Comparative assessment of phenolic composition profile and biological activities of green extract and conventional extracts of Salvia sclarea.

In recent years, there have been an attempt to develop safe and environmental friendly solvents to replace conventional solvents, and use for extraction bioactive compounds from natural sources. A current investigation involved the preparation of green, methanolic, and ultrasonic extracts of S. sclarea, and compared their phenolic profiling using HPLC-DAD, antibacterial, antioxidant, and enzyme inhibition activities. The HPLC-DAD analysis revealed that Rosmarinic acid was the main content in all extracts, with Ellagic acid only present in the green extract. The green extract exhibited superior anti-biofilm activity against S. Aureus and E. Faecalis compared to the other extracts at MIC concentration. Furthermore, the green extract also displayed the highest inhibition of swarming motility in P. Aeruginosa with inhibition range 68.0 ± 2.1 (MIC) to 19.5 ± 0.6 (MIC/4). and better enzyme inhibitory activity against BChE (with IC50 = 131.6 ± 0.98 µg/mL) and AChE (with inhibition 47.00 ± 1.50%) compared to the other extracts; while, the ultrasonic extract showed strong inhibition of violacein production by C. Violaceum with a inhibition range 05.5 ± 0.1 (MIC/32) to 100 ± 0.00 (MIC), followed by the green extract with a inhibition range 15.0 ± 0.5 (MIC/8) to 100 ± 0.00 (MIC), additionally, the ultrasonic and methanoic extracts showed significant activity against urease enzyme with (IC50 = 171.6 ± 0.95 µg/mL and IC5 0 = 187.5 ± 1.32 µg/mL) respectively. Both the green and methanolic extracts showed considerable antioxidant activities, as ß-carotene-linoleic acid (IC50 = 5.61 ± 0.47 µg/mL and 5.37 ± 0.27 µg/mL), DPPH· (IC50 = 19.20 ± 0.70 µg/mL and 16.31 ± 0.23 µg/mL), ABTS·+(IC50 = 8.64 ± 0.63 µg/mL and 6.50 ± 0.45 µg/mL) and CUPRAC (A0.5 = 17.22 ± 0.36 µg/mL and 12.28 ± 0.12 µg/mL) respectively, likewise the green extract performing better in metal chelating compared to the other extracts. The green extraction is reported as a cost effective and solvent free method for extracting natural products that produces compounds free of toxic chemicals. This could be the method to be used in the industries as a renewable method.

Citrus Honeys from Three Different Regions of Turkey: HPLC-DAD Profiling and in Vitro Enzyme Inhibition, Antioxidant, Anti-Inflammatory and Antimicrobial Properties with Chemometric Study.

The objectives of the present study are to compare the phenolic profiles and biological activities of 15 citrus honey samples from three different locations in Turkey using a chemometric approach. The HPLC-DAD analysis was used to determine phenolic profiles. Nineteen phenolic compounds were identified. Gallic acid (107.14-717.04 µg/g) was recorded as the predominant compound. AF (Antalya-Finike) had the highest antioxidant activity in ABTS⋅+ (IC50 : 18.01±0.69 mg/mL), metal chelating (IC50 : 6.20±0.19 mg/mL) and CUPRAC (A0.50 : 12.05±0.68 mg/mL) assays, while it revealed the best anti-inflammatory activity against COX-2 (17.28±0.22 %) and COX-1 (43.28±0.91 %). AM (Antalya-Manavgat) was the most active in ß-carotene-linoleic acid (IC50 : 10.05±0.19 mg/mL), anti-urease (38.90±0.69 %), anti-quorum sensing and antimicrobial activities. AKO1 (Adana-Kozan-1) in DPPH⋅ (IC50 : 34.25±0.81 mg/mL) assay, AKU1 (Antalya-Kumluca-1) in tyrosinase inhibition activity (37.73±0.38 %) assay, AKU2 (Antalya-Kumluca-2) in AChE (10.55±0.63 %) and BChE (9.18±0.45 %) inhibition activity assays showed the best activity. Chemometric tools were applied to the phenolic compositions and biological properties. PCA and HCA ensured that 15 citrus honey samples were grouped into 3 clusters. The results showed that myricetin, kaempferol, vanillin, protocatechuic acid, rosmarinic acid, rutin, vanillic acid, gallic acid, catechin and p-hydroxyphenyl acetic acid are phenolic compounds that can be used in the classification of citrus honeys.

Chemical composition, antioxidant and anticholinesterase activity of the essential oil of algerian cachrys sicula L.

