Antifungal Antibiotics from Calcarisporium thermophilum: A New Source of 15-Azahomosterol Derivatives

1990 ◽  
Vol 45 (3-4) ◽  
pp. 179-186 ◽  
Author(s):  
Paul Chrisp ◽  
Paul M. Dewick ◽  
F. Tom Boyle
Keyword(s):  
Antifungal Activity ◽  
Antifungal Metabolites ◽  
Ms Analysis ◽  
Antifungal Antibiotics ◽  
Spectral Comparison

Abstract Two antifungal metabolites isolated from Calcarisporium thermophilum were identified as 15-azahom osterols related to the compounds previously isolated from Geotrichum Jlavo-brun-neum. By full spectral comparison with authentic 15-aza-24-methylene-D-homocholesta-8,14-dien-3 β-ol (A 25822 B) from G. flavo-brunneum, the Calcarisporium metabolites were characterized as the 4a-m ethyl-and 4,4-dimethyl-analogues of A 25822 B. Several minor members of the series were also detected, and tentatively identified by MS analysis. The 15-azahom osterols exhibited good antifungal activity towards Candida parapsiliosis, though the activities were somewhat lower than that of the 4-demethyl derivative A 25822 B. Calcarisporium thermophi­lum is the second microorganism known to synthesize these unusual 15-azahomosterol deriva­tives.

scholarly journals GC-MS ANALYSIS AND ANTIFUNGAL ACTIVITY OF METHANOLIC ROOT EXTRACT OF Chenopodium album AGAINST Sclerotium rolfsii

2017 ◽  
Vol 35 (0) ◽  
Author(s):  
A. ALI ◽  
A. JAVAID ◽  
A. SHOAIB
Keyword(s):  
Antifungal Activity ◽  
Methyl Ester ◽  
Environmental Pollution ◽  
Chenopodium Album ◽  
Octadecenoic Acid ◽  
Sclerotium Rolfsii ◽  
Gas Chromatography Mass Spectrometry ◽  
Root Extract ◽  
Malt Extract ◽  
Ms Analysis

ABSTRACT Sclerotium rolfsii is a soil-borne fungal plant pathogen that causes diseases in more than 500 plant species. Chemical fungicides used to control this disease cause environmental pollution, therefore, plant derived compounds can be used as alternative to synthetic fungicides to reduce environmental pollution. Chenopodium album is a weed of family Chenopodiaceae that is used as food and also has medicinal importance. In the present study, antifungal activity of methanolic root extract of C. album was evaluated against S. rolfsii using six concentrations viz. 0.5, 1.0, 1.5, 2.0, 2.5 and 3.0 g 100 mL-1 amended in malt extract as growth medium. All the root extract concentrations significantly reduced fungal biomass by 15-58% over control. Gas chromatography-mass spectrometry (GC-MS) analysis of the methanolic root extract of C. album was performed. Six compounds were identified in methanolic root extract through GC-MS analysis. The most abundant compound was 1,2-benzenedicarboxylic acid, mono(2-ethylhexyl) ester (58.56%) followed by 9-octadecenoic acid (Z)-, methyl ester (12.75%) and 9-octadecenoic acid (Z)-, methyl ester (10.27%), which might be responsible for antifungal activity of methanolic root extract of C. album.

scholarly journals Aspergillus piperis A/5 from plum-distilling waste compost produces a complex of antifungal metabolites active against the phytopathogen Pythium aphanidermatum

2016 ◽  
Vol 68 (2) ◽  
pp. 279-289 ◽  
Author(s):  
Jelena Jovicic-Petrovic ◽  
Sanja Jeremic ◽  
Ivan Vuckovic ◽  
Sandra Vojnovic ◽  
Aleksandra Bulajic ◽  
...  
Keyword(s):  
Citric Acid ◽  
Solvent Extraction ◽  
Antifungal Activity ◽  
Aqueous Phase ◽  
Plant Pathogens ◽  
Complex Mixture ◽  
Pythium Aphanidermatum ◽  
Disease Suppression ◽  
Antifungal Metabolites ◽  
Culture Extract

