Antimicrobial and cytotoxic activities of short carbon chain unsaturated sucrose esters

Petrova, Krasimira T.; Barros, M. Teresa; Calhelha, Ricardo C.; Sokóvić, Marina; Ferreira, Isabel C.F.R.

doi:10.1007/s00044-017-2121-5

Cited by 11 publications

(10 citation statements)

References 50 publications

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“…Morin et al [67] and Siena et al [68] reported that, a variety of modified FAs are promising molecules in the treatment of cancers. Also, there were several studies dealing with anticancer, antimicrobial and anti-inflammatory activities of SE derivatives [69, 70]. Our results correlated with those reported by An and Feng [71], whose evaluated the antitumor activity of series of glucosyl esters derivatives against three cancer cells, human breast adenocarcinoma (MCF-7), human colon carcinoma (K562) and human hepatoma (HepG2).…”

Section: Resultssupporting

confidence: 88%

Singe cell oil (SCO) based bioactive compounds: II. Enzymatic synthesis of glucose fatty acid esters using SCOs as acyl group-donors and their biological activities

El-Baz

Elazzazy

Saleh

et al. 2020

Preprint

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Sugar fatty acid esters, especially glucose fatty acid esters (GEs), have broad applications in food, cosmetic and pharmaceutical industries. In this research the fatty acid moieties derived from polyunsaturated fatty acid containing single cell oils (SCOs), i.e. those produced from Cunninghamella echinulata , Umbelopsis isabellina and Nannochloropsis gaditana as well as from olive oil and an eicosapentaenoic acid (EPA) concentrate were converted into GEs by enzymatic synthesis, using lipases as biocatalysts. The GE synthesis was monitored using thin-layer chromatography, FT-IR and in situ NMR. It was found that GE synthesis carried out using immobilized Candida antarctica B lipase was very effective reaching high yields, near to 100%. It was shown that EPA-GEs were very effective against several pathogenic bacteria and their activity can be attributed to their high EPA content. Furthermore, C. echinulata-GEs were more effective against pathogens comparing to U. isabellina-GEs, probably due to the presence of gamma linolenic acid (GLA) in the lipids of C. echinulate, which is known for its antimicrobial activity, in higher concentrations. C. echinulata-GEs also showed a strong insecticidal activity against Aedes aegypti larvae, followed by EPA-GEs, olive oil-GEs, and N. gaditana-GEs. All synthesized GEs induced apoptosis of the SKOV-3 ovarian cancer cell line, with the apoptotic rate increasing significantly after 48 h. A higher percentage of apoptosis was observed in the cells treated with EPA-GEs, followed by C. echinulata-GEs, U. isabellina-GEs and olive oil-GEs. We conclude that SCOs can be used in the synthesis of GEs with interesting biological properties.

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Section: Resultssupporting

confidence: 88%

Singe cell oil (SCO) based bioactive compounds: II. Enzymatic synthesis of glucose fatty acid esters using SCOs as acyl group-donors and their biological activities

El-Baz

Elazzazy

Saleh

et al. 2020

Preprint

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“…Sucrosomial® iron is made of a ferric pyrophosphate core surrounded by a phospholipid matrix coated with the sucrose ester of fatty acids, sucrester (Gomez-Ramirez et al 2018 ). Some sucrose esters have been shown to have antimicrobial properties (Petrova et al 2017 ), however, whether this applies to sucrester is unclear and further research is needed to explain the beneficial effects of Sucrosomial® iron on the intestinal microbiome.…”