In this work, in order to explore a new Algerian medicinal plant used in traditional medicine, the essential oil of the leaves of Cachrys sicula L. (Apiaceae) collected from Algeria, obtained by hydrodistillation, was analyzed by GC/MS. Thirty-two compounds were identified accounting for 98.6% of the total oil, which is characterized by a high content of monoterpene hydrocarbons (74.8%). The main constituents of the essential oil were ß-pinene (17.9%), sabinene (17.8%), myrcene (12%), and α-pinene (11.4%). In vitro antioxidant activity of the essential oil was assayed by three methods, namely ABTS•+, metal chelating, and DPPH• assays. The antioxidant activity of the oil was higher in the ABTS•+ method. Anticholinesterase activity was screened by the Ellman method against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) which are the chief enzymes of Alzheimer's disease. The results showed mild acetylcholinesterase and good butyrylcholinesterase inhibitory effects.

Isolation and characterization of chemical constituents from Chaerophyllum bulbosum roots and their enzyme inhibitory and antioxidant effects.

Isolation and bioactive effects of the roots of Chaerophyllum bulbosum L. were firstly investigated herein. Enzyme (acetylcholinesterase, butyrylcholinesterase, urease, α-amylase, α-glucosidase, and tyrosinase) inhibitory effects of C. bulbosum root extracts were tested. Three known compounds, n-heptadecanyl eicosanoate (1), stigmasterol (2), and ß-sitosterol-3-O-ß-d-glucopyranoside (3) were isolated from C. bulbosum. Antioxidant and enzyme inhibitory effects of isolated compounds were investigated. The hexane extract (IC50: 349.58 ± 0.06 µg/mL) displayed a higher α-glucosidase inhibitory effect than the standard (IC50: 378.66 ± 0.14 µg/mL). The best inhibitory effect was found in compound 2 on AChE (46.40 ± 0.31%), BChE (56.41 ± 0.54%), and urease (92.47 ± 0.11%); compound 1 on α-amylase (22.27 ± 0.61%); and compound 3 on α-glucosidase (12.43 ± 0.25%) and tyrosinase (19.00 ± 0.16%). All isolated compounds showed moderate antioxidant effects in all assays. This study contributes to the therapeutic uses of Chaerophyllum roots and emphasizes the value of C. bulbosum species for the development of novel therapeutic agents.

Antibiofilm, antiquorum sensing and antioxidant activity of secondary metabolites from seeds of Annona senegalensis, Persoon.

The increasing resistance of bacteria to antibiotics has motivated the interest in potent natural compounds capable of disrupting bacterial cell-to-cell communication. Column chromatography of seed extract of Annona senegalensis afforded N-cerotoyltryptamine (1), asimicin (2) and ent-19-carbomethoxykauran-17-oic acid (3). The compounds were tested for their antimicrobial, antibiofilm, and anti-quorum sensing activities. The minimum inhibitory concentrations (MIC) values ranged from 50 µg/mL to 100 µg/mL for C. albicans ATCC 10239 and S. aureus ATCC 25923 E. coli ATCC 25922, C. violaceum CV026 and C. violaceum CV12472. All the compounds inhibited biofilm formations of all microorganisms tested in various percentages at MIC and MIC/2. Compound 2 also exhibited the highest antibiofilm activity against C. albicans (yeast) and E. coli with percentage inhibitions ranging from 6.3 ± 4.1 (MIC/4) to 37.9 ± 4.5 (MIC) for C. albicans and from 18.8 ± 1.1 (MIC/4) to 43.2 ± 0.5 (MIC) for E. coli. Compound 1, however, showed highest biofilm inhibition on S. aureus as the percentage inhibition varied from 26.7 ± 3.6 (MIC/4) to 43.8 ± 2.1 (MIC). Compound 2 showed highest percentage violacein inhibition on C. violaceum CV12472 ranging from 10.2 ± 0.5 (MIC/8), 65.76 ± 1.3 (MIC/2) and 100 (MIC). Compound 1 and 3 had percentage violacein formation inhibitions on C. violaceum CV12472 ranging from 9.66 ± 1.1 (MIC/4) to 100 (MIC), and from 17.4 ± 2.4 (MIC/4) to 100 (MIC), respectively. Swimming and swarming motility of P. aeruginosa PA01 strain was evaluated at three concentrations of 50, 75 and 100 µg/mL. The compounds inhibited the P. aeruginosa swimming and swarming motility at the three tested concentrations (50, 75 and 100 µg/ml) in a dose-dependent manner. The extents of inhibition of motility migration was relatively higher in the swimming model than in the swarming model for all compounds. Compound 1 exhibited the highest percentage inhibition of motility of 41.50 ± 3.5 and 39.73 ± 1.5 in swimming model and swarming model respectively at 100 µg/ml. Compound 3 showed the lowest percentage inhibition of 30.36 ± 2.0 and 23.50 ± 2.5 in swimming and swarming respectively at 100 µg/ml. At the lowest tested concentration of 50 µg/ml, it was compound 2 showing the highest inhibition of motility of 17.49 ± 0.5 and 14.29 ± 1.0 in swimming and swarming respectively. Compound 1 showed highest quorum sensing (QS) activity with QS inhibition zone of 20.0 ± 1.5 mm at MIC and 11.0 ± 1.0 mm at MIC/8 while compound 2 had the highest antimicrobial (AM) zone diameter amongst the compounds at MIC. Compound 3 was the QS inhibitory sample and did not show any QS inhibition at MIC/8 while showing its highest QS inhibition zone of 13.0 ± 1.6 mm at MIC. For antioxidant assays, no sample showed better activity than the standards. Compound 2 had highest activity with IC50 values of 87.79 ± 2.70 and 42.77 ± 1.53 µg/mL in DPPH and ß-carotene-linoleic acid assay respectively and was more active (IC50 of 97.69 ± 1.40 µg/mL) than standard quercetin (IC50 250.09 ± 0.87 µg/mL) in metal chelation assay.

