Trehalose lipids

Suzuki T, K Tanaka, I Matsubara, S Kinoshita (1969) Trehalose lipid and alpha-branched-beta-hydroxy fatty acid formed by bacteria grown on -alkanes. Agric Biol Chem 33 1619-1627. 

Fig. 3.20. Retention of CF as function of the trehalose/lipid concentration with varied dextran additions. I, no dextran 2, 0.08g dextran/g lipid . 3, 1.2 g dextran/g lipid, 4, 2.0 g dextran/g lipid (Fig. 9 from [3.37]).

Suzuki, T. 1978. Enzymatic methylation of pentachlorophenol and its related compounds by cell-free extracts of Mycobacterium sp. isolated from soil. /. Pestic. Sci. 3 441—443. Suzuki, T., K. Tanaka, I. Matsubara, and S. Kinoshita. 1969. Trehalose lipid and alpha-branched-beta-hydroxy fatty acid formed by bacteria grown on n-alkanes. Agric. Biol. Chem. 33 1619-1627. 

The rhamnolipid B (70) has the molecular structure of biosurfactants, comprising a hydrophilic part (rhamnose moiety) and a hydrophobic part ((3-hydroxydecanoate moiety) [151]. The biosurfactant property of this glycolipid was supposed to confer the ability to intercalate into and disrupt the zoospore plasma membrane [152,153]. However, other glycolipids such as sophorolipids and trehalose lipids, which have chemical properties similar to the rhamnolipids, did not show zoosporicidal activity at concentrations up to 1000 pg/ml. 

Sucrose lipid (5 1) Sucrose lipid (10 1) Trehalose lipid (5 1) Trehalose lipid (10 1)... 

TABLE 1 Characteristic Data on the Microbial Production of Rhamnose Lipids (RLs), Trehalose Corynomycolates (TL-Cs), and Anionic Trehalose Lipids (TLs), Respectively... 

An anionic trehalose lipid was first documented in 1981 from Mycobacterium paraffinicum. Two years later a similar product, 2-0-succinoyl-3,4,2 -tri-0-acyl-a,a-D-trehalose (Fig. 5, bottom) was found culturing Rhodococcus erythropolis DSM 43215 under nitrogen-limiting conditions [28]. After optimization of the process more than 30 g/L of trehalose lipids could be isolated (Table 1) [29]. In addition, similar monosuccinoyl and disuccinoyl trehalose lipids have been reported from another R. erythropolis strain, SD-74 [30,31]. 

As for medical applications two types of succinoyl trehalose lipids produced by R. erythropolis SD-74 were found to induce cell differentiation instead of cell proliferation in the human promyelocytic leukemia cell line HL60. Both compounds induced HL60 to differentiate into monocytes. Furthermore, they also inhibited protein kinase C (PKC) activities of HL60 cells indicating potential for antitumoral agents [33], Other investigations showed that... 

RL, rhamnolipid TL, anionic trehalose lipid SL, sophorolipid (classic-type) MEL, mannosyleryth-ritol lipid OSL, oligosaccharide Upid GGL, glycoglycerolipid. 

P, P-Trehalose-6,6 -dicarboxylic ester. Trehalose lipids differ in the structure of the R and R groups... 

Glycolipid-type biosurfactants are employed in a variety of applications, due to their high surface activity, biodegradability, and biocompatibility. RhamnoUpids are useful in bioremediation and enhanced oil recovery (Pinzon et al., 2009). Sophorolipids are employed in food encapsulation and, more recently, in dishwasher detergents, and have biomedical applications (Kitamoto et al, 2009 Ashby et al., 2009). Mannosylerythritol lipids have several biomedical applications, including the treatment of tumors and as antimicrobial agents (Arutchelvi et al., 2008). Mannosylerythritol lipids, sophorolipids, and several other glycolipid biosurfactants have numerous applications in cosmetics (Lourith and Kanlayavattanakul, 2009). Trehalose lipids have several environmental and biomedical applications (Franzetti et al., 2010). 

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