scholarly journals Role of Sulphur and Heavier Chalcogens on the Antioxidant Power and Bioactivity of Natural Phenolic Compounds

Biomolecules ◽  
2022 ◽  
Vol 12 (1) ◽  
pp. 90
Author(s):  
Maria Laura Alfieri ◽  
Lucia Panzella ◽  
Riccardo Amorati ◽  
Alice Cariola ◽  
Luca Valgimigli ◽  
...  

The activity of natural phenols is primarily associated to their antioxidant potential, but is ultimately expressed in a variety of biological effects. Molecular scaffold manipulation of this large variety of compounds is a currently pursued approach to boost or modulate their properties. Insertion of S/Se/Te containing substituents on phenols may increase/decrease their H-donor/acceptor ability by electronic and stereo-electronic effects related to the site of substitution and geometrical constrains. Oxygen to sulphur/selenium isosteric replacement in resveratrol or ferulic acid leads to an increase in the radical scavenging activity with respect to the parent phenol. Several chalcogen-substituted phenols inspired by Vitamin E and flavonoids have been prepared, which in some cases prove to be chain-breaking antioxidants, far better than the natural counterparts. Conjugation of catechols with biological thiols (cysteine, glutathione, dihydrolipoic acid) is easily achieved by addition to the corresponding ortho-quinones. Noticeable examples of compounds with potentiated antioxidant activities are the human metabolite 5-S-cysteinyldopa, with high iron-induced lipid peroxidation inhibitory activity, due to strong iron (III) binding, 5-S-glutathionylpiceatannol a most effective inhibitor of nitrosation processes, and 5-S-lipoylhydroxytyrosol, and its polysulfides that proved valuable oxidative-stress protective agents in various cellular models. Different methodologies have been used for evaluation of the antioxidant power of these compounds against the parent compounds. These include kinetics of inhibition of lipid peroxidation alkylperoxyl radicals, common chemical assays of radical scavenging, inhibition of the OH• mediated hydroxylation/oxidation of model systems, ferric- or copper-reducing power, scavenging of nitrosating species. In addition, computational methods allowed researchers to determine the Bond Dissociation Enthalpy values of the OH groups of chalcogen modified phenolics and predict the best performing derivative. Finally, the activity of Se and Te containing compounds as mimic of glutathione peroxidase has been evaluated, together with other biological activities including anticancer action and (neuro)protective effects in various cellular models. These and other achievements are discussed and rationalized to guide future development in the field.

Processes ◽  
2020 ◽  
Vol 8 (3) ◽  
pp. 336 ◽  
Author(s):  
Hammad Saleem ◽  
Muhammad Sarfraz ◽  
Hafiz Muhammad Ahsan ◽  
Umair Khurshid ◽  
Syed Asif Jahanzeb Kazmi ◽  
...  

This research endeavors to inspect the chemical and biological profiling of methanol and dichloromethane (DCM) extracts prepared from Abutilon figarianum Webb. Total bioactive constituents and secondary metabolites were assessed via ultra-high performance liquid chromatography (UHPLC-MS). Biological effects were evaluated via antioxidant and enzymes inhibitory assays. The methanol extract was able to give the highest phenolic (51.92 mg GAE/g extract) and flavonoid (72.59 mg QE/g extract) contents and was found to contain 11 bioactive metabolites, including flavonoid, alkaloid, phenolic and fatty acid derivatives, as accessed by UHPLC-MS analysis. Similarly, the phytochemical profiling of the DCM extract tentatively identified the 12 different secondary metabolites, most of these were fatty acid derivatives. The methanol extract was most active in the radical scavenging, reducing power and total antioxidant power assays, while dichloromethane extract showed the highest metal chelating activity. For enzyme inhibition, the DCM extract showed the highest activity against cholinesterases, glucosidase and amylase, whereas methanol extract was most active against tyrosinase. Docking studies have supported the observed biological activity, where isobergapten showed higher activity against tyrosinase (−7.63 kcal/mol) with inhibition constant (2.55 µM), as opposed to other enzymes. The observed antioxidant and inhibitory potentials of A. figarianum against the studied enzymes tend to endorse this plant as a prospective source of bioactive phytochemicals.


