Synthesis of Mannosylerythritol Lipid Analogues and their Self-Assembling Properties, Recovery Effects on Damaged Skin Cells, and Antibacterial Activity

Synthesis of three types of purpose-designed mannosylerythritol lipid (MEL)-D analogues with decanoyl groups, beta-GlcEL-D, alpha-GlcEL-D, and alpha-MEL-D, was accomplished utilizing our boron-mediated aglycon delivery (BMAD) methods. Their self-assembling properties, recovery effects on damaged skin cells, and antibacterial activity were evaluated. It was revealed, for the first time, that alpha-GlcEL-D and alpha-MEL-D only generated giant vesicles, indicating that slight differences in the steric configuration of an erythritol moiety and fatty acyl chains affect the ability to form vesicles. Analogue alpha-MEL-D exhibited significant recovery effects on damaged skin cells. Furthermore, alpha-MEL-D exhibited antibacterial activity as high as that for MEL-D, indicating that alpha-MEL-D is a promising artificial sugar-based material candidate for enhancing the barrier function of the stratum corneum, superior to a known cosmetic ingredient, and possesses antibacterial activity.

Automated summary

Three purpose-designed mannosylerythritol lipid (MEL-D) analogues with decanoyl groups, beta-GlcEL-D, alpha-GlcEL-D, and alpha-MEL-D, were synthesized using the boron-mediated aglycon delivery (BMAD) methods. Their self-assembling properties, recovery effects on damaged skin cells, and antibacterial activity were evaluated. It was found that the steric configuration of an erythritol moiety and fatty acyl chains affected the ability to form vesicles, and alpha-MEL-D showed significant recovery effects on damaged skin cells and comparable antibacterial activity to MEL-D.