Section: Discussionmentioning

confidence: 99%

Supplementation with Sucrosomial® iron leads to favourable changes in the intestinal microbiome when compared to ferrous sulfate in mice

et al. 2021

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Iron deficiency is one of the most common nutritional deficiencies worldwide and is often treated with oral iron supplements. However, commonly used supplements, including those based on ferrous iron salts, are associated with gastrointestinal side effects and unfavorable changes in the intestinal microbiome. Sucrosomial® iron is a novel iron formulation that is effective at treating iron deficiency, and with fewer gastrointestinal side effects, yet its effect on the gut microbiome has not been examined previously. Thus, we treated mice for two weeks with diets containing either Sucrosomial® iron or ferrous sulfate as the sole iron source and examined bacterial communities in the intestine using 16S Microbial Profiling of DNA extracted from feces collected both prior to and following dietary treatment. Mice treated with Sucrosomial® iron showed an increase in Shannon diversity over the course of the study. This was associated with a decrease in the abundance of the phylum Proteobacteria, which contains many pathogenic species, and an increase in short chain fatty acid producing bacteria such as Lachnospiraceae, Oscillibacter and Faecalibaculum. None of these changes were observed in mice treated with ferrous sulfate. These results suggest that Sucrosomial® iron may have a beneficial effect on the intestinal microbiome when compared to ferrous sulfate and that this form of iron is a promising alternative to ferrous iron salts for the treatment of iron deficiency.

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“…been done on their application features [33], many concerns about the nature of these molecules remain unanswered [34], leaving room for further scientific investigation and practical studies. In this respect, in vitro antimicrobial tests, ADMET, and molecular docking of the synthesized rhamnopyranoside esters were conducted and reported herein.…”

Section: Introductionmentioning

confidence: 99%

Rhamnopyranoside-Based Fatty Acid Esters as Antimicrobials: Synthesis, Spectral Characterization, PASS, Antimicrobial, and Molecular Docking Studies

et al. 2023

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The most widely used and accessible monosaccharides have a number of stereogenic centers that have been hydroxylated and are challenging to chemically separate. As a result, the task of regioselective derivatization of such structures is particularly difficult. Considering this fact and to get novel rhamnopyranoside-based esters, DMAP-catalyzed di-O-stearoylation of methyl α-l-rhamnopyranoside (3) produced a mixture of 2,3-di-O- (4) and 3,4-di-O-stearates (5) (ratio 2:3) indicating the reactivity of the hydroxylated stereogenic centers of rhamnopyranoside as 3-OH > 4-OH > 2-OH. To get novel biologically active rhamnose esters, di-O-stearates 4 and 5 were converted into six 4-O- and 2-O-esters 6–11, which were fully characterized by FT-IR, 1H, and 13C NMR spectral techniques. In vitro antimicrobial assays revealed that fully esterified rhamnopyranosides 6–11 with maximum lipophilic character showed better antifungal susceptibility than antibacterial activity. These experimental findings are similar to the results found from PASS analysis data. Furthermore, the pentanoyl derivative of 2,3-di-O-stearate (compound 6) showed better antifungal functionality against F. equiseti and A. flavus, which were found to be better than standard antibiotics. To validate the better antifungal results, molecular docking of the rhamnose esters 4–11 was performed with lanosterol 14α-demethylase (PDB ID: 3LD6), including the standard antifungal antibiotics ketoconazole and fluconazole. In this instance, the binding affinities of 10 (−7.6 kcal/mol), 9 (−7.5 kcal/mol), and 7 (−6.9 kcal/mol) were better and comparable to fluconazole (−7.3 kcal/mol), indicating the likelihood of their use as non-azole type antifungal drugs in the future.

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Antimicrobial and cytotoxic activities of short carbon chain unsaturated sucrose esters

Cited by 11 publications

References 50 publications

Singe cell oil (SCO) based bioactive compounds: II. Enzymatic synthesis of glucose fatty acid esters using SCOs as acyl group-donors and their biological activities

Singe cell oil (SCO) based bioactive compounds: II. Enzymatic synthesis of glucose fatty acid esters using SCOs as acyl group-donors and their biological activities

Supplementation with Sucrosomial® iron leads to favourable changes in the intestinal microbiome when compared to ferrous sulfate in mice

Rhamnopyranoside-Based Fatty Acid Esters as Antimicrobials: Synthesis, Spectral Characterization, PASS, Antimicrobial, and Molecular Docking Studies

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