Phytochemical contents, antioxidant effects, and inhibitory activities of key enzymes associated with Alzheimer's disease, ulcer, and skin disorders of Sideritis albiflora and Sideritis leptoclada.

In this study, urease, tyrosinase, cholinesterase inhibitory, and antioxidant activities of various extracts of Sideritis albiflora and Sideritis leptoclada were determined together with the phytochemical contents. In addition, the fatty acid compositions and phenolic compounds were investigated by gas chromatography (GC), gas chromatography-mass spectrometry (GC-MS), and high performance liquid chromatography-diode array detector (HPLC-DAD). Rosmarinic acid and caffeic acid in both Sideritis species were identified as the most abundant phenolic compounds whereas palmitic acid was found as a major fatty acid. The acetone extract of S. leptoclada indicated the highest antioxidant activity in ß-carotene-linoleic acid (IC50 : 17.23 ± 0.11 µg/ml), DPPH• (IC50 : 28.14 ± 0.05 µg/ml) and ABTS•+ (IC50 : 15.18 ± 0.02 µg/ml) assays. The acetone extract of S. albiflora (A0.50 : 32.71 ± 0.44 µg/ml) was found as the best reductant in cupric reducing antioxidant capacity (CUPRAC) assay. Against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), only the hexane extracts of Sideritis species showed moderate inhibitory activity. Moreover, all extracts of S. albiflora and the hexane extract of S. leptoclada exhibited significantly higher urease inhibitory activity than that of thiourea. Further, in vivo activity studies on extracts and isolated constituents obtained from these species are needed to understand the activity in biological systems. PRACTICAL APPLICATIONS: Multiple pharmacological studies have proven that Sideritis species is precious with significant bioactive properties. This is the first comprehensive research to determine the enzyme inhibitory and antioxidant activities of various extracts of S. albiflora and S. leptoclada with phytochemical contents. Both Sideritis species were found to be rich in rosmarinic and caffeic acids. The acetone extracts showed the highest activity in terms of antioxidant activity, while the hexane extracts exhibited superior urease inhibitory activity. These results show that Sideritis species could be used as urease inhibitors' agents and source of antioxidants in food, pharmaceutical, and cosmetic industries.

Isolation, characterization, and bioactivities of compounds from Fuscoporia torulosa mushroom.

