara, Emel Mataracı; Çınar, Ercan; Şahin, Hasan; Karahan, Selim; Sancaktepe, Kübra Karaca; Yılmaz, Mustafa Abdullah; Boğa, MehmetThyme has been used for various therapeutic purposes in many different cultures, which makes it one of the most riveting medicinal plants throughout history. From its beneficial effects on the respiratory tract or the gastrointestinal system, to its unique skin-related activities, the investigation of the medicinal properties of thyme has always been an alluring topic for researchers aiming to develop conventional medications from this traditional herb. With an incentive to contribute to the extensive thyme research, three Thymus L. species namely Thymus cariensis Hub-Mor. & Jalas (endemic), Thymus praceox subsp. grossheimii (Ronniger) Jalas, and Thymus pubescens Boiss. et Kotschy ex Celak from Turkey were deeply investigated within this study. The analysis of the phytochemical constituents of the extracts was conducted by LC-MS/MS. 12 biologically important secondary metabolites (p-coumaric acid, caffeic acid, salicylic acid, quinic acid, fumaric acid, vanillin, malic acid, rutin, apigenin, naringenin, and nicotiflorin) were detected in all extracts. Their total phenolic and flavonoid contents were calculated (11.15 ± 0.17—61.12 ± 2.59 μg PEs/mg extract, 2.53 ± 0.04—40.28 ± 0.92 μg QEs/mg extract, respectively), and the antioxidant potential of the extracts was evaluated by DPPH and ABTS radical scavenging and CUPRAC activity methods, accordingly, the extracts were shown to possess significant antioxidant activity. Among them, Thymus cariensis Hub-Mor. & Jalas was the most active with IC50 values of 34.97 ± 1.00 μg/ml and 9.98 ± 0.04 μg/ml regarding the DPPH and ABTS radical scavenging assays, respectively, and an A0.5 value of 5.80 ± 0.02 μg/ml according to CUPRAC activity method. Their anticholinesterase, antityrosinase, and antiurease activities were also tested, Thymus cariensis Hub-Mor. & Jalas (35.61 ± 1.20%) and Thymus pubescens Boiss. et Kotschy ex Celak aerial part extract (33.49 ± 1.39%) exhibited moderate antibutyrylcholinesterase activity at 200 μg/ml concentration. The results of the cell viability assay indicated that the extracts demonstrated moderate-to-low cytotoxicity on A498 human renal cell lines. Furthermore, all studied extracts exerted noteworthy antimicrobial activity, especially against Candida tropicalis (MIC values: 19.53—78.12 μg/ml). The presented data substantiates the use of thyme extracts as therapeutic agents in both ethnomedicine and conventional therapies.Öğe Towards a better understanding of commonly used medicinal plants from Turkiye: Detailed phytochemical screening and biological activity studies of two Teucrium L. species with in vitro and in silico approach(Elsevier Ireland Ltd., 2023) Ersoy, Ezgi; Süvari, Goncagül; Ercan, Selami; Özkan, Esra Eroğlu; Karahan, Selim; Tuncay, Evin Aygün; Boğa, MehmetEthnopharmacological relevance: Since ancient times, Teucrium L. species have been among the most commonly used traditional medicinal plants mainly in the Mediterranean region. From tackling gastrointestinal problems to maintaining the healthy functioning of endocrine glands, and from treating malaria to severe dermatological disorders, Teucrium species are known to have extensive therapeutic applications. Teucrium polium L. and Teucrium parviflorum Schreb. are the two members of the genus that have been used in Turkish folk medicine for various medicinal purposes. Aim of the study: To determine the phytochemical compositions of the essential oils and ethanol extracts of Teucrium polium and Teucrium parviflorum collected from different locations in Turkiye along with the investigation of in vitro antioxidant, anticancer, antimicrobial activities, and both in vitro and in silico enzyme inhibitory activities of the extracts. Materials and methods: Ethanol extracts of Teucrium polium aerial parts and roots, and aerial parts of Teucrium parviflorum were prepared. Volatile profiling of the essential oils by GC-MS, phytochemical profiling of the ethanol extracts by LC-HRMS, antioxidant activity by DPPH radical scavenging, ABTS cation radical scavenging, CUPRAC, and metal chelating activity assays, anticholinesterase, antityrosinase, antiurease, activities by different enzyme inhibitory activity assays, anticancer activity