scholarly journals Position Impact of Hydroxy Groups on Spectral, Acid–Base Profiles and DNA Interactions of Several Monohydroxy Flavanones

Molecules ◽  
2019 ◽  
Vol 24 (17) ◽  
pp. 3049 ◽  
Author(s):  
Elżbieta Łodyga-Chruścińska ◽  
Agnieszka Kowalska-Baron ◽  
Paulina Błazińska ◽  
Maria Pilo ◽  
Antonio Zucca ◽  
...  

Structure-related biological activities of flavanones are still considered largely unexplored. Since they exhibit various medicinal activities, it is intriguing to enter deeper into their chemical structures, electronic transitions or interactions with some biomolecules in order to find properties that allow us to better understand their effects. Little information is available on biological activity of flavanone and its monohydroxy derivatives in relation to their physicochemical properties as spectral profiles, existence of protonated/deprotonated species under pH changes or interaction with Calf Thymus DNA. We devoted this work to research demonstrating differences in the physicochemical properties of the four flavanones: flavanone, 2′-hydroxyflavanone, 6-hydroxyflavanone and 7-hydroxyflavanone and linking them to their biological activity. Potentiometric titration, UV–Vis spectroscopy were used to investigate influence of pH on acid–base and spectral profiles and to propose the mode of interaction with DNA. Cyclic voltammetry was applied to evaluate antioxidant potentiality and additionally, theoretical DFT(B3LYP) method to disclose electronic structure and properties of the compounds. Molecular geometries, proton affinities and pKa values have been determined. According to computational and cyclic voltammetry results we could predict higher antioxidant activity of 6-hydroxyflavanone with respect to other compounds. The values of Kb intrinsic binding constants of the flavanones indicated weak interactions with DNA. Structure–activity relationships observed for antioxidant activity and DNA interactions suggest that 6-hydroxyflavanone can protect DNA against oxidative damage most effectively than flavanone, 2′-hydroxyflavanone or 7-hydroxyflavanone.

Coatings ◽  
2021 ◽  
Vol 11 (5) ◽  
pp. 604
Author(s):  
Liyan Wang ◽  
Liang Lei ◽  
Kang Wan ◽  
Yuan Fu ◽  
Hewen Hu

Active films based on carboxymethyl chitosan incorporated corn peptide were developed, and the effect of the concentration of corn peptide on films was evaluated. Physicochemical properties of the films, including thickness, opacity, moisture content, color, mechanical properties, water vapor permeability, and oil resistance, were measured. Biological activities of the films, including the antioxidant and antibacterial activities, were characterized in terms of 2, 2-diphenyl-1-picrylhydrazyl free radical scavenging activity, reducing power, the total antioxidant activity, and the filter disc inhibition zone method. The results indicated that the incorporation of corn peptide caused interactions between carboxymethyl chitosan and corn peptide in Maillard reaction and gave rise to the films light yellow appearance. Compared with the Control, the degree of glycosylation, browning intensity, thickness, opacity, tensile strength, antioxidant activity, and antibacterial activity of films were increased, but the elongation, vapor permeability, and oil resistance of films were decreased. The films based on corn peptide and carboxymethyl chitosan can potentially be applied to food packaging.


Nova Scientia ◽  
2020 ◽  
Vol 12 (24) ◽  
Author(s):  
Rey David Vargas Sánchez ◽  
Evelin Martínez Benavidez ◽  
Javier Hernández ◽  
Gastón Ramón Torrescano Urrutia ◽  
Armida Sánchez Escalante

In this study the effect of pollen source (mesquite and catclaw) on the sensory characteristics (appearance, color, aroma, taste, consistency and visible impurities), and physicochemical properties of raw propolis, and the phenolic content and biological activities of propolis extracts (PEs) was determined. The phenolic composition of PEs was determined by the total phenolic (TPC), flavone and flavonol (FFC), and flavanone and dihydroflavonol content (FDC). The individual phenolic components were analyzed by HPLC-DAD. The antioxidant activity was determined by the ferric-reducing power (FRAP) and free-radical scavenging activity (FRS). The antibacterial activity was evaluated against Gram-positive (Staphylococcus aureus and Listeria innocua) and Gram-negative (Echerichia coli and Salmonella thyphimurium) bacteria. The results showed that sensory characteristic and physicochemical properties of mesquite and catclaw propolis complied with international quality regulations. Fifteen phenolic compounds were identified, of which pinocembrin, naringenin, galangin, chrysin and quercetin were found a high concentration (> 3 mg/g). Mesquite propolis had the highest phenolic content (TFC and FDC), as well as antioxidant activity (> 2.5 mg Fe (II) equivalent/g; > 40% of DPPH radical inhibition) and antibacterial activity against Gram-positive bacterias in the order S. aureus > L. innocua (> 50% of inhibition for both bacterias at 500 µg/mL). These results indicating that pollen source affect the sensory characteristics and physicochemical properties of propolis, as well as the biological activity of their extracts.


