Effect of seasonal variation on the chemical composition and antioxidant and antifungal activities of Convolvulus althaeoides L. leaf extracts

The composition of polyphenols, chlorophylls and carotenoids of eight extracts of Convolvulus althaeoides L. leaves, harvested in two different seasons, winter and spring, and extracted by hot extraction method using four solvents (dichloromethane, chloroform, ethyl acetate and ethanol) with increasing polarity, were evaluated along with their antioxidant and antifungal activities. Qualitative and quantitative variations were observed in the composition based on two different high performance liquid chromatography systems, liquid chromatography-photodiode array detection coupled to either atmospheric pressure chemical ionization mass spectrometry or to electrospray ionization mass spectrometry, permitting the identification of 22 polyphenols, 11 chlorophyll derivatives and 10 carotenoid compounds. Polyphenolic compounds were predominant in extracts from leaves collected in winter, whereas pigments were predominant in the spring collections. Antioxidant activities of the extracts were determined by DPPH radical scavenging method, revealing a half inhibition concentration (IC50) ranging from 0.1369 ± 0.0272 mg g−1 to 0.432 ± 0.0018 mg g−1, with no correlation to seasonal fluctuation. Concerning antifungal assays, ethyl acetate and ethanol extracts have been shown to be the most active against dermatophytes (T. rubrum, T. menthagrophytes, M. canis), with inhibiting percentages reaching 100% with 50 mg mL−1. Moreover, ethyl acetate and ethanol extracts showed a maximum inhibition potential with minimum inhibitory/fungicidal concentrations ranging from 0.78 to 6.25 mg mL−1 on Candida spp. cultures. The winter collect of these extracts showed an inhibitory effect of 90% on Candida albicans germ tubes formation, at a concentration of 3.1 mg mL−1. In conclusion, seasonality seems to influence the quality and the quantity of natural substances from leaves of C. althaeoides L., which have major importance on the antioxidant and the antifungal effectiveness

Spectroscopic, X-ray structure, radical scavenging and in vitro antifungal activities and catalytic degradation of methyl orange dye investigation of the Meso-tetrakis(p-tolyl) diprotonated porphyrin

International audienceWith the aim to fully characterize the diprotonated porphyrin: meso‑tetrakis(p-tolyl)porphyrindi-ium dichloride chloroform trisolvate with the formula [H4TTP]Cl2·3CHCl3 (2) this porphyrinic diacid species was first prepared by protonation of the meso‑tetrakis(p-tolyl)porphyrin (H2TTP, (1)). Compound 2 was studied by UV/Vis, fluorescence, IR, 1H NMR spectroscopy as well as by MALDI-TOF mass spectroscopy. The single crystal X-ray structure of 2 was a very useful technique to show the very important deformation of the porphyrin core of the diprotonated [H4TTP]2+ porphyrinic species (2) which is considered the principal cause of the important redshift of the UV/Vis and fluorescence spectra of compound 2. We used computational studies at B3LYP/6-311+G(d,p) level of theory to investigate the HOMO and LUMO molecular orbitals characteristics and calculate the global reactive parameters of compound 2 such as the electrophilicity index ψ, the chemical potential (μ), the hardness (η) and the chemical softness (S). The diacid porphyrin species (2) was tested as adsorbent of the Methyl Orange dye (MO) and also as catalyst of the degradation of this organic dye in presence of hydrogen peroxide. Biological studies on the H2TTP free base porphyrin (1) and the corresponding [H4TTP]2+ diacid species (2) were carried out in vitro in order to test their inhibitory effect against some fungal strings and the ability of these two porphyrinic compounds to scavenge 1,1-diphenyl-picrylhydrazyl DPPH radical

Synthesis, Characterization, X-ray Molecular Structure, Antioxidant, Antifungal, and Allelopathic Activity of a New Isonicotinate-Derived meso-Tetraarylporphyrin

