Lipase-catalyzed acylation of microbial mannosylerythritol lipids (biosurfactants) and their characterization

Recke, Verena K.; Beyrle, Catharina; Gerlitzki, Melanie; Hausmann, Rudolf; Syldatk, Christoph; Wray, Victor; Tokuda, Harukuni; Suzuki, Nobutaka; Lang, Siegmund

doi:10.1016/j.carres.2013.03.013

Cited by 30 publications

(13 citation statements)

References 30 publications

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“…Then, Fukuoka et al also stated MEL-A and MEL-B have performed high inhibitory effects on Micrococcus luteus, and the reason was attributed to their solubilizing effect on bilayer biomembranes [72]. Similarly, the growth of gram-positive bacteria (Bacillus megaterium and Bacillus subtilis) was restrained by MEL-A and MEL-B reported by Recke et al, and they also found MELs showed moderate antifungal effects on Candida magnoliae [73]. Besides, Okuhira et al compared the antimicrobial effects of MEL against two types of bacteria and summarized MEL selectively inhibited the proliferation of most gram-positive bacteria below the concentration of 50 µg/mL, but not gram-negative bacteria [74].…”

Section: Tobacillus Caseimentioning

confidence: 92%

Contributions of Glycolipid Biosurfactants and Glycolipid-Modified Materials to Antimicrobial Strategy: A Review

et al. 2021

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Glycolipid biosurfactants are natural amphiphiles and have gained particular interest recently in their biodegradability, diversity, and bioactivity. Microbial infection has caused severe morbidity and mortality and threatened public health security worldwide. Glycolipids have played an important role in combating many diseases as therapeutic agents depending on the self-assembly property, the anticancer and anti-inflammatory properties, and the antimicrobial properties, including antibacterial, antifungal, and antiviral effects. Besides, their role has been highlighted as scavengers in impeding the biofilm formation and rupturing mature biofilm, indicating their utility as suitable anti-adhesive coating agents for medical insertional materials leading to a reduction in vast hospital infections. Notably, glycolipids have been widely applied to the synthesis of novel antimicrobial materials due to their excellent amphipathicity, such as nanoparticles and liposomes. Accordingly, this review will provide various antimicrobial applications of glycolipids as functional ingredients in medical therapy.

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Section: Tobacillus Caseimentioning

confidence: 92%

Contributions of Glycolipid Biosurfactants and Glycolipid-Modified Materials to Antimicrobial Strategy: A Review

et al. 2021

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“…The abovementioned reports indicate that MEL biosurfactants can trigger both apoptotic and differentiation mechanisms [10,18]. In other studies, MELs have also shown excellent growth inhibition and differentiation activities against several cancer cell lines [11,[19][20][21]. Likewise, STLs have also been shown to inhibit growth and induce differentiation of human leukemia cells [18,22].…”

Section: Biosurfactants As Antitumor Agentsmentioning

confidence: 99%

Potential therapeutic applications of biosurfactants

Gudiña

Rangarajan

Sen

et al. 2013

Trends in Pharmacological Sciences

313

194

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Biosurfactants have recently emerged as promising molecules for their structural novelty, versatility, and diverse properties that are potentially useful for many therapeutic applications. Mainly due to their surface activity, these molecules interact with cell membranes of several organisms and/or with the surrounding environments, and thus can be viewed as potential cancer therapeutics or as constituents of drug delivery systems. Some types of microbial surfactants, such as lipopeptides and glycolipids, have been shown to selectively inhibit the proliferation of cancer cells and to disrupt cell membranes causing their lysis through apoptosis pathways. Moreover, biosurfactants as drug delivery vehicles offer commercially attractive and scientifically novel applications. This review covers the current state-of-the-art in biosurfactant research for therapeutic purposes, providing new directions towards the discovery and development of molecules with novel structures and diverse functions for advanced applications.

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“…This esterification reaction usually takes place in an organic solvent, producing esters with very good surfactant and emulsifier characteristics 27 . Sugar fatty acid esters are odorless, tasteless, and non‐irritating surfactants, which are very interesting features for applications in detergents, oral hygiene products, food, pharmaceutical or cosmetic formulations 31,32 . They are also biodegradable and non‐toxic to the environment.…”

Section: Introductionmentioning

confidence: 99%

“…27 Sugar fatty acid esters are odorless, tasteless, and nonirritating surfactants, which are very interesting features for applications in detergents, oral hygiene products, food, pharmaceutical or cosmetic formulations. 31,32 They are also biodegradable and non-toxic to the environment. In addition, many sugar esters suppress bacterial growth, suggesting other potential applications.…”

mentioning

confidence: 99%

Production of sugars from mixed hardwoods for use in the synthesis of sugar fatty acid esters catalyzed by immobilized‐stabilized derivatives of Candida antarctica lipase B

Gonçalves

Cansian

Tardioli

et al. 2023

Biofuels Bioprod Bioref

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The synthesis of sugar fatty acid esters (SFAEs) from lignocellulosic biomass and oleic acid (C18:1) was catalyzed by immobilized‐stabilized derivatives of Candida antarctica lipase B in a methyl ethyl ketone medium. After steam‐explosion pretreatment of mixed hardwoods and enzymatic hydrolysis at 15%wt solids, xylose and glucose were purified/concentrated to a mass ratio of ~3 to 1. These lignocellulosic sugars were superior to commercial sugars as the carbohydrate source for the esterification reaction in terms of sugar conversions. The highest conversions were obtained using 1.5% w/v of Novozyme 435 (N435, uncoated) as the biocatalyst for the synthesis of SFAEs. Coating the N435 with polyethyleneimine (PEI) prevented enzyme leakage into the reaction medium and produced 35% and 50% higher xylose and glucose conversions to SFAEs, respectively, at the same enzyme loading. After six 24 h reuse cycles with the PEI‐coated N435, xylose conversion decreased by 44%, while a 65% reduction in xylose conversion was observed with the uncoated lipase. Mass spectrometry analysis confirmed the production of xylose and glucose mono‐ and di‐esters. Our purified product presented an emulsion capacity (EC) close to that of a commercial sugar ester and the ECs of the xylose oleate, laurate, and palmitate synthesized in previous studies.

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Lipase-catalyzed acylation of microbial mannosylerythritol lipids (biosurfactants) and their characterization

Cited by 30 publications

References 30 publications

Contributions of Glycolipid Biosurfactants and Glycolipid-Modified Materials to Antimicrobial Strategy: A Review

Contributions of Glycolipid Biosurfactants and Glycolipid-Modified Materials to Antimicrobial Strategy: A Review

Potential therapeutic applications of biosurfactants

Production of sugars from mixed hardwoods for use in the synthesis of sugar fatty acid esters catalyzed by immobilized‐stabilized derivatives of Candida antarctica lipase B

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