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Roman chamomile is a wild and cultivated plant in many countries worldwide and is mainly used in folk medicine. The flower's essential oil is used in various cosmetic, perfumery and aromatherapy products. In recent years in Bulgaria, the plant has been cultivated in the experimental field of the Institute of Roses, Essential and Medical Plants, Kazanlak. The present work aims to prepare essential oil and determine its chemical composition and antioxidant activity to reveal new possibilities for its application. The essential oil was obtained under laboratory conditions by steam distillation (yield 0.14%) and its main components determined by GC/MS were: isobutyl angelate (37.22%), 2-methylbutyl angelate (18.71%), methylallyl angelate (11.85%), isobutyl isobutyrate (5.86%), pentan-2-yl 2-methylbut-2-enoate (5.48%), 2-metylbutyl isobutyrate (3.47%), and (Z)-pinocarveol (2.86%). The antioxidant activity of the essential oil was also determined by three methods -- ABTS (1.54 µM TE/g), DPPH (1.09 µM TE/g), and CUPRAC (2.26 µM TE/g). The results show that Roman chamomile can be successfully cultivated in Bulgaria. Its essential oil has an interesting chemical composition and antioxidant activity, a prerequisite for use in various food and cosmetic products, a novelty for our country. [ABSTRACT FROM AUTHOR]

The aim of this study was to evaluate the difference in amino acid composition between the cap and stem of Morchella esculenta -- a wild edible mushroom from the Batak Mountain, Bulgaria. The amino acid composition was determined by Q Exactive mass analyser equipped with TurboFlow LC system and IonMax II electrospray ionisation module (ThermoScientific Co, USA). Data acquisition and processing were carried out with XCalibur 4.2 software package. Twenty free amino acids, histidine, arginne, aspargine, glutamine, serine, aspartic acid, glutamic acid, threonin, glycine, proline, tyrosine, valine, methionine, leucine/isoleucine, phenylalanine, orndihydrochloride, tryptophane, lysine, 4-hydroxyproline and γ-amino butyric acid were determined in mushroom cap and stem. The total free amino acid (TAA) content of the cap was 26.17 mgkg-1 and that of the stem -42.75 mgkg-1. The essential to total amino acids ratios of the cap and the stem were 0.15 and 0.25, respectively. The most substantial difference between Morchella esculenta cap and stem was established in omithine -- 263%, followed by serine -- 18.93% and aspargine -- 20.28%. The smallest differences in the amino acid composition between cap and stem were demonstrated in proline -- 102.77% followed by glutamine -- 104.33% and glumatic acid -- 93.12% Of all 20 amino acids, only 6 were found in larger amounts in the cap than in the stem. The results showed the free amino acid content of the analysed wild edible mushroom was considerable, and that they may be important compounds contributing to the typical mushroom taste, nutritional value, and potent antioxdant properties. [ABSTRACT FROM AUTHOR]

Herein we report an alternative eco-friendly method for the synthesis of 1,2,3,4-tetrahydroisoquinoline sulfonamide derivatives. All obtained compounds were screened for their in vitro inhibition of albumin denaturation, antioxidant, antitryptic and antibacterial activity, and have shown significant results. The lipophilicity was established using both reversed-phase thin layer chromatography and in silico calculations.

Medicinal plants of Achillea millefolium group in Bulgarian wild flora are widely used in both traditional medicine and pharmaceutical, cosmetic and nutritive industries. They are intensively collected from the natural habitats, thus leading to a number of negative effects, such as ecological risk of extinction of native sources and high heterogeneity of the collected market samples. We explored the possibilities for field cultivation of wild A. millefolium group species as a promising approach to produce homogenous samples of valuable plants without damage to the natural environment. Our preliminary studies have identified as promising two species of A. millefolium group in Bulgaria - A. collina and A. asplenifolia. The species A. collina and A. asplenifolia, each with two populations, were studied, while cv. "Proa", bred for field cultivation, was used as a standard. Seeds were collected from the natural habitats and those of cv. Proa were purchased from the firm "Pharmasaat GmbH", Germany. Seedlings were produced in a greenhouse and then transferred to the experimental field of the Institute of Plant Physiology and Genetics near Sofia. Plants were harvested at full blossoming stage. Essential oil yield and chamazulene content in the oil, contents of total flavonoids and chlorogenic (3-O-caffeoyl quinic) acid as well as antiradical and antioxidant activities in flower heads were determined. Principal Component Analysis (PCA) of data was performed. The results showed that field-grown plants of the studied A. millefolium group species produced significant amounts of bioactive compounds, particularly flavonoids and chlorogenic acid which highly correlated with the antiradical activity. PCA pointed to the relatedness of populations within each species, and the distant positions of the species. The populations of A. asplenifolia were distinguished by higher contents of total flavonoids, essential oil, chamazulene and chlorogenic acid as well as by higher antiradical and antioxidant activities as compared to A. collina, while being closer by all parameters to cv. "Proa". The data point to A. asplenifolia as a promising species for field cultivation. [ABSTRACT FROM AUTHOR]

