Characterization Of Bioactive Metabolites Research Articles

A comparative metabolomic investigation of different sections of Sicilian Citrus x limon (L.) Osbeck, characterization of bioactive metabolites, and evaluation of in vivo toxicity on zebrafish embryo.

Citrus fruits are a diverse and economically important group of fruit crops known for their distinctive flavors and high nutritional value. Their cultivation and consumption contribute significantly to the global agricultural economy and offer a wide range of health benefits. Among the genetic diversity of citrus species, Citrus x limon (L.) Osbeck is particularly relevant due to its chemical composition and potential health benefits. Two cultivars from the Sicily region (southern Italy) were compared for their phenolic content and preliminary antioxidant activity to select the distinctive extract with potential biological activity. A detailed characterization revealed the occurrence of phenolics, coumarins, and flavonoids. The quantification of metabolites contained in the selected extract was performed by an ultrahigh-performance liquid chromatographic method coupled with an ultraviolet detector. Different concentrations were tested in vivo through the fish embryo acute toxicity test, and the 50% lethal dose of 107,833µgmL-1 was calculated. Finally, the effect of the extract on hatching was evaluated, and a dose-dependent relationship with the accelerated hatching rate was reported, suggesting a Femminello Zagara Bianca green peel upregulating effect on the hatching enzymes. PRACTICAL APPLICATION: Citrus fruits and their products continue to be one of the natural food sources with the highest waste output. In this study, we demonstrate how food industry waste, particularly lemon peel, is rich in bioactive compounds with anti-inflammatory and antioxidant properties that may be used in the nutraceuticals industry.

Characterization of Bioactive Metabolites and Antioxidant Activities in Solid and Liquid Fractions of Fresh Duckweed (Wolffia globosa) Subjected to Different Cell Wall Rupture Methods.

Fresh Wolffia globosa, the smallest flowering plant well-known for its favorable nutrient composition and rich content of bioactive compounds, was subjected to boiling, freeze-thawing, and mechanical crushing to reduce its excessive (95-96%) moisture level and consequent drying time. The resultant three wolffia matrixes were filtered through a plankton net to fractionate into the residue and the filtrate. The proximate composition, bioactive metabolites, antioxidant activity, and characterization of bioactive metabolites by LC-ESI-QTOF-MS/MS and Fourier transform infrared spectroscopy were made from oven-dried residues and filtrates. Among residues, crude protein (29.84%), crude lipid (5.77%), total carotenoids (TCC; 722.8 μg/g), and vitamin C (70.02 mg/100 g) were the highest (p < 0.05) for freeze-thawing against higher ash (7.99%), total phenolic content (TPC; 191.47 mg GAE g-1 dry weight), total flavonoid content (TFC; 91.54 mg QE g-1 dry weight), DPPH activity (47.46%), and ferric reducing antioxidant power (FRAP) activity (570.19 μmol FeSO4 equiv/mg) for the crushed counterpart and Chl-b in residues from boiling. No significant variation was evident in the total tannin content (TTC). Among filtrates, higher total phenolic content (773.29 mg GAE g-1 dry weight), TFC (392.77 mg QE g-1 dry weight), TTC (22.51 mg TAE g-1), and antioxidant activity as DPPH activity (66.46%) and FRAP (891.62 μmol FeSO4 equiv/mg) were evident for boiling, while that from crushing exhibited the highest TCC (1997.38 μg/g DM). LC-ESI-QTOF-MS/MS analysis identified 72 phenolic compounds with the maximum in residue (33) and filtrate (33) from freeze-thawing, followed by crushing (18 and 19) and boiling (14 and 13) in order, respectively. The results indicated that the predrying cell rupturing method significantly impacted quantitative, as well as qualitative compositions of residues and filtrates from fresh wolffia.

