ChemInform Abstract: Furandiones from an Endophytic Aspergillus terreus Residing in Malus halliana

Gu, Wen; Qiao, Chao

doi:10.1002/chin.201315199

Cited by 6 publications

(12 citation statements)

References 1 publication

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“…Due to the isolation of lesser amount we were not able to perform biological activities of these compounds, but the butenolides have gained special attention as α-glucosidase, cytotoxic and antiinflammatory agents. [28][29][30] Previous research has identified them as distinguishing characteristics of αglucosidase inhibitory actions. Recently butenolides showed the promising activity against the influenza viruses.…”

Section: Resultsmentioning

confidence: 99%

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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Section: Resultsmentioning

confidence: 99%

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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“…Enantia chlorantha Oliv. Brine shrimp larvae cytotoxicity and bacterial activity [171] Expansol C (197) Penicillium expansum…”

Section: Tiliacora Triandramentioning

confidence: 99%

Endophytic Fungi as a Source of Novel Metabolites

2015

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“…Compounds 37 and 38 showed significant cytotoxicity against PC3 (prostate cancer) cell line with IC 50 30.6 and 32.2 lM, respectively. Among the isolated compounds was trypacidin (40) which displayed activity against PC3 with IC 50 19.9 lM. Trypacidin also exhibited cytotoxicity against PC3D (multiple drug resistance cells), A549, and NCI-H460 with IC 50 39.6, 33.8, and 31 lM, respectively.…”

Section: Endophyte-host Interactionmentioning

confidence: 99%

“…Compounds 45 and 46 exhibited moderate cytotoxicity against human colorectal carcinoma SW1116 cells with IC 50 values of 57.5 and 71.0 lM, respectively. [40] N- (5,6,9,11a-Tetrahydro-1,2,3-trihydroxy-6-methyl-9-oxo-6aH-cyclohepta[a]naphthalen-6a-yl)acetamide (47) was isolated from an Aspergillus spp. endophyte from the seeds of Gloriosa superba and was found to possess activity comparable to the standard anticancer drugs mitomycin-C and 5-FU when tested against six cancer cell lines.…”

Section: Endophyte-host Interactionmentioning

confidence: 99%

“…The endophytic fungus Aspergillus terreus MHL‐P22, isolated from the leaves of Malus halliana , produced two furandiones, asperterones B ( 45 ) and C ( 46 ), in liquid culture. Compounds 45 and 46 exhibited moderate cytotoxicity against human colorectal carcinoma SW1116 cells with IC 50 values of 57.5 and 71.0 μ m , respectively . N ‐(5,6,9,11a‐Tetrahydro‐1,2,3‐trihydroxy‐6‐methyl‐9‐oxo‐6a H ‐cyclohepta[ a ]naphthalen‐6a‐yl)acetamide ( 47 ) was isolated from an Aspergillus spp.…”

Section: Introductionmentioning

confidence: 99%

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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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ChemInform Abstract: Furandiones from an Endophytic Aspergillus terreus Residing in Malus halliana

Abstract: isolation and structure elucidation of two new furandione derivatives, asperterone B (I) and C (II), which show moderate cytotoxic activities against the human colorectal carcinoma SW1116

Cited by 6 publications

References 1 publication

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

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

Endophytic Fungi as a Source of Novel Metabolites

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

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