by SRB cell viability assay, and antimicrobial activity against a standard panel of bacteria and fungi by the microbroth dilution technique. Molecular docking studies were performed by Autodock Vina (Ver. 1.1.2). Results: The studied extracts were found to be quite rich in various biologically important volatile and phenolic compounds. (−)-Epigallocatechin gallate, which is a molecule renowned for having great therapeutic potential, was the major compound of all extracts. Teucrium polium aerial parts extract was revealed as a great source for naringenin with 16327 ± 685.23 μg/g extract. All extracts exerted significant antioxidant activity by different methods. All extracts demonstrated antibutrylcholinesterase, antityrosinase, and antiurease activities by in vitro and in silico assays. Teucrium polium roots extract stood out with remarkable tyrosinase and urease inhibitory and cytotoxic activities. Conclusion: The obtained results from this multi-disciplinary study proves that the traditional use of these two Teucrium species is justified, and the mechanisms behind are enlightened.Öğe Volatile and phenolic profiling of a traditional medicinal plant, Hypericum empetrifolium with in vitro biological activities(Elsevier Ireland LTD, 2021) Boğa, Mehmet; Ersoy, Ezgi; Özkan, Esra Eroğlu; Çınar, Ercan; Kara, Emel Mataracı; Cantürk, Yeter Yeşil; Zengin, GökhanEthnopharmacological relevance: Hypericum empetrifolium Willd is a member of the Hypericaceae family, mainly known in southern Greece, and western Turkey. Being a centuries-old medicinal plant, the aerial parts of the plant have been used for the treatment of herpes, kidney stones, gastric ulcer, and also for their anti-helminthic, and diuretic purposes traditionally. Aim of the study: The current study aimed to investigate the phytochemical profiles of the essential oil, and two ethanol extracts prepared from the aerial parts (H. empetrifolium aerial parts extract HEA), and roots of the plant (H. empetrifolium roots extract HER), and to provide data on antioxidant, anticholinesterase, antityrosinase, antiurease, cytotoxic, and antimicrobial activities of the extracts. Materials and methods: In this study, volatile and phenolic compounds of the HEA and HER were analyzed by GC MS and LC-MS/MS, respectively. Antioxidant potential of the extracts was clarified by using DPPH radical scavenging assay, ABTS cation radical assay, and the CUPRAC assay. Acetylcholinesterase, butyrylcholinesterase, urease, and tyrosinase inhibitory activity assays were used to determine enzyme inhibition capacity of the extracts. Cytotoxic activity of the extracts was established by using XTT assay. The antimicrobial activity of the extracts was determined by the microbroth dilution technique. Results: The major compounds of the essential oil were revealed as alloaromodendrene (24.7%), alpha-pinene (14.7%), beta-pinene (10.7%), and alpha-terpineol (7.7%) by the GC-MS analysis. According to the LC-MS/MS analysis results, quinic acid was the most abundant constituent in both extracts with 20612.42 +/- 169.02 mu g/g extract in HEA extract, and with 2254.34 +/- 18.49 mu g/g extract in HER extract, respectively. The HEA extract was also found to be rich in terms of chlorogenic acid (5583.14 +/- 38.52 mu g/g extract), isoquercitrin (3076.77 +/- 40.92 mu g/g extract), and malic acid (2822.90 +/- 31.90 mu g/g extract). HEA extract exhibited a significant antioxidant effect with an IC50 value of 11.98 +/- 0.22 mu g/mL according to the DPPH radical scavenging assay. Similar results were obtained with the ABTS cation radical assay, and the CUPRAC assay. HER extract showed a strong butyrylcholinesterase inhibitory effect with 88.69 +/- 0.62% at 200 mu g/mL concentration. Both extracts were considered to have moderate anti-tyrosinase activity compared to the standard at 200 mu g/mL. The best antimicrobial activity was obtained for HEA against C. parapsilosis with an MIC value of 4.88 mu g/mL. HEA also exhibited antifungal activity against C. tropicalis with 19.53 mu g/mL. Only HER exhibited low cytotoxicity on A498 renal cell lines with 60.6% cell viability. Conclusion: Unquestionably, H. empetrifolium Willd has ethnopharmacological importance according to these results, and further investigations are required to evaluate other therapeutic properties of the plant.