2019 ◽  
Vol 14 (5) ◽  
pp. 1934578X1984413 ◽  
Author(s):  
Soraia I. Falcão ◽  
Mélissa Lopes ◽  
Miguel Vilas-Boas

Propolis is a natural product derived from plant resins collected by honeybees and used in the beehive as a construction and defensive material. The broad spectrum of biological activities is dependent on the chemical diversity of its composition which is determined by the floral sources at the site of collection. For the first time, the chemical composition of Guinean propolis as well as its physicochemical properties, phenolic composition, and antioxidant activity was assessed. Eight compounds were identified through LC/DAD/ESI-MS n , mostly isoflavonoids, resembling Nigerian and Brazilian red propolis from the genus Dalbergia.


2018 ◽  
Vol 2018 ◽  
pp. 1-14 ◽  
Author(s):  
Xiaolong Ji ◽  
Yingbin Shen ◽  
Xudan Guo

Polysaccharides obtained fromGynostemma pentaphyllum(Thunb.) Makino have promising prospects in functional food and nutraceuticals due to its broad range of biological activities including antioxidant, immunomodulatory, antitumor, hepatoprotective, neuroprotective, and antifatigue activities. These beneficial biological activities are related to chemical composition and structure of theG. pentaphyllumpolysaccharides. The molecular weight, monosaccharide composition, and chemical structures could be influenced by both different extraction/purification techniques employed to obtain polysaccharide enriched products. The purpose of this article is to review previous and current literature regarding the extraction, purification, structural characterization, and biological activity ofG. pentaphyllumpolysaccharides. This review provides a useful bibliography for the further investigation, production, and application ofG. pentaphyllumpolysaccharides as functional foods and nutraceuticals.


Author(s):  
Yingkai Liu ◽  
Yuqing Jian ◽  
Mengru Cao ◽  
Bin Wang ◽  
Yixing Qiu ◽  
...  

: Seco-tetracyclic and seco-pentacyclic triterpenoids are a special class of triterpenoids with ring/rings cleaved on the original skeleton structures. A class of important triterpene derivatives, seco-tetracyclic and seco-pentacyclic triterpenoids, have long stimulated the interest and attention of botanists and natural products chemists. There is no systematic and comprehensive review for them. This review is focused on the phytochemical investigations and biological activities of seco-tetracyclic and seco-pentacyclic triterpenoids from nature, covering the literature from 2000-2019. This review describes 310 seco-tetracyclic and 139 seco-pentacyclic triterpenoids discovered from 154 species belong to 97 genera, which cover the chemical structures, types, sources, and bioactivities of compounds. The literature from 2000-2019 is reviewed and 208 references are cited.


2021 ◽  
Vol 3 (5) ◽  
Author(s):  
Peter Cavazos ◽  
David Gonzalez ◽  
Jocelyn Lanorio ◽  
Ruby Ynalvez

AbstractThe use of plants as sources for novel antimicrobial as well as antioxidant agents offers advantages. Plants are readily accessible and inexpensive, extracts or compounds from plant sources often demonstrate high level of biological activities. Previous studies have reported antibacterial and antifungal activities within the Fabaceae family that included Acacia species. This study aims to determine presence of antibacterial activity, antioxidant activity, and the secondary metabolites of sequential solvent extracts (acetone, methanol, and acetic acid) of Acacia berlandieri and Acacia rigidula leaves. The antibacterial activity was investigated using a disc diffusion assay. The ferric thiocyanate method was used to assess the ability of all extracts to prevent oxidation. Qualitative phytochemical tests, NMR, IR, and UV–Vis spectroscopy were done to identify potential secondary metabolites. P. alcalifaciens (p < 0.001), E. faecalis (p < 0.01), S. aureus (p < 0.001), and Y. enterocolitica (p < 0.001) were significantly inhibited by A. rigidula extracts when compared to A. berlandieri extracts. A. rigidula’s acetone extract exhibited the significantly (p < 0.001) highest inhibition of peroxidation, 42%. Qualitative phytochemical tests showed positive results for presence of phenols, flavonoids, saponins, terpenes and tannins. NMR, IR, and UV–Vis spectroscopy revealed chemical structures found in flavonoids, saponins, terpenes and tannins, supporting the results of qualitative phytochemical tests. A. berlandieri and A. rigidula leaf extracts have revealed presence of medicinally valued bioactive components. The results of this study provide a basis for further investigations of the A. rigidula leaf extracts. A. rigidula leaf extracts have the potential to serve as a source of novel antimicrobial and antioxidant agents. Graphic abstract


