Synthesis of Lanostane‐Type Triterpenoid N‐Glycosides and Their Cytotoxicity against Human Cancer Cell Lines |
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Authors: | Motohiko Ukiya Teppei Hayakawa Kouta Okazaki Maiko Hikawa Hiroyuki Akazawa Wei Li Kazuo Koike Makoto Fukatsu |
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Institution: | 1. College of Science and Technology, Nihon University, Chiyoda‐ku, Tokyo, Japan;2. Faculty of Pharmaceutical Science, Toho University, Funabashi‐shi, Chiba, Japan |
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Abstract: | Seventeen lanostane‐type triterpenoid derivatives ( 2 – 18 ), including 11N‐glycosides ( 8 – 18 ), were synthesized from the natural triterpenoid, lanosterol ( 1 ), and were evaluated for their cytotoxicity against the human cancer cell lines, HL‐60, A549, and MKN45, as well as the normal human lung cells, WI‐38. Among them, N‐β‐d ‐2‐acetamido‐2‐deoxyglucoside ( 10 ) showed cytotoxicity against HL‐60, A549, MKN45, and WI‐38 cells (IC50 0.0078 – 2.8 μm ). However, N‐β‐d ‐galactoside ( 12 ) showed cytotoxicity against HL‐60 and MKN45 cells (IC50 0.0021 – 4.0 μm ), but not the normal WI‐38 cells. Furthermore, Western blot analysis suggested that 12 induces apoptosis by activation of caspases‐3, 8, and 9. These results will be useful for the synthesis of other tetracyclic triterpenoids or steroid N‐glycosides to increase their cytotoxicity and apoptosis‐inducing activities. |
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Keywords: | terpenoid glycosylation N‐glycoside cytotoxicity apoptosis |
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