Synthesis of Mannosylerythritol Lipid Analogues and their Self‐Assembling Properties, Recovery Effects on Damaged Skin Cells, and Antibacterial Activity
| Autor: | 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 |
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| Rok vydání: | 2022 |
| Předmět: | |
| Zdroj: | Chemistry – A European Journal. 28 |
| ISSN: | 1521-3765 0947-6539 |
| DOI: | 10.1002/chem.202201733 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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