International audienceThe present article describes the synthesis of an isonicotinate-derived meso-arylporphyrin, that has been fully characterized by spectroscopic methods (including fluorescence spectroscopy), as well as elemental analysis and HR-MS. The structure of an n-hexane monosolvate has been determined by single-crystal X-ray diffraction analysis. The radical scavenging activity of this new porphyrin against the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical has been measured. Its antifungal activity against three yeast strains (C. albicans ATCC 90028, C. glabrata ATCC 64677, and C. tropicalis ATCC 64677) has been tested using the disk diffusion and microdilution methods. Whereas the measured antioxidant activity was low, the porphyrin showed moderate but encouraging antifungal activity. Finally, a study of its effect on the germination of lentil seeds revealed interesting allelopathic properties

Botanical and Genetic Identification Followed by Investigation of Chemical Composition and Biological Activities on the Scabiosa atropurpurea L. Stem from Tunisian Flora

Scarce information about the phenolic composition of Scabiosa atropurpurea L. is available, and no carotenoid compounds have been reported thus far. In this study the phenolic and carotenoid composition of this plant was both investigated and associated bioactivities were evaluated. Aiming to obtain extracts and volatile fractions of known medicinal plants to valorize them in the pharmaceutical or food industries, two techniques of extraction and five solvents were used to determine the biologically active compounds. Gas chromatography coupled to flame ionization and mass spectrometry and liquid chromatography coupled to photodiode array and atmospheric pressure chemical ionization/electrospray ionization mass spectrometry highlighted the presence of 15 volatiles, 19 phenolics, and 24 natural pigments in Scabiosa atropurpurea L. stem samples; among them, the most abundant were 1,8-cineole, chlorogenic acid, cynaroside, and lutein. Bioactivity was assessed by a set of in vitro tests checking for antioxidant, antibacterial, antifungal, and allelopathic (against Brassica oleracea L. and Lens culinaris Medik) effects. Scabiosa atropurpurea L. stem extracts presented a considerable antioxidant, antibacterial, and allelopathic potential, with less antifungal effectiveness. These results indicate that the volatile fractions and extracts from S. atropurpurea L. stem could be considered as a good source of bioactive agents, with possible applications in food-related, agriculture, and pharmaceutical fields. Genetic investigations showed 97% of similarity with Scabiosa tschiliensis, also called Japanese Scabiosa

Chemical Composition, Antifungal and Anti-Biofilm Activities of Volatile Fractions of Convolvulus althaeoides L. Roots from Tunisia

The antifungal drugs currently available and mostly used for the treatment of candidiasis exhibit the phenomena of toxicity and increasing resistance. In this context, plant materials might represent promising sources of antifungal agents. The aim of this study is to evaluate for the first time the chemical content of the volatile fractions (VFs) along with the antifungal and anti-biofilm of Convolvulus althaeoides L. roots. The chemical composition was determined by gas chromatography coupled to a flame ionization detector and mass spectrometry. In total, 73 and 86 chemical compounds were detected in the n-hexane (VF1) and chloroform (VF2) fractions, respectively. Analysis revealed the presence of four main compounds: n-hexadecenoic acid (29.77%), 4-vinyl guaiacol (12.2%), bis(2-ethylhexyl)-adipate (9.69%) and eicosane (3.98%) in the VF extracted by hexane (VF1). n-hexadecenoic acid (34.04%), benzyl alcohol (7.86%) and linoleic acid (7.30%) were the main compounds found in the VF extracted with chloroform (VF2). The antifungal minimum inhibitory concentrations (MICs) of the obtained fractions against Candida albicans, Candida glabrata and Candida tropicalis were determined by the micro-dilution technique and values against Candida spp. ranged from 0.87 to 3.5 mg/mL. The biofilm inhibitory concentrations (IBF) and sustained inhibition (BSI) assays on C. albicans, C. glabrata and C. tropicalis were also investigated. The VFs inhibited biofilm formation up to 0.87 mg/mL for C. albicans, up to 1.75 mg/mL against C. glabrata and up to 0.87 mg/mL against C. tropicalis. The obtained results highlighted the synergistic mechanism of the detected molecules in the prevention of candidosic biofilm formation