3 years ago

Ribocyclophanes A–E, Glycosylated Cyclophanes with Antiproliferative Activity from Two Cultured Terrestrial Cyanobacteria

Ribocyclophanes A–E, Glycosylated Cyclophanes
with Antiproliferative Activity from Two Cultured Terrestrial Cyanobacteria
Qi Shen, Aleksej Krunic, Jimmy Orjala, Steven M. Swanson, Joanna E. Burdette, Bernard D. Santarsiero, Daniel S. May, Hahk-Soo Kang
The cell extracts of two cultured freshwater Nostoc spp., UIC 10279 and UIC 10366, both from the suburbs of Chicago, showed antiproliferative activity against MDA-MB-231 and MDA-MB-435 cancer cell lines. Bioassay-guided fractionation led to the isolation of five glycosylated cylindrocyclophanes, named ribocyclophanes A–E (15) and cylindrocyclophane D (6). The structure determination was carried out by HRESIMS and 1D and 2D NMR analyses and confirmed by single-crystal X-ray crystallography. The structures of ribocyclophanes A–E (15) contain a β-d-ribopyranose glycone in the rare 1C4 conformation. Among isolated compounds, ribocyclophane D (4) showed antiproliferative activity against MDA-MB-435 and MDA-MB-231 cancer cells with an IC50 value of less than 1 μM.

Publisher URL: http://dx.doi.org/10.1021/acs.jnatprod.7b00954

DOI: 10.1021/acs.jnatprod.7b00954

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