SECONDARY METABOLITE OF Aspergillus fumigatus, ENDOPHYTIC FUNGI OF THE MEDICINAL PLANT Garcinia griffithii (original) (raw)
Natural Product Research, 2016
Chemical investigation of Aspergillus japonicus CAM231, isolated from the leaf of Garcina preussii collected in Cameroon, yielded two new compounds; one pyrone derivative, hydroxy neovasinin (1) and one phenol derivative, asperolan (2), together with two known compounds neovasifurarone B (3) and variecolin (4). The structures of the two new compounds were established using intensive NMR spectroscopy and HRMS spectra in comparison with data found in literature. The structure of compound 1 was confirmed by singlecrystal X-ray crystallographic analysis in combination with NOESY experiment. The new compounds were screened for their cytotoxic and antibacterial properties; however, the tested compounds displayed no significant activities.
Biological activities of extracts from endophytic fungi isolated from Garcinia plants
2007
Sixty-five crude extracts from 51 selected endophytic fungi isolated from Garcinia species were tested for various bioactivities. Eighty per cent of the fungal extracts from fermentation broths and mycelia displayed bioactivities: antimycobacterial (76.9%), antimalarial (14.1%), antiviral (16.7%), antioxidant (22.2%), antiproliferation (11.1% against NCI-H187 and 12.7% against KB cells), and cytotoxicity to Vero cells (40.0%). Based on internal transcribed spacer rRNA sequence analysis, 15 bioactive isolates were identified as Aspergillus, Botryosphaeria, Curvularia, Fusicoccum, Guignardia, Muscodor, Penicillium, Pestalotiopsis, and Phomopsis spp. One isolate (N24) was matched with an unidentified fungal endophyte. These results indicate that endophytic fungi isolated from Garcinia plants in Thailand are potential sources of various bioactive natural products.
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...
Molekul, 2016
The compound from endophytic fungi of Aspergillus sp. from leaves of kunyit putih (Curcuma zedoaria (Berg.) Roscoe) has been isolated. Isolation begins with cultivation ofAspergillus sp. in 18 L PDB’s media (Potato Dextrose Broth) for 28 days. The liquid cultivation medium was extracted by partitioning method using ethylacetate and then evaporated. The extract was separated and purified by chromatography techniques. Elucidation stucture of the isolated compound was analysis by spectroscopic method NMR 1D and 2D. Antibacterial activity of isolated compound was tested using the disc diffusion method at concentrations 2500, 1000, 500, and 125 ppm. The isolated compounds obtained in the form of a yellow oil (24.30 mg). The 13C NMR spectrum indicated 24 signals of carbon and base on analysis spectrum DEPT 135 showed 5 signal methynes carbon, 1 signals methylene, 9 signals of methyl and 9 signals quarternary carbon. These signals from 1H and 13C-NMR suggested that this compound contained ...
Novel Research in Microbiology Journal
The morbidity and mortality rates from Pseudomonas aeruginosa infections are increasing, due to the development of drug-resistant strains. This study aimed to explore the secondary metabolites of endophytic fungi of Garcinia kola for their antibacterial activities against P. aeruginosa. The endophytic fungi associated with healthy leaves of G. kola were isolated using the standard methods. These fungi were subjected to solid-state fermentation on rice media at 28 o C for 21 d. The fungal secondary metabolites were extracted using ethyl acetate, and then concentrated under vacuum. The fungal crude extracts were screened for their antibacterial activities against clinical and laboratory strains of P. aeruginosa, using the agar diffusion method. The bioactive components of the fungal extracts were identified using High-Performance Liquid Chromatography-Diode Array Detector (HPLC-DAD) analysis. Three endophytic fungi mainly; Aspergillus sp., Fusarium sp. and Colletotrichum sp. were isolated. At concentration of 1 mg/ml, extracts of the three fungi displayed antipseudomonal activities against all the isolates, except for a P. aeruginosa isolate recovered from urine. Results of the HPLC-DAD analysis revealed the presence of several active compounds such as; indole-3-acetic acid, phydroxybenzoic acid, and protocatechuic acid, among others in the fungal extracts. These compounds have been previously reported to have significant antimicrobial properties. This study reveals that endophytic fungi associated with G. kola leaves possess promising anti-pseudomonal potential.
Isolation and biological activity of compounds from Garcinia preussii
Pharmaceutical Biology, 2014
Context: Plants of the genus Garcinia (Clusiaceae) are traditionally used to relieve stomachaches, toothaches, and as a chew stick. Objective: In order to determine which compounds were responsible for these activities, a phytochemical investigation of the fruits and leaves of Garcinia preussii Engl. was pursued. Materials and methods: Plants were extracted by solvents of various polarities. Compounds isolation was then carried out using chromatography methods (medium-and high-pressure liquid chromatography, open column and thin-layer chromatography). The isolated compounds were identified and characterized by using 1D and 2D NMR spectroscopies. The antioxidant activity was evaluated using DPPH , ABTS À , ALP, and ORAC assays. The antimicrobial activity was assayed against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Enterococcus faecalis by determining the minimum inhibitory concentration (MIC) value. The cytotoxic activity of most of the isolated compounds was evaluated on a small panel of human cancer cell lines (DU145, HeLa, HT-29, and A431) using the XTT method. Results: The phytochemical investigation of G. preussii led to the isolation of eight known compounds, six benzophenones and two flavonoids. These compounds were tested for their biological activities. 1, 2, 3, 4, 7 and 8 demonstrated a high free radical scavenging activity with ER 50 ranging from 0.1 to 0.7. The antimicrobial activity was shown only against Gram-positive bacteria for 1, 4, and 5. A moderate cytotoxic activity with IC 50 ranging from 7 to 50 mM was observed, except for 6 which was not active. Conclusion: These results appear to support some of the properties reported for Garcinia species.
