Bioactivity-Guided Isolation of Antimicrobial and Antioxidant Metabolites from the Mushroom Tapinella atrotomentosa

Béni, Zoltán; Dékány, Miklós; Kovacs, Beatrix; Csupor-Löffler, Boglárka; Zomborszki, Zoltán Péter; Kerekes, Erika Beáta; Szekeres, András; Urbán, Edit; Hohmann, Judit; Ványolós, Attila

doi:10.3390/molecules23051082

Cited by 31 publications

(26 citation statements)

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“…For the antimicrobial analyses, the pure synthesized compounds were dissolved in MeOH and diluted with H 2 O to reach concentration levels up to 400 and 40 µg/mL with a final MeOH content of 10%. Then, these test solutions were investigated in a microdilution assay with two Gram-positive bacteria (Bacillus subtilis SZMC 0209 and Staphylococcus aureus SZMC 14611), two Gram-negative bacteria (Escherichia coli SZMC 6271 and Pseudomonas aeruginosa SZMC 23290), and two yeast strains (Candida albicans SZMC 1533 and C. krusei SZMC 1352) according to the M07-A10 CLSI guideline [76] and our previous work [57,77]. For the assay, the suspensions of the microbes were prepared from overnight cultures that were cultivated in a ferment broth (bacteria: 10 g/L peptone, 5 g/L NaCl, 5 g/L yeast extract; yeast: 20 g/L peptone, 10 g/L yeast extract, and 20 g/L glucose) at 37 • C, and their concentrations were set to 2 × 10 5 cells/mL with sterile media.…”

Section: Antimicrobial Analysesmentioning

confidence: 99%

“…(3R,3aR,6R,7aS)-6-Methyl-3-((((R)-1-phenylethyl)amino)methyl)octahydrobenzofuran-3-ol(7) Yield: 65%, white crystals, m.p. :[77][78][79][80][81] • C. [α] 20 D = +27.0 (c 0.25, MeOH). 1 H NMR (500 MHz, CDCl 3 ): δ = 0.78-0.87 (1H, m), 0.86 (3H, d, J = 6.5 Hz), 0.98-1.06 (1H, m), 1.12-1.18 (1H, m), 1.38 (3H, d, J = 6.6 Hz), 1.45-1.50 (1H, m), 1.51-1.63 (3H, m), 1.66-1.72 (1H, m), 2.00-2.05 (1H, m), 2.42 (1H, d, J = 12.1 Hz), 2.77 (1H, d, J = 12.1 Hz), 3.64 (1H, d, J = 9.5 Hz), 3.70 (1H, d, J = 9.6 Hz), 3.79 (1H, q, J = 6.5 Hz), 4.37 (1H, q, J = 3.0 Hz), 7.25-7.35 (5H, m).…”

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confidence: 99%

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Synthesis and Application of 1,2-Aminoalcohols with Neoisopulegol-Based Octahydrobenzofuran Core

et al. 2019

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A library of 1,2-aminoalcohol derivatives with a neoisopulegol-based octahydrobenzofuran core was developed and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The allylic chlorination of (+)-neoisopulegol, derived from natural (-)-isopulegol followed by cyclization, gave the key methyleneoctahydrobenzofuran intermediate. The stereoselective epoxidation of the key intermediate and subsequent oxirane ring opening with primary amines afforded the required 1,2-aminoalcohols. The ring closure of the secondary amine analogues with formaldehyde provided spiro-oxazolidine ring systems. The dihydroxylation of the methylenetetrahydrofuran moiety with OsO 4 /NMO (4-methylmorpholine N-oxide) resulted in the formation of a neoisopulegol-based diol in a highly stereoselective reaction. The antimicrobial activity of both the aminoalcohol derivatives and the diol was also explored. Molecules 2020, 25, 21 2 of 14 antimalarial [26-28], and antileishmanial [29] agents. The 1,2-aminoalcohol function is found in a broad range of β-adrenergic blockers that are used extensively in the management of cardiovascular disorders [30], including hypertension, angina pectoris and cardiac arrhythmias, and other disorders that are related to the sympathetic nervous system [31,32]. 1,2-aminoalcohols have also been demonstrated to be excellent chiral auxiliaries and chiral catalysts in asymmetric synthesis [33]. To achieve new, efficient, and commercially available chiral catalysts, natural chiral terpenes, such as α-pinene [34-38], β-pinene [34,39], (-)-3-carene [39,40], (-)-verbenone [41,42], (-)-fenchone [43,44], (+)-camphor [43,45,46], and (-)-menthone [47] have proven to be excellent sources for the synthesis of bifunctional chiral compounds and heterocycles.In the present work, we set out to create a compound library with a (+)-neoisopulegol-based octahydrobenzofuran core and 1,2-aminoalcohol moieties. The synthesis started from commercially available (-)-isopulegol and then utilizing the resulting 1,2-aminoalcohol derivatives as chiral catalysts in the enantioselective addition of diethylzinc to benzaldehyde. Furthermore, the antimicrobial activities of the synthesized compounds were also tested on multiple bacterial and fungal strains. Results Synthesis of Key Intermediate 3Key intermediate (-)-3-methylenetetrahydrofuran 3 was prepared from commercially available (-)-isopulegol 1 by oxidizing its hydroxyl function, followed by the stereoselective reduction of the resulting carbonyl group, thus providing (+)-neoisopulegol 2 [48][49][50][51]. The allylic chlorination of (+)-neoisopulegol 2 was followed by the cyclization-produced (-)-methylenetetrahydrofuran 3 [52-55], which was transformed into (−)-methylenetetrahydrofuran 4 by allylic oxidation after applying the literature method [55,56] (Figure 1).

