Cynotofuranoside A-C: Uncommon C21-steroidal furanosides derived from the acid hydrolysate of Cynanchum otophyllum roots. (25th May 2022)

• Record Type: Journal Article
• Authors: Li, Xiao-San; Long, Juan; Chen, Mei-Fang; Wang, Qi-Lin; Liang, Xiao-Yan; Zheng, Jia-Chon; Xing, Rui; Yang, Xue-Mei; Huang, Yong-Mei; Luo, Hui
• Is Part Of: Tetrahedron letters. Volume 98(2022)
• Publication Date: 2022-05-25
• Subjects: Cynanchum otophyllum -- Acid hydrolysate -- C21-steroidal furanosides -- Cytotoxicity; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2022.153812
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Three uncommon C21 -steroidal furanosides derived from the acid hydrolysate of Cynanchum otophyllum roots. Their structures were elucidated by extensive spectroscopic analysis including NMR and HR-ESI-MS. Their 2, 6-dideoxy-aldohexose units were located at C-3 of C21 -steroidal aglycone in the form of furan ring. Compound 1 and 3 showed the moderate cytotoxicity against HepG2 with IC50 of 43.15 and 34.36 μM, respectively. Abstract: Cynotofuranoside A-C (1 –3 ), three previously undescribed C21 -steroidal furanosides were isolated from the acid hydrolysate of Cynanchum otophyllum roots. Their structures were elucidated by extensive spectroscopic analysis including UV, IR, 1D and 2D NMR and HR-ESI-MS. Compounds 1 –3 represented the first examples of 2, 6-dideoxy-aldohexose in the form of furan ring attaching to 3 β -OH of natural occurring C21 -steroidal aglycones. The cytotoxicity of these compounds against human cancer MCF-7, HCT-116, HeLa, and HepG2 cells were evaluated. Compounds 1 and 3 showed moderate cytotoxic activities against HepG2 cancer cells with IC50 values of 43.15 and 34.36 μM, respectively.