Adding compost to soil can result in plant disease suppression through the mechanisms of antagonistic action of compost microflora against plant pathogens. The aim of the study was to select effective antagonists of Pythium aphanidermatum from compost, to assess the effect of its extracellular metabolites on the plant pathogen, and to characterize antifungal metabolites. The fungal isolate selected by a confrontation test was identified as Aspergillus piperis A/5 on the basis of morphological features and the internal transcribed spacer (ITS) region, ?-tubulin and calmodulin partial sequences. Liquid chromatography-mass spectroscopy (LC-MS) analysis showed that gluconic and citric acid were the most abundant in the organic culture extract. However, the main antifungal activity was contained in the aqueous phase remaining after the organic solvent extraction. The presence of considerable amounts of proteins in both the crude culture extract as well as the aqueous phase remaining after solvent extraction was confirmed by SDS-PAGE. Isolated Aspergillus piperis A/5 exhibits strong antifungal activity against the phytopathogen Pythium aphanidermatum. It secretes a complex mixture of metabolites consisting of small molecules, including gluconic acid, citric acid and itaconic acid derivatives, but the most potent antifungal activity was associated with proteins resistant to heat and organic solvents. Our findings about the activity and characterization of antagonistic strain metabolites contribute to the understanding of the mechanism of interaction of antifungal metabolites as well as fungal-fungal interaction. The obtained results provide a basis for further application development in agriculture and food processing.

scholarly journals Antifungal Evaluation and Molecular Docking Studies of Olea europaea Leaf Extract, Thymus vulgaris and Boswellia carteri Essential Oil as Prospective Fungal Inhibitor Candidates

Molecules ◽  
2021 ◽  
Vol 26 (20) ◽  
pp. 6118
Author(s):  
Hanaa S. Omar ◽  
Soheir N. Abd El-Rahman ◽  
Sheikha M. AlGhannam ◽  
Mohamed S. Sedeek
Keyword(s):  
Molecular Docking ◽  
Antifungal Activity ◽  
Essential Oil ◽  
Olea Europaea ◽  
Leaf Extract ◽  
Thymus Vulgaris ◽  
Chemical Compositions ◽  
Docking Analysis ◽  
Ms Analysis ◽  
Olea Europaéa

Background: The present study investigated the antifungal activity and mode of action of four Olea europaea leaf extracts, Thymus vulgaris essential oil (EO), and Boswellia carteri EO against Fusarium oxysporum. Methods:Fusarium oxysporum Lactucae was detected with the internal transcribed spacer (ITS) region. The chemical compositions of chloroform and dichloromethane extracts of O. europaea leaves and T. vulgaris EO were analyzed using GC-MS analysis. In addition, a molecular docking analysis was used to identify the expected ligands of these extracts against eleven F. oxysporum proteins. Results: The nucleotide sequence of the F. oxysporum Lactucae isolate was deposited in GenBank with Accession No. MT249304.1. The T. vulgaris EO, chloroform, dichloromethane and ethanol efficiently inhibited the growth at concentrations of 75.5 and 37.75 mg/mL, whereas ethyl acetate, and B. carteri EO did not exhibit antifungal activity. The GC-MS analysis revealed that the major and most vital compounds of the T. vulgaris EO, chloroform, and dichloromethane were thymol, carvacrol, tetratriacontane, and palmitic acid. Moreover, molecular modeling revealed the activity of these compounds against F. oxysporum. Conclusions: Chloroform, dichloromethane and ethanol, olive leaf extract, and T. vulgaris EO showed a strong effect against F. oxysporum. Consequently, this represents an appropriate natural source of biological compounds for use in healthcare. In addition, homology modeling and docking analysis are the best analyses for clarifying the mechanisms of antifungal activity.

scholarly journals Chemical structure and antifungal activity of mint essential oil components

2020 ◽  
Vol 85 (9) ◽  
pp. 1149-1161
Author(s):  
Dragana Plavsic ◽  
Marija Skrinjar ◽  
Djordje Psodorov ◽  
Lato Pezo ◽  
Ivan Milovanovic ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Essential Oil ◽  
Chemical Structure ◽  
Coefficient Of Determination ◽  
Mentha Piperita ◽  
Training Cycle ◽  
Ms Analysis ◽  
Structure Retention ◽  
Quantitative Structure Retention Relationship ◽  
Essential Oil Compounds