Chromatographic purification of Fuscoporia torulosa extracts resulted in the isolation and characterization of a new steroid, 5α,8α-epidioxyergosta-6,22-dien-3ß-il-palmitate (1) and 10 known compounds (2-11). The structures of compounds were elucidated by IR, NMR, MS analyses, and comparison with literature data. Cytotoxic activities against MCF-7 (breast cancer), PC-3 (prostate cancer), and 3T3 (nontumor) of the extracts and cytotoxic, antioxidant, cholinesterase, and tyrosinase inhibitory activities of all isolated compounds were evaluated. The methanol extract and Compound 8 showed the best cytotoxicity against MCF-7, whereas the hexane extract and Compound 4 displayed the highest cytotoxicity against PC-3. Compounds 10 and 11 displayed higher antioxidant activity than α-tocopherol and butylated hydroxyanisole (BHA) which are used as standards in ABTS•+ , DPPH• , and cupric reducing antioxidant capacity (CUPRAC) assays. Also, cholinesterase inhibitory activity against acetylcholinesterase (AChE) and butrylcholinesterase (BChE), Compounds 4 and 8 were determined as the most active compounds. Among all isolated compounds, Compound 11 exhibited the highest tyrosinase inhibitory activity. PRACTICAL APPLICATIONS: Mushrooms have various important medicinal properties. A detailed study was made to identify the bioactive constituents of Fuscoporia torulosa mushroom and a new (1) and 10 known compounds (2-11) were isolated. Compounds 10 and 11 showed higher antioxidant activity than standards. The methanol extract and Compound 8 exhibited high cytotoxic activity against MCF-7. Compound 8 indicated potent BChE inhibitory activity. This study suggests that natural compounds isolated from F. torulosa mushroom could be used as promising anticancer, antioxidant, and anticholinesterase agents.

Chemical Profile, In Vitro Enzyme Inhibitory, and Antioxidant Properties of Stereum Species (Agaricomycetes) from Turkey.

Recently, mushroom species have been the focus of researchers' interest because of several bioactivities. The aim of this study was to investigate the chemical profile and biological activities of various extracts of two Stereum species (S. rugosum and S. sanguinolentum). Antioxidant activity was tested using ß-carotene-linoleic acid, DPPH scavenging, ABTS·+ scavenging, cupric-reducing antioxidant capacity (CUPRAC), and metal chelating assays. The extracts were also tested for their enzyme inhibitory activities against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). HPLC-DAD was applied for the analysis of phenolic compounds, and fatty acid compositions were determined using GC and GC-MS. When fumaric acid and catechin hydrate were found as the most abundant phenolic compounds in both Stereum species, oleic acid and palmitic acid were identified as major fatty acids. Both of the studied Stereum methanol extracts were determined as the most active in ß-carotene-linoleic acid, DPPR, ABTS·+, and CUPRAC assays; the n-hexane extracts were found to be most active in metal chelating and AChE inhibitory activity assays. In addition, the methanol extract of S. sanguinolentum (IC50: 34.26 ± 0.31 µg/mL) showed higher ABTS·+ scavenging activity than α-tocopherol (IC50: 38.51 ± 0.54 µg/mL). The acetone extracts were found as potent inhibitors against BChE. These results suggest that Stereum species could be an antioxidant source and cholinesterase agent in pharmaceutic, food, and cosmetics industries.

Chemical composition, antioxidant, anticholinesterase, antimicrobial and antibiofilm activities of essential oil and methanolic extract of Anthemis stiparum subsp. sabulicola (Pomel) Oberpr.

Anthemis species are traditionally used to treat infectious and inflammatory processes, among others clinical disturbances. In the current study, the chemical composition, the total phenolic and flavonoid contents, the antioxidant, anticholinesterase, antimicrobial, and antibiofilm activities of Anthemis stiparum subsp. sabulicola aerial parts methanolic extract (As-ME) and essential oil (As-EO) were investigated. The chemical composition of As-EO was established by GC-MS and GC-FID. Total phenolic and flavonoid contents of As-ME were spectrophotometrically determined. Diphenyl-1-picrylhydrazyl (DPPH●) radical scavenging, cupric reducing antioxidant capacity (CUPRAC) and ß-carotene bleaching assays were applied to evaluate the antioxidant potential. The anticholinesterase activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes were carried out spectrophotometrically. The antimicrobial activity was assessed by Minimal Inhibitory Concentration (MIC) using broth microdilution method against 7 ATCC® bacterial and one ATCC® yeast reference strains. The antibiofilm effect was determined quantifying the percentage of adhesion inhibition. GC-MS and GC-FID identified 72 compounds (99.02%), being As-EO predominantly constituted by germacrene D (11.13%), t-cadinol (11.01%), camphor (6.73%), spathulenol (6.50%) and isoamyl salicylate (6.45%). The total phenolic and flavonoid contents of As-ME were 13.6 ±â€¯0.03 and 5.9 ±â€¯0.04 pyrocatechol equivalents and quercetin equivalents, respectively. In ß-carotene-linoleic acid assay, As-ME showed the best lipid peroxidation inhibition activity with an IC50 = 9.96 µg/mL followed by As-EO with an IC50 = 619.98 µg/mL. In contrast, in DPPH assay, As-ME and As-EO showed moderate to low activity with an IC50 = 92.69 µg/mL for As-ME and 917.69 µg/mL for As-EO. While in CUPRAC assay, As-EO and As-ME indicated a less to moderate reducing activity. As-ME inhibited AChE (IC50 = 490.46 µg/mL) and BChE (IC50 = 142.07 µg/mL), while As-EO was inactive against AChE and revealed a discreet inhibitory action against BChE (IC50 = 212.14 µg/mL). As-ME displayed better antimicrobial activity than As-EO, being active against Staphylococcus aureus (ATCC® 25923) and Bacillus subtilis (ATCC® 6633), with MIC of 1.56 mg/mL. An expressive fungal adhesion inhibition (80.02%) on Candida albicans (ATCC® 10239) was detected with As-ME at 6.25 mg/mL. These results showed that A. stiparum subsp. sabulicola is a natural source of active compounds with antibiotic and antibiofilm effects against S. aureus and B. subtilis, and C. albicans, respectively, and also presents antioxidant and anticholinesterase properties.

