scholarly journals An Updated Review on the Secondary Metabolites and Biological Activities of Aspergillus ruber and Aspergillus flavus and Exploring the Cytotoxic Potential of Their Isolated Compounds Using Virtual Screening

2021 ◽  
Vol 2021 ◽  
pp. 1-11
Author(s):  
Fadia S. Youssef ◽  
Abdel Nasser B. Singab
Keyword(s):  
Secondary Metabolites ◽  
Aspergillus Flavus ◽  
Topoisomerase Ii ◽  
High Resolution Mass Spectrometry ◽  
Antioxidant Activities ◽  
Biological Activities ◽  
2D Nmr ◽  
Aspergillus Species ◽  
Cytotoxic Potential ◽  
In Silico Studies

The secondary metabolites and biological activities of Aspergillus ruber and Aspergillus flavus were comprehensively reported. About 70 compounds were isolated from both species that belong to different classes using conventional and advanced chromatographic techniques and unambiguously elucidated employing one- and two-dimensional nuclear magnetic resonance (1D and 2D NMR) and high resolution mass spectrometry (HRMS). Some of them displayed promising antiviral, anti-inflammatory, and antioxidant activities. In silico studies were conducted on human cyclin-dependent kinase 2 (CDK-2), human DNA topoisomerase II (TOP-2), and matrix metalloprotinase 13 (MMP-13) in an effort to explore the cytotoxic potential of the diverse compounds obtained from both Aspergillus species. 1,6,8-Trihydroxy-4-benzoyloxy-3-methylanthraquinone (23) revealed the most firm fitting with the active pockets of CDK-2 and MMP-13; meanwhile, variecolorin H alkaloid (14) showed the highest fitting within TOP-2 with ∆G equals to −36.51 kcal/mole. Thus, fungal metabolites could offer new drug entities for combating cancer. Relevant data about both Aspergillus species up to August 2020 were gathered from various databases comprising Scifinder (https://scifinder.cas.org/scifinder/login) for secondary metabolite-related studies; meanwhile, for biology-related articles, data were collected from both PubMed (http://www.ncbi.nlm.nih.gov/pubmed/) and Web of Knowledge (http://www.webofknowledge.com) as well.

scholarly journals Chemical Composition and Biological Activities of Metabolites from the Marine Fungi Penicillium sp. Isolated from Sediments of Co To Island, Vietnam

Molecules ◽  
2019 ◽  
Vol 24 (21) ◽  
pp. 3830
Author(s):  
Hong Le ◽  
Quynh Do ◽  
Mai Doan ◽  
Quyen Vu ◽  
Mai Nguyen ◽  
...  
Keyword(s):  
Minimum Inhibitory Concentration ◽  
Secondary Metabolites ◽  
Inhibitory Concentration ◽  
Biological Activities ◽  
2D Nmr ◽  
Inhibitory Effect ◽  
Marine Microorganisms ◽  
Penicillium Species ◽  
E Coli ◽  
Strong Inhibitory Effect

Marine microorganisms are an invaluable source of novel active secondary metabolites possessing various biological activities. In this study, the extraction and isolation of the marine sediment Penicillium species collected in Vietnam yielded ten secondary metabolites, including sporogen AO-1 (1), 3-indolecarbaldehyde (2), 2-[(5-methyl-1,4-dioxan-2-yl)methoxy]ethanol (3), 2-[(2R-hydroxypropanoyl)amino]benzamide (4), 4-hydroxybenzandehyde (5), chrysogine (6), 3-acetyl-4-hydroxycinnoline (7), acid 1H-indole-3-acetic (8), cyclo (Tyr-Trp) (9), and 2’,3’-dihydrosorbicillin (10). Their structures were identified by the analysis of 1D and 2D NMR data. Among the isolated compounds, 2-[(5-methyl-1,4-dioxan-2-yl)methoxy]ethanol (3) showed a strong inhibitory effect against Enterococcus faecalis with a minimum inhibitory concentration value of 32 µg/mL. Both 2-[(2R-hydroxypropanoyl)amino]benzamide (4) and 4-hydroxybenzandehyde (5) selectively inhibited E. coli with minimum inhibitory concentration values of 16 and 8 µg/mL, respectively. 2’,3’-Dihydrosorbicillin (10) potentially inhibited α-glucosidase activity at a concentration of 2.0 mM (66.31%).

