Erectsterates A and B, a pair of novel highly degraded steroid derivatives from the South China Sea soft coral Sinularia erecta
Jiao Liu, Xin Wu, Min Yang, Yu-Cheng Gu, Li-Gong Yao, Xia-Juan Huan, Ze-Hong Miao, Hui Luo, Yue-Wei Guo
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.
Circular dichroism, Absolute configuration, Stereochemistry, Natural products, Medicinal, Biochemistry