Gulcin, İlhami; Mutlu, Muzaffer; Bingol, Zeynebe; Ozden, Eda Mehtap; Mirzaee, Ziba; Goren, Ahmet C.; Köksal, Ekrem

This investigation explored the chemical constituents and biological activities of the steam-distilled oil of L. usitatissimum (SDOLU), employing sophisticated techniques including LC-HRMS, GC-MS, and GC-FID. The analysis identified a diverse array of 17 phenolic compounds, with linoleoyl chloride (64.05%) and linoleic acid (10.39%) as the major fatty acid components. The SDOLU demonstrated remarkable antioxidant capacity, effectively neutralizing free radicals in both DPPH• (IC50: 19.80 μg/mL) and ABTS•+ (IC50: 57.75 μg/mL) scavenging assays, alongside robust electron-donating activity in reducing ability tests. Moreover, the SDOLU showed significant inhibition of key enzymes implicated in metabolic and neurodegenerative disorders, including α-amylase (IC50: 531.44 μg/mL), acetylcholinesterase (IC50: 13.23 μg/mL), and carbonic anhydrase II (IC50: 281.02 μg/mL). Collectively, these results highlight the SDOLU as a valuable natural source of multifunctional bioactivities with potential applications in combating oxidative stress and enzyme-related global diseases. Further studies are warranted to validate its therapeutic efficacy and expand its industrial utilization.

Durmaz, Lokman; Kiziltas, Hatice; Guven, Leyla; Karagecili, Hasan; Alwasel, Saleh; Gulcin, İlhami

Magnofluorine, a secondary metabolite commonly found in various plants, has pharmacological potential; however, its antioxidant and enzyme inhibition effects have not been investigated. We investigated the antioxidant potential of Magnofluorine using bioanalytical assays with 2,2-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS•+), N,N-dimethyl-p-phenylenediamine dihydrochloride (DMPD•+), and 1,1-diphenyl-2-picrylhydrazyl (DPPH•) scavenging abilities and K3[Fe(CN)6] and Cu2+ reduction abilities. Further, we compared the effects of Magnofluorine and butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), α-Tocopherol, and Trolox as positive antioxidant controls. According to the analysis results, Magnofluorine removed 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals with an IC50 value of 10.58 μg/mL. The IC50 values of BHA, BHT, Trolox, and α-Tocopherol were 10.10 μg/mL, 25.95 μg/mL, 7.059 μg/mL, and 11.31 μg/mL, respectively. Our results indicated that the DPPH· scavenging effect of Magnofluorine was similar to that of BHA, close to that of Trolox, and better than that of BHT and α-tocopherol. The inhibition effect of Magnofluorine was examined against enzymes, such as acetylcholinesterase (AChE), α-glycosidase, butyrylcholinesterase (BChE), and human carbonic anhydrase II (hCA II), which are linked to global disorders, such as diabetes, Alzheimer’s disease (AD), and glaucoma. Magnofluorine inhibited these metabolic enzymes with Ki values of 10.251.94, 5.991.79, 25.411.10, and 30.563.36 nM, respectively. Thus, Magnofluorine, which has been proven to be an antioxidant, antidiabetic, and anticholinergic in our study, can treat glaucoma. In addition, molecular docking was performed to understand the interactions between Magnofluorine and target enzymes BChE (D: 6T9P), hCA II (A:3HS4), AChE (B:4EY7), and α-glycosidase (C:5NN8). The results suggest that Magnofluorine may be an important compound in the transition from natural sources to industrial applications, especially new drugs.

Durmaz, Lokman; Erturk, Adem; Akyüz, Mehmet; Kose, Leyla Polat; Uc, Eda Mehtap; Bingol, Zeynebe; Saglamtas, Ruya; Alwasel, Saleh; Gulcin, İlhami

Coumestrol (3,9-dihydroxy-6-benzofuran [3,2-c] chromenone) as a phytoestrogen and polyphenolic compound is a member of the Coumestans family and is quite common in plants. In this study, antiglaucoma, antidiabetic, anticholinergic, and antioxidant effects of Coumestrol were evaluated and compared with standards. To determine the antioxidant activity of coumestrol, several methods—namely N,N-dimethyl-p-phenylenediamine dihydrochloride radical (DMPD•+)-scavenging activity, 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulphonate) radical (ABTS•+)-scavenging activity, 1,1-diphenyl-2-picrylhydrazyl radical (DPPH•)-scavenging activity, potassium ferric cyanide reduction ability, and cupric ion (Cu2+)-reducing activity—were performed. Butylated hydroxyanisole (BHA), Trolox, α-Tocopherol, and butylated hydroxytoluene (BHT) were used as the reference antioxidants for comparison. Coumestrol scavenged the DPPH radical with an IC50 value of 25.95 µg/mL (r2: 0.9005) while BHA, BHT, Trolox, and α-Tocopherol demonstrated IC50 values of 10.10, 25.95, 7.059, and 11.31 µg/mL, respectively. Evaluating these results, Coumestrol had a similar DPPH•-scavenging effect to BHA and Trolox, better than BHT and α-Tocopherol. In addition, the inhibition effects of Coumestrol were tested against the metabolic enzymes acetylcholinesterase (AChE), butyrylcholinesterase (BChE), carbonic anhydrase II (CA II), and α-glycosidase, which are associated with some global diseases such as Alzheimer’s disease (AD), glaucoma, and diabetes. Coumestrol exhibited Ki values of 10.25 ± 1.94, 5.99 ± 1.79, 25.41 ± 1.10, and 30.56 ± 3.36 nM towards these enzymes, respectively.

