Study on Phenolic and Organic Acid Compositions and Antioxidant and Enzyme Inhibition Activities of Agaricomycetes Mushroom Species from Turkey.

Mushrooms stand out as one of nature's best gifts among the natural product sources with their diversity, therapeutic values and increasing popularity. In this study, antioxidant (ABTS·+ scavenging, ß-carotene-bleaching, cupric-reducing antioxidant capacity (CUPRAC), DPPH· scavenging, and metal chelating assays), and enzyme (buty-rylcholinesterase (BChE) and acetylcholinesterase (AChE), α-amylase and α-glucosidase) inhibition activities of the extracts obtained from Coprinus comatus (O.F. Müll.) Pers., Cerrena unicolor (Bull.) Murrill, Inocutis rheades (Pers.) Fiasson & Niemela and Leptoporus mollis (Pers.) Quél. mushroom species were investigated. The presence of phenolic and organic acid compounds associated with the bioactive properties of the mushroom species was determined by HPLC-DAD. Fumaric acid was found to be prominent compound in C. comatus (43.90 µg/g dw) and C. unicolor (659.9 µg/g dw), vanillin in L. mollis (19.48 µg/g dw), and p-coumaric acid in I. rheades (21.32 µg/g dw). L. mollis methanol extract, as well as higher antioxidant activity than the standards in CUPRAC and ß-carotene-bleaching assays, was noted as superior antioxidant active in all assays (except metal chelating). C. comatus possessed the highest inhibition activity on α-amylase (IC50: 0.23 mg/mL for methanol extract), AChE (IC50: 125.50 µg/mL for hexane extract), and BChE (IC50: 61.03 µg/mL for methanol extract). Also, C. comatus methanol (IC50: 0.09 mg/mL) and L. mollis hexane (IC50 : 0.11 mg/ mL) extracts were better α-glucosidase inhibition active than the acarbose (IC50: 0.37 mg/mL). Our study ascertained that the studied mushroom species are particularly sources of biochemically active compounds with therapeutic potential.

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.

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.

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 Composition, Antioxidant, Anticholinesterase and Anti-Tyrosinase Activities of Essential Oils of Two Sideritis Species from Turkey.

Sideritis species have been known as medicinal plants since ancient times, and used as tea in Mediterranean countries such as Turkey, Greece, and Spain. They are also used for the treatment of several ailments such as a cough, common cold, and gastrointestinal disorders. The aim of the present study was to perform the chemical composition, antioxidant, anticholinesterase, and anti-tyrosinase activities of the essential oils of Sideritis albiflora and S. leptoclada. ß-caryophyllene (21.2%) and Germacrene D (17.9%) were identified as the major compounds in S. albiflora and S. leptoclada essential oils, respectively. The essential oil of S. albiflora showed the highest lipid peroxidation inhibitory (IC50: 73.8 ± 0.8 µg/mL), DPPH free radical scavenging (28.3±0.1%), ABTS cation radical scavenging (IC50: 50.6 ± 1.0 µg/mL), reducing power (A0.05: 181.7 ± 0.6 µg/mL), acetylcholinesterase (22.1 ± 0.4%), butyrylcholinesterase (IC50: 157.2 ± 0.9 µg/mL) and tyrosinase (15.2 ± 0.4%) inhibitory activities. Moreover, S. albiflora essential oil had rich total phenolic and flavonoid contents indicating 41.5 ± 0.8 µg PEs/mg and 21.4 ± 1.0 µg QEs/mg respectively. This study suggests that consumption of Sideritis species as tea may protect one against melanogenesis, amnesia, and oxidative stress without any observable side effect.

Phenolic profiles, antioxidant, and anticholinesterase activities of three Gloeophyllum species with chemometric approach.

This study's aim was to determine the antioxidant and anticholinesterase activities of Gloeophyllum odoratum, Gloeophyllum sepiarium, and Gloeophyllum trabeum species with phenolic profiles. The major compound in G. odoratum (101.6 µg/g) and G. sepiarium (92.61 µg/g) mushrooms was fumaric acid, while ferulic acid was found as the main compound in G. trabeum (11.67 µg/g). The methanol extracts of Gloeophyllum species exhibited the highest activity in CUPRAC, DPPH• , ß-carotene-linoleic acid, and ABTS•+ assays while the n-hexane extracts showed the highest activity in the metal chelating assay. Also, the methanol extract of G. odoratum (IC50 : 32.16 ± 0.28 µg/mL) was found to be highly active than its antioxidant standard α-tocopherol (IC50 : 38.51 ± 0.54 µg/mL) in the ABTS•+ radical scavenging assay. All the studied Gloeophyllum species extracts were found to be moderate inhibitors against AChE, whereas G. sepiarium n-hexane extract (69.70 ± 1.92%) and G. odoratum n-hexane extract (58.08 ± 1.36%) exhibited potent BChE inhibitory activity. PRACTICAL APPLICATIONS: The results of these studies demonstrated that the methanol and the n-hexane extracts had a potential application as alternative natural products for pharmaceutical, food, and cosmetic industries. In addition, the chemometric analysis by principal component analysis and hierarchical clustering analysis techniques could be used for the classification of the extracts of Gloeophyllum according to their bioactivity results. This is the first comprehensive study on phenolic profiles and bioactivities of G. odoratum, G. sepiarium, and G. trabeum mushroom species.

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.

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.