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Rhamnolipid the Glycolipid Biosurfactant: Emerging Trends and Promising Strategies in the Feld of Biotechnology and Biomedicine Priyanka Thakur1†, Neeraj K

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Rhamnolipid the Glycolipid Biosurfactant: Emerging Trends and Promising Strategies in the Feld of Biotechnology and Biomedicine Priyanka Thakur1†, Neeraj K Thakur et al. Microb Cell Fact (2021) 20:1 https://doi.org/10.1186/s12934-020-01497-9 Microbial Cell Factories REVIEW Open Access Rhamnolipid the Glycolipid Biosurfactant: Emerging trends and promising strategies in the feld of biotechnology and biomedicine Priyanka Thakur1†, Neeraj K. Saini2†, Vijay Kumar Thakur3, Vijai Kumar Gupta3,4* , Reena V. Saini5 and Adesh K. Saini5,6* Abstract Rhamnolipids (RLs) are surface-active compounds and belong to the class of glycolipid biosurfactants, mainly produced from Pseudomonas aeruginosa. Due to their non-toxicity, high biodegradability, low surface tension and minimum inhibitory concentration values, they have gained attention in various sectors like food, healthcare, phar- maceutical and petrochemicals. The ecofriendly biological properties of rhamnolipids make them potent materials to be used in therapeutic applications. RLs are also known to induce apoptosis and thus, able to inhibit proliferation of cancer cells. RLs can also act as immunomodulators to regulate the humoral and cellular immune systems. Regarding their antimicrobial property, they lower the surface hydrophobicity, destruct the cytoplasmic membrane and lower the critical micelle concentration to kill the bacterial cells either alone or in combination with nisin possibly due to their role in modulating outer membrane protein. RLs are also involved in the synthesis of nanoparticles for in vivo drug delivery. In relation to economic benefts, the post-harvest decay of food can be decreased by RLs because they prevent the mycelium growth, spore germination of fungi and inhibit the emergence of bioflm formation on food. The present review focuses on the potential uses of RLs in cosmetic, pharmaceutical, food and health-care industries as the potent therapeutic agents. Keywords: Rhamnolipids, Antimicrobial agents, Antitumor agents, Biosurfactants, Immunomodulators Background as in the environmental remediation [3, 4]. Initially, pet- Surfactants are group of amphipathic compounds hav- rochemical based synthetic detergents were used in the ing hydrophobic and hydrophilic moieties with the industries, but they are toxic and non-biodegradable. But potential to lessen the surface and interfacial tensions their negative efects on the environment made research- in molecules [1, 2] which makes them very suitable for ers to introduce biosurfactants which are surface-active lubrication, emulsifcation, foaming, detergency and dis- compounds having low toxicity and high biodegradabil- persing agents and thus, can be efectively used by food, ity. Biosurfactants can be synthesized either enzymati- petroleum, agriculture, pharmaceutical industries as well cally or can be isolated from microorganisms [1–3, 5]. Biosurfactants harbour hydrophobic (saturated/ unsaturated fatty acids) and hydrophilic (amino acids/ *Correspondence: [email protected]; [email protected] peptides, anions/cations, di-/polysaccharides) moie- †Priyanka Thakur and Neeraj K. Saini contributed equally to this work ties which are synthesized by fungi, bacteria, yeast. Tey 3 Biorefning and Advanced Materials Research Center, Scotland’s Rural College (SRUC), Kings Buildings, West Mains Road, Edinburgh EH9 3JG, UK decrease the surface and interfacial tensions in solid/liq- 5 Department of Biotechnology, MMEC, Maharishi Markandeshwar uid, liquid/liquid, liquid/gas phases [6–8]. Diverse prop- (Deemed to be University), Mullana, Haryana 133207, India erties of biosurfactants namely high biodegradability, low Full list of author information is available at the end of the article toxicity, low critical micelle concentration (cmc), low cost © The Author(s) 2021. This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creat iveco mmons .org/licen ses/by/4.0/. The Creative Commons Public Domain Dedication waiver (http://creat iveco mmons .org/publi cdoma in/ zero/1.0/) applies to the data made available in this article, unless otherwise stated in a credit line to the data. Thakur et al. Microb Cell Fact (2021) 20:1 Page 2 of 15 production, and tolerance to extreme conditions (high mannosylerythritol lipids, cellobiose lipids, monoacyl- temperature and salinity, low and high pH) make them glycerol, diglycosyl