Mechanistic Insights into the Selective Synthesis of 4H-Pyran Derivatives On-Water Using Naturally Occurring Alginate from Sargassum muticum: Experimental and DFT Study.

The naturally occurring sodium alginate (SA) biopolymer from the Sargassum muticum (Yendo) Fensholt was employed as a green organocatalyst for the synthesis of 4H-pyran derivatives. The naturally extracted macromolecule was fully characterized using different analyses, including nuclear magnetic resonance (NMR), Fourier-transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), and Energy Dispersive X-ray Analysis (EDX). The catalytic activity of SA was investigated in the one-pot reaction between aldehydes, malononitrile, and 1,3-dicarbonyl compounds in water at room temperature, and the corresponding 2-amino-3-cyano-4H-pyran derivatives were obtained with good to excellent yields. This organocatalyst was easily separated from the reaction mixture and reused for at least two consecutive cycles without a significant loss of its catalytic activity or selectivity. From the mechanistic point of view, density functional theory (DFT) and NCI analyses were performed for the first time to explain the regioselectivity outcomes for the synthesis of 2-amino-3-cyano-4H-pyran derivatives using SA as a green organocatalyst.

Chemical Composition and In Vitro Antioxidant and Antimicrobial Activities of the Marine Cyanolichen Lichina pygmaea Volatile Compounds.

Volatile compounds from the marine cyanolichen Lichina pygmaea, collected from the Moroccan Atlantic coast, were extracted by hydrodistillation and their putative chemical composition was investigated by gas chromatography coupled to mass spectrometry (GC/MS). Based on the obtained results, Lichina pygmaea volatile compounds (LPVCs) were mainly dominated by sesquiterpenes compounds, where γ-himachalene, ß-himachalene, (2E,4E)-2,4 decadienal and α-himachalene were assumed to be the most abundant constituents, with percentage of 37.51%, 11.71%, 8.59% and 7.62%, respectively. LPVCs depicted significant antimicrobial activity against all tested strains (Staphylococcus aureus CCMM B3, Pseudomonas aeruginosa DSM 50090, Escherichia coli ATCC 8739 and Candida albicans CCMM-L4) with minimum inhibitory concentration (MIC) values within the range of 1.69-13.5 mg/mL. Moreover, this LPVC showed interesting scavenging effects on the 2,2-diphenyl-1-picrylhydrazyl radical with an IC50 of 0.21 mg/mL. LPVCs could be an approving resource with moderate antimicrobial potential and interesting antioxidant activity for cosmetics and pharmaceutical applications.

Gracilaria gracilis (Gracilariales, Rhodophyta) from Dakhla (Southern Moroccan Atlantic Coast) as Source of Agar: Content, Chemical Characteristics, and Gelling Properties.

Agar is a sulfated polysaccharide extracted from certain marine red algae, and its gel properties depend on the seaweed source and extraction conditions. In the present study, the seaweed Gracilaria gracilis (Gracilariales, Rhodophyta) from Dakhla (Moroccan Atlantic Coast) was investigated for its agar content, structure, and gel properties. The agar yields of G. gracilis were 20.5% and 15.6% from alkaline pretreatment and native extraction, respectively. Agar with alkaline pretreatment showed a better gelling property supported by higher gel strength (377 g·cm-2), gelling (35.4 °C), and melting (82.1 °C) temperatures with a notable increase in 3,6-anhydro-galactose (11.85%) and decrease in sulphate (0.32%) contents. The sulfate falling subsequent to alkaline pretreatment was verified through FT-IR spectroscopy. The 13C NMR spectroscopy showed that alkaline-pretreated agar has a typical unsubstituted agar pattern. However, native agar had a partially methylated agarose structure. Overall, this study suggested the possibility of the exploitation of G. gracilis to produce a fine-quality agar. Yet, further investigation may need to determine the seasonal variability of this biopolymer according to the life cycle of G. gracilis.

Isolation and FTIR-ATR and 1H NMR Characterization of Alginates from the Main Alginophyte Species of the Atlantic Coast of Morocco.

Alginates are widely used as gelling agents in textile print pastes, medical industries, impression material in dentistry, and anticoagulant material in toothpaste. In the present study, the content and spectroscopic characterization (1H NMR and FT-IR) of the sodium alginates were investigated in the eight brown seaweeds Sargassum muticum, Fucus vesiculosus f. volubilis, Carpodesmia tamariscifolia, Bifurcaria bifurcata, Laminaria ochroleuca, Cystoseira humilis, Saccorhiza polyschides, and Fucus guiryi harvested from the NW Atlantic coast of Morocco. The results proved that the most studied algae depicted alginate yields higher than 18% dry weight. The FT-IR analysis showed that the spectra of the extracted alginates exhibited significant similarities to the commercial alginate from Sigma-Aldrich. The 1H NMR spectroscopy indicated that the extracted alginates have a high content of ß-d-mannuronic (M) than α-l-guluronic acid (G) with M/G ratio values ranging from 1.04 to 4.41. The homopolymeric fractions FMM are remarkably high compared to the FGG and heteropolymeric fractions (FGM = FMG) especially for F. guiryi, C humilis, C. tamariscifolia, L. ochroleuca, and S. polyschides. Nevertheless, the heteropolymeric fractions (FGM/FMG) are quite abundant in the alginates of S. muticum, F. vesiculosus f. volubilis, and B. bifurcata accounting for more than 52% of the polymer diads. Based on these results, the investigated algal species (except Fucus guiryi and Bifurcaria bifurcata) could be regarded as potential sources of alginates for industrial uses.

Spatiotemporal variation of the epifaunal assemblages associated to Sargassum muticum on the NW Atlantic coast of Morocco.

Epifaunal assemblages inhabiting the non-indigenous macroalga Sargassum muticum (Yendo) Fensholt were investigated on two physically distinct intertidal rocky (S1) and sandy (S2) sites along the Atlantic coast of Morocco. The objective of this study was to test whether the habitat-forming marine alga S. muticum invasive in these sites supported different epifaunal assemblages under different environmental conditions and through time. The gastropods Steromphala umbilicalis, S. pennanti, and Rissoa parva and the isopod Dynamene bidentata were the most contributive species to the dissimilarity of epifaunal assemblage structure between both sites throughout seasons. SIMPER analysis showed a dissimilarity of 58.3-78.5% in the associated species composition of S. muticum between study sites with respect to sampling season. Species diversity and total abundance were significantly higher at the rocky site compared to the sandy site. PERMANOVA analyses showed significant differences of associated epifaunal assemblage structure for the season and site interaction. Accordingly, site and season were determinant factors conditioning the role of habitat in structuring epifaunal assemblages.