2020 ◽  
Vol 10 (2) ◽  
pp. 145-152 ◽  
Author(s):  
Imane Rihab Mami ◽  
Rania Belabbes ◽  
Mohammed El Amine Dib ◽  
Boufeldja Tabti ◽  
Jean Costa ◽  
...  

Background: Carthamus caeruleus belongs to the Asteraceae family. The roots are traditionally used as healing agents. They help to heal burns and treat skin diseases. They are also used against joint inflammation and are very effective against diseases such as irritable bowel syndrome for cancer patients. Objectives: The purpose of this work was i) to study the chemical composition of i) the essential oil and hydrosol extract of Carthamus caeruleus, ii) to isolate the major component of both extracts and iii) to evaluate their antioxidant, antifungal and insecticidal activities. Methods: The essential oil and hydrosol extract obtained from the roots were studied by GC and GC/MS. The antioxidant activities were performed using two different methods i) Radical scavenging activity (DPPH) and ii) the Ferric-Reducing Antioxidant Power (FRAP), using BHT as a positive control. Whereas, the antifungal activity of the essential oil and Carlina oxide was investigated against plant fungi. The fumigation toxicity of C. caeruleus essential oil besides Carlina oxide was evaluated against adults of Bactrocera oleae better known as the olive fly. Results: The essential oil and hydrosol extract were mainly represented by acetylenic compounds such as carline oxide and 13-methoxy carline oxide. Carlina oxide was isolated and identified by 1H and 13C NMR spectroscopic means. The results showed that Carlina oxide presented interesting antioxidant and antifungal properties, while C. caeruleus root essential oil had better insecticidal activity. Furthermore, Carlina oxide has demonstrated promising in vivo antifungal activity to control infection of apples by Penicillium expansum. Conclusion: Carlina oxide can be used as a natural food preservative and alternative to chemical fungicides to protect stored apple against Penicillium expansum.


Plants ◽  
2021 ◽  
Vol 10 (6) ◽  
pp. 1191
Author(s):  
Mahak Majeed ◽  
Tanveer Bilal Pirzadah ◽  
Manzoor Ahmad Mir ◽  
Khalid Rehman Hakeem ◽  
Hesham F. Alharby ◽  
...  

The study aimed at evaluating the antioxidant profile of a medicinal epiphyte Viscum album L. harvested from three tree species, namely, Populus ciliata L, Ulmus villosa L., and Juglans regia L. The crude extracts were obtained with ethanol, methanol, and water and were evaluated for the total phenol content (TPC), total flavonoid content (TFC), and antioxidant activities using total reducing power (TRP), ferric reducing antioxidant power (FRAP), 1, 1-diphenyl 1-2-picryl-hydrazyl (DPPH), superoxide radical scavenging (SOR), and hydroxyl radical scavenging (•OH) assays. Our results showed that crude leaf extracts of plants harvested from the host Juglans regia L. exhibited higher yields of phytochemical constituents and noticeable antioxidative properties. The ethanolic leaf samples reported the highest phenols (13.46 ± 0.87 mg/g), flavonoids (2.38 ± 0.04 mg/g), FRAP (500.63 ± 12.58 μM Fe II/g DW), and DPPH (87.26% ± 0.30 mg/mL). Moreover, the highest values for TRP (4.24 ± 0.26 μg/mL), SOR (89.79% ± 0.73 mg/mL), and OH (67.16% ± 1.15 mg/mL) were obtained from aqueous leaf extracts. Further, Pearson correlation was used for quantifying the relationship between TPC, TFC, and antioxidant (FRAP, DPPH, SOR, OH) activities in Viscum album L. compared to their hosts. It was revealed that the epiphyte showed variation with the type of host plant and extracting solvent.


