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Structures of sophorolipids types produced by Candida species

Structures of sophorolipids types produced by Candida species

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Biosurfactants are natural compounds with surface activity and emulsifying properties produced by several types of microorganisms and have been considered an interesting alternative to synthetic surfactants. Glycolipids are promising biosurfactants, due to low toxicity, biodegradability, and chemical stability in different conditions and also becau...

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... The BS classes include glycolipids, lipopeptides, and lipoproteins (Desai and Banat, 1997). Amongst all, the low molecular weight BS are the most studied (Paulino et al., 2016). Glycolipid consists of a long fatty acid chain with carbohydrate compounds (Müller and Hausmann, 2011). ...
... Rhamnolipids, a class of glycolipids produced by P. aeruginosa, composed of a rhamnosyl head group and 3-(hydroxyalkanoyloxy)alkanoic acid fatty acid tail, have previously been shown to play several roles in virulence. For example, rhamnolipids' amphiphilic structure allows them to reduce water surface tension, making them a potent biosurfactant (74). They also facilitate P. aeruginosa immune evasion through supporting the development of biofilms (75) and through inhibiting phagocytosis by macrophages and polymorphonuclear leukocytes, even at sublethal concentrations (27,28,76). ...
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Pseudomonas aeruginosa is an opportunistic human pathogen that has developed multi- or even pan-drug resistance toward most frontline and last resort antibiotics, leading to increasing frequency of infections and deaths among hospitalized patients, especially those with compromised immune systems. Further complicating treatment, P. aeruginosa produces numerous virulence factors that contribute to host tissue damage and immune evasion, promoting bacterial colonization and pathogenesis. In this study, we demonstrate the importance of rhamnolipid production in host-pathogen interactions. Secreted rhamnolipids form micelles that exhibited highly acute toxicity toward murine macrophages, rupturing the plasma membrane and causing organellar membrane damage within minutes of exposure. While rhamnolipid micelles (RMs) were particularly toxic to macrophages, they also caused membrane damage in human lung epithelial cells, red blood cells, Gram-positive bacteria, and even noncellular models like giant plasma membrane vesicles. Most importantly, rhamnolipid production strongly correlated with P. aeruginosa virulence against murine macrophages in various panels of clinical isolates. Altogether, our findings suggest that rhamnolipid micelles are highly cytotoxic virulence factors that drive acute cellular damage and immune evasion during P. aeruginosa infections.
... Currently, biobased surfactants account for about 25% of the global surfactant and detergent market [1], with an estimated value of USD 14.3 billion in 2023, and an anticipated growth to USD 26.2 billion by 2033 [2]. Gly-colipids represent the most important sector of the biosurfactant market, as they have great potential to replace fossil fuel derived surfactants [3,4]. Sugar derived fatty acid esters (SFAEs), a particular class of glycosylated lipids, are odorless, flavorless, nontoxic, possess antimicrobial activity, excellent emulsifying properties and foaming ability, exhibiting high biodegradability and biocompatibility. ...
... Microbial glycolipids are low molecular weight amphiphilic compounds (500-1000 kDa) structurally sub-divided into rhamnose lipids, trehalose dimycolates, trehalose lipids, succinoyl-trehalolipids, trehalose tetraesters, dicorynomycolates, fructose lipids, sophorose lipids, mannosylerythritol lipids, xylose lipids, cellobiose lipids, liamocins, polyol lipids, sugarbased bioemulsifiers, glycoglycerolipids, monoacylglycerols, galactosyl-diglycerides, diglycosyl diglycerides, lipomannosyl-mannitols, lipomannans, and lipoarabino-mannanes, as reported by Kitamoto et al., [34] Arutchelvi et al., [35] and Paulino et al. [36] Certain mannophosphoinositides, mannose proteins and mannose lipids are also investigated. [37] To date, nearly 250 glycolipids have been reported. ...
