Novel cholestane glycosides from the bulbs of Ornithogalum saundersiae and their cytostatic activity on leukemia HL-60 and MOLT-4 cells

✍ Scribed by Minpei Kuroda; Yoshihiro Mimaki; Yutaka Sashida; Toshihiko Hirano; Kitaro Oka; Akira Dobashi; Hong-yu Li; Nobuyuki Harada

• Book ID: 104207994
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 828 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)00750-3

✦ Synopsis

Two novel 24(23--~22)abeo-cholestane glycosides with a six-membered hemiacetal ring system and a five-membered acetal ring system (2, 3), designated as saundersioside A and B, respectively, together with a new 16,23-epoxy-5~-cholestane glycoside (1) were isolated from the bulbs of Ornithogalum saundersiae. Their structures were determined by detailed analysis of the IH and 13C NMR spectra, including various two-dimensional spectroscopy, and acid-catalyzed hydrolysis. The conformations of the 16,23-epoxy moiety of 1 and the six-membered hemiacetal moiety of 2 and 3 were studied through molecular mechanics and molecular dynamics calculation methods. Compound 3 bearing ap-methoxybenzoyl group at the saccharide part showed potent cytostatic activity on leukemia HL-60 and MOLT-4 cells, and the effect to HL-60 cells was revealed to be mediated partially through induction of apoptosis by cell morphology and DNA fragmentation.