Microbial synthesis of sophorolipids.
Microbial synthesis of sophorolipids
MICROBIAL SYNTHESIS OF RHAMNOLIPIDS BY …
Addition of synthetic surfactants or MS resulted in increased mobility and solubility of CH, which is essential for effective microbial degradation122.
Sophorolipids appear to act as membrane-perturbing agents. Other membrane-perturbing agents have been shown to display spermicidal and virucidal properties (). The membrane partitioning of these compounds is critically involved in their microbicidal activity. However, this property does not strictly follow a simple model (). The lipid composition of cell membranes plays a crucial role in the membrane-perturbing activity of compounds. The presence and abundance of cholesterol, for instance, has the greatest influence (). In this regard, in spite of their general similarity, sperm, microbial, and somatic cell membranes have several distinguishing features which provide the basis for design of a selective microbicidal spermicide.
(201 1 ) recently reviewed the microbial synthesis of sophorolipids
This study clearly demonstrates that certain sophorolipids and modified forms thereof have excellent spermicidal and anti-HIV activity. SAR analysis showed that the acetylation of SL sophorose head groups is a key structural parameter that determines the potency of these molecules. Esterifying the carboxyl groups of SL fatty acids had a similar impact on specific activity. The ability to manipulate the biological properties of SLs over such a broad range with the small number of natural and modified SL structures thus far studied indicates that a much broader SAR analysis for this family of compounds would be of great value. For instance, the importance of acetylating SL sophorose head groups demonstrated in this work leads one to question what would be the effect of substituting acetate with propionate, butyrate, or charged moieties, such as sulfate or phosphate groups. Furthermore, only a few simple n-alkyl groups have thus far been esterified to the carboxyl group of SL fatty acids. The results of this study suggest that expanding the range of SL-related structures and assessing their biological properties will provide a deeper knowledge of SAR. Through these activities there is good reason to believe that SL-based compounds with significantly enhanced microbicidal, spermicidal, or other desirable biological attributes but with lower irritating properties will result.
Sophorolipids (SLs) are a group of microbial glycolipids produced by yeasts, such as Candida bombicola, Yarrowia lipolytica, Candida apicola, and Candida bogoriensis (). They occur naturally as disaccharide sophoroses linked glycosidically to the hydroxyl group at the penultimate carbon of primarily C18-chain-length fatty acids (Fig. ). First described in 1961, sophorolipids occur as mixtures of macrolactone (structures 1 to 4 [Fig. ]) and open ring (structures 5 to 8 [Fig. ]) that are acetylated to various extents at the primary hydroxyl position of the sophorose ring (Fig. ) (, ). Analytical studies revealed that at least eight structurally different sophorolipids are produced during fermentation (). Previous publications by R. Gross’s laboratory describe chemoenzymatic transformations for the synthesis of pure compounds from the natural mixture. This resulted in a family of new SL analogs that extend and diversify structural features present in the natural compounds (, ). We have also shown that the natural SL mixture, selected pure isolates, and/or SL derivatives have antibacterial and antifungal activity (, ), function as immunomodulators for the treatment of endotoxic (septic) shock by cytokine downregulation (), and display anticancer activity (). Maingault () further proposed that sophorolipids be used to treat skin diseases. The present study documents in vitro spermicidal and anti-HIV virucidal activities for a series of SL analogs.
Structure of surfactant phases in water
Chen J, Song X, Zhang H, Qu Y. 2006b. Production, structure elucidation and anticancer properties of sophorolipid from Wickerhamiell adomercqiae. Enzyme Microb. Tech. 39, 501–506.
Felse PA, Shah V, Chan J, Rao KJ, Gross RA. 2007. Sophorolipid biosynthesis by Candida bombicola from industrial fatty acid residues. Enzyme Microb. Tech. 40, 316–323.
Important dates in the history of lipids ..
―Sophorolipids , Microbial Glycolipids with Anti-Human
Laboratory of Biocatalysis & Bioprocessing - RPI
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Selective Production of Acid-form Sophorolipids ..
Production and characterization of methyl ester sophorolipids with 22-carbon-fatty acids
Microbial production of biosurfactants and their importance
Subsequent acrylation of the new non-natural lactonic form of SL, catalyzed by Novozym 435, led to formation of the C-6ʹ monoacryl derivative (Bisht et al, 2000). Thus, a mono-acryl compound with potential to be used for introduction into polymers via free radical polymerization was synthesized. This series of sophorolipid analogues was further extended in a study by Singh et al (2003) to prepare a series of sophorolipid amides.
Microbial production of biosurfactants and their importance: ..
Studies were also performed in collaboration with the Eastern Virginia Medical School (Gustavo F. Doncel M.D.) to explore the dual use of sophorolipids for protection against the human immunodeficiency virus (HIV)/AIDS disease as well as their efficacy and safety as a vaginal topical microbicide (Shah et al, 2005). The sophorolipid diacetate ethyl ester derivative is the most potent spermicidal and virucidal agent of the series of SLs studied. Its virucidal activity against HIV and sperm-immobilizing activity against human semen are similar to those of nonoxynol-9. However, it also induces sufficient vaginal cell toxicity to raise concerns about its applicability for long-term microbicidal contraception. Further work is planned to further elucidate structure-activity relationship to create new sophorolipid analogs with less cytotoxicity and higher activity.
Sophorolipid | Wiki | Everipedia
Interestingly, spectral analysis of this compound showed that a synthetic analogue of microbially produced macrolactone was formed. Sophorolactone differs from the natural sophorolipid lactone in that the fatty acid carboxyl carbon is linked to the C-6ʺ hydroxyl, not to the C-4ʺ hydroxyl.
Today sophorolipids are considered promising bio ..
Giessen, TW, Silver, PA. (2016). Converting a natural protein compartment into a nanofactor for the size-constrained synthesis of antimicrobial silver nanoparticles. ACS Synth. Biol. 5(12), 1497-1504.
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