Novel lactones from Aspergillus versicolor (original) (raw)
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Isolation of Bioactive Compounds from Aspergillus terreus LS07
Indonesian Journal of Chemistry, 2014
This study aims to search for the active components from Aspergillus terreus LS07 which isolated from an Indonesian soil. Bioassay-guided fractionations of the ethyl acetate (EtOAc) extract against α-glucosidase and DPPH free radical to give four isolated compounds: oleic acid (1), ergosterol (2), butyrolactone I (3), and butyrolactone II (4). The structures of these metabolites were assigned on the basis of detailed spectroscopic analysis. Oleic acid (1) was showed significant activity toward α-glucosidase with IC50 value of 8.54 μM, but not for antioxidant. Butyrolactone I (3) and II (4) were showed significant activities against the α-glucosidase with their IC50 values at 52.17 and 96.01 μM, and those against DPPH free radicals at 51.39 and 17.64 μM, respectively. On the other hand, ergosterol (2) did not show any activities.
2013
During the research for bioactive secondary metabolites from microorganisms, the endophytic fungi Aspergillus fumigatus sp. isolate R7 was found to produce a set of promising bioactive compounds (1-10) after its large scale fermentation, working up and purification using a series of chromatographic techniques. Structural elucidation of the yielded compounds using intensive studies of their NMR ( 1 H, 13 C& 2D NMR) and mass (EI MS, ESI MS) spectrometry confirmed them as linoleic acid (1), R(-)-glycerol monolinoleate (2), bis-dethio-(bis-methyl-thio)-gliotoxin (3), fumiquinazoline-F (4), fumiquinazoline-D (5), (Z,Z)-N,N’-[1-[(4-Hydroxy-phenyl)methylene]-2-[(4-methoxy-phenyl)-methylene]-1,2-ethanediyl]-bis-formamide (6), pyrazoline-3-one trimer (7), Tricho-9-ene-2a,3a,11a,16-tetraol (8), 2’-deoxy-thymidine (9), and cerebroside A (10). In this article, taxonomical characterization, fermentation, structural characterization of the obtained metabolites were reported together with their an...
Isolation of Bioactive Metabolites from Soil Derived Fungus-Aspergillus fumigatus
Microorganisms
Fungi produce numerous secondary metabolites with intriguing biological properties for the health, industrial, and agricultural sectors. Herein, we report the high-yield isolation of phenolic natural products, N-formyl-4-hydroxyphenyl-acetamide 1 (~117 mg/L) and atraric acid 2 (~18 mg/L), from the ethyl acetate extract of the soil-derived fungus, Aspergillus fumigatus. The structures of compounds 1 and 2 were elucidated through the detailed spectroscopic analysis of NMR and LCMS data. These compounds were assayed for their antimicrobial activities. It was observed that compounds 1 and 2 exhibited strong inhibition against a series of fungal strains but only weak antibacterial properties against multi-drug-resistant strains. More significantly, this is the first known instance of the isolation of atraric acid 2 from a non-lichen fungal strain. We suggest the optimization of this fungal strain may exhibit elevated production of compounds 1 and 2, potentially rendering it a valuable so...
Acta Chromatographica, 2018
Eight compounds were isolated and identified from the soil-inhabiting fungus Aspergillus fumigatus 3T-EGY, namely, stearic acid (1), α-linolenic acid (2), physcion (3), di-(2-ethylhexyl) phthalate (4), 2,4,5,17-tetramethoxy pradimicin lactone (5), 3,5-dihydroxy-7-O-α-rhamnopyranoyl-2H-chromen-2-one (6), juglanthraquinone A-5-O-D-rhodosamine-(4′→1″)-2-deoxy-D-glucose (4″→1″′)-cinerulose B (7), and micropeptin (8). Their structures were determined on the basis of one-dimensional (1D-) and two-dimensional nuclear magnetic resonance (2D-NMR) [ 1 H-, 13 C-NMR, 1 H-1 H COSY (COrrelated SpectroscopY), and 1 H-13 C HMBC (Heteronuclear Multiple Bond Correlation) spectroscopy]. Compound 7 showed moderate in vitro antimicrobial activity against three pathogenic strains with inhibition zones values were ranged from 9.0 to 10.66 mm compared to neomycin as a positive control with inhibition zones values were ranged from 14.0 to 19.0 mm.
