scholarly journals Antimicrobial Properties of Spent Hops Extracts, Flavonoids Isolated Therefrom, and Their Derivatives

Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 2059 ◽  
Author(s):  
Agnieszka Bartmańska ◽  
Ewa Wałecka-Zacharska ◽  
Tomasz Tronina ◽  
Jarosław Popłoński ◽  
Sandra Sordon ◽  
...  

Hop cones preparations possess a wide range of biological activities including antimicrobial properties. In this work, we evaluated the effect of various organic extracts obtained from spent hops, as well as six hops flavonoids and their twenty natural and synthetic derivatives on human and plant microbial pathogens. Methylene chloride, acetone, ethyl acetate, and methanol were used as extractants. Seven flavonoids, among them two natural (α,β-dihydroxanthohumol and 8-prenylnaringenin) showed significant activity against methicillin sensitive and resistant Staphylococcus aureus and Staphylococcus epidermidis strains with the lowest MIC80 value of 0.5 µg/mL. The crude ethyl acetate, acetone, and methanol extracts from the spent hops exhibited antifungal activity against Fusarium oxysporum, F. culmorum, and F. semitectum with the lowest MIC50 of 0.5 mg/mL, while the methylene chloride extract exerted antifungal activity against Botrytis cinerea with the MIC50 of 1 mg/mL. The preparation obtained after the removal of xanthohumol from the spent hops crude extracts retained up to 95% of activity. These findings suggest that various spent hops extracts may be effective agents for the control of plant pathogens of economic importance, like Botrytis cinerea and Fusarium oxysporum, while some compounds from spent hops or their derivatives may become useful for staphylococcal infections.

2021 ◽  
Vol In Press (In Press) ◽  
Author(s):  
Sedigheh Akbarnezhad Ghareh Lar ◽  
Nakisa Zarrabi Ahrabi ◽  
Yasin SarveAhrabi

Background: Acinetobacter bumanni is one of the most common opportunistic pathogens in health centers that is resistant to many antibiotics due to biofilm production. 1, 3, 4-oxadiazoles have a wide range of biological activities. Objectives: The aim of this research was to examine the impact of new 1, 3, 4-oxadiazole derivatives on the expression of biofilm-associated surface protein (Bap), playing an important role in promoting the biofilm formation ability of A. baumannii strains. Methods: Derivatives of 1, 3, 4-oxadiazole were synthesized through a one-step synthesis. A. baumannii strains were identified and isolated in the laboratory. The antimicrobial properties of the synthesized materials against the isolated strains were investigated. DNA, RNA, and cDNA were extracted, and the relative expression of BAP gene in A. baumannii isolates was evaluated by real-time polymerase chain reaction. Results: The compound with methoxyphenyl functional group with MIC = 62.50 mg/mL had the best inhibitory performance among all derivatives. Also, the combination of 4i reduced the expression of the Bap gene by about 24 times, but it had no effect on the expression of the 16srRNA housekeeping gene. Conclusions: 1, 3, 4-oxadiazole derivatives, especially the methoxyphenyl functional group, act as an inhibitor of bacterial biofilm formation and have the potential to be used in the pharmaceutical and biological industries.


2020 ◽  
Vol 17 (34) ◽  
pp. 528-540
Author(s):  
Ekhlas Q JASIM ◽  
Hawraa K DHAIF ◽  
Munther A MUHAMMAD-ALI

