Phytochemical profile, enzyme inhibition, antioxidant, and antibacterial activity of Rosa pimpinellifolia L.: A comprehensive study to investigate the bioactivity of different parts (whole fruit, pulp, and seed part) of the fruit.

The pharmaceutical and nutraceutical potentials of whole fruit, pulp and seeds of Rosa pimpinellifolia L. were evaluated. Forty-two phenolic compounds and two triterpenoids were identified in extracts by LC-MS/MS and GC-MS, respectively. The most prominent compounds were ellagic acid, catechin, epicatechin, tannic acid, quercetin, oleanolic acid, and ursolic acid. The highest enzyme inhibitory activities of the extracts (94.83%) were obtained against angiotensin-converting enzyme and were almost equal to those of the commercial standard (lisinopril, 98.99%). Whole fruit and pulp extracts (IC50:2.47 and 1.52 µg DW/mL) exhibited higher antioxidant capacity than the standards (α-tocopherol, IC50:9.89 µg DW/mL). The highest antibacterial activity was obtained against Bacillus cereus (MIC: 256 µg/mL) for the whole fruit extract. Correlation analyses were conducted to find the correlation between individual phenolics and enzyme inhibitory activities. The results showed the remarkable future of not only the edible part but also the seeds of black rose hips in phytochemical and functional aspects.

Cream production and biological in vivo/in vitro activity assessment of a novel boron-based compound derived from quercetin and phenyl boronic acid.

Boronic acids constitute an important class of synthetic intermediates due to their high chemical stability, ease of use, moderate organic Lewis acid properties, reduced reactivity profiles and numerous biological activities such as antibacterial and antioxidant. The present study documents the synthesis and characterization of a novel boronic ester compound (3,5,7-trihydroxy-2- (2-phenyl benzo [d] [1,3,2] dioxaborol-5-yl) -4H-chromen-4-a) which was derived from phenyl boronic acid and quercetin. The new boron-based compound was used in the cream formulation after evaluating its antioxidant, antibacterial, anti-enzyme, anticancer activities and electrochemical oxidation behaviour. Furthermore, the cream has been dermatologically and microbiologically tested. Also, histological evaluation of the agent was estimated on multiple rat organs by hematoxylin-eosin staining method. Antioxidant potential of the new compound was tested by ABTS cation radical (IC50: 0.11 ± 0.01 µg/mL), DPPH free radical scavenging (IC50: 0.14 ± 0.01 µg/mL), and CUPRAC (A0.5: 1.73 ± 0.16 µg/mL) methods, respectively. The compound determined to have a dominant antioxidant activity. In addition, the synthesized compound had no toxic effect on the healthy cell line (PDF), while having a very high (IC50: 18.76 ± 0.62 µg/mL) cytotoxic effect on the cancerous cell line (MCF-7). In general, the compound showed moderate acetylcholinesterase enzyme activity (IC50: 115.63 ± 1.16 µg/mL), high butyrylcholinesterase (IC50: 3.12 ± 0.04 µg/mL), antiurease (IC50: 1.10 ± 0.06 µg/mL), and antithyrosinase (IC50: 11.52 ± 0.46 µg/mL) enzyme activities. In addition, the compound was found to be effective against Escherichia coli (ATCC 25922) bacteria studied at concentrations of 6.50 mg/mL. Moreover, the test results of the boronic ester compound used in the cream formulation demonstrated that it was microbiologically and dermatologically appropriate. Histologic analysis showed that the control group and experimental group were at similar properties without significant change. The phenyl boronic acid derivative compound synthesized from quercetin may have higher biological activity potential than quercetin. Due to the high biological activity potential of the synthesized compound, it has the potential to be used in food, feed, pharmaceutical and cosmetic industries.

Determination of essential oil and biological activities of Hypericum ternatum Poulter and H. scabrum L. species collected from different localities: is H. scabrum an alternative to multifunctional species ST JOHN'S WORT (H. perforatum)?

The importance of Hypericum L. species, being used in traditional medicine, in the scientific world is increasing day by day. Hypericum species are plants that have been used in the treatment of many diseases for a long time and have healing properties. In the current study, the essential oil compositions of Hypericum scabrum L. and H. ternatum Poulter collected from different localities in Turkey were determined by GC-MS/FID. In addition, their antioxidant, cytotoxic, and antimicrobial activities with their enzyme inhibitory potentials (cholinesterase, urease, tyrosinase, elastase, and collagenase) were investigated. Also, in vitro and in silico studies of the major components of the species have been carried out on the studied enzymes. It was determined that four H. scabrum samples mainly contained α-pinene (55.99%-62.80%) while three H. ternatum samples contained 2-methyloctane (9.45%-22.39%) and α-pinene (12.75%-33.08%). While H. scabrum essential oils possessed significant biological activity potential except for the antimicrobial activity, H. ternatum samples did not. All essential oil samples of H. scabrum exhibited a high cytotoxic effect (IC50 21.67 ± 0.34 to 34.67 ± 0.45 µg/mL) against colon cancer cell line (HT-29) and indicated higher acetyl-(Inhibiton% 83.30 ± 1.90 to 93.08 ± 1.04) and butyryl-cholinesterase (Inhibiton% 80.58 ± 1.19 to 93.28 ± 1.99) inhibitory activity than the standard compound, galantamine. Furthermore, all samples of H. scabrum showed high tyrosinase (Inhibiton% 69.00 ± 1.64 to 95.25 ± 1.42) and elastase (Inhibiton% 27.58 ± 0.34 to 36.69 ± 0.18) inhibitory effects. These biological activity results indicated that H. scabrum essential oil could be used in the cosmetic and pharmaceutical industries.

