Cholesaponins A-F, six new rare cholestane saponins including two unprecedented 14-methyl C28 cholestane saponins from Solanum xanthocarpum. (12th March 2022)

• Record Type: Journal Article
• Authors: Xu, Zhen-Peng; Liu, Yan; Wang, Si-Yi; Li, Xiao-Mao; Lu, Dong-Xu; Li, Zi-Wei; Pan, Juan; Kuang, Hai-Xue; Yang, Bing-You
• Is Part Of: Tetrahedron. Volume 109(2022)
• Publication Date: 2022-03-12
• Subjects: Solanum xanthocarpum -- Natural products -- Structure elucidation -- Saponins -- Cytotoxicity; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2022.132674
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Phytochemical investigation of Solanum xanthocarpum fruits resulted in the isolation of eight rare cholestane saponins, including six new ones (1 –6 ) and two known ones (7 –8 ). Especially, cholesaponins A and B (1 –2 ) were unusual 14-methyl C28 cholestane saponins discovered for the first time. The chemical structures of 1 –6 were characterized by extensive 1D NMR and 2D NMR and mass analyses. The bioassay screening revealed that most compounds showed varying cytotoxic activity degrees against five human cancer cell lines (A-549, HepG2, MGC-803, LN-229, and SMMC-7721). Graphical abstract: Image 1 Highlights: Six new rare cholestane saponins were obtained from Solanum xanthocarpum fruits. Cholesaponins A and B with the 14-methyl C28 cholestane new carbon skeleton. Plausible biosynthesis pathway of cholesaponin A-B was speculated. Cholesaponin B (2 ) showed significant cytotoxicity (IC50 = 2.60–6.33 μ M).