Plants ◽  
2021 ◽  
Vol 10 (6) ◽  
pp. 1054
Author(s):  
Ivana Carev ◽  
Cengiz Sarikurkcu

Background: Genus Stachys is one of the largest of the Lamiaceae family, having around 300 different plant species inhabiting areas with temperate and warm climates. The Stachys species in Turkey are represented with 81 taxa; 51 of them being endemic. Plants of the Stachys genus have been known for their biological activity and their use in ethnomedicine. Methods: The dominant components of S. cretica ssp. anatolica aqueous and methanol extracts were studied with the LC-MS/MS technique. Results: Chlorogenic acid, apigenin-7-glucoside and verbascoside present as the dominant polyphenols found in studied extracts. The prominent biological activity of the studied S. cretica ssp. anatolica methanol and aqueous extracts showed strong antioxidant activity and inhibition of enzymes tyrosinase and α-amylase, involved in skin disorders and diabetes mellitus type II. Conclusions: This study has proven that the aqueous and methanol extracts of S. cretica ssp. anatolica have prominent antioxidant activity, due to a high abundance of polyphenols. The strong antioxidant properties of S. cretica ssp. anatolica extracts show promising application for the pharmaceutical, food, and cosmetics industries.


2021 ◽  
Vol 2021 ◽  
pp. 1-12
Author(s):  
Naoual El Menyiy ◽  
Meryem Bakour ◽  
Asmae El Ghouizi ◽  
Soukaina El Guendouz ◽  
Badiaa Lyoussi

This research is aimed at determining the physicochemical properties (resin, wax, balsams, pH, moisture, ash, and mineral contents) of propolis samples collected from different geographical areas in Morocco, as well as evaluating the antioxidant and antibacterial activities of these samples. The results showed the following values for physicochemical analysis: resin (17.42-58.01%), wax (21.31-70.12%), balsam (0.27-2.12%), pH (3.7-5.3), moisture (1.02-3.65%), and ash (0.72-5.01%). The phenolic and flavone/flavonol contents of samples were ranged between 6.74 mg FAE/g and 149.13 mg FAE/g and between 1.19 mg QE/g and 108.11 mg QE/g, respectively. The sample P3 presented also the strongest radical scavenging activity toward DPPH, ABTS free radicals, and FRAP assay with IC50 values of 0.021, 0.026, and 0.042 mg/mL, respectively. All propolis samples showed significant inhibitory effects against all tested microorganisms with MICs ranging from 0.28 mg/mL to 1.12 mg/mL for Gram-negative strains and from 0.002 mg/mL to 1.12 mg/mL for Gram-positive strains. A strong correlation was found between resin, total phenolic compounds, flavones/flavonols, and antioxidant activity. Linear discriminant analysis revealed that the samples studied were divided into two groups which were differentiated by the data of antioxidant activity, mineral contents, and antibacterial activity. It can be concluded that the physicochemical properties, mineral content, and biological activities of Moroccan propolis depend on their geographical and botanical origin.


Author(s):  
Juanyan Fang ◽  
Muhammad Rafiullah ◽  
Hafiz Muhammad Afzal Siddiqui

Background: Sierpinski graphs S(n,k) are largely studied because of their fractal nature with applications in topology, chemistry, mathematics of Tower of Hanoi, and computer sciences. Applications of molecular structure descriptors are a standard procedure that are used to correlate the biological activity of molecules with their chemical structures and thus can be helpful in the field of pharmacology. Objective: The aim of this article is to establish analytically closed computing formulae for eccentricity-based descriptors of Sierpinski networks and their regularizations. These computing formulae are useful to determine a large number of properties like thermodynamic properties, physicochemical properties, chemical and biological activity of chemical graphs. Methods: At first, vertex sets have been partitioned on the basis of their degrees, eccentricities, and frequencies of occurrence. Then these partitions are used to compute the eccentricity-based indices with the aid of some combinatorics. Results: The total eccentric index and eccentric-connectivity index have been computed. We also compute some eccentricity-based Zagreb indices of the Sierpinski networks. Moreover, a comparison has also been presented in the form of graphs. Conclusion: These computations will help the readers to estimate the thermodynamic properties, physicochemical properties of chemical structures, which are of fractal nature and can not be dealt with easily. A 3D graphical representation is also presented to understand the dynamics of the aforementioned topological descriptors.


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