Antioxidant, anticholinesterase and antibacterial activities of Stachys guyoniana and Mentha aquatica.

CONTEXT: Stachys guyoniana Noë ex. Batt. and Mentha aquatica L. are two Algerian Lamiaceae used in folk medicine. OBJECTIVE: To investigate their antioxidant, anticholinesterase and antibacterial activities. MATERIAL AND METHODS: n-Butanol (BESG), ethyl acetate (EESG) and chloroform (CESG) extracts of S. guyoniana and methanol (MEMA) and chloroform (CEMA) aerial part extracts of M. aquatica and methanol (MERMA) and acetone (AERMA) roots extracts of M. aquatica were evaluated for their antioxidant activity by the ß-carotene-linoleic acid, DPPH• and ABTS•+ scavenging, CUPRAC and metal chelating assays. The anticholinesterase activity was tested against AChE and BChE. The antibacterial activity was assessed by MICs determination against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Salmonella heidelberg, Klebsiella pneumoniae, Enterobacter aerogenes and Morganella morganii strains. RESULTS: In the ß-carotene test, the CESG (IC50: 2.3 ± 1.27 µg/mL) exhibited the highest activity. The BESG was the best scavenger of DPPH• (IC50: 2.91 ± 0.14 µg/mL). In the ABTS test, AERMA was the most active (IC50: 4.21 ± 0.28 µg/mL). However, with the CUPRAC, the BESG exhibited the best activity (A0.50: 0.15 ± 0.05 µg/mL) and was active in metal chelating assay with 48% inhibition at 100 µg/mL. The BESG was the best AChE inhibitor (IC50: 5.78 ± 0.01 µg/mL) however, the AERMA showed the highest BChE inhibitory activity (IC50: 19.23 ± 1.42 µg/mL). The tested extracts exhibited a good antibacterial activity. CONCLUSION: This study demonstrated good antioxidant, anticholinesterase and antibacterial potential of S. guyoniana and M. aquatica, which fits in well with their use in folk medicine.

A new fatty acid ester from an edible mushroom Rhizopogon luteolus.

Phytochemical investigation of the Rhizopogon luteolus Fr. led to the isolation of one new fatty acid ester, 3-hydroxy-2,4-dimethylheptacosyl acetate (1) together with two known compounds tetracosanoic acid (2) and ergosterol (3). 1D and 2D NMR, and MS techniques were used for structural elucidation. Phenolic and fatty acid compositions were identified using HPLC-DAD and GC-MSD, respectively. Fumaric acid was the major phenolic acid, whereas linoleic, stearic and oleic acids were the most abundant fatty acids. Antioxidant and anticholinesterase activities of the extracts and compounds (1-3) were tested spectrophotometrically. Among the extracts, hexane extract showed the highest activity in all tests, particularly in ß-carotene-linoleic acid assay (IC50: 16.65 ± 1.12 µg/mL). Furthermore, compound 3 exhibited higher antioxidant and anticholinesterase activities. The study indicates that R. luteolus can be used in food, cosmetic and pharmaceutical industries.

Phytochemicals from Dodonaea viscosa and their antioxidant and anticholinesterase activities with structure-activity relationships.