scholarly journals γ-Butyrolactones from Aspergillus Species: Structures, Biosynthesis, and Biological Activities

2017 ◽  
Vol 12 (5) ◽  
pp. 1934578X1701200 ◽  
Author(s):  
Sabrin R. M. Ibrahim ◽  
Gamal A. Mohamed ◽  
Amgad I.M. Khedr
Keyword(s):  
Secondary Metabolites ◽  
Biological Activities ◽  
Rich Source ◽  
Aspergillus Species ◽  
Aromatic Rings ◽  
Naturally Occurring ◽  
Fungal Secondary Metabolites

Recently, numerous metabolites possessing uncommon structures and potent bioactivity have been isolated from strains of fungi collected from diverse environments. The genus Aspergillus is known as a rich source of γ-butyrolactones. These are a group of fungal secondary metabolites, consisting of a five-membered lactone bearing two aromatic rings, which shows a great variety of biological activities. This review summarizes the research on the biosynthesis, source, and biological activities of the naturally occurring γ-butyrolactones that have been isolated from Aspergillus species published over the last decades. More than 75 compounds are described and 65 references are cited.

scholarly journals Identification of a Proanthocyanidin from Litchi Chinensis Sonn. Root with Anti-Tyrosinase and Antioxidant Activity

Biomolecules ◽  
2020 ◽  
Vol 10 (9) ◽  
pp. 1347
Author(s):  
Matthew Saive ◽  
Manon Genva ◽  
Thibaut Istasse ◽  
Michel Frederich ◽  
Chloé Maes ◽  
...  
Keyword(s):  
Antioxidant Activities ◽  
Biological Activities ◽  
Chemical Characterization ◽  
2D Nmr ◽  
Ethnobotanical Study ◽  
Traditional Use ◽  
Litchi Chinensis ◽  
Isolated Compound ◽  
First Time

This work follows an ethnobotanical study that took place in the island of Mayotte (France), which pointed out the potential properties of Litchi chinensis Sonn. roots when used to enhance skin health and appearance. Through in vitro testing of a crude methanolic extract, high anti-tyrosinase (skin whitening effect) and antioxidant activities (skin soothing effect) could be measured. HPLC successive bio-guided fractionation steps allowed the purification of one of the compounds responsible for the biological activities. The isolated compound was characterized by UV, IR, MS and 2D-NMR, revealing, for the first time in Litchi chinensis Sonn. roots, an A-type proanthocyanidin and thus revealing a consensus among the traditional use shown by the ethnobotanical study, in vitro biological activities and chemical characterization.

Secondary Metabolites from the Barks of Eucommia ulmoides and Their Bioactivities

2019 ◽  
Vol 41 (1) ◽  
pp. 169-169
Author(s):  
Wen Yan Liu Wen Yan Liu ◽  
Zi Ling Zi Ling ◽  
Dong Dong ◽  
Ke Huan Li Ke Huan Li ◽  
Jian Hua Shao Jian Hua Shao ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Antioxidant Activities ◽  
Ethanol Extract ◽  
2D Nmr ◽  
Eucommia Ulmoides ◽  
Antioxidant Power ◽  
Ic50 Values ◽  
Ferric Reducing Antioxidant Power ◽  
Intense Activity

Eucommia ulmoides Oliv., exhibiting diverse bioactivities including antimicrobial, antioxidant, neuroprotective, anti-tumor and anti-inflammatory properties, has long been known as an active ingredient commonly used in antihypertensive herbal prescriptions in China. The 95% ethanol extract of the barks of E. ulmoides showed antimicrobial and antioxidant activities and then was isolated by bioactivity-guided fractionation to obtain a new cinnamyl glucoside, 1-O-trans-cinnamoyl-β-D-apiofuranosyl-(1→6)-β-D-glucopyranose (1), together with twenty known secondary metabolites (2–21). And their structures were identified by extensive spectroscopic analyses, including 1D and 2D NMR, UV, IR and HRESIMS, and chemical methods. All secondary metabolites were evaluated for their antimicrobial and antioxidant activities in vitro. Compounds 7, 8, 11, and 21 exhibited moderately antimicrobial activity. In the antioxidant activity assay, compounds 3, 7, 11, and 14 showed intense activity in ferric reducing antioxidant power (FRAP) with the values of 9.82 mmol/g, 19.25 mmol/g, 14.52 mmol/g, and 12.58 mmol/g in comparison to Trolox (9.02 mmol/g). And compounds 2, 11, and 14–16 showed more potent activity with IC50 values ranging from 18.34 to 24.36 M than Trolox (26.35 M) in ABTS+• scavenging assay.