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... Among low-molecular-weight BSs, glycolipids constitute the group that has been most thoroughly studied. They are made up of a hydrophobic moiety that contains long fatty acid chains and a hydrophilic moiety that contains saccharides of various sugars, including glucose, galactose, mannose, glucuronic acid, rhamnose, or sophorose (Paulino et al. 2016). Rhamnolipids, sophorolipids, mannosylerythritol lipids, trehalose lipids, cellobiose lipids, and glucose lipids are some of the further subgroups of glycolipid BSs (Inès and Dhouha 2015). ...
Chapter
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... The pH of the soil fluctuates as a result of the addition of inorganic fertilisers, low moisture levels, and intermediate metabolites produced by the HC degradation process (Van Horn et al. 2014;Liu et al. 2016;Chaudhary and Kim 2019). The synthesis of acidic aromatic compounds or acidic surfactants may have caused pH fluctuations that were consistent with rates of microbial activity and abundance (Peng et al. 2008;Paulino et al. 2016;Potts et al. 2018). ...
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... Even though biosurfactants are naturally formed, they are renowned for their emulsifying abilities in pharmaceuticals and vaccines. Therefore, when combined with traditional antigens for the treatment of COVID-19 disease, these surfactants contain immunological adjuvants that are both non-toxic and non-pyrogenic (Paulino et al., 2016). Consequently, these demonstrate that surfactants of biological origin play a significant role as immunosuppressive drugs and may be utilized extensively as a combine therapy toward reducing the inflammatory reactions brought on by coronavirus infection. ...
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... Depending on the charge and mass, the surfactants are classified into four distinct groups namely, cationic, anionic, non-ionic and zwitterionic (Safdel et al., 2017). But the major classification of biosurfactants is represented in Table 2. Based on the structure, these microbial metabolites are classified into low or high molecular weight biosurfactants, which are further classified into different subcategories (Paulino et al., 2016) (Table 2). They are widely classified into five types: glycolipids (rhamnolipids, sophorolipids, trehaloplipids), lipopeptides (lichenysins, iturins, fengycins and surfactins), phospholipids, fatty acids (emulsan and liposan) (Desai and Banat, 1997;Henkel and Hausmann, 2019) (Table 2). ...
... Glycolipids and lipopeptides fall under the category of low molecular weight biosurfactants, which exhibit good stability and possess major applications in the fields of food, therapeutic, cosmetics, agriculture and environment (Mnif and Ghribi, 2015;Paulino et al., 2016;Vijay et al., 2022). Glycolipids are structurally heterogeneous in nature, made up of glycosyl and lipid moieties. ...
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Globally, the rapid increase in the human population has given rise to a variety of industries, which have produced a variety of wastes. Due to their detrimental effects on both human and environmental health, pollutants from industry have taken centre stage among the various types of waste produced. The amount of waste produced has therefore increased the demand for effective waste management. In order to create valuable chemicals for sustainable waste management, trash must be viewed as valuable addition. One of the most environmentally beneficial and sustainable choices is to use garbage to make biosurfactants. The utilization of waste in the production of biosurfactant provides lower processing costs, higher availability of feedstock and environmental friendly product along with its characteristics. The current review focuses on the use of industrial waste in the creation of sustainable biosurfactants and discusses how biosurfactants are categorized. Waste generation in the fruit industry, agro-based industries, as well as sugar-industry and dairy-based industries is documented. Each waste and wastewater are listed along with its benefits and drawbacks. This review places a strong emphasis on waste management, which has important implications for the bioeconomy. It also offers the most recent scientific literature on industrial waste, including information on the role of renewable feedstock for the production of biosurfactants, as well as the difficulties and unmet research needs in this area.
... The antimicrobial activity of SLs can be influenced depending on the concentration, treatment time, composition of fatty acids, the predominance of acidic and lactonic forms, and the sugar group of the molecule (Morya et al., 2013;Lydon et al., 2017). In general, lactonic SLs are more efficient at reducing surface tension and are better antimicrobial agents (Shah et al., 2007;Paulino et al., 2016), whereas acidic SLs have better foaming properties (Lang et al., 2000). Acetyl groups can also lower the hydrophilicity of SLs and enhance their antiviral and cytokine stimulating effects (Shah et al., 2005). ...