Comprehensive Metabolite Fingerprinting of Australian Black and Green Olives and Their Antioxidant and Pharmacokinetics Properties

Polyphenols, especially flavonoids, are well-known for their bioactive antioxidant properties. Therefore, this study aimed to analyze Australian black (ripe) and green olives (unripe) for phenolic and non-phenolic metabolites, antioxidant activities, and pharmacokinetic properties. Liquid chromatography–mass spectrometry coupled with quadrupole–time of flight (LC–ESI–QTOF–MS/MS) was applied to elucidate the composition, identification, and characterization of bioactive metabolites from Australian olives. This study identified 110 metabolites, including phenolic acids, flavonoids, stilbenes, lignans, and other compounds (phenolic terpenes, tyrosols, fatty acids, and terpenoids). Luteolin (flavonoid) and verbascoside (hydroxycinnamic acid) are identified with higher concentrations in black olives. Black (ripe) olives were measured at a higher TPC (10.94 ± 0.42 mg GAE/g) and total antioxidant potential than green olives. The pharmacokinetic properties (absorption, distribution, metabolism, excretion, toxicity) of phenolic compounds for human health were evaluated to predict the potential of the most abundant metabolites in olives. Gastrointestinal absorption and Caco-2 cell permeability of metabolites in olives were also predicted. This study will develop into further research to identify the Australian olives’ therapeutic, nutraceutical, and phytopharmaceutical potential.

Antioxidant activity and protective effect of the outer scales hydroalcoholic extract of Allium cepa L. var. Tropea on toxicity damage induced by Cadmium in Caco-2 cells.

The characterization of bioactive metabolites and the protective effects against Cadmium (Cd) of the hydroalcoholic extract from Allium cepa var. Tropea (Tropea red onion) in human Caco-2 colon adenocarcinoma cells and in vitro antioxidant effects were investigated. Tropea red onion extract showed high levels of bioactive compounds and a strong activity as radical scavenger and inhibitor of lipid peroxidation. The most abundant specialized metabolites were quercetin derivatives. In addition, the extract inhibited NO release in a dose-dependent manner. Exposure of Cd treated human Caco-2cells to the Tropea red onion extract resulted in a higher cytoprotection with a significant falloff of cells damage produced by Cd. The effect of Tropea red onion evaluated with the MTT assay and LDH test, was time-dependent and more evident after 24h of treatment. Caco-2cells treated with the Tropea red onion extract and CdCl2 at 24h showed a significant cytoprotection at concentrations equal to 50μg/mL + 25μM and 100μg/mL + 25μM while at 72h at a concentration of 25μg/mL + 25μM. We observed with MTT and LDH assays that treatment of cells with Tropea red onion extract at 24h was able to significantly prevent Cd-induced cytotoxicity alone.

UHPLC-QToF-MS characterization of bioactive metabolites from Quercus robur L. grown in South Africa for antioxidant and antidiabetic properties

The leaves and stem bark extracts of Quercus robur L. grown in South Africa have been investigated for their bioactive metabolites using UHPLC-QToF-MS. The UHPLC-QToF-MS profiling of the various extracts revealed the presence of twenty-seven compounds. These compounds were majorly grouped into flavonoids, phenolic acid and triterpenoids such as alnusiin, (+)-catechin, cis-3,4-leucopelargonidin, (-)-gallocatechin, ellagic acids, gallic acid, luteoforol, kaempferol-3-o-(6-o-cis-coumaryl)glucoside, myricitrin, neohesperidin, neriifolin, pheophorbide a, pheophytin a, procyanidin B5, pedunculagin, quercetin 3-O-[beta-D-xylosyl-(1- > 2)-beta-D-glucoside and quercitrin. The aqueous bark extract had the highest total phenol content (TPC) (320 mg GAE/g DW) and total flavonoids content (TFC) (505 mg QE/g DW), whereas the 80% aqueous acetone leaves extract had the highest proanthocyanidins levels (Pro) (433 CE/g DW). The 80% aqueous acetone extract had the best 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) scavenging capability with an IC50 value of 8.16 µg/mL. The 80% aqueous ethanol extract had the highest 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) scavenging ability with an IC50 value of 7.73 µg/mL. The aqueous leaves extract had the best ferric reducing antioxidant power assay (FRAP) ability with values of 558 µg/mL GAE. The most significant inhibitory effects on digestive enzyme activity were obtained with the 80% aqueous methanol bark and aqueous bark extracts at the concentration of 7.81 µg/mL, yielding inhibition values of 62 and 97% on α-amylase and α-glucosidase, respectively higher than the positive control used (acarbose). These findings calls attention to the phytochemical content, antioxidant and inherent antidiabetic activity of Q. robur L. grown in South Africa and therefore potentiate its potential application in the food and pharmaceutical industries, with a focus in the prevention of diabetes.