2020 ◽  
Vol 42 (1) ◽  
pp. 109-109
Author(s):  
Hao Zang Hao Zang ◽  
Qian Xu Qian Xu ◽  
Luyun Zhang Luyun Zhang ◽  
Guangqing Xia Guangqing Xia ◽  
Jiaming Sun and Junyi Zhu Jiaming Sun and Junyi Zhu

A series of hydroxytyrosol (HT) derivatives were synthesized by modification of alcohol hydroxyl group of HT, twenty-five target compounds were obtained and characterized by NMR and HRMS. The antioxidant activities of those compounds were evaluated in three different assays. Except 3e and 3y, all other compounds demonstrated significant 2,2and#39;-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) free radical cation scavenging activity ranging from IC50 3.4 to 24.4 μM, which were more potent than L-ascorbic acid (IC50=24.8 μM). Compounds 3b-3d, 3f-3k, 3m-3x were better than Trolox (18.3 M). Moreover, the ferric reducing antioxidant power (FRAP) of all compounds were discovered to be more potent than L-ascorbic acid (40.7 mmol/g), except 3e, all other compounds (141.5-202.1 mmol/g) were better than Trolox (94.7 mmol/g). Compounds 3a-3d, 3f-3j, 3l-3m, 3o, 3q, 3t, 3v-3y exhibited more potent hydroxyl radical scavenging activity (IC50=245.1-475.1 M) than L-ascorbic acid (554.4 M) and Trolox (500.4 M). Compounds 3q, 3t and 3y exhibited more potent -Glucosidase inhibition activity (39.1-52.4 M) than Acarbose (60.9 M). Compounds 3a, 3d, 3f-3m, 3s-3t, 3v-3y showed some acetylcholinesterase inhibition activities, compounds 3a, 3d, 3f-3j, 3l-3m, 3o-3p, 3s-3t, 3w showed some butyrylcholinesterase inhibition activities.


2018 ◽  
Vol 2018 ◽  
pp. 1-7 ◽  
Author(s):  
Kenza Ammor ◽  
Dalila Bousta ◽  
Sanae Jennan ◽  
Bahia Bennani ◽  
Abdellah Chaqroune ◽  
...  

The aim of this study is to investigate in vitro antioxidant and antibacterial activities of the aqueous and hydroethanolic extracts for aerial parts of Herniaria hirsuta. Extracts were screened for their possible antioxidant activities by three tests: DPPH free radical-scavenging, reducing power, and molybdenum systems. The screening of antibacterial activity of extracts was individually evaluated against sixteen bacteria species using a disc diffusion method. Flavonoids, total phenols, and tannins content were performed for both extracts. It shows higher content in the hydroethanolic extract. The hydroethanolic extract showed a significant antioxidant activity for the three methods studies to the aqueous extract, but nonsignificant results compared to the reference (BHT). However, both extracts have negative effect on the strains studies for the antibacterial activity.


Antioxidants ◽  
2019 ◽  
Vol 8 (12) ◽  
pp. 632 ◽  
Author(s):  
Gabriele Rocchetti ◽  
Biancamaria Senizza ◽  
Gokhan Zengin ◽  
Murat Ali Okur ◽  
Domenico Montesano ◽  
...  

