Journal
STEROIDS
Volume 161, Issue -, Pages -Publisher
ELSEVIER SCIENCE INC
DOI: 10.1016/j.steroids.2020.108681
Keywords
Sinularia erecta; Steroidal derivative; Cytotoxicity; Baeyer-Villiger oxidation
Funding
- National Key Research and Development Program of China [2018YFC0310903]
- Natural Science Foundation of China [81991521, 81520108028, 21672230]
- Drug Innovation Major Project [2018ZX09711-001-001-009]
- SKLDR/SIMM Project [SIMM1903ZZ-04]
- Syngenta-SIMM-PhD Studentship Project
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Two novel steroidal derivatives, erectsterates A (1) and B (2), a pair of epimers at C-10, were isolated from the South China Sea soft coral Sinularia erecta. Their structures were established by extensive spectroscopic analysis and deduction from biosynthesis route. Compounds 1 and 2 are rare steroids with a highly degradation in ring B and an ester linkage between A and C/D rings, similar with the known compounds chaxines B (3) and D from an edible mushroom Agrocybe chaxingu. To the best of our knowledge, this is the first report of such kind of steroid from soft coral. And a different biosynthetic route from the reported approach of chaxines was proposed in this paper. Interestingly, the ring C of 1 and 2 was formally oxidized by Baeyer-Villiger reaction to provide an unprecedented seven-membered lactone moiety in ring C of steroid. The in vitro anti-proliferative activities of 2 were evaluated against A549, HT-29, SNU-398 and Capan-1 cell lines. The results indicated that it showed weak cytotoxicity against the tested four cell lines.
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