Aspernolides F and G, new butyrolactones from the endophytic fungus Aspergillus terreus

Ibrahim, Sabrin R. M.; Elkhayat, Ehab S.; Mohamed, Gamal A.; Khedr, Amgad I. M.; Fouad, Mostafa A.; Kotb, Mohamed H.R.; Ross, Samir A.

doi:10.1016/j.phytol.2015.09.006

Cited by 85 publications

(45 citation statements)

References 33 publications

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“…All the isolated compounds were tested for their anti-microbial activity at concentrations of 20-0.8 μg/mL against Candida albicans ATCC 90028, Candida glabrata ATCC90030, Candida krusei ATCC 6258, Asperigillus fumigates ATCC 90906, methicillin-resistant Staphylococcus aureus ATCC 33591, Cryptococcus neoformans ATCC 90113, Staphylococcus aureus ATCC 2921, Escherichia coli ATCC 35218, Klebsiella pneumonia ATCC 13883, Pseudomonus aeruginosa ATCC 27853 and Mycobacterium intracellulare ATCC 23068 using modified versions of the CLSI/NCCLS methods (Ibrahim et al 2012a, 2015a, b). …”

Section: Methodsmentioning

confidence: 99%

“…The anti-leishmanial activity of the isolated metabolites was tested in vitro against L. donovani promastigotes as previously described (Ibrahim et al 2012a, 2015a, b). Pentamidine and amphoterecin B were used as positive controls.…”

Section: Methodsmentioning

confidence: 99%

“…The cell line was obtained from the American Type Culture Collection (ATCC, Rockville, MD). The cell viability was determined using Neutral Red dye according to a previous method with modification (Borenfreund et al 1990; Mohamed et al 2013; Ibrahim et al 2015a, b). Doxorubicin was used as a positive control, whereas DMSO was used as the negative control.…”

Section: Methodsmentioning

confidence: 99%

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New ursane triterpenoids from Ficus pandurata and their binding affinity for human cannabinoid and opioid receptors

et al. 2016

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Phytochemical investigation of Ficus pandurata Hance (Moraceae) fruits has led to the isolation of two new triterpenoids, ficupanduratin A [1β-hydroxy-3β-acetoxy-11α-methoxy-urs-12-ene] (11) and ficupanduratin B [21α-hydroxy-3β-acetoxy-11α-methoxy-urs-12-ene] (17), along with 20 known compounds: α-amyrin acetate (1), α-amyrin (2), 3β-acetoxy-20-taraxasten-22-one (3), 3β-acetoxy-11α-methoxy-olean-12-ene (4), 3β-acetoxy-11α-methoxy-12-ursene (5), 11-oxo-α-amyrin acetate (6), 11-oxo-β-amyrin acetate (7), palmitic acid (8), stigmast-4,22-diene-3,6-dione (9), stigmast-4-ene-3,6-dione (10), stigmasterol (12), β-sitosterol (13), stigmast-22-ene-3,6-dione (14), stigmastane-3,6-dione (15), 3β,21β-dihydroxy-11α-methoxy-olean-12-ene (16), 3β-hydroxy-11α-methoxyurs-12-ene (18), 6-hydroxystigmast-4,22-diene-3-one (19), 6-hydroxystigmast-4-ene-3-one (20), 11α,21α-dihydroxy-3β-acetoxy-urs-12-ene (21), and β-sitosterol-3-O-β-D-glucopyranoside (22). Compound 21 is reported for the first time from a natural source. The structures of the 20 compounds were elucidated on the basis of IR, 1D (1H and 13C), 2D (1H–1H COSY, HSQC, HMBC and NOESY) NMR and MS spectroscopic data, in addition to comparison with literature data. The isolated compounds were evaluated for their anti-microbial, anti-malarial, anti-leishmanial, and cytotoxic activities. In addition, their radioligand displacement affinity on opioid and cannabinoid receptors was assessed. Compounds 4, 11, and 15 exhibited good affinity towards the CB2 receptor, with displacement values of 69.7, 62.5 and 86.5 %, respectively. Furthermore, the binding mode of the active compounds in the active site of the CB2 cannabinoid receptors was investigated through molecular modelling.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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New ursane triterpenoids from Ficus pandurata and their binding affinity for human cannabinoid and opioid receptors

et al. 2016

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“…71 was active against C. neoformans and MRSA with IC 50 values of 5.19 and 6.39 lg/ml, respectively. [56] Five ergot alkaloids, fumigaclavines D -H (73 -77), were isolated from the endophytic Aspergillus fumigatus. Compounds 75 and 77 were the most active against Veillonella parvula, an anaerobic bacterium, with an MIC of 16 lg/ml.…”