diglycerides, lipomannosyl-manni- efective to be used over petro-chemical surfactants [4, tols, galactosyl-diglyceride, lipoarabinomannanes and 9–11]. Moreover, these biosurfactants also show antitu- lipomannans [3, 8]. In the recent past, rhamnolipids are mor and antimicrobial activity [12, 13]. Biosurfactants extensively studied because of their lower range in both are classifed based on the following criteria: (a) ionic surface tension (28 to 30 mN/m) as well as critical micel- charge, (b) molecular weight, (c) secretion type (adhesion lar concentration (10 to 200 mg/L) and, high emulsifying to microbes, intra and extracellular) and (d) chemical indexes from 60–70% as well as their high production in structure [8]. Amongst all, the low molecular weight bio- very short duration [16]. surfactants are mostly studied and further divided into glycolipids and lipopeptides group [3]. Rhamnolipids (RLs) RLs are one of the most studied microbial amphip- Glycolipid biosurfactants athic biosurfactants which was reported as “oily gly- Glycolipids are the most worked out biosurfactants of colipids” by Bergstrom et al. in 1946 [17, 18]. Tey have low molecular weight and are synthesized from hydro- two moieties: Rhamnose (also known as glycon part) carbons, industrial wastes, frying and olive oil wastes and lipid (also known as aglycon part) (Fig. 1) [4, 19]. [8]. Structural composition of glycolipid biosurfactants Rhamnose moiety is hydrophilic in nature compris- consists of hydrophilic moiety having carbohydrate ing of mono or di (L)-rhamnose molecules which are compounds like glucose, mannose, galactose, trehalose, linked together through α-1,2-glycosidic linkage. Te rhamnose, sophorose and hydrophobic moiety having lipid moiety is hydrophobic in nature and comprises long fatty acid chain [14, 15]. Glycolipids are shown to of one or more saturated/unsaturated β-hydroxy fatty be very efcient against various bacteria, viruses, myco- acids chains of C C lengths, linked together with 8− 24 plasma and fungus because of their potent role in desta- an ester bond (Fig. 1) [16, 19]. Both moieties are linked bilizing the biological membranes via the generation of via glycosidic linkage [19]. By using varieties of sugar or ion channels and pores [8]. Glycolipids activate/inhibit hydrocarbons, diferent organisms can produce approxi- enzyme for various biotechnological processes by mod- mately sixty congeners or homologs of rhamnolipids ulating the enzyme activities. Tey are also used in cos- [19–23]. Gram-negative bacterium Pseudomonas aer- metics because of their moisturization ability as well as uginosa (PA) is the most predominant species which because of their anti-adhesive property which inhibit the produces four familiar rhamnolipids, viz. 3-[3-(2-O-α- bioadhesion of any bacteria [8]. L-Rhamnopyranosyl-α-L-rhamnopyranosyloxy) Glycolipid biosurfactants are further subdivided decanoyloxy]decanoic acid (Rha2-C10-C10), into rhamnolipids, trehalose lipids, sophorolipids, 3-[(6-Deoxy-α-L-mannopyranosyl)oxy]decanoic acid Fig. 1 Flow chart showing rhamnolipid moieties Thakur et al. Microb Cell Fact (2021) 20:1 Page 3 of 15 (Rha-C10), 3-[3-(α-L-Rhamnopyranosyloxy)decanoy- the synthesis of mono-RL by using dTDP-1-rhamnose loxy]decanoic acid (Rha-C10-C10) and 3-[(2-O-α-L- and 3-(3-hydroxyalkanoyloxy) alkanoic acid as precursors Rhamnopyranosyl-α-L-rhamnopyranosyl)oxy] decanoic [30]. (c) RhlC rhamnosyltransferase directs the condensa- acid (Rha2-C10) [16, 22]. tion of mono-RLs and dTDP-1-rhamnose to synthesize di-rhamnolipids [31]. Biosynthesis of rhamnolipids Rhamnolipids production is transcripShreya delete Diferent carbon sources can afect the supply of basic from heretionally regulated through quorum sensing precursors for the biosynthesis of rhamnolipids and signals [32–34]. RhlI and LasI enzymes are responsible because of this reason, diferent PA strains produce for the synthesis of autoinducer molecules; autoinducer variants of rhamnolipid [24]. A complex genetic net- molecules when outreach the thresshold concentration work is required for RLs production including the rhl persuade the rhl genes expression by binding to their reg- genes (A, B and C), quorum sensing and, three main ulatory proteins LasI and RhlR [26, 35, 36]. steps which give rise to dTDP-l-rhamnose and vari- ants of 3-(3-hydroxyalkanoyloxy) alkanoic acid (primar- Applications of gycolipids biosurfactant: ily β-Hydroxydecanoyl-β-Hydroxydecanoate; HAA) [4, rhamnolipids 23, 25]. Te three steps (as shown in Fig. 2) are: (a) RhlA RLs have tremendous applications [37–40]. Rhamnolip- enzyme transfers
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