Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents

Campana, Raffaella; Merli, Alessio; Verboni, Michele; Biondo, Francesca; Favi, Gianfranco; Duranti, Andrea; Lucarini, Simone

doi:10.3390/ph12040186

Cited by 24 publications

(33 citation statements)

References 47 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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“…The purification of the residue was done by column chromatography (cyclohexane/ethyl acetate 6:4) and gave 6-O-monolauroyl-glucose as a white solid. (0.163 g, Yield: 80%) [28]. 1 Triethylamine (18.3 mL, 130.9 mmol) was added to a stirred suspension of trehalose 1 (1.12 g, 3.27 mmol) in dichloromethane (15 mL).…”

Section: Synthesis Of Glucose Monolauratementioning

confidence: 99%

Quercetin Loaded Monolaurate Sugar Esters-Based Niosomes: Sustained Release and Mutual Antioxidant—Hepatoprotective Interplay

et al. 2020

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Flavonoids possess different interesting biological properties, including antibacterial, antiviral, anti-inflammatory and antioxidant activities. However, unfortunately, these molecules present different bottlenecks, such as low aqueous solubility, photo and oxidative degradability, high first-pass effect, poor intestinal absorption and, hence, low systemic bioavailability. A variety of delivery systems have been developed to circumvent these drawbacks, and among them, in this work niosomes have been selected to encapsulate the hepatoprotective natural flavonoid quercetin. The aim of this study was to prepare nanosized quercetin-loaded niosomes, formulated with different monolaurate sugar esters (i.e., sorbitan C12; glucose C12; trehalose C12; sucrose C12) that act as non-ionic surfactants and with cholesterol as stabilizer (1:1 and 2:1 ratio). Niosomes were characterized under the physicochemical, thermal and morphological points of view. Moreover, after the analyses of the in vitro biocompatibility and the drug-release profile, the hepatoprotective activity of the selected niosomes was evaluated in vivo, using the carbon tetrachloride (CCl 4 )-induced hepatotoxicity in rats. Furthermore, the levels of glutathione and glutathione peroxidase (GSH and GPX) were measured. Based on results, the best formulation selected was glucose laurate/cholesterol at molar ratio of 1:1, presenting spherical shape and a particle size (PS) of 161 ± 4.6 nm, with a drug encapsulation efficiency (EE%) as high as 83.6 ± 3.7% and sustained quercetin release. These niosomes showed higher hepatoprotective effect compared to free quercetin in vivo, measuring serum biomarker enzymes (i.e., alanine and aspartate transaminases (ALT and AST)) and serum biochemical parameters (i.e., alkaline phosphatase (ALP) and total proteins), while following the histopathological investigation. This study confirms the ability of quercetin loaded niosomes to reverse CCl 4 intoxication and to carry out an antioxidant effect.Pharmaceutics 2020, 12, 143 2 of 18 and anticancer activities [1][2][3]. These intrinsic properties, together with their biocompatibility and remarkable antioxidant activity, have attracted researchers' attention to explore potential therapeutic applications [4,5].Quercetin (3, 30, 4, 5, 7-pentahydroxyflavone) is probably the most studied bioflavonoid, belonging to the family of flavonols; its therapeutic applications include hepatoprotection [6], prevention of neural cell apoptosis [7] and cancer chemo-prevention and treatment [8].Quercetin acts as strong antioxidant by scavenging free radicals and transition metal ions, thus decreasing the process of lipid peroxidation, which is responsible for the development of many diseases, e.g., cardiovascular and neurodegenerative diseases, as well as liver damage [9][10][11].However, quercetin therapeutic applications present challenges due to (i) low aqueous solubility, (ii) photo and oxidative degradability, (iii) high first-pass effect, (iv) poor intestinal absorption and, hence, low systemic...

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“…The antimicrobial activities of sugar fatty acid esters produced by lipase-catalyzed synthesis and of chemically synthesized aromatic lactose esters have also been tested. The highest inhibition for Escherichia coli, Listeria monocytogenes, Staphylococcus aureus and Salmonella enteritidis was exhibited by mannose C10 ester and lactose biphenylacetate [19]. The antioxidant properties of sugar cane juice phenolic extracts of cinnamic, caffeic and sinapic acid were demonstrated by inhibition of spontaneous peroxidation of rat brain homogenates, suggesting the potential of such compounds for oxidative stress therapy [20].…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Synthesis of New Aromatic Esters of Mono- and Oligosaccharides

et al. 2020

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An efficient and convenient chemoenzymatic route for the synthesis of novel phenolic mono-, di- and oligosaccharide esters is described. Acetal derivatives of glucose, sucrose, lactose and inulin were obtained by chemical synthesis. The fully characterized pure sugar acetals were subjected to enzymatic esterification with 3-(4-hydroxyphenyl) propionic acid (HPPA) in the presence of Novozyme 435 lipase as a biocatalyst. The aromatic esters of alkyl glycosides and glucose acetal were obtained with good esterification yields, characterized by mass spectrometry (MALDI-TOF MS), infrared spectroscopy (FTIR) and nuclear magnetic resonance spectroscopy (1H NMR, 13C NMR). The synthesis of aromatic esters of disaccharide acetals was successful only for the enzymatic esterification of sucrose acetal. The new chemoenzymatic route allowed the synthesis of novel aromatic esters of inulin as the inulin monoacetal monoester and diester and the inulin diacetal monoester with a polymerization degree of two, as well as the inulin monoacetal monoester with a degree of polymerization of three, were obtained by enzymatic acylation of inulin acetals with HPPA. These compounds could represent a new class of sugar ester surfactants with enhanced bioactivity, antioxidative and antimicrobial properties and with potential application in drug delivery systems.

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Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents

Cited by 24 publications

References 47 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

Quercetin Loaded Monolaurate Sugar Esters-Based Niosomes: Sustained Release and Mutual Antioxidant—Hepatoprotective Interplay

Chemoenzymatic Synthesis of New Aromatic Esters of Mono- and Oligosaccharides

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