Section: Endophyte-host Interactionmentioning

confidence: 99%

“…71 was active against C . neoformans and MRSA with IC 50 values of 5.19 and 6.39 μg/ml, respectively . Five ergot alkaloids, fumigaclavines D – H ( 73 – 77 ), were isolated from the endophytic Aspergillus fumigatus .…”

Section: Introductionmentioning

confidence: 99%

Metabolomic Tools to Assess the Chemistry and Bioactivity of Endophytic Aspergillus Strain

Tawfike

Tate

Abbott

et al. 2017

Chemistry & Biodiversity

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Endophytic fungi associated with medicinal plants are a potential source of novel chemistry and biology that may find applications as pharmaceutical and agrochemical drugs. In this study, a combination of metabolomics and bioactivity-guided approaches were employed to isolate secondary metabolites with cytotoxicity against cancer cells from an endophytic Aspergillus aculeatus. The endophyte was isolated from the Egyptian medicinal plant Terminalia laxiflora and identified using molecular biological methods. Metabolomics and dereplication studies were accomplished by utilizing the MZmine software coupled with the universal Dictionary of Natural Products database. Metabolic profiling, with aid of multivariate data analysis, was performed at different stages of the growth curve to choose the optimized method suitable for up-scaling. The optimized culture method yielded a crude extract abundant with biologically-active secondary metabolites. Crude extracts were fractionated using different high-throughput chromatographic techniques. Purified compounds were identified by HR-ESI-MS, 1D- and 2D-NMR. This study introduced a new method of dereplication utilizing both high-resolution mass spectrometry and NMR spectroscopy. The metabolites were putatively identified by applying a chemotaxonomic filter. We also present a short review on the diverse chemistry of terrestrial endophytic strains of Aspergillus, which has become a part of our dereplication work and this will be of wide interest to those working in this field.

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Biological Activity and Phytochemical Analysis of Dicranum scoparium against the Bacterial Disease for Honey Bee

Karaoğlu

Yaylı

Erik

et al. 2022

Chemistry & Biodiversity

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Bacterial diseases, such as American Foulbrood (AFB) and European Foulbrood (EFB), are known to have catastrophic effects on honey bees (if left to spread, can wipe out entire colonies), leading to severe financial losses in the beekeeping industry. The aim of this study was to evaluate the pharmacological properties of methanol extract and its fractions (ethyl acetate, hexane, water) derived from Dicranum scoparium Hedw., which could be utilized as a potential drug to prevent the bacterial diseases (AFB and EFB) affecting the honey bees. For this purpose, crude methanol extract and ethyl acetate/hexane/water fractions were prepared from the aerial part of D. scoparium, collected from Trabzon province. Bio‐guided fractionation of the extract and its fractions led to the first‐time isolation of five compounds. The structure of all compounds was elucidated by nuclear magnetic resonance (NMR) spectroscopy, ultraviolet (UV) spectral analysis, Fourier‐transform infrared spectroscopy (FT‐IR), liquid chromatography quadrupole time‐of‐flight mass spectroscopy (LC‐QToF‐MS), and by comparison of their NMR data with that of literature. The analysis of these compounds revealed significant antibacterial and sporicidal activities against bacteria causing larval diseases in honey bees. The antibacterial activity of these compounds ranged from 0.6 to 60 μg/mL against AFB and EFB causing bacteria. Therefore, the natural raw extract and fractions of D. scoparium could be used as potential therapeutic agents against bacterial agents affecting honey bees.

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Aspernolides F and G, new butyrolactones from the endophytic fungus Aspergillus terreus

Cited by 85 publications

References 33 publications

New ursane triterpenoids from Ficus pandurata and their binding affinity for human cannabinoid and opioid receptors

New ursane triterpenoids from Ficus pandurata and their binding affinity for human cannabinoid and opioid receptors

Metabolomic Tools to Assess the Chemistry and Bioactivity of Endophytic Aspergillus Strain

Biological Activity and Phytochemical Analysis of Dicranum scoparium against the Bacterial Disease for Honey Bee

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