The objective of this research was to determine chemical composition and to evaluate the antifungal activity of essential oil of Mentha piperita. By the application of GC/MS analysis of essential mint oil, 27 components were identified. The major components were menthol (39.9 %), menton (23.51 %), menthyl acetate (7.29 %), 1.8-cineol (5.96 %), isomenton (5.24 %), isomenthol (3.17 %), trans-caryophyllene (2.88 %), limonene (2.14 %), pulegon (1.38 %), beta-pinene (1.14 %) and piperiton (1.03 %). The quantitative structure? retention relationship (QSRR) was employed to predict the retention time (RT) of Mentha piperita essential oil compounds obtained in GC/MS analysis, using twelve molecular descriptors selected by genetic algorithm. The selected descriptors were used, as inputs of an artificial neural network, to build an RT predictive QSRR model. The coefficient of determination was 0.983, during training cycle, indicating that this model could be used for prediction of RT values for essential oil compounds in Mentha piperita essential oil extracts. Essential oil of Mentha piperita showed antifungal activity on all tested isolates in the minimal inhibitory concentration range of 0.2?1.7 ?l/ml and a minimal fungicidal concentration (MFC) range of 1.7?454.5 ?l/ml. The most powerful antifungal activity of mint was observed in C. cladosporioides of MFC value 1.7 ?l/ml. P. aurantiogriseum showed the lowest sensitivity of MFC value 454.5 ?l/ml.

scholarly journals The study of the antifungal activity of the Bacillus subtilis BZR 336g strain under the conditions of periodic cultivation with the addition of citric acid, corn extract and some microelements

2020 ◽  
Vol 21 ◽  
pp. 00015
Author(s):  
Anzhela Asaturova ◽  
Evgeny Gyrnets ◽  
Valeria Allakhverdian ◽  
Mikhail Astakhov ◽  
Ksenia Saenko
Keyword(s):  
Bacillus Subtilis ◽  
Citric Acid ◽  
Antifungal Activity ◽  
Liquid Culture ◽  
Complex Interaction ◽  
Crystalline Hydrate ◽  
Antifungal Metabolites ◽  
Qualitative And Quantitative ◽  
Test Culture ◽  
Combined Use

We studied the antifungal activity of the Bacillus subtilis BZR 336g strain against the test culture of the fungus Fusarium oxysporum var. orthoceras App. et Wr. BZR 6, depending on the addition of citric acid crystalline hydrate, a microelements solution and corn extract to the liquid nutrient medium. It was found that citric acid at a concentration of 15 g/l improves the bioavailability of microelements and increases antifungal activity. Corn extract and microelements without the formation of a chelate form with citric acid do not affect the fungicidal properties of B. subtilis BZR 336g. However, the corn extract at a concentration of 3 g / l increases the titer of bacteria in the liquid culture from 2 ± 0.1 × 108 to 1 ± 0.08 × 108 CFU/ml. The combined use of the studied components allowed us to achieve a significant increase in the antifungal activity of B. subtilis BZR 336g by 3.1 times. At the same time, the effect of synergism in their complex interaction was noted, which is probably due to a qualitative and quantitative change in the composition of B. subtilis BZR 336g antifungal metabolites.

In Vitro Antifungal Activity of Clove Oil against Candida Albicans Isolated from Clinical Samples

2018 ◽  
Vol 11 (2) ◽  
pp. 4021-4025
Author(s):  
Noura Berakdar ◽  
Abdulkarim Radwan
Keyword(s):  
Candida Albicans ◽  
Antifungal Activity ◽  
In Vitro Study ◽  
Inhibition Zone ◽  
University Hospital ◽  
Vaginal Candidiasis ◽  
Clinical Samples ◽  
Clove Oil ◽  
Antifungal Antibiotics

The main goal of this study was to investigate the antifungal activity of clove oil against candida albicans of vaginal candidiasis in females from Syria. An in vitro study was carried out using the following Candida albicans strains involved in vaginal candidiasis using the well diffusion (WD) testing.Candida albicans (ATCC 90028) and 15 strains were compiled from Aleppo University Hospital. These strains were collected from women having vaginal candidiasis. The antifungal activity of clove oil was determined in the form of inhibition zone using antifungal assay by agar WD testing.In all experiments, the obtained results indicated that clove oil has inhibitory effects on Candida albicans (ATCC 90028) and against15 fungal strains. This study showed that clove oil was active against the tested Candida albicans strains. Clove oil was more effective against Candida albicans compared to the antifungal antibiotics nystatin, ketoconazole and itraconazol. Clove oil may have potential for use in the development of clinically useful antifungal preparations. Therefore, clove oil might be clinically effective in the natural prevention treatment of vaginal candidiasis.       