Herein, we report the synthesis of a series of new compounds by combining 2-aminobenzothiazole with various profens. The compounds were characterized using techniques such as 1 H- and 13 C-NMR, FT-IR spectrometry, and high-resolution mass spectrometry (HRMS), with detailed HRMS analysis conducted for each molecule. Their biological activities were tested in vitro, revealing significant anti-inflammatory and antioxidant effects, comparable to those of standard reference compounds. Lipophilicity was experimentally determined through partition coefficient (R M ) measurements. To understand their binding affinity, molecular docking studies were perfsormed to analyze interactions with human serum albumin (HSA). The stability of these predicted complexes was further evaluated through molecular dynamics simulations. The results highlight the compounds' promising biological activity and strong affinity for HSA. The new hybrid molecule between 2-ABT and ketoprofen 3b demonstrates significant promise based on the experimental data and is further supported by in silico calculations. Compound 3b exhibits the best hydrogen peroxide scavenging activity among the tested compounds, with an IC 50 of 60.24 μg/mL. Furthermore, 3b also displays superior anti-inflammatory activity, with an IC 50 of 54.64 μg/mL, making it more effective than the standard ibuprofen (76.05 μg/mL).

In this study, we present the synthesis of five novel compounds by combining flurbiprofen with various substituted 2-phenethylamines. The synthesized derivatives underwent comprehensive characterization using techniques such as 1 H- and 13 C-NMR spectroscopy, UV-Vis spectroscopy, and high-resolution mass spectrometry (HRMS). Detailed HRMS analysis was performed for each of these newly created molecules. The biological activities of these compounds were assessed through in vitro experiments to evaluate their potential as anti-inflammatory and antioxidant agents. Furthermore, the lipophilicity of these derivatives was determined, both theoretically using the c Log P method and experimentally through partition coefficient (R M ) measurements. To gain insights into their binding affinity, we conducted an in silico analysis of the compounds' interactions with human serum albumin (HSA) using molecular docking studies. Our findings reveal that all of the newly synthesized compounds exhibit significant anti-inflammatory and antioxidant activities, with results statistically comparable to the reference compounds. Molecular docking studies further explain the observed in vitro results, shedding light on the molecular mechanisms behind their biological activities. Using in silico method, toxicity was calculated, resulting in LD 50 values. Depending on the administration route, the novel flurbiprofen derivatives show lower toxicity compared to the standard flurbiprofen.

Helichrysum italicum has piqued the interest of many researchers in recent years, mostly for its essential oil, but increasingly for its polyphenolic content as well. In the current study, we examine the polyphenolic composition of H. italicum grown in Bulgaria. The polyphenolic complex was fractionated with solvents of various polarities, including hexane, chloroform, ethyl acetate, and butanol, in order to assess the biological impact of the components. HPLC-PDA and UHPLC-MS/MS were used to examine all fractions. The green coffee fingerprint profile was employed as a "surrogate standard" in the polyphenolic components detection approach. From the UHPLC-MS/MS analysis, we identified 60 components of the polyphenolic complex such as quercetin 3- O -glucuronide, quercetin acetyl-glycoside, isorhamnetin acetyl-glycoside, isorhamnetin caffeoyl-glycoside, quercetin caffeoyl-malonyl-glycoside, isorhamnetin coumaroyl-glycoside, coumaroyl-caffeoylquinic acid, and diCQA-acetyl-derivative were first reported in the composition of H. italicum . The biological activity of the fractions was evaluated in vitro and in silico , which included the fight against oxidative stress (hydrogen peroxide scavenging activity (HPSA), hydroxyl radical scavenging activity (HRSA), metal-chelating activity (MChA)) and nitrosative (nitric oxide scavenging activity) (NOSA)), in vitro anti-inflammatory, and anti-arthritic activity. Results are presented as IC 50 ± SD μg/mL. The analysis showed that the EtOAc fraction was characterized by highest HPSA (57.12 ± 1.14 μg/mL), HRSA (92.23 ± 1.10 μg/mL), MChA (5.60 ± 0.17 μg/mL), and NOSA (89.81 ± 2.09 μg/mL), while the hexane and chloroform fractions showed significantly higher in vitro anti-inflammatory activity (30.48 ± 2.33 μg/mL, 62.50 ± 1.69 μg/mL) compared to the standard ibuprofen. All three fractions showed potential anti-arthritic activity (102.93 ± 8.62 μg/mL, 108.92 ± 4.42 μg/mL, 84.19 ± 3.89 μg/mL).

