Sophorolipids Decrease IgE Production in U266 Cells by Downregulation of BSAP (Pax5), TLR-2, STAT3 and IL-6

Hagler, M.; Smith‐Norowitz, Tamar A.; Chice, Seto; Wallner, Sabine R.; Viterbo, Domenico; Mueller, Cathy M.; Gross, Richard A.; Nowakowski, Maja; Schulze, Robert; Zenilman, Michael E.; Bluth, Martin H.

doi:10.1016/j.jaci.2006.12.399

Cited by 32 publications

(21 citation statements)

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“…In addition, earlier research by our group established many SL small molecule derivatives that are anti-inflammatory. [30][31][32][33][34] Thus, it is worthwhile to explore in future studies whether polyLSLs or their degradation products still possess this property that is highly desirable for biomaterial applications such as implants. Besides, sophorose derivatives were reported to bind lectins with high to mild affinity.…”

Section: Resultsmentioning

confidence: 99%

“…[26][27][28][29] Furthermore, our laboratory working with collaborators reported SLs have excellent potential as therapeutic agents. [30][31][32][33][34] When pure oleic acid is used as the lipid feedstock to produce SLs by fermentation, the main product is an unusual diacetylated lactonic sophorolipid, LSL[6'Ac, 6"Ac], shown in Scheme-1. Earlier work exploring the conversion of SLs to glycopolymers involved the use of a multi-step synthetic approach giving SL pendant groups appended to an acrylate main chain 35 and lipase-catalyzed ROP of lactonic SLs that gave low molecular weight products.…”

Section: Introductionmentioning

confidence: 99%

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Poly(sophorolipid) Structural Variation: Effects on Biomaterial Physical and Biological Properties

Peng

Muñoz-Pinto²,

Chen

et al. 2014

Biomacromolecules

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Diacetylated lactonic sophorolipids (polyLSL[6'Ac,6″Ac]), a biosurfactant, can be efficiently polymerized by ring-opening metathesis polymerization (ROMP). In this paper, enzyme-mediated chemical transformations are developed to regioselectively modify LSL[6'Ac,6″Ac] at sophorose primary hydroxyl positions (6' and 6″). The resulting modified LSLs were polymerized to expand polyLSL structural diversity, that is, polyLSL[6'OH,6″Ac], polyLSL[6'OH,6″OH], polyLSL[6'Bu,6″Ac], polyLSL[6'N3,6″Ac], and polyLSL[6'MA,6″Ac]. Controlled placement of azide and methacrylate at sophorolipid moieties enables the use of "click" reactions to introduce bioactive groups. Thermal analyses of polyLSLs showed that the acylation pattern at sugar moieties has a remarkable effect on chain stiffness and crystallinity. Films of polyLSL[6'Ac,6″Ac], polyLSL[6'OH,6″Ac], and polyLSL[6'Bu,6″Ac] exhibited nonbrittle behaviors with compressive elastic moduli ranging from ∼1.5 to ∼4.9 MPa. PolyLSLs were cytocompatible with human mesenchymal stem cells (h-MSCs), and examination of material-induced osteogenic cell lineage progression uncovered a dependence on polyLSL substitution at sophorose 6'-sites. This research reveals opportunities to regulate polyLSL physical properties and cell response behaviors by variation in substituents at polyLSL sophorolipid moieties.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Poly(sophorolipid) Structural Variation: Effects on Biomaterial Physical and Biological Properties

Peng

Muñoz-Pinto²,

Chen

et al. 2014

Biomacromolecules

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“…For example, they were used as treatment in vivo to decrease sepsis‐related mortality in experimental sepsis . Moreover, recent studies demonstrated that SLs possess antibacterial , antiviral , and anti‐inflammatory properties. In order to enhance or modulate these properties, modification of SL structure has been attempted during their microbial production by varying the lipophilic substrates in fermentation media and by genetic engineering to alter the biosynthetic pathway .…”

Section: Introductionmentioning

confidence: 99%

Sophorolipids: Expanding structural diversity by ring‐opening cross‐metathesis

Peng

Totsingan

Meier

et al. 2014

Euro J Lipid Sci & Tech

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Lactonic sophorolipids (LSL) are glycolipid biosurfactants produced in large quantity by yeast fermentation. Chemical or enzymatic modification of naturally produced sophorolipids is an effective route to improve their functional properties. For the first time, ring-opening cross metathesis (RO/CM) was used to convert natural LSL to a unique family of modified sophorolipids. Reaction conditions for RO/CM of LSL with n-alkyl acrylates, trans-3-hexene, 1-hexene and ethylene were investigated. For the RO/CM of n-alkyl acrylates with LSL, %-conversions greater than 95% within 1 h resulted from conducting reactions in THF at 60°C using 5 mol% of Grubbs second generation ruthenium based catalyst (M2). The RO/CM reaction of LSL with ethylene performed at 3 bar under an ethylene atmosphere using Grubbs first generation (G1) (10 mol%) as the catalyst in dichloromethane (room temperature, 5 h) gave complete conversion of LSL to the corresponding ring-opened product. Ethanolysis of LSL RO/CM products generated a series of medium chain (C10-C14) SL-surfactants and fatty acid co-products. Values of surface tension reduction at the air-water interface versus Log (C) for modified SLs were measured by the Wilhelmy plate method. Minimum surface tension values varied as a function of the hydrophobic character of modified SLs. The modified SL from RO/CM with 1-hexene (SL-14) gave the largest surface tension reduction and lowest CMC (to 34 mN/m and 0.15 mM, respectively) and showed a similar surface tension reduction behavior as n-dodecyl-b-D-maltoside (Mal-C12). Increasing the number of carbons in the hydrophobic segment for the homologous series of n-alkyl sophorosides results in an almost linear decrease in log(CMC), with B ¼ 0.18 AE 0.03. This number is smaller than that of other related surfactants such as alkyl-b-D-glycosides and alkyl-b-D-maltosides.Practical applications: Modified sophorolipids can be used in a wide variety of applications such as stabilization of oil-in-water dispersions, antimicrobials and various cleaning operations.

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“…The mechanisms involved in these studies included a decrease in nitric oxide production and proinflammatory cytokines [2,5,7]. Recent studies in our laboratory also demonstrated the utility of sophorolipids in atopic disease [11]; sophorolipids were able to decrease IgE production in a dose-dependent manner and used mechanisms involving the reduction of IgErelated genes, including BSAP (Pax5) and IL-6 among others [12]. In all cases, there were no deleterious effects to the host or somatic cell lines in vitro and in vivo at therapeutic doses.…”

Section: Discussionmentioning

confidence: 98%