Like other members of the Colchicum genus, C. szovitsii subsp. szovitsii is also of medicinal importance in Turkish traditional medicine. However, its biological properties have not been fully investigated. Herein, we focused on the evaluation of the in vitro antioxidant and enzyme inhibitory effects of flower, root and leaf extracts, obtained using different extraction methods. In addition, a comprehensive (poly)-phenolic and alkaloid profiling of the different extracts was undertaken. In this regard, ultra-high-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UHPLC-QTOF-MS) allowed us to putatively annotate 195 polyphenols and 87 alkaloids. The most abundant polyphenols were flavonoids (83 compounds), whilst colchicine and 2-demethylcolchicine were some of the most widespread alkaloids in each extract analyzed. However, our findings showed that C. szovitsii leaf extracts were a superior source of both total polyphenols and total alkaloids (being, on average 24.00 and 2.50 mg/g, respectively). Overall, methanolic leaf extracts showed the highest (p < 0.05) ferric reducing antioxidant power (FRAP) reducing power (on average 109.52 mgTE/g) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging (on average 90.98 mgTE/g). Interestingly, each C. szovitsii methanolic extract was more active than the water extracts when considering enzymatic inhibition such as against tyrosinase, glucosidase, and acetylcholinesterase (AChE). Strong correlations (p < 0.01) were also observed between polyphenols/alkaloids and the biological activities determined. Multivariate statistics based on supervised orthogonal projections to latent structures discriminant analysis (OPLS-DA) allowed for the detection of those compounds most affected by the different extraction methods. Therefore, this is the first detailed evidence showing that C. szovitsii subsp. szovitsii might provide beneficial effects against oxidative stress and the associated chronic diseases. Nevertheless, the detailed mechanisms of action need to be further investigated.


2017 ◽  
Vol 2017 ◽  
pp. 1-9 ◽  
Author(s):  
Yaejin Woo ◽  
Hyeji Lee ◽  
Yong-Seob Jeong ◽  
Ga Young Shin ◽  
Ja Gyeong Oh ◽  
...  

This study aimed to evaluate the antioxidant activity of various plant extracts. A total of 94 kinds of edible plant extracts obtained from the Korea Plant Extract Bank were screened for cytotoxicity, following which the total phenolic content of 24 shortlisted extracts was determined. Of these, extracts from three plants, namely, Castanea crenata (CC) leaf, Camellia japonica (CJ) fruit, and Viburnum dilatatum (VD) leaf, were examined for antioxidant capabilities by measuring radical scavenging activity, ferric reducing/antioxidant power, and lipid peroxidation inhibitory activity. In addition, cellular antioxidant activities of the three extracts were assessed by a cell-based dichlorofluorescein assay and antioxidant response element (ARE) reporter activity assay. The results demonstrated that all three extracts concentration-dependently scavenged free radicals, inhibited lipid peroxidation, reduced the cellular level of reactive oxygen species, and increased ARE-luciferase activity, indicating antioxidant enzyme-inducing potential. In particular, CJ extract showed significantly greater antioxidative activity and antimigratory effect in a breast cancer cell line compared to CC and VD extracts. Hence, CJ extract deserves further study for its in vivo functionality or biologically active constituents.


Author(s):  
K. K. Sha’a

Antioxidant activities and nutritional composition are essential ingredients normally considered in the choice of vegetables for human consumption. Leafy vegetables in particular, are regarded as protective foods in human diet due to their many health benefits. The aim of this research was to carry out the quantitative phytochemical screening, the antioxidant activities of extracts and determine the nutritional content of Cucurbita maxima and Vigna unguiculata leaves. Quantitative phytochemical screening were conducted using standard techniques. 2, 2-diphenyl-1-picrylhydrazyl (DPPH) and ferric reducing antioxidant power (FRAP) assays were used to determine antioxidant activities of these extracts. Nutritional composition was determined using standard procedures.  Quantitative analysis revealed the phytochemicals in C. maxima and V. unguiculata as; saponins (1.03%, and 1.34%), tannins (3.49% and 2.60%), terpenoids (0.0% and 0.47%), flavonoids (2.81% and 4.11%), alkaloids (5.72% and 3.5%), phenols (4.02% and 3.83%) respectively. There was a significant (p=0.05) difference in radical scavenging activity of ethanol leaf extract of V. unguiculata comprared to C. maxima. In FRAP both plants’ extract revealed a good antioxidant reducing power at 100mg/ml (range 0.40 to 0.5 absorbance) at 700nM. Antioxidant activities of extracts is attributed to their flavonoid and phenolic contents. Proximate analysis revealed the nutrients for C. maxima and V. unguiculata as; crude protein (11.58% and 14.83%), crude fat (0.47% and 0.61%), ash (4.11% and 3.72%), crude fiber (6.95 and 4.68%), moisture (1.03% and 1.38%), carbohydrate (75.86% and 74.78%) respectively. This shows that the leaves are a good source of energy to both humans and animals. Also, both vegetables revealed good percentages of proteins which can be used to compliment other sources of protein.


