Digipregnosides A–C, three novel rearranged 11, 12-secopregnane glycosides, and digipregnosides D and E, 12, 20-epoxypregnane glycosides from the seeds of Digitalis purpurea. (27th April 2021)

• Record Type: Journal Article
• Authors: Takatori, Kazuhiro; Kuroda, Minpei; Mishima, Masaki; Matsuo, Yukiko; Mimaki, Yoshihiro
• Is Part Of: Tetrahedron letters. Volume 70(2021)
• Publication Date: 2021-04-27
• Subjects: Digitalis purpurea -- Rearranged 11, 12-secopregnane glycoside -- 12, 20-epoxypregnane glycoside -- SBC-3 cells; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2021.153020
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Rearranged 11, 12-secopregnane glycosides, digipregnosides A—C (1 –3 ) were isolated. 12, 20-Epoxypregnane glycosides, digipregnosides D (4 ) and E (5 ) were isolated. Compounds 1 and 4 showed tumor selective cytotoxicity against SBC-3 cells. Compounds 1 and 4 activated caspase-3/7 and induced apoptosis in SBC-3 cells. Abstract: Three novel rearranged 11, 12-secopregnane glycosides—named, digipregnosides A (1 ), B (2 ), and C (3 )—and two novel 12, 20-epoxypregnane glycosides—named, digipregnosides D (4 ) and E (5 )—were isolated from the seeds of Digitalis purpurea . Their structures were determined based on extensive spectroscopic analysis, including long-range heteronuclear single quantum multiple bond correlation (HSQMBC) spectral data, and the results of hydrolytic cleavage. Compounds 1 and 4 showed tumor selective cytotoxicity against SBC-3 small cell lung carcinoma cells at a sample concentration of 0.001 μM and induced apoptotic cell death in SBC-3 cells with IC50 values of 1.3 ± 0.16 and 0.17 ± 0.072 μM respectively.