Context Dodonaea viscosa (L.) Jacq (Sapindaceae) has been used in traditional medicine as antimalarial, antidiabetic and antibacterial agent, but further investigations are needed. Objective This study determines the antioxidant and anticholinesterase activities of six compounds (1-6) and two crystals (1A and 3A) isolated from D. viscosa, and discusses their structure-activity relationships. Materials and methods Antioxidant activity was evaluated using six complementary tests, i.e., ß-carotene-linoleic acid; DPPH(•), ABTS(•+), superoxide scavenging, CUPRAC and metal chelating assays. Anticholinesterase activity was performed using the Elman method. Results Clerodane diterpenoids (1 and 2) and phenolics (3-6) - together with three crystals (1A, 3A and 7A) - were isolated from the aerial parts of D. viscosa. Compound 3A exhibited good antioxidant activity in DPPH (IC50: 27.44 ± 1.06 µM), superoxide (28.18 ± 1.35% inhibition at 100 µM) and CUPRAC (A0.5: 35.89 ± 0.09 µM) assays. Compound 5 (IC50: 11.02 ± 0.02 µM) indicated best activity in ABTS assay, and 6 (IC50: 14.30 ± 0.18 µM) in ß-carotene-linoleic acid assay. Compounds 1 and 3 were also obtained in the crystal (1A and 3A) form. Both crystals showed antioxidant activity. Furthermore, crystal 3A was more active than 3 in all activity tests. Phenol 6 possessed moderate anticholinesterase activity against acetylcholinesterase and butyrylcholinesterase enzymes (IC50 values: 158.14 ± 1.65 and 111.60 ± 1.28 µM, respectively). Discussion and conclusion This is the first report on antioxidant and anticholinesterase activities of compounds 1, 2, 5, 6, 1A and 3A, and characterisation of 7A using XRD. Furthermore, the structure-activity relationships are also discussed in detail for the first time.

Chemical constituents of essential oil of endemic Rhanterium suaveolens Desf. growing in Algerian Sahara with antibiofilm, antioxidant and anticholinesterase activities.

Twenty compounds were detected in the essential oil of Rhanterium suaveolens representing 98.01% of the total oil content. Perillaldehyde (45.79%), caryophyllene oxide (24.82%) and ß-cadinol (5.61%) were identified as the main constituents. In ß-carotene-linoleic acid assay, both the oil and the methanol extract exhibited good lipid peroxidation inhibition activity, with IC50 values of 17.97 ± 5.40 and 11.55 ± 3.39 µg/mL, respectively. In DPPH and CUPRAC assays, however, the methanol extract exhibited a good antioxidant activity. The highest antibiofilm activity has been found 50.30% against Staphylococcus epidermidis (MU 30) at 20 µg/mL for essential oil and 58.34% against Micrococcus luteus (NRRL B-4375) at 25 mg/mL concentration for methanol extract. The in vitro anticholinesterase activity of methanol extract showed a moderate acetylcholinesterase inhibitory (IC50 = 168.76 ± 0.62 µg/mL) and good butyrylcholinesterase inhibitory (IC50 = 54.79 ± 1.89 µg/mL) activities. The essential oil was inactive against both enzymes.

Compounds from Sedum caeruleum with antioxidant, anticholinesterase, and antibacterial activities.

CONTEXT: This is the first study on the phytochemistry, antioxidant, anticholinesterase, and antibacterial activities of Sedum caeruleum L. (Crassulaceae). OBJECTIVE: The objective of this study is to isolate the secondary metabolites and determine the antioxidant, anticholinesterase, and antibacterial activities of S. caeruleum. MATERIALS AND METHODS: Six compounds (1-6) were isolated from the extracts of S. caeruleum and elucidated using UV, 1D-, 2D-NMR, and MS techniques. Antioxidant activity was investigated using DPPH(•), CUPRAC, and ferrous-ions chelating assays. Anticholinesterase activity was determined against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes using the Ellman method. Antibacterial activity was performed according to disc diffusion and minimum inhibitory concentration (MIC) methods. RESULTS: Isolated compounds were elucidated as ursolic acid (1), daucosterol (2), ß-sitosterol-3-O-ß-D-galactopyranoside (3), apigenin (4), apigetrin (5), and apiin (6). The butanol extract exhibited highest antioxidant activity in all tests (IC50 value: 28.35 ± 1.22 µg/mL in DPPH assay, IC50 value: 40.83 ± 2.24 µg/L in metal chelating activity, and IC50 value: 23.52 ± 0.44 µg/L in CUPRAC), and the highest BChE inhibitory activity (IC50 value: 36.89 ± 0.15 µg/L). Moreover, the chloroform extract mildly inhibited (MIC value: 80 µg/mL) the growth of all the tested bacterial strains. DISCUSSION AND CONCLUSION: Ursolic acid (1), daucosterol (2), ß-sitosterol-3-O-ß-D-galactopyranoside (3), apigenin (4), apigetrin (5), and apiin (6) were isolated from Sedum caeruleum for the first time. In addition, a correlation was observed between antioxidant and anticholinesterase activities of bioactive ingredients of this plant.

