scholarly journals Crystal Structure, Spectroscopic Characterization, Antioxidant and Cytotoxic Activity of New Mg(II) and Mn(II)/Na(I) Complexes of Isoferulic Acid

Materials ◽  
2021 ◽  
Vol 14 (12) ◽  
pp. 3236
Author(s):  
Monika Kalinowska ◽  
Ewelina Gołębiewska ◽  
Liliana Mazur ◽  
Hanna Lewandowska ◽  
Marek Pruszyński ◽  
...  

The Mg(II) and heterometallic Mn(II)/Na(I) complexes of isoferulic acid (3-hydroxy-4-methoxycinnamic acid, IFA) were synthesized and characterized by infrared spectroscopy FT-IR, FT-Raman, electronic absorption spectroscopy UV/VIS, and single-crystal X-ray diffraction. The reaction of MgCl2 with isoferulic acid in the aqueous solutions of NaOH resulted in synthesis of the complex salt of the general formula of [Mg(H2O)6]⋅(C10H9O4)2⋅6H2O. The crystal structure of this compound consists of discrete octahedral [Mg(H2O)6]2+ cations, isoferulic acid anions and solvent water molecules. The hydrated metal cations are arranged among the organic layers. The multiple hydrogen-bonding interactions established between the coordinated and lattice water molecules and the functional groups of the ligand stabilize the 3D architecture of the crystal. The use of MnCl2 instead of MgCl2 led to the formation of the Mn(II)/Na(I) complex of the general formula [Mn3Na2(C10H7O4)8(H2O)8]. The compound is a 3D coordination polymer composed of centrosymmetric pentanuclear subunits. The antioxidant activity of these compounds was evaluated by assays based on different antioxidant mechanisms of action, i.e., with •OH, DPPH• and ABTS•+ radicals as well as CUPRAC (cupric ions reducing power) and lipid peroxidation inhibition assays. The pro-oxidant property of compounds was measured as the rate of oxidation of Trolox. The Mg(II) and Mn(II)/Na(I) complexes with isoferulic acid showed higher antioxidant activity than ligand alone in DPPH (IFA, IC50 = 365.27 μM, Mg(II) IFA IC50 = 153.50 μM, Mn(II)/Na(I) IFA IC50 = 149.00 μM) and CUPRAC assays (IFA 40.92 μM of Trolox, Mg(II) IFA 87.93 μM and Mn(II)/Na(I) IFA 105.85 μM of Trolox; for compounds’ concentration 10 μM). Mg(II) IFA is a better scavenger of •OH than IFA and Mn(II)/Na(I) IFA complex. There was no distinct difference in ABTS•+ and lipid peroxidation assays between isoferulic acid and its Mg(II) complex, while Mn(II)/Na(I) complex showed lower activity than these compounds. The tested complexes displayed only slight antiproliferative activity tested in HaCaT human immortalized keratinocyte cell line within the solubility range. The Mn(II)/Na(I) IFA (16 μM in medium) caused an 87% (±5%) decrease in cell viability, the Mg salt caused a comparable, i.e., 87% (±4%) viability decrease in a concentration of 45 μM, while IFA caused this level of cell activity attenuation (87% ± 5%) at the concentration of 1582 μM (significant at α = 0.05).

Author(s):  
Gerard Bessan Dossou-Agoin ◽  
Habib Ganfon ◽  
Fidèle Assogba ◽  
Adam Gbankoto ◽  
Joachim Gbenou ◽  
...  