scholarly journals ANTIOXIDANT ACTIVITY AND PHENOLIC CONTENTS OF SEVEN BROWN SEAWEED FROM DJIBOUTI COAST

2019 ◽  
pp. 42-44
Author(s):  
ABDIRAHMAN ELMI FOURREH ◽  
FATOUMA MOHAMED ABDOUL-LATIF ◽  
MOUSTAPHA NOUR IBRAHIM ◽  
ALI MERITO ALI
Keyword(s):  
Antioxidant Activity ◽  
Secondary Metabolites ◽  
Dry Matter ◽  
Phenolic Content ◽  
Antioxidant Activities ◽  
Biological Activities ◽  
Brown Seaweed ◽  
Antioxidant Potential ◽  
Phenolic Contents ◽  
Dpph Method

Objective: This study focuses on the antioxidant potential of Djibouti brown seaweed and their phenolic contents. Methods: We evaluated the antioxidant potential by DPPH method (1,1-diphenyl-2-picrylhydrazyl) and their phenolic contents of seven Djibouti seaweed: Cytoseira myrica, Padina pavonica, Sargassum fluitans, Sargassum ilifolium, Sargassum sp, Turbinaria triquetra and Turbinaria turbinata. Also, we searched the secondary metabolites of these seaweeds. Results: We obtain a higher antioxidant activity at 60,7±0,9 % and a higher phenolic content at 199,01±0,5 μg equivalent phloroglucinol (PGE)/g dry matter for Padina pavonica. A good linear correlation (R2 = 0,898) is observed between the antioxidant activity and the phenolic content of the seaweed studied. Also, two Padina pavonica collected in two different locations have different biochemical concentrations and antioxidant activity, suggesting the influence of the marine environment on the biosynthesis of secondary metabolites and the biological activities of seaweed. The present study shows the presence of tannins, saponosides, flavonoids and steroid-terpenes. Conclusion: The species studied show interesting antioxidant activities and can be consumed to prevent oxidative stress.

scholarly journals Biofilm Mode of Cultivation Leads to an Improvement of the Entomotoxic Patterns of Two Aspergillus Species

2020 ◽  
Vol 8 (5) ◽  
pp. 705
Author(s):  
Frédéric Francis ◽  
Florent Druart ◽  
José Diana Di Mavungu ◽  
Marthe De Boevre ◽  
Sarah De Saeger ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Secondary Metabolite ◽  
Aspergillus Flavus ◽  
Aspergillus Oryzae ◽  
Proteomic Analysis ◽  
Cyclopiazonic Acid ◽  
Aspergillus Species ◽  
Metabolite Profiles

Two fungi, i.e., Aspergillus flavus Link and Aspergillus oryzae (Ahlb.) E. Cohn, were cultivated according to two methodologies, namely submerged and biofilm cultures with the primary aim to use their secondary metabolites the supernatant CL50, and CL90 varied between 1.3% (v/v) to 12.7% (v/v) for incubation times from 24 to 72 h. While the A. flavus supernatant entomotoxicity was higher than this of A. oryzae, the biofilm culture application increased the efficiency of the former. Proteomic analysis of the supernatants revealed discrepancies among the two species and modes of cultivation. Furthermore, the secondary metabolite profiles of both Aspergillus cultures were verified. Aspergillic acid, beta-cyclopiazonic acid, cyclopiazonic acid, ferrineospergillin, flavacol, and spermadin A were most predominant. Generally, these secondary metabolites were present in higher concentrations in the supernatants of A. flavus and biofilm cultures. These molecular identifications correlated positively with entomotoxic activity. Noteworthy, the absence of carcinogenic aflatoxins was remarkable, and it will allow further valorization to produce A. flavus to develop potential biopesticides.

scholarly journals Facile One-Pot Multicomponent Synthesis of Pyrazolo-Thiazole Substituted Pyridines with Potential Anti-Proliferative Activity: Synthesis, In Vitro and In Silico Studies

