Development of novel sophorolipids with improved cytotoxic activity toward MDA-MB-231 breast cancer cells

Isabel A C Ribeiro, Célia M C Faustino, Patrí S. Guerreiro, Raquel F M Frade, Maria do Rosário Bronze, Matilde F. Castro, Maria H L Ribeiro

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40 Citations (Scopus)


Sophorolipids (SLs) are glycolipid biosurfactants, produced as a mixture of several compounds by some nonpathogenic yeast. In the current study, separation of individual SLs from mixtures with further evaluation of their surface properties and biologic activity on MDA-MB-321 breast cancer cell line were investigated. SLs were biosynthesized by Starmerella bombicola in a culture media supplemented with borage oil. A reverse-phase flash chromatography method with an automated systemcoupled with a prepacked cartridgewas used to separate and purify themain SLs. Compositional analysis of SLs was performed by high-performance liquid chromatography with electrospray ionization mass spectrometry and tandem mass spectrometry. The following diacetylated lactonic SLs were isolated and purified: C18:0, C18:1, C18:2, and C18:3. The critical micelle concentration (CMC) and surface tension at CMC (γCMC) of the purified SLs showed an increase with the number of double bonds. High cytotoxic effect against MDA-MB-231 cells was observed with C18:0 and C18:1 lactonic SLs. The cytotoxic effects of C18:3 lactonic SL on cancerous cells were for the first time studied. This cytotoxic effect was considerably higher than the promoted by acidic SLs; however, it induced a lower effect than the previously mentioned SLs, C18:0 and C18:1. To our knowledge, for the first time, C18:1 lactonic SL, in selected concentrations, proved to be able to inhibit MDA-MB-231 cell migration without compromising cell viability and to increase intracellular reactive oxygen species.

Original languageEnglish
Pages (from-to)155-165
Number of pages11
JournalJournal of Molecular Recognition
Issue number3
Publication statusPublished - 2015


  • Breast cancer
  • Cytotoxicity
  • MDA-MB-231 cells
  • Sophorolipid
  • Starmerella bombicola
  • Surface tension


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