Aims: The leafy stem and fruit of P.murex have been reported to be used in folk medicine to treat male reproductive system ailments. This study was undertaken to assess the antioxidant potential of the aqueous extracts of P.murex leafy stem and fruit. Methodology: Extracts were prepared by macerating the powder in water. Total phenolics amount were determined by Folin-Ciocalteu reagent, flavonoids were quantified by aluminum chloride method and total tannin content was estimated by hexacyanoferric method. The in vitro antioxidant activity of the extracts were assessed through 2,2´-diphenyl-1-picrylhydrazyl (DPPH) scavenging assay, reducing power assay, hydrogen peroxide (H2O2) inhibition assay and lipid peroxidation assay. Results: Total phenolic compounds, flavonoids and tannins content were respectively equal to 48.91± 1.67 µg/mg Gallic Acid Equivalents (GAE); 56.01± 0.90 µg/mg Rutin Equivalents (RUE); 16.92± 1.22 µg/mg Tannic Acid Equivalents (TAE) for the leafy stem extract while they were equal to 26.26± 0.54 µg/mg GAE; 47.88± 2.39 µg/mg RUE; 7.94± 0.31 µg/mg TAE for the fruit. The leafy stem extract exhibited a more pronounced DPPH scavenging activity, reducing power, hydrogen peroxide scavenging activity and lipid peroxidation activity than the fruit extract. Conclusion: The antioxidant activity of the leafy stem aqueous extract was significantly more potent than that of the fruit extract. Further studies will find out the extracts pharmacological efficacy and innocuity.


2009 ◽  
Vol 4 (9) ◽  
pp. 1934578X0900400 ◽  
Author(s):  
Mehmet Öztürk ◽  
Ufuk Kolak ◽  
Mehmet Emin Duru ◽  
Mansur Harmandar

The aerial parts of Micromeria juliana (L.) Bentham ex Reichb. were extracted with light petroleum, acetone and methanol, successively. The antioxidant activity of different concentrations of the extracts was evaluated using different antioxidant tests, namely total antioxidant (lipid peroxidation inhibition activity), DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging, ferric reducing power, and metal chelating. Total antioxidant activity was determined using the β-carotene-linoleic acid assay. Unexpectedly, the light petroleum extract exhibited strong lipid peroxidation inhibition activity. The extract was fractionated on a silica gel column and the antioxidant activity of the fractions was determined by the β-carotene-linoleic assay at 25 μg/mL concentration. The fractions that exhibited more than 50% inhibition activity were analysed by GC and GC/MS; thus, the structure of fourteen compounds were elucidated. In addition, acetyl- and butyrylcholinesterase inhibitory activities of the extracts were also determined in vitro. The light petroleum and acetone extracts were found to have mild butyrylcholinesterase inhibitory activity.


2011 ◽  
Vol 6 (10) ◽  
pp. 1934578X1100601 ◽  
Author(s):  
Sunday O. Okoh ◽  
Olayinka T. Asekun ◽  
Oluwole B. Familoni ◽  
Anthony J. Afolayan

Morinda lucida (L.) Benth. (Rubiacae) is used in traditional medicine in many West African countries for the treatment of various human diseases. The leaves and roots of this plant were subjected to hydrodistillation to obtain volatile oils which were analyzed by high resolution GC/MS. Fifty compounds were identified in the leaf volatile oil and the major compounds were α-terpinene (17.8%) and β–bisabolene (16.3%). In the root oil, 18 compounds were identified, the major constituents being 3-fluoro- p-anidine (51.8%) and hexadecanoic acid (12.0%). Antioxidant activities of the oils were examined using the DPPH, ABTS, reducing power and lipid peroxidation assays. All assays were concentration dependent with varying antioxidant potentials. The antioxidant activity of the root volatile oil of M. lucida was similar to that of the standard drugs used.


2011 ◽  
Vol 6 (9) ◽  
pp. 1934578X1100600 ◽  
Author(s):  
Xiaozhen Wang ◽  
Xican Li ◽  
Dongfeng Chen

