2024 Volume 24 Issue 11 Pages 475-481
Mannosylerythritol lipids (MELs) are a class of amphipathic molecules with a hydrophilic 4-O-β-d-mannopyranosyl-erythritol skeleton and two hydrophobic fatty acyl chains. So far, our group has accomplished the systematic and stereoselective total synthesis of 20 kinds of S-MEL-A-D (C6, C8, C10, C12, C14) with different fatty acid chain lengths and different patterns of Ac groups at C4’ and C6’ of the mannose moiety and a structure-activity relationship (SAR) study of the recovery effects on damaged skin cells was performed. As a result, it was found that S-MELs with C10 fatty chain length showed high recovery effects on damaged skin cells. Here, to create candidate molecules for new cosmeceuticals, we designed and synthesized four kinds of MEL analogues, R-MEL-A, S-mannosylthreitol lipid (MTL)-A, R-MTL-A, and α-S-MEL-A, using our previously reported boron-mediated aglycon delivery (BMAD) method and a neighboring group-assisted glycosylation method. Among them, R-MTL-A showing the highest selective cytotoxicity against human skin squamous carcinoma cells also exhibits an efficient recovery effect on damaged skin cells, indicating that R-MTL-A has potential as a lead compound for new cosmeceuticals.