Fatih Polat, M.

One of the main areas of interest of synthetic organic chemistry is the rapid construction of small molecules with proven diverse biological activities for the development of new strategies to cure human health. In particular, the development of novel synthetic strategies is the most important option for reaching the molecular scaffolds of active molecules of natural origin. Balsacone A and asebogenin are compounds that exhibit a wide variety of important biological activities. In this respect, it has become very important to develop new strategies for the construction of biologically active natural and synthetic balsacone analogues. In particular, balsacone derivatives with hydroxy-substituted dihydrochalcone skeletons can be isolated from plant sources or obtained by hemi-syntheses using bio-sourced precursors. An efficient synthetic strategy to synthetically obtain balsacone A is the aim of the present study that considers the limited natural availability of these molecules as well as other factors, such as cost and time. Starting with phloroglucinol, a nine-step synthesis of the precursor of balsacone A was achieved at a 10% overall yield. Furthermore, asebogenin, which has a dihydrochalcone structure and plays a key role in the synthesis of balsacone A, was synthesised with a good yield.

Kızıltaş, Hatice; Bingol, Zeynebe; Gören, Ahmet Ceyhan; Kose, Leyla Polat; Durmaz, Lokman; Topal, Fevzi; Alwasel, Saleh H.; Gulcin, İlhami

Kınkor (Ferulago stellata) is Turkish medicinal plant species and used in folk medicine against some diseases. As far as we know, the data are not available on the biological activities and chemical composition of this medicinal plant. In this study, the phytochemical composition; some metabolic enzyme inhibition; and antidiabetic, anticholinergic, and antioxidant activities of this plant were assessed. In order to evaluate the antioxidant activity of evaporated ethanolic extract (EEFS) and lyophilized water extract (WEFS) of kınkor (Ferulago stellata), some putative antioxidant methods such as DPPH· scavenging activity, ABTS•+ scavenging activity, ferric ions (Fe3+) reduction method, cupric ions (Cu2+) reducing capacity, and ferrous ions (Fe2+)-binding activities were separately performed. Furthermore, ascorbic acid, BHT, and α-tocopherol were used as the standard compounds. Additionally, the main phenolic compounds that are responsible for antioxidant abilities of ethanol and water extracts of kınkor (Ferulago stellata) were determined by liquid chromatography-high-resolution mass spectrometry (LC-HRMS). Ethanol and water extracts of kınkor (Ferulago stellata) demonstrated effective antioxidant abilities when compared to standards. Moreover, ethanol extract of kınkor (Ferulago stellata) demonstrated IC50 values of 1.772 µg/mL against acetylcholinesterase (AChE), 33.56 ± 2.96 µg/mL against α-glycosidase, and 0.639 µg/mL against α-amylase enzyme respectively.

Ozgen, Ufuk; Sevindik, Handan; Kazaz, Cavit; Yigit, Demet; Kandemir, Ali; Secen, Hasan; Calis, Ihsan

Sonchus erzincanicus (Asteraceae) is an endemic species in Turkey, where six Sonchus species grow. In this study, a phytochemical study was performed on the aerial parts of the plant. The study describes the isolation and structure elucidation of five flavonoids and two a-ionone glycosides from S. erzincanicus. The compounds were isolated using several and repeated chromatographic techniques from ethyl acetate and aqueous phases that were partitioned from a methanol extract obtained from the plant. 5,7,3',4'-Tetrahydroxy-3- methoxyflavone (1) and quercetin 3-O-ß-D-glucoside (2) were isolated from the ethyl acetate phase, while corchoionoside C 6'-O-sulfate (3), corchoionoside C (4), luteolin 7-O-glucuronide (5) and luteolin 7-O-ß-Dglucoside (6), apigenin 7-O-glucuronide (7) were isolated from the aqueous phase. Corchoionoside C 6'-O-sulfate (3), isolated for the first time from a natural source, was a new compound. The structures of the compounds were elucidated by means of 1H-NMR, 13C-NMR, 2D-NMR (COSY, HMQC, HMBC) and ESI-MS.