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3103
Author(s):  
Islam H. El El Azab ◽  
Rania B. Bakr ◽  
Nadia A. A. Elkanzi
Keyword(s):  
Cell Lines ◽  
In Silico ◽  
Topoisomerase Ii ◽  
Human Cancer ◽  
Docking Simulation ◽  
Cytotoxic Potential ◽  
One Pot ◽  
In Silico Docking ◽  
In Silico Studies

Pyrazolothiazole-substituted pyridine conjugates are an important class of heterocyclic compounds with an extensive variety of potential applications in the medicinal and pharmacological arenas. Therefore, herein, we describe an efficient and facile approach for the synthesis of novel pyrazolo-thiazolo-pyridine conjugate 4, via multicomponent condensation. The latter compound was utilized as a base for the synthesis of two series of 15 novel pyrazolothiazole-based pyridine conjugates (5–16). The newly synthesized compounds were fully characterized using several spectroscopic methods (IR, NMR and MS) and elemental analyses. The anti-proliferative impact of the new synthesized compounds 5–13 and 16 was in vitro appraised towards three human cancer cell lines: human cervix (HeLa), human lung (NCI-H460) and human prostate (PC-3). Our outcomes regarding the anti-proliferative activities disclosed that all the tested compounds exhibited cytotoxic potential towards all the tested cell lines with IC50 = 17.50–61.05 µM, especially the naphthyridine derivative 7, which exhibited the most cytotoxic potential towards the tested cell lines (IC50 = 14.62–17.50 µM) compared with the etoposide (IC50 = 13.34–17.15 µM). Moreover, an in silico docking simulation study was performed on the newly prepared compounds within topoisomerase II (3QX3), to suggest the binding mode of these compounds as anticancer candidates. The in silico docking results indicate that compound 7 was a promising lead anticancer compound which possesses high binding affinity toward topoisomerase II (3QX3) protein.

scholarly journals A Comprehensive Review of Bioactive Peptides from Marine Fungi and Their Biological Significance

Marine Drugs ◽  
2019 ◽  
Vol 17 (10) ◽  
pp. 559 ◽  
Author(s):  
Fadia S. Youssef ◽  
Mohamed L. Ashour ◽  
Abdel Nasser B. Singab ◽  
Michael Wink
Keyword(s):  
Natural Products ◽  
Marine Fungi ◽  
High Resolution Mass Spectrometry ◽  
Biological Activities ◽  
Biological Significance ◽  
2D Nmr ◽  
Biological Assessment ◽  
Lipid Lowering ◽  
Marine Microorganisms ◽  
Bioactive Natural Products

Fungal marine microorganisms are a valuable source of bioactive natural products. Fungal secondary metabolites mainly comprise alkaloids, terpenoids, peptides, polyketides, steroids, and lactones. Proteins and peptides from marine fungi show minimal human toxicity and less adverse effects comparable to synthetic drugs. This review summarizes the chemistry and the biological activities of peptides that were isolated and structurally elucidated from marine fungi. Relevant fungal genera including Acremonium, Ascotricha, Aspergillus, Asteromyces, Ceratodictyon, Clonostachys, Emericella, Exserohilum, Microsporum, Metarrhizium, Penicillium, Scytalidium, Simplicillium, Stachylidium, Talaromyces, Trichoderma, as well as Zygosporium were extensively reviewed. About 131 peptides were reported from these 17 genera and their structures were unambiguously determined using 1D and 2D NMR (one and two dimensional nuclear magnetic resonance) techniques in addition to HRMS (high resolution mass spectrometry). Marfey and Mosher reactions were used to confirm the identity of these compounds. About 53% of the isolated peptides exhibited cytotoxic, antimicrobial, and antiviral activity, meanwhile, few of them showed antidiabetic, lipid lowering, and anti-inflammatory activity. However 47% of the isolated peptides showed no activity with respect to the examined biological activity and thus required further in depth biological assessment. In conclusion, when searching for bioactive natural products, it is worth exploring more peptides of fungal origin and assessing their biological activities.

scholarly journals Chemical composition, antioxidant and hepatoprotective activities of methanol extracts from leaves ofTerminalia belliricaandTerminalia sericea(Combretaceae)

