Synthesis of Mannosylerythritol Lipid Analogues and their Self-Assembling Properties,Recovery Effects on Damaged Skin Cells,and Antibacterial Activity |
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| Authors: | Takanori Kondo Chihiro Yasui Ikkei Miyajima Dr. Taisuke Banno Prof. Dr. Kouichi Asakura Dr. Tokuma Fukuoka Dr. Kazunori Ushimaru Dr. Maito Koga Dr. Azusa Saika Dr. Tomotake Morita Dr. Yoshiaki Takahashi Chigusa Hayashi Dr. Masayuki Igarashi Prof. Dr. Daisuke Takahashi Prof. Dr. Kazunobu Toshima |
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| Affiliation: | 1. Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522 Japan;2. Research Institute for Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST) 5-2 Tsukuba Central, 1-1 Higashi, Tsukuba, Ibaraki, 305-8565 Japan;3. Institute of Microbial Chemistry (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo, 141-0021 Japan |
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| 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. |
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| Keywords: | antibacterial activity damaged skin cells giant vesicle mannosylerythritol lipid recovery effect self-assembly |
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