In the present work, we have investigated the polyphenolic composition of Chenopodium botrys from Bulgaria. The polyphenols were fractionated with solvents of varying polarity ( n -hexane, chloroform, ethyl acetate, and n -butanol). The fractions were analyzed by HPLC-PDA and UHPLC-MS. The ethyl acetate fraction contained mono- and di-glycosides of quercetin, di-glycosides of kaempferol, and isorhamnetin and monoglycosides of hispidulin and jaceosidine. We found quercetin triglycosides in the butanol fraction. The ethyl acetate and butanol fractions contained 168.82 mg/g Extr and 67.21 mg/g Extr of quercetin glycosides, respectively. The main components of the polyphenolic complex in C. botrys were 6-methoxyflavones (355.47 mg/g Extr), which were found in the chloroform fraction. The flavonoids pectolinarigenin, demethylnobiletin, and isosinensetin, and the glycosides of quercetin (triglycosides, acylglycosides), kaempferol, isorhamnetin, hispidiulin, and jaceosidine, were discovered and reported in Chenopodium botrys for the first time. We used in vitro methods to assess the biological activity against oxidative stress (hydrogen peroxide scavenging activity (HPSA) and hydroxyl radical scavenging activity (HRSA)), nitrosative stress (nitric oxide scavenging activity (NOSA)), anti-inflammatory activity (IAD inhibition), and anti-tryptic activity (ATA). Quercetin mono- and di-glycosides exhibited greater HPSA and HRSA (IC 50 = 39.18, 105.03 µg/mL), while 6-methoxyflavones had a greater NOSA (IC 50 = 146.59 µg/mL). The same components showed the highest ATA (IC 50 ranging from 116.23 to 202.44 µg/mL).

The genus Nepeta , belonging to the family Lamiaceae, includes about 300 species, most of which are used in folk medicine due to their pronounced biological properties. The aim of the present study was to evaluate the agrobiological characteristics of Nepeta transcaucasica ( N. transcaucasica ) Grossh. and Nepeta cataria ( N. cataria ) L., cultivated in Bulgaria, and obtain their essential oils and determine their antimicrobial and antioxidant activities. The agrobiological characteristics of the two species growing in Kazanlak were analyzed; therefore, high variability in the population of N. transcaucasica and comparative homogeneity in N. cataria was shown. The species N. transcaucasica contained 0.28% essential oil with main components β-citronellol (52.05%), eucalyptol (7.34%), β-citronellal (6.06%), germacrene D (5.45%), ( Z )-β-ocimene (5.14%), and β-caryophyllene (3.06%). The species N. cataria consisted of 0.19% essential oil with main components β-citronellol (26.31%), geraniol (15.92%), neral (11.45%), nerol (9.56%), carvacrol (6.04%), and β-citronellal (5.35%). The antibacterial activity against Gram-positive bacteria Listeria monocytogenes and Staphylococcus aureus and Gram-negative bacteria Escherichia coli ( E. coli ) and Salmonella enterica subsp. enterica serovar Abony was determined. The essential oils showed antimicrobial activity only against E. coli . The diameters of the inhibition zones were found to be 26 mm for the species N. transcaucasica and 10 mm for the species N. cataria . The antioxidant activity of the two essential oils was also determined by four different methods, DPPH, ABTS, FRAP, and CUPRAC, with the highest values for the ABTS radical, for the species N. transcaucasica (48.72 μM TE/mL), and the species N. cataria (310 μM TE/mL)., Competing Interests: The authors declare no competing financial interest., (© 2023 The Authors. Published by American Chemical Society.)

Herein, we report the obtaining of new hybrid molecules of amphetamine with different profens (amfens). The obtained amfens are characterized by their melting points, UV, 1 H-, 13 C-NMR, and HRMS spectra. A complete and detailed mass spectral analysis of the newly obtained derivatives of amphetamine with ibuprofen, flurbiprofen, ketoprofen, naproxen, and carprofen was performed. In vitro inhibition of albumin denaturation of each new compound was assessed, and they showed significant activity. The IC 50 values of the obtained amphetamine-profen derivatives ranged from 92.81 to 159.87 µg/mL. This indicates that the new hybrids inherit the anti-inflammatory properties of profens. Using in silico method, the toxicity was also calculated. The obtained results are given in LD 50 values. Depending on the route of administration, the amfens are less toxic compared to the standard amphetamine.

Maintaining a strong antioxidant system is essential for preventing drought-induced oxidative stress. Thus, in the present study we investigated the role of some non-enzymic and enzymic antioxidants in desiccation tolerance of Haberlea rhodopensis. The effects of high light upon desiccation on antioxidant capacity was estimated by comparing the response of shade and sun plants. The significant enhancement of the antioxidant capacity at 8% RWC corresponded to an enormous increase in flavonoid content. The important role of ascorbate-glutathione cycle in overcoming oxidative stress during drying of H. rhodopensis was established. The antioxidant capacity increased upon dehydration of both shade and sun plants but some differences in non-enzymatic and enzymatic antioxidants were observed. Investigations on the role of polyphenols in desiccation tolerance are scarce. In the present study the polyphenol profiles (fingerprints) of the resurrection plant Haberlea rhodopensis, including all components of the complex are obtained for the first time. It was clarified that the polyphenol complex of H. rhodopensis includes only two types of glycosides - phenylethanoid glucosides and hispidulin 8-C-glucosides. Upon desiccation the polyphenol content increase and the main role of phenylethanoid glucosides in the protection of H. rhodopensis was revealed., (Copyright © 2017 Elsevier Masson SAS. All rights reserved.)