Furandiones from an Endophytic &lt;i&gt;Aspergillus terreus&lt;/i&gt; Residing in &lt;i&gt;Malus halliana&lt;/i&gt;

Gu, Wen; Qiao, Chao

doi:10.1248/cpb.c12-00643

Cited by 18 publications

(2 citation statements)

References 21 publications

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“…According to our research, only four phenyl-and benzyl-disubstituted maleimides have been isolated, asperimides A-D, from a tropical endophytic fungus Aspergillus terreus [12]. Trisubstituted butenolides exhibit diverse biological activities such as antibacterial [13], cytotoxic [14,15], antiinflammatory [16], and antioxidant [17] activities.…”

Section: Introductionmentioning

confidence: 99%

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Bioactive Aspergteroids G–J from Soft-Coral-Associated Symbiotic and Epiphytic Fungus Aspergillus terreus EGF7-0-1

et al. 2023

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Two new disubstituted maleimides, aspergteroids G–H (1–2), and two trisubstituted butenolides aspergteroids I–J (3–4), along with four known analogs, were isolated and structurally identified from the fermentation extract of soft-coral-associated symbiotic and epiphytic fungus Aspergillus terreus EGF7-0-1. The structures of the new compounds were established mainly via spectroscopic data analyses, and their absolute configurations were determined via X-ray diffraction analysis and comparison of the calculated and experimental electronic circular dichroism. Myocardial protection assays showed that compounds 1, 2, 5, and 6 possess protective effects against tert-butyl hydroperoxide (TBHP)-induced H9c2 (rat myocardial cells) apoptosis at low concentrations. Based on the analyses of the protein–protein interaction (PPI) network and Western blotting, compound 1 may inhibit the apoptosis and inflammatory response of cardiomyocytes after TBHP induction and improve the antioxidant capacity of cardiomyocytes. We speculate that the anti-inflammatory response of compound 1 is suppressed by the glycogen synthase kinase-3 beta (GSK-3β), downregulated by the NOD-like receptor thermal protein domain associated protein 3 (NLRP3) inflammasome activation, and suppressed by the expression of cysteinyl aspartate specific proteinase-3 (caspase-3) and B-cell lymphoma-2 associated X protein (Bax).

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Section: Introductionmentioning

confidence: 99%

“…Bioengineering 2023, 10, x FOR PEER REVIEW 2 of 13 endophytic fungus Aspergillus terreus [12]. Trisubstituted butenolides exhibit diverse biological activities such as antibacterial [13], cytotoxic [14,15], anti-inflammatory [16], and antioxidant [17] activities.…”

Section: Introductionmentioning

confidence: 99%

Bioactive Aspergteroids G–J from Soft-Coral-Associated Symbiotic and Epiphytic Fungus Aspergillus terreus EGF7-0-1

et al. 2023

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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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Isolation of Thioinosine and Butenolides from a Terrestrial Actinomycetes sp. GSCW‐51 and Their in Silico Studies for Potential against SARS‐CoV‐2

Tousif

Nazir

Khalid

et al. 2022

Chemistry & Biodiversity

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In our continuous screening for bioactive microbial natural products, the culture extracts of a terrestrial Actinomycetes sp. GSCW‐51 yielded two new metabolites, i. e., 5‐hydroxymethyl‐3‐(1‐hydroxy‐6‐methyl‐7‐oxooctyl)dihydrofuran‐2(3H)‐one (1), 5‐hydroxymethyl‐3‐(1,7‐dihydroxy‐6‐methyloctyl)dihydrofuran‐2(3H)‐one (2), and two known compounds; 5′‐methylthioinosine (3), and 5′‐methylthioinosine sulfoxide (4), which are isolated first time from any natural source, along with four known compounds (5–8). The structures of the new compounds were deduced by HR‐ESI‐MS, 1D and 2D NMR data, and in comparison with related compounds from the literature. Additionally, owing to the current COVID‐19 pandemic situation, we also computationally explored the therapeutic potential of our isolated compounds against SARS‐CoV‐2. Compound 4 showed the best binding energies of −6.2 and −6.6 kcal/mol for Mpro and spike proteins, respectively. The intermolecular interactions were also studied using 2‐D and 3‐D imagery, which also supported the binding energies as well as put several insights under the spotlight. Furthermore, Lipinski's rule of 5 was used to predict the drug likeness of compounds 1–4, which indicated all compounds obey Lipinski's rule of 5. The study of bioavailability radars of the compounds 1–4 also confirmed their drug likeness properties where all the five crucial drug likeness parameters are in color area, which is safe to be used as drugs. Our isolation and computational findings highly encourage the scientific community to do further in vitro and in vivo studies of compounds 1–4.

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Furandiones from an Endophytic <i>Aspergillus terreus</i> Residing in <i>Malus halliana</i>

Cited by 18 publications

References 21 publications

Bioactive Aspergteroids G–J from Soft-Coral-Associated Symbiotic and Epiphytic Fungus Aspergillus terreus EGF7-0-1

Bioactive Aspergteroids G–J from Soft-Coral-Associated Symbiotic and Epiphytic Fungus Aspergillus terreus EGF7-0-1

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

Isolation of Thioinosine and Butenolides from a Terrestrial Actinomycetes sp. GSCW‐51 and Their in Silico Studies for Potential against SARS‐CoV‐2

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