Effect of Adiantum philippense Extract on Biofilm Formation, Adhesion With Its Antibacterial Activities Against Foodborne Pathogens, and Characterization of Bioactive Metabolites: An in vitro-in silico Approach.

Adiantum philippense (A. philippense), an ethnomedicinally important fern, has become an interesting herb in the search for novel bioactive metabolites, which can also be used as therapeutic agents. Primarily, in this study, A. philippense crude extract was screened for its phytochemical constituents, antagonistic potential, and effect on bacterial adhesion and biofilm formation against common food pathogens. Phytochemical profiling of A. philippense was carried out by using High Resolution-Liquid Chromatography and Mass Spectroscopy (HR-LCMS) followed by antibacterial activity via agar cup/well diffusion, broth microdilution susceptibility methods, and growth curve analysis. Antibiofilm potency and efficacy were assessed on the development, formation, and texture of biofilms through light microscopy, fluorescent microscopy, scanning electron microscopy, and the assessment of exopolysaccharide production. Correspondingly, a checkerboard test was performed to evaluate the combinatorial effect of A. philippense and chloramphenicol. Lastly, molecular docking studies of identified phytochemicals with adhesin proteins of tested food pathogens, which helps the bacteria in surface attachment and leads to biofilm formation, were assessed. A. philippense crude extract was found to be active against all tested food pathogens, displaying the rapid time-dependent kinetics of bacterial killing. A. philippense crude extract also impedes the biofilm matrix by reducing the total content of exopolysaccharide, and, likewise, the microscopic images revealed a great extent of disruption in the architecture of biofilms. A synergy was observed between A. philippense crude extract and chloramphenicol for E. coli, S. aureus, and P. aeruginosa, whereas an additive effect was observed for S. flexneri. Various bioactive phytochemicals were categorized from A. philippense crude extract using HR-LCMS. The molecular docking of these identified phytochemicals was interrelated with the active site residues of adhesin proteins, IcsA, Sortase A, OprD, EspA, and FimH from S. flexneri, S. aureus, P. aeruginosa, and E. coli, respectively. Thus, our findings represent the bioactivity and potency of A. philippense crude extract against food pathogens not only in their planktonic forms but also against/in biofilms for the first time. We have also correlated these findings with the possible mechanism of biofilm inhibition via targeting adhesin proteins, which could be explored further to design new bioactive compounds against biofilm producing foodborne bacterial pathogens.

The antibacterial and antibiofilm activity of sea anemone (Stichodactyla haddoni) against antibiotic-resistant bacteria and characterization of bioactive metabolites

Sea anemones produce many biologically active compounds including neurotoxins, pore-forming toxins, phospholipases and proteinase inhibitors. The Persian Gulf is an unexplored environment and maybe a rich source of marine natural products. The aim of this study is screening and identification of bioactive metabolites from Stichodactyla haddoni (Haddon’s sea anemone) collected at the Persian Gulf. The crude extract of the sea anemone (tentacle, disc and total body) was obtained by methanol solvent. The antibacterial assays were carried out by the disc diffusion method. The antibiofilm activity (biofilm formation, biofilm destruction and reduction of metabolic activity) of the sea anemone extracts was evaluated by microtiter plate method. The bioactive compounds were identified by GC–MS analysis. Data showed that the best antibacterial effect (relate to P. aeruginosa) is obtained from extracts of “total body” section. Values of minimum inhibitory concentration and minimum bactericidal concentration show that the maximum antibacterial activity takes place at 10–20 mg/ml concentration. Three parts of sea anemone exhibit different inhibition against biofilm of bacteria, in particular, inhibition of biofilm observed by the tentacle, disc and total body against P. aeruginosa, K. pneumonia and A. baumannii, respectively. Biofilm of P. aeruginosa was the most sensitive and the biofilm of B. cereus was the most resistant structure between all pathogenic bacteria. The best reduction in the metabolic activity was observed in P. aeruginosa and K. pneumonia among tested bacteria. Aliphatic compounds were predominant bioactive metabolites in this sea anemone. The marine animal and especially sea anemone produce useful bioactive compounds that can be used to prevent bacterial biofilm; application of bioactive materials, reported in this study, can be proposed for future studies.

