Synthesis of Lanostane‐Type Triterpenoid N‐Glycosides and Their Cytotoxicity against Human Cancer Cell Lines

Synthesis of Lanostane‐Type Triterpenoid N‐Glycosides and Their Cytotoxicity against Human Cancer Cell Lines

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...

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Bibliographic Details
Published in:Chemistry & biodiversity Vol. 15; no. 7; pp. e1800113 - n/a
Main Authors: Ukiya, Motohiko, Hayakawa, Teppei, Okazaki, Kouta, Hikawa, Maiko, Akazawa, Hiroyuki, Li, Wei, Koike, Kazuo, Fukatsu, Makoto
Format: Journal Article
Language:English
Published: Switzerland Wiley Subscription Services, Inc 01-07-2018
Subjects:
Airborne particulates
Apoptosis
Biotechnology
Cancer
Cytotoxicity
Glycosides
glycosylation
Lanosterol
Lungs
N‐glycoside
Synthesis
terpenoid
Toxicity
Triterpenoids
Tumor cell lines
apoptosis
glycosylation
N-glycoside
terpenoid
cytotoxicity
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Summary: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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ISSN:1612-1872
1612-1880
DOI:10.1002/cbdv.201800113