PeerJ ◽  
2019 ◽  
Vol 7 ◽  
pp. e6322 ◽  
Author(s):  
Mansour Sobeh ◽  
Mona F. Mahmoud ◽  
Rehab A. Hasan ◽  
Mohamed A.O. Abdelfattah ◽  
Samir Osman ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Antioxidant Activities ◽  
Binding Free Energy ◽  
Biological Activities ◽  
Flavonoid Glycosides ◽  
Leaf Extracts ◽  
Apoptotic Pathway ◽  
In Silico Docking ◽  
Terminalia Bellirica ◽  
Interaction Surface

BackgroundPlants belonging to the genusTerminaliasuch asTerminalia belliricaandTerminalia sericeaare used traditionally to treat several diseases and health disorders. Up to this date, the roots ofTerminalia sericeaand the fruits ofTerminalia belliricaare the mostly studied plant parts. The phytochemical composition and the biological activities of the leaves of both species are not well identified so far.MethodsThe secondary metabolites ofTerminalia belliricaandTerminalia sericealeaves were identified using HPLC-PDA-MS/MS. The antioxidant activities of the leaves extracts were determined by DPPH and FRAP assays. The hepatoprotective potential was evaluated in rats with D-galactosamine induced liver damage. The effect of the extracts on the expression of the anti-apoptotic marker Bcl-2 was measured in an immunohistochemical study. The most abundant compounds identified in the studied extracts were docked into Bcl-2: Bim (BH3) interaction surface using molecular operating environment software.ResultsA total of 85 secondary metabolites were identified in the leaf extracts of both species. Ellagitannins such as corilagin, chebulagic acid, galloylpunicalagin, and digalloyl-hexahydroxydiphenoyl-hexoside were found to be the major components inTerminalia belliricawhereas flavonoid glycosides including quercetin rutinoside and quercetin galloyl-glucoside were highly abundant inTerminalia sericea. The studied extracts exhibited pronounced antioxidant activities, moderate anti-apoptotic and hepatoprotective potential. In silico docking experiments revealed that the compounds abundant in the extracts were able to bind to Bcl-2: Bim (BH3) interaction surface with an appreciable binding free energy.DiscussionThe antioxidant and hepatoprotective activities exhibited by the studied extracts might be attributed to the high content of the polyphenols. The anti-apoptotic activity could be due to the interference with the apoptotic pathway mediated by Bcl-2: Bim interaction. These findings support the medicinal relevance ofTerminalia belliricaandTerminalia sericeaand provide a rational base for their utilization in folk medicine.

scholarly journals 1,4-Disubstituted 1H-1,2,3-Triazoles for Renal Diseases: Studies of Viability, Anti-Inflammatory, and Antioxidant Activities

2020 ◽  
Vol 21 (11) ◽  
pp. 3823
Author(s):  
Ching-Yi Cheng ◽  
Ashanul Haque ◽  
Ming-Fa Hsieh ◽  
Syed Imran Hassan ◽  
Md. Serajul Haque Faizi ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Metabolic Diseases ◽  
Mesangial Cells ◽  
Antioxidant Activities ◽  
Biological Activities ◽  
Renal Diseases ◽  
No Production ◽  
In Silico Studies ◽  
Cox 2 ◽  
Anti Inflammatory

Inflammation is a hallmark of many metabolic diseases. We previously showed that ferrocene-appended 1H-1,2,3-triazole hybrids inhibit nitric oxide (NO) production in in vitro models of lipopolysaccharide-induced inflammation in the BV-2 cell. In the present study, we explored the viability, anti-inflammatory, and antioxidant potential of ferrocene-1H-1,2,3-triazole hybrids using biochemical assays in rat mesangial cells (RMCs). We found that, among all the ferrocene-1H-1,2,3-triazole hybrids, X2–X4 exhibited an antioxidant effect on mitochondrial free radicals. Among all the studied compounds, X4 demonstrated the best anti-inflammatory effect on RMCs. These results were supplemented by in silico studies including molecular docking with human cytosolic phospholipase A2 (cPLA2) and cyclooxygenase 2 (COX-2) enzymes as well as absorption, distribution, metabolism, excretion, and toxicity (ADMET) profiling. Besides, two new crystal structures of the compounds have also been reported. In addition, combining the results from the inducible nitric oxide synthase (iNOS), cPLA2, COX-2, and matrix metalloproteinase-9 (MMP-9) enzymatic activity analysis and NO production also confirmed this argument. Overall, the results of this study will be a valuable addition to the growing body of work on biological activities of triazole-based compounds.

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