Characterization of Bioactive Metabolites of Endophytic Fusarium solani Isolated from Withania somnifera

This study was conducted to characterize and explore the endophytic fungi of Withania somnifera plant for their bioactive potential. A total of 70 segments of W. somnifera were screened and the highest species richness, as well as frequency of colonization was found in root determined as 25%. Endophytic fungi shown significant antibacterial activity against Staphylococcus aureus, E.coli, Proteus sp, Klebsiella pneumoniae and Pseudomonas sp. and were identified as Corynespora cassicola, Fusarium solani and Penicillium chrysogenum. The minimum inhibitory concentration (MIC) by the micro dilution broth was in the range of 21-82 μg/mL. Isolates revealed the presence of different phytochemicals, which includes, terpenoids, tannins, alkaloids and flavonoids. Based on its antibacterial, antioxidant and cytotoxic potential, Fusarium solani was selected, characterized genotypically by 28S rDNA typing and the sequence was deposited in NCBI database under accession number KJ193849. Fusarium solani was found to possess higher relative percentage reducing power of about 90.62% than that of Corynespora cassicola (57.47%) and Penicillium chrysogenum (52.37%) and the absorbance value obtained is comparable with the control. Percentage cell viability on cultured HeLa cell lines was determined as 6.25 μg/mL (64.74%), 12.5 μg/mL (61.08%), 25 μg/mL (58.68%), 50 μg/mL (53.24%), and 100 μg/mL (49.94%).There was significant reduction in the viability of cancer cells at 100 μg/mL. GC-MS analysis of the HPTLC fractions of Fusarium solani showed a wide range of compounds and the compounds taraxasterol, acenaphthylene, 3,4-oxadiazole, benzenamine were pharmaceutically important.

Isolation and characterization of bioactive metabolites from Xylaria psidii, an endophytic fungus of the medicinal plant Aegle marmelos and their role in mitochondrial dependent apoptosis against pancreatic cancer cells

BackgroundThe genus Xylaria has been reported as a rich source of biologically active secondary metabolites. In the present study, an endophytic fungus Xylaria psidii has been isolated from the leaf sample of Aegle marmelos (L.) Corr., characterized on the basis of its morphological features and sequence data for the ITS region (KU291350) of the nuclear ribosomal DNA. Biological screening of ethyl acetate extract of Xylaria psidii displayed a potential therapeutic effect on pancreatic cancer cells. HypothesisThis study was designed systematically to explore Xylaria psidii, an endophytic fungus for the identification of biologically active secondary metabolites against pancreatic cancer cells. MethodsWhile exploring the bioactive secondary metabolites, a sensitive and reliable LC-MS based dereplication approach was applied to identify four compounds A-D from fungal extract. Further bioactivity guided isolation of fungal extract yielded two major metabolites 1 and 2. The structures of 1 and 2 have been determined by detailed spectroscopic analysis including MS, NMR, IR and UV data and similarity with published data. Xylarione A (1) is new whereas (−) 5-methylmellein (2) is reported for the first time from X. psidii. Both the isolated compounds were screened for their effect on the viability and proliferation against a panel of cancer cell lines (MCF-7, MIA-Pa-Ca-2, NCI-H226, HepG2 and DU145) of different tissue origin. ResultsCompounds 1 and 2 exhibited cytotoxicity against pancreatic cancer (MIA-Pa-Ca-2) cells with IC50 values of 16.0 and 19.0 µm, respectively. The cell cycle distribution in MIA-Pa-Ca-2 cells, confirmed a cell cycle arrest at the sub-G1 phase. Cell death induced by 1 and 2 displayed features characteristic of apoptosis. Flow cytometry based analysis of 1 and 2 using Rhodamine-123 displayed substantial loss of mitochondrial membrane potential in a concentration dependent manner by both the compounds. ConclusionResults conclude that the isolated compounds 1 and 2 are responsible for the activity shown by crude ethyl acetate extract and may act as potential leads for medicinal chemists for designing more potent analogs.