Isoferulic acid (3-hydroxy-4-methoxycinnamic acid, IFA), the isomer of ferulic acid (4-hydroxy-3-methoxycinnamic acid), is a rare phenolic acid occurring in Rhizoma Cimicifugae. Unlike ferulic acid, which has been well investigated, the antioxidant activity of IFA has not been measured. In this study, IFA was systematically evaluated for its in vitro antioxidant activity for the first time. IC50 values were calculated of 7.30±0.57, 4.58±0.17, 1.08±0.01, 8.84±0.43, 7.69±0.39, 1.57±0.2, 13.33±0.49 μg/mL, respectively, for lipid peroxidation, DPPH (1,1-diphenyl-2-picrylhydrazyl radical) and ABTS (3-ethylbenzthiazoline-6-sulfonic acid diammonium salt) radical scavenging, reducing power on Fe3+ and Cu2+ ions, and hydroxyl and superoxide anion radical scavenging. Comparison with the IC50 values with those of the positive controls, Trolox and butylated hydroxyanisole (BHA), it can be concluded that isoferulic acid is an effective natural antioxidant in both lipid and aqueous media.


2014 ◽  
Vol 900 ◽  
pp. 267-274 ◽  
Author(s):  
Jie Wei ◽  
Jia Shi ◽  
Jun Gao ◽  
Zhi Quan Zhou ◽  
Jun Gang Fan

Sorbus sibirica fruits, popularly consumed as tea, is believed to promote healthy, relieve a cough. The literature reporting pharmacological studies related to Sorbus sibirica is very limited. Thus, The antioxidant activities of extracts from Sorbus sibirica fruits were evaluated using various in vitro assays including total flavonoid contents, total antioxidant activity, reducing power, lipid peroxidation inhibitory activity, scavenging hydroxyl and superoxide anion free radicals activity, and protective effects against DNA and protein damages. We selected the process of ultrasound-assisted extraction for total flavonoids from Sorbus sibirica fruits according to the extraction rate of total flavonoids. Results showed that the content of total flavonoids was 0.82 g per 100 g dry fruits sample obtained with ultrasound-assisted extraction method. The extracts exhibited strong scavenging capability with respect to hydroxyl and superoxide anion free radicals, and effectively inhibited the lipid peroxidation of polyunsaturated fatty acids. They also had good reducing power and protection against DNA and protein damage. Therefore, they might offer an important source of effective natural antioxidants in the food and cosmetic industries.


2015 ◽  
Vol 71 (11) ◽  
pp. m197-m198 ◽  
Author(s):  
Alfredo A. Morales-Tapia ◽  
Raúl Colorado-Peralta ◽  
Angélica M. Duarte-Hernández ◽  
Angelina Flores-Parra ◽  
José María Rivera

In the title polymeric complex salt, {[Ni(C8H4NO2)(C10H8N2)(H2O)3](C8H4NO2)}n, the NiIIcation is coordinated by a 4-cyanobenzoate anion, two 4,4′-bipyridine ligands and three water molecules in a distorted N2O4octahedral geometry. The 4,4′-bipyridine ligands bridge the NiIIcations to form polymeric chains of the title complex cations, propagating along thec-axis direction. The dihedral angle between the pyridine rings of the 4,4′-bipyridine ligand is 24.9 (6)°. In the crystal, the uncoordinating 4-cyanobenzoate anions link with the complex cationsviaO—H...O hydrogen bonds into a three-dimensional supramolecular architecture. Weak C—H...O, C—H...N interactions and π–π stacking [centroid-to-centroid distances = 3.566 (4) and 3.885 (4) Å] are also observed in the crystal.


Author(s):  
Leye Jonathan Babatola ◽  
Oluwakemisola B. Oshanimi ◽  
Olanrewaju M. Oluba ◽  
Lawrence Okoror ◽  
Adewale Agboola Odutuga

