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

Takanori Kondo, Chihiro Yasui, Ikkei Miyajima, Taisuke Banno, Kouichi Asakura, Tokuma Fukuoka, Kazunori Ushimaru, Maito Koga, Azusa Saika, Tomotake Morita, Yoshiaki Takahashi, Chigusa Hayashi, Masayuki Igarashi, Daisuke Takahashi, Kazunobu Toshima

Research output: Contribution to journalArticlepeer-review

Abstract

Synthesis of three types of purpose-designed mannosylerythritol lipid (MEL)-D analogues with decanoyl groups, β-GlcEL-D, α-GlcEL-D, and α-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 α-GlcEL-D and α-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 α-MEL-D exhibited significant recovery effects on damaged skin cells. Furthermore, α-MEL-D exhibited antibacterial activity as high as that for MEL-D, indicating that α-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.

Original languageEnglish
Article numbere202201733
JournalChemistry - A European Journal
Volume28
Issue number55
DOIs
Publication statusPublished - 2022 Oct 4

Keywords

  • antibacterial activity
  • damaged skin cells
  • giant vesicle
  • mannosylerythritol lipid
  • recovery effect
  • self-assembly

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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