scholarly journals Antifungal Metabolites From Alternaria atrans: An Endophytic Fungus in Psidium guajava

2019 ◽  
Vol 14 (5) ◽  
pp. 1934578X1984411 ◽  
Author(s):  
Zhi Yang ◽  
Wen-Jia Dan ◽  
Yi-Xiao Li ◽  
Guang-Rui Peng ◽  
An-Ling Zhang ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Medicinal Plant ◽  
Inhibitory Activity ◽  
Colletotrichum Gloeosporioides ◽  
Fusaric Acid ◽  
Alternaria Solani ◽  
Psidium Guajava ◽  
Inhibitory Effect ◽  
Solid Culture ◽  
Antifungal Metabolites

Six metabolites (1–6), including 1 new fusaric acid derivative, designated atransfusarin (1), and 5 known compounds, (3 R,6 R)-3-benzyl-6-isopropyl-4-methylmorpholine-2,5-dione (2), daucoterol (3), adenosine (4), cerebroside B (5), and 2,3-dihydroxypropyl ( Z,Z)-9,12-octadecadienate (6), were isolated from the solid culture of an endophytic Alternaria atrans MP-7, associated with the medicinal plant Psidium guajava. The structure of the new compound was elucidated by spectral data. The antifungal test indicated that (3 R,6 R)-3-benzyl-6-isopropyl-4-methylmorpholine-2,5-dione (2) showed obvious inhibitory activity against Alternaria solani, Colletotrichum gloeosporioides, and Phyricularia grisea. Compared to fusaric acid (1a), even though the antifungal activity of atransfusarin (1) against A. solani, C. gloeosporioides, and P. grisea was greatly decreased, its inhibitory effect against Botrytis cinerea was still retained.

scholarly journals Chromatographic profiles of antifungal exo- and endometabolites of Bacillus velezensis

2021 ◽  
Vol 2(26) ◽  
pp. 191-199
Author(s):  
T.M. Sidorova ◽  
◽  
A.M. Asaturova ◽  
V.V. Allakhverdyan ◽  
◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Fusarium Oxysporum ◽  
Phytopathogenic Fungi ◽  
Antagonistic Activity ◽  
Active Metabolites ◽  
Fungicidal Action ◽  
Antifungal Metabolites ◽  
Alternaria Sp ◽  
Tlc Analysis

The antifungal activity of the Bacillus bacteria is based on their ability to produce metabolites. Therefore, when selecting a strain that produces an effective biofungicide, it is necessary to assess the metabolism of bacteria. The aim of this work is to isolate exo- and endometabolites of the promising B. velezensis BZR 336g and B. velezensis BZR 517 strains and assess their antifungal activity. Studies were carried out in 2020–2021. The object of the study is a liquid culture of the B. velezensis BZR 336g and B. velezensis BZR 517 strains. Methods of liquid extraction, ascending thin layer chromatography (TLC), bioautography with a test-culture of Fusarium oxysporum var. orthoceras and Alternaria sp. fungi were used to analyze metabolites. The ability of the strains to accumulate a complex of active metabolites showing antifungal effect from fungistatic to fungicidal action was revealed. On the bioautogram of exometabolites, we found two most pronounced zones (Rf 0.18 and 0.29) of Fusarium oxysporum var. orthoceras BZR P1 growth inhibition (fungicide). Zones with Rf 0.58 for B. velezensis BZR 336g and Rf 0.70 for B. velezensis BZR 517 correspond to the test fungus growth retardation (fungistatic). Significant suppression of Alternaria sp. BZR P8 growth was also observed in two zones (Rf 0.18 and 0.29). The use of surfactin, iturin A, fengycin (Sigma-Aldrich®) in the TLC analysis made it possible to detect similar lipopeptides in the composition of metabolite complexes produced by the studied bacteria. It should be noted that the studied strains differed both in their ability to produce metabolites of different structure (can be found when analyzing chromatograms under ultraviolet light) and in their effect on phytopathogenic fungi in vitro. This may indicate possible differences in the mechanism of antagonistic activity of bacteria against phytopathogenic fungi. Thus, B. velezensis BZR 336g and B. velezensis BZR 517 produce a significant set of antifungal metabolites and can be used as strains to produce effective biofungicides.

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