Schiff bases (SB) are an important type of organic compounds and have a wide range of biological activities due to commercial and pharmaceutical trading uses. The different activities of these compounds induced the researchers to synthesized and studied new types of these compounds. Two series of Schiff base derivatives were synthesized by the condensation reactions of substituted aldehydes salicylaldehyde, 4-(N,Ndimethylamino) benzaldehyde or 2,4-dimethoxybenzaldehyde with 2-amino-5-iodobenzoic acid (1:1) or with 3,5- diamenobenzoic acid (1:2) in ethanol absolute as a solvent. Different analytical techniques characterized the structure of the synthesized Schiff bases; for instance, Fourier transform infrared FT-IR and proton nuclear magnetic resonance 1H-NMR. The purity of the synthesized compounds was tested by elemental microanalysis CHN and thin layer chromatography TLC. The structural properties of the studied molecules were investigated theoretically by performing density functional theory (DFT) using the HyperChem software. The lipophilicity of the tested compounds showed that the compounds 2c, 2b, 2a, and 1c have logP values less than (5), 2.90, 3.78, 3.82 and 4.57, respectively, whereas, 1b and 1a have logP values higher than (5), 5.01 and 5.03, respectively. The Mulliken charge distribution showed that the carbonyl oxygen atom of the carboxylic group is more negative (~ - 0.4) as compared to other oxygen atoms (~ -0.3) in all selected compounds. Frontier molecular orbitals energy diagram and their bandgap provided indications about chemical reactivity and kinetic stability of the molecules. The synthesized compounds were tested for antifungal effects against Aspergillus niger and Candida albicans, which indicated that the compounds had good antifungal activity.


2012 ◽  
Vol 59 (2) ◽  
pp. 51-58 ◽  
Author(s):  
Alicja Saniewska ◽  
Anna Jarecka ◽  
Zbigniew Biały ◽  
Marian Jurzysta

Antifungal activity of total saponins originated from roots of <i>Medicago hybrida</i> (Pourret) Trautv. were evaluated <i>in vitro</i> against six pathogenic fungi and eight individual major saponin glycosides were tested against one of the most susceptible fungi. The total saponins showed fungitoxic effect at all investigated concentrations (0.01%, 0.05% and 0.1%) but their potency was different for individual fungi. The highest saponin concentration (0.1%) was the most effective and the inhibition of <i>Fusarium oxysporum</i> f. sp. <i>callistephi</i>, <i>Botrytis cinerea</i>, <i>Botrytis tulipae</i>, <i>Phoma narcissi</i>, <i>Fusarium oxysporum</i> f. sp. <i>narcissi</i> was 84.4%, 69.9%, 68.6%, 57.2%, 55.0%, respectively. While <i>Fusarium oxysporum</i> Schlecht., a pathogen of <i>Muscari armeniacum</i>, was inhibited by 9.5% only. Eight major saponin glycosides isolated from the total saponins of <i>M. hybrida</i> roots were tested against the mycelium growth of <i>Botrytis tulipae</i>. The mycelium growth of the pathogen was greatly inhibited by hederagenin 3-O-<i>β</i>-D-glucopyranoside and medicagenic acid 3-O-<i>β</i>-D-glucopyranoside. Medicagenic acid 3-O-<i>β</i>-D-glucuronopyranosyl-28-O-<i>β</i>-D-glucopyranoside and oleanolic acid 3-O-[<i>β</i>-D-glucuronopyranosyl(1→2)-<i>α</i>-L-galactopyranosyl]-28-O-<i>β</i>-D-glucopyranoside showed low fungitoxic activity. Medicagenic acid 3-O-a-D-glucopyranosyl- 28-O-β-D-glucopyranoside, hederagenin 3-O-[α-L- hamnopyranosyl(1→2)-β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl]- 28-O-α-D-glucopyranoside and hederagenin 3-O-<i>β</i>-D-glucuronopyranosyl-28-O-<i>β</i>-D- lucopyranoside did not limit or only slightly inhibited growth of the tested pathogen. While 2<i>β</i>, 3<i>β</i>-dihydroxyolean-12 ene-23-al-28-oic acid 3-O-<i>β</i>-D-glucuronopyranosyl-28-O-<i>β</i>-D-glucopyranoside slightly stimulated mycelium growth of <i>B. tulipae</i>.


