Synthesis of Mannosylerythritol Lipid Analogues and their Self‐Assembling Properties, Recovery Effects on Damaged Skin Cells, and Antibacterial Activity. Issue 55 (1st August 2022)

• Record Type: Journal Article
• Authors: Kondo, Takanori; Yasui, Chihiro; Miyajima, Ikkei; Banno, Taisuke; Asakura, Kouichi; Fukuoka, Tokuma; Ushimaru, Kazunori; Koga, Maito; Saika, Azusa; Morita, Tomotake; Takahashi, Yoshiaki; Hayashi, Chigusa; Igarashi, Masayuki; Takahashi, Daisuke; Toshima, Kazunobu
• Is Part Of: Chemistry. Volume 28:Issue 55(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-08-01
• Subjects: antibacterial activity -- damaged skin cells -- giant vesicle -- mannosylerythritol lipid -- recovery effect -- self-assembly; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202201733
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Abstract : Antibacterial artificial sugar‐based material : Synthesis of three types of mannosylerythritol lipid (MEL)‐D analogues with decanoyl groups, β‐GlcEL‐D, β‐GlcEL‐D, and α‐MEL‐D, was accomplished. Their self‐assembling properties, recovery effects on damaged skin cells, and antibacterial activity were evaluated. The results indicated α‐MEL‐D is a promising artificial sugar‐based material candidate for enhancing the barrier function of the stratum corneum with possessing antibacterial activity.