Synthese and characterization of boronic acid functionalized macroporous uniform poly(4-chloromethylstyrene-co-divinylbenzene) particles and its use in the isolation of antioxidant compounds from plant extracts.

Aminophenyl boronic acid (APBA) carrying uniform-macroporous poly(chloromethylstyrene-co-divinylbenzene), poly(CMS-co-DVB) particles were synthesized for selective separation of cis-diol-containing flavonoids from plant extracts. For this purpose, 2.5 µm polystyrene seed particles were first swelled by a mixture of dibutyl phthalate (DBP), toluene and dodecanol, then by a monomer mixture including CMS and DVB. The repolymerization of the monomer phase in the swollen seed particles provided macroporous and uniform particles, approximately 7 µm in size. Chlorine atoms on the surface of these particles were derivatized with APBA to gain affinity properties for flavonoids containing vicinal hydroxyl groups. Model adsorption studies showed that these particles selectively adsorbed quercetin and rutin containing cis-diol groups, but did not adsorb apigenin similar to quercetin and not carrying cis-diol groups. These particles were also tested in adsorption/desorption studies for ethanol and ethyl acetate extracts of the Hypericum perforatum (HP) stems to obtain high antioxidant mixtures. With ethanol extract, the antioxidant activity of the desorption solution was a bit higher than that of the post-adsorption solutions. However, the DPPH radical scavenging activity of the desorption solution decreased with respect to the original extract and post-adsorption solutions. A similar result was obtained for the antioxidant activity of the desorption solution using ethyl acetate extract. An interesting result was obtained that DPPH radical scavenging activity of the post-adsorption solution was higher than that of the original ethyl acetate extract and desorption solutions. These results were attributed to selective adsorption of antioxidant characterized cis-diol-containing apolar molecules much more rather than that radical scavenger characterized polar molecules.

In vitro antioxidant, anticholinesterase and antimicrobial activity studies on three Agaricus species with fatty acid compositions and iron contents: a comparative study on the three most edible mushrooms.

The fatty acids of Agaricus essettei, Agaricus bitorquis and Agaricus bisporus were investigated by using GC and GC-MS. The dominant fatty acids were found to be linoleic (61.82-67.29%) and palmitic (12.67-14.71%) acids among the 13 fatty acids detected in the oils. Total unsaturation for the oils was calculated as 77.50%, 77.44%, and 79.72%, respectively. In vitro antioxidant, anticholinesterase and antimicrobial activities were also studied. The ethyl acetate extract of Agaricus bitorquis showed the highest activity in ß-carotene-linoleic acid, DPPH(·) and ABTS(·)(+) assays, while the hexane extract of Agaricus bisporus exhibited the best metal chelating activity. The ethyl acetate and hexane extract of Agaricus bitorquis and the hexane extract of Agaricus essettei showed meaningful butyrylcholinesterase activity being close to that of galantamine. The extracts were found to be effective on Gram (+) bacteria, especially against Micrococcus luteus, Micrococcus flavus, Bacillus subtilis and Bacillus cereus. In conclusion, Agaricus bitorquis and Agaricus essettei demonstrated higher iron content, and better antioxidant, anticholinesterase and antimicrobial activities than those of Agaricus bisporus commonly consumed mushroom. Hence, Agaricus species, particularly Agaricus bitorquis might be useful as antioxidant agents and moderate anticholinesterase agents, and their extracts will probably be used for development of dietary foods, food products and additives.

Chemical composition of the essential oil and hexane extract of Salvia chionantha and their antioxidant and anticholinesterase activities.

