17, 20-Epoxysteroids from octocoral Isis hippuris (Linnaeus, 1758). (12th October 2022)

• Record Type: Journal Article
• Authors: Huang, Yi-Qi; Chen, Po-Jen; Yang, San-Nan; Chien, Su-Ying; Zheng, Li-Guo; Wen, Zhi-Hong; Kuo, Liang-Mou; Sung, Ping-Jyun
• Is Part Of: Tetrahedron letters. Volume 108(2022)
• Publication Date: 2022-10-12
• Subjects: Isis hippuris -- Hippuristeroketal -- Hippuristerone -- Cytotoxicity -- X-ray; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2022.154142
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: 17, 20-epoxysteroids, hippuristeroketal B (1 ), hippuristerones A (2 ) and I (3 ), were isolated from octocoral Isis hippuris . The absolute stereochemistry of steroids 1 –3 was determined by single-crystal X-ray diffraction analysis. Hippuristerone A (2 ) exhibited cytotoxic effect against HT-29 and DLD-1 cancer cells. Abstract: Three 17, 20-epoxysteroids, including a new metabolite, hippuristeroketal B (1 ), as well as two known compounds, hippuristerones A (2 ) and I (3 ), have been isolated from octocoral Isis hippuris collected off the waters of Taiwan. The structure of steroid 1 was deduced by extensive 1D and 2D NMR studies. The absolute stereochemistry of steroids 1 –3 was determined by single-crystal X-ray diffraction analysis. Steroid 2 exhibited cytotoxic effect against HT-29 and DLD-1 cancer cells with IC50 values of 11.39 and 12.86 μM, respectively.