2019 ◽  
Vol 17 (1) ◽  
pp. 79-84 ◽  
Author(s):  
Elvira Rifovna Shakurova ◽  
Darina Alexandrovna Pozdnyakova ◽  
Elena Valeryevna Tretyakova ◽  
Lyudmila Vyacheslavovna Parfenova

Background: A wide range of biological activity, relatively low toxicity and multiple pharmacological effects of triterpenoids are major advantages of these compounds in the prevention and treatment of various diseases. They include the lupane- type triterpenoids that proved to be a promising platform for the synthesis of analogs with a wide range of biological activities, including anti-inflammatory, antitumor, antiparasitic and antiviral properties. The main disadvantage complicating the use of all known derivatives of lupane acids in medical practice is low bioavailability associated with poor solubility in biologic fluids, limiting their effective interaction with the biological targets. Objective: The objective of this study is the synthesis of new amphiphilic betulin derivatives on the base of pyridinium salts with antifungal and antibacterial activity. Methods: In this study we have developed an effective one-pot method for the preparation of new quaternized pyridine derivatives 4-6 of the betulinic series based on the reaction of the initial triterpenes 1-3 with the Tempo+Br3 - reagent in the pyridine. The synthesized and initial compounds were tested for their antimicrobial and antifungal activity. Results: The data presented in this document indicate that all synthesized compounds 4-6 exhibited high activity against both gram-positive Staphylococcus aureus bacteria and gram-negative Pseudomonas aeruginosa strains, as well as Candida albicans and Cryptococcus neoformans fungi with the >90% coverage of the inhibition zone. The best result in a series of compounds 4-6 was found for the derivative 6 at the minimum inhibitory concentration of 1 µg/ml against S. aureus bacteria, C. albicans and C. neoformans fungi at the concentration of 8 µg/ml. Conclusion: Thus, we have demonstrated the first example of the pyridine quaternization using the betulin triterpenoids as the lipophilic substrates and Tempo+Br3 - cation. The obtained quaternized pyridine analogs of betulin triterpenes showed high antibacterial and antifungal activity in comparison with the initial compounds.


Author(s):  
Manoj N. Bhoi ◽  
Mayuri A. Borad ◽  
Neha K. Panchal ◽  
Hitesh D. Patel

The benzothiazole and Schiff base moieties are crucial functionalities due to their wide variety of biological activities and have a wide range of therapeutic properties. Keeping in view the importance of these organic moieties, a new series of 2-Aminobenzothiazole containing novel Schiff bases derivatives were synthesized by sequential reaction. The structures of the synthesized compounds were confirmed by their analytical and spectral data. The synthesized compounds were evaluated for their in vitro antibacterial activity against gram positive and gram negative bacteria. Synthesized compounds showed significant activity against microorganisms, which can be correlated with the privileged heterocyclic structural scaffolds.


2020 ◽  
Vol 9 (2) ◽  
pp. 1111-1116

The current study investigated the phytochemical analysis, chemical composition, antioxidant, cytotoxic and antifungal activity of Trichilia emetica seed extracts. Preliminary phytochemical screening and quantification were realized by GC-MS. Consecutive extractions (methanol, ethanol, ethyl acetate, hexane, chloroform and distilled water) were carried out and phytochemical tests performed to represent the variety of phytochemicals. Seed extracts variably displayed alkaloids, cardiac glycosides, phenols, sterols, terpenoids and flavonoids but there was no indication of saponins and tannins in all extracts. The biological investigation of the methanolic extract showed significant biological activities. The results obtained revealed that methanol extract has presented significant IC50 =5.94 µg/mL radical scavenging activity. Minimum inhibitory concentration (MIC) of hexane and chloroform fractions displayed antifungal activity (40.95-100 and 76.27-100.11, respectively) against all three fungal pathogens, whilst the methanol extract inhibited C. krusei and C. parapsilosis and the ethyl acetate inhibited C. parapsilosis only. The results obtained revealed the medicinal importance of the plant and methanol extract of T. emetica would aid researchers to exploit as potential antifungal and antioxidant agent.


