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
,
,
,
,
,
,
,
,
,
,
,
,
,
,
,
, as well as
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.
Genus
represents a widely spread genus of fungi that is highly popular for possessing potent medicinal potential comprising mainly antimicrobial, cytotoxic and antioxidant properties. They are highly ...attributed to its richness by alkaloids, terpenes, steroids and polyketons. This review aimed to comprehensively explore the diverse alkaloids isolated and identified from different species of genus
that were found to be associated with different marine organisms regarding their chemistry and biology. Around 174 alkaloid metabolites were reported, 66 of which showed important biological activities with respect to the tested biological activities mainly comprising antiviral, antibacterial, antifungal, cytotoxic, antioxidant and antifouling activities. Besides, in silico studies on different microbial proteins comprising DNA-gyrase, topoisomerase IV, dihydrofolate reductase, transcriptional regulator TcaR (protein), and aminoglycoside nucleotidyl transferase were done for sixteen alkaloids that showed anti-infective potential for better mechanistic interpretation of their probable mode of action. The inhibitory potential of compounds vs. Angiotensin-Converting Enzyme 2 (ACE2) as an important therapeutic target combating COVID-19 infection and its complication was also examined using molecular docking. Fumigatoside E showed the best fitting within the active sites of all the examined proteins. Thus,
species isolated from marine organisms could afford bioactive entities combating infectious diseases.
In continuation of our antecedent work against COVID-19, three natural compounds, namely, Luteoside C (130), Kahalalide E (184), and Streptovaricin B (278) were determined as the most promising ...SARS-CoV-2 main protease (Mpro) inhibitors among 310 naturally originated antiviral compounds. This was performed via a multi-step in silico method. At first, a molecular structure similarity study was done with PRD_002214, the co-crystallized ligand of Mpro (PDB ID: 6LU7), and favored thirty compounds. Subsequently, the fingerprint study performed with respect to PRD_002214 resulted in the election of sixteen compounds (7, 128, 130, 156, 157, 158, 180, 184, 203, 204, 210, 237, 264, 276, 277, and 278). Then, results of molecular docking versus Mpro PDB ID: 6LU7 favored eight compounds (128, 130, 156, 180, 184, 203, 204, and 278) based on their binding affinities. Then, in silico toxicity studies were performed for the promising compounds and revealed that all of them have good toxicity profiles. Finally, molecular dynamic (MD) simulation experiments were carried out for compounds 130, 184, and 278, which exhibited the best binding modes against Mpro. MD tests revealed that luteoside C (130) has the greatest potential to inhibit SARS-CoV-2 main protease.
The antioxidant and enzyme inhibitory potential of fifteen cycloartane-type triterpenes' potentials were investigated using different assays. In the phosphomolybdenum method, cycloalpioside D (
) ...(4.05 mmol TEs/g) showed the highest activity. In 1,1-diphenyl-2-picrylhydrazyl (DPPH*) radical and 2,2'-azino-bis(3-ethylbenzothiazoline)-6-sulfonic acid (ABTS) cation radical scavenging assays, cycloorbicoside A-7-monoacetate (
) (5.03 mg TE/g) and cycloorbicoside B (
) (10.60 mg TE/g) displayed the highest activities, respectively. Oleanolic acid (
) (51.45 mg TE/g) and 3-
-β-d-xylopyranoside-(23
,24
)-16β,23;16α,24-diepoxycycloart-25(26)-en-3β,7β-diol 7-monoacetate (
) (13.25 mg TE/g) revealed the highest reducing power in cupric ion-reducing activity (CUPRAC) and ferric-reducing antioxidant power (FRAP) assays, respectively. In metal-chelating activity on ferrous ions, compound
displayed the highest activity estimated by 41.00 mg EDTAE/g (EDTA equivalents/g). The tested triterpenes showed promising AChE and BChE inhibitory potential with 3-
-β-d-xylopyranoside-(23
,24
)-16β,23;16α,24-diepoxycycloart-25(26)-en-3β,7β-diol 2',3',4',7-tetraacetate (
), exhibiting the highest inhibitory activity as estimated from 5.64 and 5.19 mg GALAE/g (galantamine equivalent/g), respectively. Compound
displayed the most potent tyrosinase inhibitory activity (113.24 mg KAE/g (mg kojic acid equivalent/g)). Regarding α-amylase and α-glucosidase inhibition, 3-
-β-d-xylopyranoside-(23
,24
)-16β,23;16α,24-diepoxycycloart-25(26)-en-3β,7β-diol (
) (0.55 mmol ACAE/g) and compound
(25.18 mmol ACAE/g) exerted the highest activities, respectively. In silico studies focused on compounds
,
, and
as inhibitors of tyrosinase revealed that compound
displayed a good ranking score (-7.069 kcal/mole) and also that the ΔG free-binding energy was the highest among the three selected compounds. From the ADMET/TOPKAT prediction, it can be concluded that compounds
and
displayed the best pharmacokinetic and pharmacodynamic behavior, with considerable activity in most of the examined assays.