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Section: Antimicrobial Analysesmentioning

confidence: 99%

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confidence: 99%

Synthesis and Application of 1,2-Aminoalcohols with Neoisopulegol-Based Octahydrobenzofuran Core

et al. 2019

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“…It has been found that mushrooms also have various pharmacological properties in addition to their nutritional value. Previous studies have reported that mushrooms had antioxidant, antimicrobial, anticancer, antiproliferative, DNA-protective, antiallergic, analgesic, antitumor, immunosuppressive, antiatherogenic, hypoglycemic, anti-inflammatory, hepatoprotective activities (Yang et al 2008, Hetland et al 2011, Patel and Goyal 2012, Ren et al 2012, Li et al 2013, Soares et al 2013, Sun et al 2014, Elsayed et al 2014, Yıldız et al 2015, Bal et al 2017, Béni et al 2018. Also, it has been found that Lycoperdon sp.…”

Section: Introductionmentioning

confidence: 96%

The Antioxidant potential of ethanolic extract of edible mushroom Lycoperdon molle Pers. (Agaricomycetes)

Bal¹,

Akgül²,

Sevindik³

2019

Eurasian Journal of Forest Science

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Mushroom play an important role in the decay of organic cover in forest ecosystems. In addition, mushrooms which are forest products are consumed as food. This study aims to determine the antioxidant activity of ethanol (EtOH) extract from edible Lycoperdon molle Pers. mushroom collected from Antalya (Turkey). Total antioxidant status (TAS), total oxidant status (TOS) and the oxidative stress index (OSI) were analyzed using Rel Assay Diagnostics kits. In addition, free radical scavenging activity was determined using the DPPH method. As a result of the studies, TAS, TOS and OSI values of L. molle were 1.855±0.072, 2.201±0.085 and 0.119±0.008, respectively. The free radical scavenging activity of the fungus was at a normal level in comparison to the standards used, i.e. rosmarinic and caffeic acids. Consequently, it was determined that L. molle may be used as a source of natural antioxidants. As a result, it was determined that edible L. molle, which is one of the forest products, has antioxidant potential in addition to its nutritional properties.

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“…More than 300 types of mushrooms with different biological activities have been identified as folk medicines in the literature. Mushrooms are rich in several bioactive compounds such as polysaccharides, phenols, terpenoids, and ergosterols which have exhibited several activities including anti‐diabetic, immunity‐stimulating, antitumor, antioxidant, antimicrobial, antihyperlipidemic, anti‐hypercholesterolemic, hepatoprotective, and anti‐inflammatory activities (Beni et al, ; Cheung, ; Duru & Tel Çayan, ; Kim, Park, Min, & Shim, ; Lindequist, ; Maljuric et al, ; Nguyen, Im, Choi, Shin, & Lee, ; Song et al, ; Wasser & Weis, ).…”

Section: Introductionmentioning

confidence: 99%

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

Tel‐Çayan

2019

J Food Biochem

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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•, β‐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.

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Bioactivity-Guided Isolation of Antimicrobial and Antioxidant Metabolites from the Mushroom Tapinella atrotomentosa

Cited by 31 publications

References 21 publications

Synthesis and Application of 1,2-Aminoalcohols with Neoisopulegol-Based Octahydrobenzofuran Core

Synthesis and Application of 1,2-Aminoalcohols with Neoisopulegol-Based Octahydrobenzofuran Core

The Antioxidant potential of ethanolic extract of edible mushroom Lycoperdon molle Pers. (Agaricomycetes)

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

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