2018 ◽  
Vol 22 (2) ◽  
pp. 140-147 ◽  
Author(s):  
Bimala Subba ◽  
Susila Thapa

Phytochemical and biological activities of methanolic extract of seven plants viz. Scindapsus officinalis Schott. , Lepisorus loriformis, Nicotiana tabacum L., Clematis buchananiana DC., Astilbe rivularis D. Don, Potentilla fulgens Wall. ex Hook and Taxus wallichiana Zucc. were carried out. The brine shrimp bioassay showed that N. tabacum, A. rivularis, and P. fulgens were pharmacologically active. The antibacterial potential was studied against Staphylococcus aureus (gram positive bacteria) and Escherichia coli (gram negative bacteria) using Agar Well Diffusion Method. Roots of P. fulgens showed inhibition against gram positive bacteria while the rhizome of A. rivularis showed inhibition against both gram positive and gram negative bacteria. Antioxidant activity was evaluated by 2, 2-diphenyl-1-picryl hydrazyl (DPPH) free radical scavenging activity and ferric reducing antioxidant power FRAP assay. Both assays showed that P. fulgens has high antioxidant activities with (IC50 =15.57 ± 3.6) lower than standard ascorbic acid.  Journal of Institute of Science and TechnologyVolume 22, Issue 2, January 2018, Page: 140-147


2014 ◽  
Vol 31 (4) ◽  
pp. 245-252 ◽  
Author(s):  
Jovana Veljković ◽  
Jelena Brcanović ◽  
Aleksandra Pavlović ◽  
Snežana Mitić ◽  
Biljana Kaličanin ◽  
...  

Summary While there is a large number of scientific papers reporting chemical composition and biological activities of Aronia melanocarpa, there is a lack information regarding the commercially available bagged tea. In order to supply new information on the antioxidant activity of the Aronia melanocarpa tea infusions, the aim of this study was to evaluate individual phenolic compounds which could be responsible for antioxidant activities of these beverages. Selected anthocyanins (cyanidin-3-O-galactoside, cyanidin-3-O-glucoside, cyanidin- 3-O-arabinoside, and cyanidin-3-O-xyloside), gallic acid, caffeic acid, rutin, morin, and protocatechuic acid were simultaneously detected from commercially available tea infusions using a High Performance Liquid Chromatographic (HPLC) method. The antioxidant activity was measured using five in vitro spectrophotometric methods: 1,1-diphenyl- 2-picrylhydrazyl radical scavenging activity (DPPH), 2,2'-azino-bis (3-ethylbenzthiazoline- 6-sulphonic acid) radical cation scavenging activity (ABTS), ferric reducing-antioxidant power (FRAP) and reduction power (RP)Fe(III) to Fe(II). Obtained results showed that anthocyanins, predominantly of cyanidin-3-O-galactoside, are the major class of polyphenolic compounds in tea infusions. Among phenolic acids the most abundant is caffeic acid. A significant correlation between DPPH and ABTS and FRAP and RP suggested that antioxidant components in these beverages were capable scavenging free radicals and reducing oxidants. Generally, these beverages had relatively high antioxidant capacities and could be important dietary sources of antioxidant phenolics for the prevention of diseases caused by oxidative stress.


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