The metabolic variation in the essential oil composition of
leaves obtained from different seasons was quantitatively and qualitatively determined employing GC/MS (Gas Chromatography coupled with ...Mass Spectrometry) and GC/FID (Gas chromatography equipped with flame ionization detector) techniques. It displayed the existence of 97 constituents accounting for 94.19%, 92.27%, 91.95% and 92.63% for POS (spring), POM (summer), POA (autumn) and POW (winter) whole essential oils.
-Caryophyllene constituting the main metabolite in the oil in the different seasons. To better visualize the differences between them, GC data were exposed to chemometric analysis. A PCA (principal component analysis) score plot revealed the closeness of POS and POW. Molecular modelling on collagenase, elastase and hyaluronidase enzymes active centres shows that different compounds existing in the essential oil of
leaves shows binding to the active sites with variable degrees that suggested its anti-ageing potential. Palmitic acid displayed the highest fitting for both the collagenase and elastase active centres in both pH-based and rule-based ionization methods with ∆G equals -78.27 and -44.77 kcal/mol, respectively; meanwhile, heptacosane showed the highest fitting score in the hyaluronidase centre with ∆G = -43.78 kcal/mol. In vitro assays consolidates the obtained modelling studies in which essential oil shows considerable anti-elastase and anti-hyaluronidase potential as evidenced by their IC
values being 49.3 and 37.7 μg/mL, respectively; meanwhile, the essential oil of
leaves displayed mild anti-collagenase potential. Thus, it can be concluded that
could serve as a promising anti-ageing naturally occurring drug that could be effectively incorporated by pharmaceutical industries in cosmetics combating ageing and skin wrinkling.
The chemical composition of
bark essential oil (PRO) was qualitatively and quantitatively determined using GC/FID and GC/MS. The anti-inflammatory activity was assessed in vitro by evaluating the ...binding percentages on the cannabinoids and opioids receptors. Bleomycin (BLM)-induced pulmonary inflammation in
mice was adopted to assess PRO anti-inflammatory efficacy in vivo. In silico molecular modelling of its major components was performed on human glucocorticoids receptor (GR). Seventy-five components were identified in which longifolene (33.13%) and palmitic acid (9.34%) constituted the predominant components. No binding was observed on cannabinoid receptor type 1 (CB1), whereas mild binding was observed on cannabinoid receptor type 2 (CB2),
,
, and
receptors accounting for 2.9%, 6.9%, 10.9% and 22% binding. A significant in vivo activity was evidenced by reduction of the elevated malondialdehyde (MDA), nitric oxide (NO), myeloperoxidase (MPO), interleukin-6 (IL-6), and tumor necrosis factor-
(TNF-
) levels by 55.56%, 55.66%, 64.64%, 58.85% and 77.78% with concomitant elevation of superoxide dismutase (SOD) and catalase (CAT) activities comparable to BLM-treated group at 100 mg/kg body weight. In silico studies showed that palmitic acid exerted the fittest binding. PRO could serve as a potent anti-inflammatory natural candidate that should be supported by further clinical trials.
Tabebuia impetiginosa (Bignoniaceae) was traditionally used for memory enhancement and central nervous system (CNS) stimulation.
Aim of the study: This study aims to create a metabolic profile of the ...ethyl acetate fraction of T. impetiginosa (TEF) and investigate for the first time its neuroprotective potential on cyclophosphamide (CP)-induced chemobrain, validating its traditional use.
Metabolite profiling of TEF was performed using Liquid Chromatography coupled with Quadrupole Time of Flight-Mass/Mass Spectrometry (LC-qTOF-MS/MS). For the in vivo study, CP (200 mg/kg, i.p.) was administered to induce cognitive impairment in rats; TEF (30 mg/kg, p.o.) was administered throughout the 14 days of the experiment to assess its role in mitigating CP-induced neuronal deficits. Behavioral tests including locomotor, Y-maze, and passive avoidance tests were conducted. Additionally, biochemical markers such as reduced glutathione (GSH), malondialdehyde (MDA), tumor necrosis factor-α (TNF-α), and caspase-3 immunoexpression were assessed in the hippocampus area.