2021 ◽  
Vol 10 (1) ◽  
Author(s):  
Luce Mattio ◽  
Giorgia Catinella ◽  
Marcello Iriti ◽  
Lisa Vallone

Stilbenoids (resveratrol and its derivatives) are secondary metabolites produced by plants as defence mechanism to microbial infection. These compounds are known for their anti-inflammatory action and health benefits in preventing a wide range of disorders (e.g. cancer and cardiovascular diseases). However, their antimicrobial properties are less investigated. A series of 8 stilbenoid compounds were synthesized and their antifungal activity against 19 wild strains of filamentous fungi and yeasts (isolated from the environment and food) was tested in vitro. Using an agar diffusion assay, compounds were tested at the concentration of 100 μg/ml on filamentous fungi and yeasts at 104 CFU/ml. The results showed that tested derivatives possess moderate antifungal activity: in particular, monomeric stilbenoids 3’-hydroxy-pterostilbene and piceatannol, and dimeric stilbenoids (±)-trans-δ-viniferin and pallidol were active against mycotoxigenic fungi.


Molecules ◽  
2021 ◽  
Vol 26 (16) ◽  
pp. 4937
Author(s):  
Narcisa Mandras ◽  
Janira Roana ◽  
Daniela Scalas ◽  
Simonetta Del Re ◽  
Lorenza Cavallo ◽  
...  

The epidemiology of yeast infections and resistance to available antifungal drugs are rapidly increasing, and non-albicans Candida species and rare yeast species are increasingly emerging as major opportunistic pathogens. In order to identify new strategies to counter the threat of antimicrobial resistant microorganisms, essential oils (EOs) have become an important potential in the treatment of fungal infections. EOs and their bioactive pure compounds have been found to exhibit a wide range of remarkable biological activities. We investigated the in vitro antifungal activity of nine commercial EOs such as Thymus vulgaris (thyme red), Origanum vulgare (oregano), Lavandula vera (lavender), Pinus sylvestris (pine), Foeniculum vulgare (fennel), Melissa officinalis (lemon balm), Salvia officinalis (sage), Eugenia caryophyllata (clove) and Pelargonium asperum (geranium), and some of their main components (α-pinene, carvacrol, citronellal, eugenol, γ-terpinene, linalool, linalylacetate, terpinen-4-ol, thymol) against non-albicans Candida strains and uncommon yeasts. The EOs were analyzed by GC-MS, and their antifungal properties were evaluated by minimum inhibitory concentration and minimum fungicidal concentration parameters, in accordance with CLSI guidelines, with some modifications for EOs. Pine exhibited strong antifungal activity against the selected non-albicans Candida isolates and uncommon yeasts. In addition, lemon balm EOs and α-pinene exhibited strong antifungal activity against the selected non-albicans Candida yeasts. Thymol inhibited the growth of all uncommon yeasts. These data showed a promising potential application of EOs as natural adjuvant for management of infections by emerging non-albicans Candida species and uncommon pathogenic yeasts.


2014 ◽  
Vol 5 (2) ◽  
Author(s):  
Widya Lestari

Endophytic fungi are a group of fungi whose part or whole life is in living plant tissue and usually does not harm the host. Endophytic fungi generally produce secondary metabolites that have beneficial biological activities such as anti-cancer compounds, antifungi or antibacterials. Control of plant diseases caused by Rigidoporus microporus and Ganoderma boninense can be done by using biological agents, namely by using endophytic fungi. This fungus has metabolite compounds that can inhibit the growth of Rigidoporus microporus and Ganoderma boninense. This study aims to determine what content is found in endophytic mushroom extracts isolated from rubber plants (Hevea brasiliensis). Endophytic fungi are extracted by maceration using methanol and ethyl acetate solvents. The extract was tested for antifungal activity using diffusion method. The content of secondary metabolites was tested by phytochemical test. The results of endophytic fungal extraction with methanol and ethyl acetate solvents resulted in antifungal activity with inhibitory zones in a row namely WL01: 2.19 and 2.15 mm Fungi Isolates on Ganoderma boninense while 3.09 mm WL02 against Rigidoporus microporus Based on the phytochemical test results, endophytic fungal extract with methanol and ethyl acetate solvents showed the presence of alkaloid, flavonoid, phenol and saponin. Keywords: endofit, fungi, hevea, secondary metabolites


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