The essential oil and methyl ester of hexane extract of Salvia chionantha Boiss. were analysed by GC and GC-MS. Totally, 54 components were detected in the essential oil and all of them were fully determined. Germacrene D (25.03%), ß-caryophyllene (8.71%), spathulenol (5.86%) and α-humulene (4.82%) were identified as the major compounds. In the methylated hexane extract, 3-hydroxy hexadecanoic acid (39.39%), 3-hydroxy tetradecanoic acid (12.66%) and palmitic acid (12.02%) were the major fatty acids elucidated. The antioxidant activity of the essential oil and the hexane extract was determined by using four complementary test systems; namely, ß-carotene-linoleic acid, DPPH() scavenging, ABTS(+)* scavenging, and CUPRAC assays. In ß-carotene-linoleic acid assay, the extract showed 81.2±0.1% lipid peroxidation inhibition at 0.8 mg/mL concentration, while in ABTS(+)* assay the essential oil exhibited 77.4±0.5% inhibition at same concentration. Since, acetylcholinesterase and butyrylcholinesterase enzymes are taking place in pathogenesis of Alzheimer's disease, in vitro anticholinesterase activity of the essential oil and the extract was also studied spectrophotometrically. At 0.5mg/mL concentration, the essential oil showed moderate acetylcholinesterase (56.7±1.9%) and butyrylcholinesterase (41.7±2.9%) inhibitory activity, while the extract was only exhibited activity (63.1±0.8%) against butyrylcholinesterase enzyme. Hence, the essential oil may be useful as a moderate anticholinesterase agent, particularly against acetylcholinesterase.

GC-MS analysis of the antioxidant active fractions of Micromeria juliana with anticholinesterase activity.

The aerial parts of Micromeria juliana (L.) Bentham ex Reichb. were extracted with light petroleum, acetone and methanol, successively. The antioxidant activity of different concentrations of the extracts was evaluated using different antioxidant tests, namely total antioxidant (lipid peroxidation inhibition activity), DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging, ferric reducing power, and metal chelating. Total antioxidant activity was determined using the beta-carotene-linoleic acid assay. Unexpectedly, the light petroleum extract exhibited strong lipid peroxidation inhibition activity. The extract was fractionated on a silica gel column and the antioxidant activity of the fractions was determined by the beta-carotene-linoleic assay at 25 microg/mL concentration. The fractions that exhibited more than 50% inhibition activity were analysed by GC and GC/MS; thus, the structure of fourteen compounds were elucidated. In addition, acetyl- and butyryl-cholinesterase inhibitory activities of the extracts were also determined in vitro. The light petroleum and acetone extracts were found to have mild butyrylcholinesterase inhibitory activity.

The effect of temperature on the essential oil components of Salvia potentillifolia obtained by various methods.

The chemical compositions of the essential oils of Salvia potentillifolia (Lamiaceae) were analyzed by GC and GC-MS. The oils were obtained by four different methods (hydrodistillation, steam distillation, and two extraction methods) to investigate the effect of temperature on the volatile compounds. In total, 121 components were detected in the various oils. The major compounds characterized were alpha-pinene (30.2, 31.2, 10.6, and 14.8%) and beta-pinene (15.0, 14.6, 7.6, and 11.4%), respectively. Surprisingly, the percentage concentrations of alpha-pinene and beta-pinene in the hydrodistilled and steam distilled oils were high, even though prepared at high temperature, whereas the contents of both compounds were lower in the essential oils obtained by the extraction methods prepared without added heat. The percentage concentration of 8,13-epoxy-labda-14-en-2-one, a diterpenoid, in the extracted essential oil was 22 times higher than in the hydrodistilled and steam distilled essential oils. However, the concentrations of cis-p-menth-2-en-1-ol was four times, and beta-bourbonene and beta-caryophyllene two times superior than their percentage concentrations in the hydrodistilled and steam distilled essential oils.

GC-MS analysis and antimicrobial activity of essential oil of Stachys cretica subsp. smyrnaea.

The essential oil from the aerial parts of Stachys cretica L. subsp. smyrnaea Rech. fil. (Lamiaceae), endemic to Turkey, was investigated by using GC and GC-MS. Thirty-four of 37 components, represented 99.7% of the total oil, were identified. The major components of the essential oil were trans-beta-caryophyllene (51.0%), germacrene-D (32.8%), a-humulene (3.1%), delta-cadinene (2.1%) and delta-elemene (2.1%). The antimicrobial activity of the essential oil, trans-beta-caryophyllene and five different extracts of the aerial parts of S. cretica L. subsp. smyrnaea were investigated by the standard disc diffusion method. The essential oil and trans-beta-caryophyllene exhibited antibacterial and antifungal activities. The activity increased with increasing concentrations of the essential oil and the extracts. The essential oil showed antimicrobial activity, particularly against Pseudomonas aeruginosa and Bacillus subtilis. The extracts exhibited either moderate or no activity.