This study is sought to determine the antioxidant activity and protective ability of aqueous and methanol extractible phytochemicals from Euphorbia heterophylla leaves on lipid peroxidation induced in rat brain by pro-oxidant, in vitro. The extracts of the leaves were prepared, and the ability of the extracts is to inhibit 25 µM FeSO4 induced lipid peroxidation in isolated rats’ brain, were determined. Thereafter, total phenol content, reducing power (FRAP), Fe (II) chelating, and DPPH* free radical scavenging ability of the extracts was determined and considered as an index of antioxidant activity. The results revealed that the extracts inhibit malondialdehyde (MDA) production in the basal and pro-oxidant induced lipid peroxidised rats in a dose-dependent manner, [methanol 80.11%, aqueous 70.3%] with the methanol extract (MEE) significantly (P< 0.05) than that of aqueous extract (AEE). The methanol extract (0.74 ± 0.6 mg/g) had higher total phenol contents than the aqueous (0.57 ± 1.2 mg/g); likewise the methanol extract had higher reducing power (0.08 ± 0.2, 0.03 ± 0.1 mg/g), but had no significant difference in Fe (II) chelating ability (EC50= 0.34, 0.36) with DPPH* scavenging ability (EC50=0.075, 0.075). This antioxidant properties and the protective effect of this leaf could be harnessed in the management and prevention of degenerative diseases in association with oxidative stress.


2009 ◽  
Vol 15 (1) ◽  
pp. 41-46 ◽  
Author(s):  
G. Oboh ◽  
A.O. Ademiluyi ◽  
A.A. Akindahunsi

The effect of fermentation on the polyphenol distribution and antioxidant activity of four underutilized legumes [Cajanus cajan L. Millsp (Pigeon pea), Vigna subterranea L. Verdc (Bambara groundnut), Sphenostylis stenocarpa Harms (African yam bean), and Phaseolus vulgaris L. (Kidney bean)] were investigated. The beans were cooked (12 h), soaked in boiled water (12 h), dehulled, and then cooked again (2 h). The cotyledons were drained, wrapped in jute sacks and left to ferment at 37°C (4 days) to produce condiments. The distribution of free and bound phenolic compounds in the fermented and unfermented beans was determined; thereafter the free radical scavenging ability, reducing power, and the ability of the free and bound phenolic compounds of the fermented and unfermented beans to inhibit lipid peroxidation were determined. The results of the study revealed that fermentation caused a significant increase (p<0.05) in the free soluble phenol content of the legumes, while there was a significant decrease (p<0.05) in the bound phenol content of the legumes. Free soluble phenol from both the fermented and unfermented legumes had a significantly (p<0.05) higher reducing power (except C. cajan), free radical scavenging ability (except C. cajan) and inhibition of lipid peroxidation than bound phenolic extract. However, free soluble phenolic compounds from the fermented beans had a significantly higher (p<0.05) reducing power, free radical scavenging ability, and inhibition of lipid peroxidation than free soluble phenols from unfermented beans. Hence, it was concluded that, fermentation could increase the free soluble phenolic content of the underutilized legumes tested and consequently enhance the antioxidant activities of the legumes; fermented V. subterranea was found to be the most promising condiment with antioxidant activity.


2019 ◽  
Vol 97 (12) ◽  
pp. 824-832 ◽  
Author(s):  
Kamel Harrouche ◽  
Asma Lahouel ◽  
Mebrouk Belghobsi ◽  
Bernard Pirotte ◽  
Smail Khelili

A series of 1,2,4-benzothiadiazine-1,1-dioxides bearing a sulfonylthiourea moiety were synthesized, characterized, and screened for their antioxidant activity, using six antioxidant analytical assays comparatively to reference compounds, ascorbic acid and quercetin. The results indicated that several compounds demonstrated strong antioxidant activity in DPPH, ABTS, H2O2, and lipid peroxidation assays where some of them were either as active as or more active than reference compounds. However, all compounds were largely less active than references compounds in the reducing power assay. The results indicated that the thiourea moiety probably played a crucial role in the antioxidant activity of the target compounds, as a thiolate ion. The most favorable R1 groups were the hydrogen atom and methyl group, followed by phenyl and benzyl groups, whereas the most favorable R2 group was iPr, followed by the phenyl and methyl groups. The combination of benzothiadiazine ring with sulfonylthiourea moieties led to valuable new antioxidants, which could be used in the treatment or the prevention of certain diseases or in the field of cosmetics, which needs further investigations in the future.


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