Organic and Medicinal Chemistry Letters, 2012
The chemical constituents and biological activities of the terrestrial Aspergillus flavipes MM2 isolated from Egyptian rice hulls are reported. Seven bioactive compounds were obtained, of which one sterol: ergosterol (1), four butyrolactones: butyrolactone I (2), aspulvinone H (3), butyrolactone-V (6) and 4,4'-diydroxypulvinone , along with 6-methylsalicylic acid (4) and the cyclopentenone analogue; terrien (5). Structures of the isolated compounds were deduced by intensive studies of their 1D & 2D NMR, MS data and comparison with related structures. The strain extract and the isolated compounds (1-7) were biologically studied against number of microbial strains, and brine shrimp for cytotoxicity. In this article, the taxonomical characterization of A. flavipes MM2 along with its upscale fermentation, isolation and structural assignment of the obtained bioactive metabolites, and evaluate their antimicrobial and cytotoxic activities were described.
The aim of this research was analysis of the bioactive chemical products and evaluation of antibacterial and antifungal activity of Aspergillus terreus. Bioactives (chemical compounds often referred to as secondary metabolites) were analyzed using gas chromatography-mass spectroscopy (GC-MS) technique, then the in vitro antibacterial and antifungal activity of the methanolic extract was evaluated. Forty seven bioactive compounds were identified in the methanolic extract of Aspergillus terreus. Crude extract of Gramineae poaceae plant was very highly active (7.47±0.14) mm. The results of anti-bacterial activity produced by Aspergillus terreus showed that the volatile compounds were highly effective to suppress the growth of Streptococcus pneumonia. Aspergillus terreus produce many important secondary metabolites with high biological activities. Based on the significance of employing bioactive compounds in pharmacy to produce drugs for the treatment of many diseases, the purification of compounds produced by Aspergillus terreus species can be useful.
Food Additives & Contaminants: Part A, 2014
The filamentous fungus Aspergillus flavus is one of the most important species in the Aspergillus genus and is distributed worldwide as a prevalent aflatoxin-producing food and feed contaminant. A. flavus contains more than 55 gene clusters that are predicted to encode proteins involved in secondary metabolite production. One of these, cluster 27, contains a polyketide synthase (pks27) gene that encodes a protein that is highly homologous to the aflatoxin cluster PKS. Comparative metabolomics, using ultra-high performance liquid chromatography (UHPLC) coupled to high resolution Orbitrap mass spectrometry (MS) was used to detect metabolites differentially expressed in the A. flavus wild-type and Δpks27 mutant strains. Metabolite profiling was aided by a statistical differential analysis of MS data using SIEVE software. This differential analysis combined with accurate mass data from the Orbitrap and ion trap multiple stage MS allowed four metabolites to be identified that were produced only by the wild-type culture. These included asparasone A (358 Da), an anthraquinone pigment, and related anthraquinones with masses of 316, 340 and 374 Da. These latter three compounds had similar fragmentation patterns to that of asparasone A. The 316 Da anthraquinone is particularly interesting because it is most likely formed by incorporation of seven malonyl-CoA units rather than the eight units required for the formation of asparasone A. The 340 and 374 Da metabolites are the dehydration and an oxy-derivative of asparasone A, respectively. Asparasone A was also identified in extracts from several other Aspergillus species.
epi-Aszonalenins A, B, and C from Aspergillus novofumigatus
ChemInform, 2006
Three new benzodiazepines have been isolated from an unusual chemotype of Aspergillus novofumigatus: epi-aszonalenins A, B, and C. The structures were elucidated by use of one-and two-dimensional NMR spectroscopic techniques and HR ESI MS. The relative configuration was established on the basis of a single crystal X-ray diffraction study of epi-aszonalenin A and the absolute configuration was determined by optical rotation comparison with the literature data. The absolute configurations of epi-aszonalenins B and C were determined by circular dichroism comparison to epi-aszonalenin A.