Isolation and Characterization of Bioactive Metabolites from Fruiting Bodies and Mycelial Culture of Ganoderma oerstedii (Higher Basidiomycetes) from Mexico.

Various species of the genus Ganoderma have been used for centuries according to oriental tradition as a source of medicines and nutrients. A chemical study of the fruiting bodies and mycelial culture of G. oerstedii was carried out with the idea of isolating and characterizing active natural components present to make use of their potential pharmaceutical application in Mexico. The fruiting bodies and mycelial culture of G. oesrtedii were lyophylized and extracted one after the other with hexane, chloroform, and methanol. Following this process, each substance was extracted separately by using column chromatography. From fruiting bodies eight metabolites, five sterols (ergosta-7,22-dien-3β-ol, ergosterol peroxide, ergosterol, cerevisterol, and ergosta-7,22-dien-3-one) as well as three terpene compounds (ganodermanondiol, ganoderic acid Sz, and ganoderitriol M) were obtained from fruiting bodies. From the mycelial culture three metabolites, two sterols (ergosterol and cerevisterol), and a new terpene compound (ganoderic acetate from the acid) were obtained. These structures were established based on a spectroscopic analysis mainly using nuclear magnetic resonance and a comparison with data already established.

Production and characterization of bioactive metabolites from piezotolerant deep sea fungus Nigrospora sp. in submerged fermentation.

To produce and characterize bioactive metabolites from piezotolerant marine fungus Nigrospora sp. in submerged fermentation. A distinct marine strain, Nigrospora sp. NIOT has been isolated from a depth of 800 m at the Arabian Sea. The 18S rRNA and internal transcribed spacers (ITS) analysis demonstrates its close association with the genus Nigrospora. Effect of pH, temperature, salinity, carbon source and amino acids was studied to optimize the fermentation conditions. Optimal mycelia growth and secondary metabolites production were observed at 6·0-8·0 pH, 20-30°C temperature, 7·5% salinity, sucrose as carbon source and tryptophan as amino acid source. The extracellular secondary metabolites exhibited high antimicrobial activities against both gram-positive and gram-negative pathogenic bacteria with minimal inhibitory concentration (MIC) values higher than 30 μg ml(-1). Strongest cytotoxicity was observed in all cell lines tested, GI50 (growth inhibition by 50%) was calculated to be 1·35, 3·2, 0·13 and 0·35 μg ml(-1) against U937, MCF-7, A673 and Jurkat, respectively. Fourier transform infrared spectroscopy (FTIR) and gas chromatography-mass spectrometry (GC-MS) analyses of secondary metabolites confirmed the production of antimicrobial and anticancer substances. A piezotolerant fungus Nigrospora sp. NIOT isolated from deep sea environment was successfully cultured under submerged fermentation. The secondary metabolites produced from this organism showed potent antimicrobial and anticancer activities with immediate application to cosmetics and pharmaceutical industries. This is the first study exploring Nigrospora sp. from 800 m in marine environment. This deep sea fungus under optimized culture conditions effectively produced bioactive secondary metabolites such as griseofulvin, spirobenzofuran and pyrone derivatives at higher concentrations.

Taxonomy and Characterization of Bioactive Metabolites from a New Marine Microorganism Strain MLA-21

Taxonomy and Characterization of Bioactive Metabolites from a New Marine Microorganism Strain MLA-21

ChemInform Abstract: Isolation and Characterization of Bioactive Metabolites from Marine‐Derived Filamentous Fungi Collected from Tropical and Sub‐tropical Coral Reefs.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Isolation and characterization of bioactive metabolites from marine-derived filamentous fungi collected from tropical and sub-tropical coral reefs.

Two new compounds, paecilospirone (1) and phomopsidin (2), and seven known compounds, chaetoglobosin A (3), griseofulvin (4), fusarielin A (5), fusapyrone (6), deoxyfusapyrone (7), and verrucarins J (8) and L acetate (9), have been isolated and characterized from marine-derived fungi collected in tropical and sub-tropical coral reef environments. The utility of marine-derived fungi as a source of bioactive secondary metabolites is discussed.