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Two experiments were conducted to evaluate the effects of dietary sophorolipids (SLs) supplementation as antibiotic alternatives on growth performance and gut health of chickens infected with Eimeria maxima. In experiment 1, 336 (zero-day-old) male broilers were used. The chickens were weighed and randomly allocated to the following six treatments groups with 7 chickens/cage and 8 cages/treatment: control group that received a basal diet (NC), positive control group that received a basal diet and was challenged with E. maxima (PC), PC+C18:1 lactonic diacetyled SL (SL1), PC+C18:1 deacetyled SL (SL2), PC+C18:1 monoacetyled SL (SL3), and PC+C18:1 diacetyled SL (SL4). Each SL (200 mg/kg feed) was added to the corresponding treatment group. In experiment 2, 588 (zero-day-old) male broilers were used. The chickens were randomly allocated to the following experimental groups with 10 or 11 chickens/cage and 8 cages/treatment: NC, PC, PC+monensin at 90 mg/kg feed (MO), PC+SL1 at 200 mg/kg feed (SL1 200), PC+SL1 at 500 mg/kg feed (SL1 500), PC+SL4 at 200 mg/kg feed (SL4 200), and PC+SL4 at 500 mg/kg of feed (SL4 500). The chickens and feed were weighed at 0, 7, 14, 20 and 22 d to determine growth performance. In both experiments, all chickens except the NC group were orally infected with E. maxima (10,000 oocysts/chicken) at day 14. One chicken per cage was euthanized at day 20 to sample jejunal tissue to measure lesion scores, cytokines, and tight junction (TJ) proteins. Excreta samples were collected daily between day 20 and 22 to measure oocyst numbers. Data were analyzed using Mixed Model (PROC MIXED) in SAS. In experiment 1, SLs did not affect the growth of broiler chickens, but SL4 decreased (P < 0.05) the lesion score and oocyst number compared to PC chickens. In terms of cytokines and TJ protein gene expression, SLs increased (P < 0.05) IL-1β, IL-6, IL-17F, IL-4, IL-13, occludin and ZO1 levels compared to PC chickens. In experiment 2, monensin increased (P < 0.05) body weight, and decreased (P < 0.05) the lesion score and oocyst number compared to the PC group. SL4 500 increased (P < 0.05) average daily gain and feed conversion ratio but decreased (P < 0.05) lesion score and fecal oocyst number. SL4 decreased (P < 0.05) IL-6, IL-17F, TNFSF-15, IL-2, and IL-10 levels but increased (P < 0.05) occludin and ZO-1 levels. Overall, dietary SL supplementation, especially SL4, improved growth and gastrointestinal functionality of young broiler chickens, demonstrating significant potential as an antibiotic alternative.
... 22 Glycolipids secreted by strains are often a series of homologues with different structures and different proportions. 29 Ma et al., in the study on P. aeruginosa DN1, obtained a mixture of six rhamnolipid homologues. 30 The yield and proportion of these homologues depend on factors such as medium composition, culture temperature, pH, substrate, microbial species, and so forth. ...
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A strain of Lysinibacillus sp., named as Y316, can degrade heavy fractions such as resins and asphaltenes in oil sand. We used Y316 to degrade oil sand samples for 35 days. After bacterial degradation, the oil sand degradation efficiency was 5.88%, while the degradation efficiency of the control group was only 0.29% under the same conditions. Compared with the control group, the saturated content of oil sand in the degradation group increased from 9.56 to 14.39%. After degradation, the resin and asphaltene fractions decreased by 5.34 and 4.77%, respectively. The results of the vaporizable fraction analysis also confirmed the degradation of heavy fractions and the formation of light fractions. After 35 days of degradation, the vaporizable fractions of saturates increased by 3.76 times. The results indicate that Y316 has great significance for improving the quality of oil sands and assisting in oil sand exploitation.