Acta Amazonica, 2018
Tuberculosis (TB) remains one of the most deadly communicable infectious diseases, causing 1.4 million deaths in 2015 worldwide due to many conditions, including the inadequate treatment and the emergence of multidrug-resistant strains of the causal agent, Mycobacterium tuberculosis. Therefore, drugs developed from natural sources, as microorganisms and plant extracts, are a frequent target for the research and discovery of antimicrobial compounds. The current study started the characterization of compounds produced by an Aspergillus fumigatus isolated from copaíba (Copaifera multijuga) that efficiently inhibits M. tuberculosis by releasing the compounds into the fermentation broth under specific culture conditions. A preliminary assay was carried out with a correlate species, M. smegmatis, aiming to detect an antimicrobial effect related to A. fumigatus fermentation broth. The direct use of this substrate in antibiosis assays againstM. tuberculosis H 37 Rv strain (ATCC 27294) allowed the detection of antimicrobial activity with a minimal inhibitory concentration of 256 μg mL-1 , demonstrating that purification processes developed by the Biotage Flash Chromatography System are robust and reliable techniques for purification of compounds from natural sources. Also, this chromatographic system can be used in combination with specific biochemical tests, improving the search for reliable results. We conclude that this fraction can express a broad action range, inhibiting both Mycobacterium species used as target organisms.
Secondary metabolites and bioactivity of two fungal strains
Purpose The investigation of two fungal strains isolated from Egyptian habitats, namely, the endophytic Fusarium poae FUN1 and the terrestrial Penicillium italicum FUN2 to illustrate their chemical constituents and their bioactivities. Materials and methods See General instrumental procedures. Results Linoleic acid (1), indole-3-acetic acid methyl ester (2) and Nb-acetyltryptamine (3) were produced by F. poae FUN1, whereas P. italicum FUN2 also delivered linoleic acid (1) in addition to cis-cyclo-(prolyl,valyl) (4). The structures of compounds (1)–(4) were elucidated by 1D and 2D NMR, MS data and through comparison with literature reports. In this article, the taxonomical characterization of both fungal strains, their upscale fermentation and the antimicrobial and cytotoxic activities tested have been described. Conclusion Two different fungal strains, endophytic F. poae FUN1 and terrestrial P. italicum FUN2, were intensively studied biologically and chemically. Four bioactive compounds (1)–(4) were isolated, and structurally confirmed by intensive studies of NMR and MS. The antimicrobial and cytotoxic activities of the fungal extracts and their delivered compounds were studied. This might be helpful for the cure of recent diseases, and drug-resistant phenomena as well as in the development of pharmaceutical, agrochemical and biochemical agents and their lead compounds.
Natural product research, 2015
Endophytic fungi are considered as a good source to produce important secondary metabolites with interesting bioactivities. In a continuation of our studies towards the search for environmentally friendly bioactive compounds from Sri Lankan flora, we investigated the secondary metabolites produced by the endophytic fungi Aspergillus sp. isolated from the seeds of the popular edible fruit Limonia acidissima L. of the family Rutaceae. The pure culture of the Aspergillus sp. was grown on potato dextrose broth media. After 4 weeks fermentation, fungal media were extracted with organic solvents. Chromatographic separation of the fungal extracts over silica gel, Sephadex LH-20 and RP-HPLC furnished flavasperone (1), rubrofusarin B (2), aurasperone A (3), fonsecinone D (4) and aurasperone B (5). Compounds 1-4 showed moderate activities in brine shrimp toxicity assay. This is the first report of the (13)C NMR data of compounds 4 and 5.
Secondary metabolites from stem bark of Garcinia beccarii pierre and Garcinia cuneifolia pierre
2017
The genus Garcinia is from the family Guttiferae of evergreen trees and shrubs distributed in tropical Asia, Africa and Polynesia. The genus Garcinia is known to be a rich source of polyisoprenylated benzophenones and xanthones. Medium scale extractions of the grounded stem bark of Garcinia beccarii Pierre and Garcinia cuneifolia Pierre were conducted by using the solvent extraction method at room temperature for three days. The extracts afforded some xanthones and triterpenoids. These compounds were isolated by using various chromatographic techniques and their structures were elucidated by using spectroscopy techniques such as NMR, GC-MS and FTIR. Bioassays such as cytotoxic activities and antimicrobial screenings were investigated by using on the crude extracts of the two plants. Four xanthones namely rubraxanthone, trapezifolixanthone, α-mangostin and β-mangostin were isolated from the chloroform and ethyl acetate extracts of the stem bark of Garcinia beccarii Pierre. Two xantho...