Essential Oil, Aroma, and Fatty Acid Profiles of Five Endemic Salvia Taxa from Turkey with Chemometric Analysis.

The essential oil, aroma, and fatty acid compositions of Salvia cerino-pruinosa var. cerino-pruinosa, S. cerino-pruinosa var. elazigensis, S. pseudeuphratica, S. rosifolia, and S. kurdica collected in 2015, 2016, and 2017 were analysed by GC-FID, GC/MS/Head Space and GC/MS. The results were evaluated chemometrically for principal component analyses and hierarchical clustering analyses using Minitab program. The main components of their essential oils have been determined as germacrene-D (41.79 % highest for these species), camphor (55.80 %), linalool (33.38 %), caryophyllene oxide (32.99 %), 1,8-cineole (26.30 %) and geraniol acetate (31.63 %), while for aroma 1,8-cineole (45.95 % highest for these species), camphor (58.54 %), D-limonene (40.83 %), linalool (27.67 %) and cis-linalool oxide (25.87 %). Oleic (72.65 % highest for these species), erucic (44.61 %), 2-palmitoleic (42.17 %) and nervonic (32.61 %) acids were determined as major components of their fatty acids. According to the PCA and HCA, the essential oil components of these Salvia taxa unaffected by the years, and accordingly, the Salvia taxa grouped among themselves.

Selective in-vitro Enzymes' Inhibitory Activities of Fingerprints Compounds of Salvia Species and Molecular Docking Simulations.

Recently Nutrition and Food Chemistry researches have been focused on plants and their products or their secondary metabolites having anti-alzheimer, anti-cancer, anti-aging, and antioxidant properties. Among these plants Salvia L. (Lamiaceae) species come into prominence with their booster effects due to high antioxidant contents, which have over 900 species in the world and 98 in Turkey. Some Salvia species are already in use as herbal treatment of vessel stiffness, Dementia like problems and cancer. Recently some species of Salvia are of extensive research topic. In this study, inhibitory potentials of secondary metabolites, rosmarinic acid, salvigenin, salvianolic acid A and B, tanshinone I and IIA, cyrtotanshinone, dihydrotanshinone I, carnosic acid, carnosol, and danshensu sodium salt were investigated against acetylcholinesterase, butyrylcholinesterase, urease and tyrosinase enzymes both in-vitro and in slico in detail. Elevated inhibitory effects on acetyl- and butyryl-cholinesterase of dihydrotanshinone I (IC50: 1.50 ± 0.02 and 0.50 ± 0.01 µg/mL, respectively), carnasol (IC50: 11.15 ± 0.05 ve 3.92 ± 0.03 µg/mL) and carnosic acid (IC50: 31.83 ± 0.65 ve 4.12±0.04 µg/mL) were observed. Furthermore, all other secondary metabolites were active against butyrylcholinesterase. Anti-urease (42.41 ± 0.85%) and anti-tyrosinase (39.82 ± 1.16%) activities of tanshinone I were also observed. Potential inhibitory effects of these molecules on target proteins were investigated using DOCK and molecular dynamics calculations. Dock score analysis and Lipinski parameters were demonstrated that these ligands are potential inhibitors against relevant enzymes. Our findings suggest that Salvia species can be utilized as a ptential source of anti-alzheimer active compounds for designing novel products.

A Detailed Biological and Chemical Investigation of Sixteen Achillea Species' Essential Oils via Chemometric Approach.

Representatives of the Achillea genus are widely used as foods or nutraceuticals. Considering the increasing demand for herbal dietary supplements with health promoting effects, the objective of this research was to evaluate the chemical composition and biological activities of the essential oils obtained from sixteen Achillea species (A. biebersteinii, A. wilhelmsii subsp. wilhelmsii, A. aleppica subsp. zederbaueri, A. vermicularis, A. monocephala, A. nobilis, A. goniocephala, A. sintenisii, A. coarctata, A. kotschyi subsp. kotschyi, A. millefolium subsp. millefolium, A. lycaonica, A. spinulifolia, A. teretifolia, A. setacea, and A. schischkinii). Anticholinesterase, antiurease, antityrosinase enzymes inhibition, antioxidant, antimicrobial, toxic and cytotoxic activities of obtained essential oils were investigated. DPPH activities were found to be very low in all studied samples, while ABTS and CUPRAC antioxidant activities were found to be moderate. In addition, all samples were found to have moderate anticholinesterase and antimicrobial effects. It has been determined that the studied species have low cytotoxicity and high toxicity. Besides, chemical composition of the essential oils were determined by GC/MS and the results were chemometrically analyzed. The chemometric analyses of Achillea species collected from nine different regions were accomplished by principal component analysis (PCA) and hierarchical cluster analysis (HCA) techniques. According to the PCA analysis, A. nobilis subsp. neilreichii was found to be different from all studied species in terms of essential oil composition. The major components found in these species were piperitone, camphor, α-terpinene, eucalyptol, artemisia ketone, endo-borneol, ß-eudesmol and verbenol. The fact that camphor was toxic and found in majority of the studied species stands out as a remarkable result.