Forty-four phytoconstituents were tentatively identified in TEF, mainly iridoids and organic acids. TEF showed significant memory enhancement as evidenced by the increase in step-through latency in the passive avoidance test by 1.5 folds and the increase in sequence alternation percentage (SAP) in the Y-maze test by 67.3%, as compared to CP-group. Moreover, it showed pronounced antioxidant and anti-inflammatory potentials evidenced by the significant elevation in reduced glutathione (GSH) levels by 80% and a pronounced decline in MDA and TNF-α levels by 24% and 45%, respectively relative to the CP group. TEF treatment restored normal hippocampal histological features and attenuated apoptotic caspase-3 expression by 70% compared to the CP group.
TEF can act as a promising natural scaffold in managing the chemobrain induced by CP in cancer patients.
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•Metabolic profiling of its ethyl acetate fraction (TEF) was done by LC/MS/MS.•Forty-four compounds were identified in TEF mainly iridoids and organic acids.•TEF exhibited pronounced antioxidant and anti-inflammatory potentials.•It also showed promising neuroprotective effect in in vivo chemobrain model.
Thunbergia erecta (Benth.) was traditionally used as anxiolytic, sedative and antidepressant.
The study aimed to characterize T. erecta leaf ethyl acetate fraction of alcohol extract (TEAF) and ...evaluate its neuroprotective effect on doxorubicin and cyclophosphamide-induced chemobrain.
Chemical profiling of TEAF was done using (Liquid chromatography coupled with mass (LC-ESI-MS/MS). In vivo chemobrain model was performed by cognitive impairment induced by doxorubicin and cyclophosphamide. Behavioral assessments included moris water maze, y maze, novel object recognition task and passive avoidance tests. Histological examination and oxidative stress markers were investigated. Protein expression of HMDGB1/RAGE/pNF-κB pathway markers was done using western blotting. All results were applied to hippocampus and prefrontal cortex of rats. Molecular docking was done within the active sites of Human Receptor for Advanced Glycation Endproducts (RAGE) using Discovery studio software.
Twenty-one phytoconstituents, mostly polyphenolics, were characterized in TEAF of which eleven compounds were tentatively identified for the first time from T. erecta leaves where rosmarinic acid (11) represents the most prevailing compound. TEAF resulted in a marked dose-dependent amelioration of the histopathological changes evidenced by normal histological structure demonstrated in the hypocampal gesture of rats. TEAF demonstrated an enhanced memory and learning functioning in the different behavioral tests assessed especially at 200 mg/kg. It showed significant long-term spatial memory enhancement manifested by 50.32% increase in probe trial relative to chemobrain-induced group. It showed pronounced antioxidant activity evidenced by the significant elevation of prefrontal cortical and hippocampal reduced glutathione levels by 2.45 and 2.65 folds, respectively relative to the chemobrain-induced group. The pronounced reduction in hydrogen peroxide (1.24–1.93 folds) and malondialdehyde levels (1.42–2.60 folds) with significant elevation of catalase activity (12.65–31.47%) induced by TEAF supported its potent antioxidant activity. TEAF reversed the inflammatory cytokines release induced by chemotherapy via its interference with HMGB1/RAGE pathway suppressing the expression of HMBG1, RAGE, p65 (NF-kB), and IL-1β. In silico studies showed that rosmarinic acid displayed the best fitting at the active site of RAGE (ΔG = −40.39 kcal/mol).
Thunbergia erecta can act as a promising remedy for chemobrain that further consolidates its traditional importance.
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Lobularia libyca (L. libyca) is a traditional plant that is popular for its richness in phenolic compounds and flavonoids. The aim of this study was to comprehensively investigate the phytochemical ...profile by liquid chromatography, electrospray ionization and tandem mass spectrometry (LC-ESI-MS), the mineral contents and the biological properties of L. libyca methanol extract. L. libyca contains significant amounts of phenolic compounds and flavonoids. Thirteen compounds classified as flavonoids were identified. L. libyca is rich in nutrients such as Na, Fe and Ca. Moreover, the methanol extract of L. libyca showed significant antioxidant activity without cytotoxic activity on HCT116 cells (human colon cancer cell line) and HepG2 cells (human hepatoma), showing an inhibition zone of 13 mm in diameter. In silico studies showed that decanoic acid ethyl ester exhibited the best fit in β-lactamase and DNA gyrase active sites; meanwhile, oleic acid showed the best fit in reductase binding sites. Thus, it can be concluded that L. libyca can serve as a beneficial nutraceutical agent, owing to its significant antioxidant and antibacterial potential and due to its richness in iron, calcium and potassium, which are essential for maintaining a healthy lifestyle.
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