Phytochemical and biological investigations on two Nepeta species: Nepeta heliotropifolia and N. congesta subsp. cryptantha.

In the present study, the essential oil and aroma compositions of Nepeta heliotropifolia (NH) and N. congesta subsp. cryptantha (NC) were determined by gas chromatography-mass spectrometry (GC-MS) and gas chromatography-flame ionization detector (GC/FID), and their phenolic compounds by liquid chromatography-tandem mass spectrometry (LC-MS/MS). In addition, antioxidant, cytotoxic, anticholinesterase, urease, and tyrosinase activities of essential oils obtained from NH and NC aerial parts and ethanol extracts prepared from different parts of NH and NC were investigated. The major constituent of water-distilled essential oils was found to be germacrene D (36.7% and 38.5%, respectively), and their main aroma component was eucalyptol (48.0% and 24.7%, respectively). Among the studied parts of NH and NC, their flowers extracts were found to be the richest in phenolic compounds and in which the most abundant compound was rosmarinic acid (8,909.91 and 4,317.20 µg/g, respectively). NH and NC flower extracts exhibited also strong antioxidant activity in DPPH, ABTS, and CUPRAC assays. Among the tested samples, NH essential oil indicated the best cytotoxic effect against PDF, HT-29, and MCF-7 (IC50 52.34, 25.89, and 44.70 µg/ml, respectively), and the highest butyrylcholinesterase (77.21 ± 1.12% inhibition) and moderate acetylcholinesterase (41.36 ± 0.69% inhibition) inhibitory activities. PRACTICAL APPLICATIONS: This is the first report on the essential oil and aroma compositions, the phenolic compounds, the antioxidant with total phenolic and flavonoid contents, cytotoxic, anticholinesterase, urease, and tyrosinase activities of Nepeta heliotropifolia and N. congesta subsp. cryptantha, except for their essential oil compositions. The reported results suggested that Nepeta heliotropifolia and N. congesta subsp. cryptantha flowers being rich in rosmarinic acid and having strong antioxidant potential, and NH essential oil possessing significant cytotoxic and butyrylcholinesterase inhibitory effect could be source for nutraceutical, food, and drug industries.

A comprehensive LC-MS/MS method validation for the quantitative investigation of 37 fingerprint phytochemicals in Achillea species: A detailed examination of A. coarctata and A. monocephala.

The current study aims to optimize and validate a comprehensive LC-MS/MS method for the quantification of 37 phytochemicals (15 phenolic acids, 17 flavonoids, 3 non-phenolic organic acids, 1 phenolic aldehyde and 1 benzopyrene) in Achillea species. Though Achillea species were chosen as real life samples, the current method is applicable to a wide range of plant species. The developed method was fully validated in terms of linearity, accuracy (recovery), inter-day and intra-day precision (repeatability), limits of detection and quantification (LOD/LOQ) and relative standard uncertainty (U% at 95% confidence level (k = 2)). Reversed-phase ultrahigh performance liquid chromatography was optimized to achive optimum separation for 37 phytochemical compounds and to overcome the suppression effects. MS detection was performed using a triple quadrupole mass spectrometer and negative or positive ionization modes were optimized for each analyte. Multiple reaction monitoring (MRM) was used to quantify the analytes, related molecular ions and transition ions were optimized. Phytochemical screening of ethanol and methanol-chloroform extracts of root and aerial parts of A. coarctata and A. monocephala were performed by using the developed and validated LC-MS/MS method. Root and aerial parts of both species have considerable amounts of certain phenolic-nonphenolic acids (quinic, malic, fumaric, chlorogenic and vanillic acids) and flavonoids (rutin, hesperidin, isoquercitrin, apigetrin, luteolin, apigenin). Additionally, total phenolic and flavonoid amounts, antioxidant (DPPH free radical scavenging assay, ABTS radical cation decolorization assay, ß-carotene lipid peroxidation test system and CUPRAC cupper reduction capacity methods), anticholinesterase, tyrosinase, urease inhibition and cytotoxic activities (on HeLa (Human Cervical Carcinoma Cell Line) of A. coarctata and A. monocephala were also investigated. It has been determined that the studied Achillea species, that are rich in total phenolic-flavonoid and chlorogenic acid contents, have high antioxidant and cytotoxic potential at the same time. According to the results of LC-MS/MS, antioxidant and cytotoxic activity studies, after detailed chemical investigation and toxicity studies on these species, A. coarctata and A. monocephala may be promoted as promising sources of natural agents and used for the development of nutraceuticals or functional food ingredients in future.