Merocyclophanes A and B, Antiproliferative Cyclophanes from the Cultured Terrestrial Cyanobacterium Nostoc sp.
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Date
2012-07Author
Kang, Hahk-Soo
Santarsiero, Bernard D.
Kim, Hyunjung
Krunic, Aleksej
Shen, Qi
Swanson, Steven M.
Chai, Hee-Byung
Kinghorn, A. Douglas
Orjala, Jimmy
Publisher
ElsevierMetadata
Show full item recordAbstract
The cell extract of a cultured terrestrial Nostoc sp. (UIC 10062), obtained from a sample collected at Grand Mere State park in Michigan, displayed antiproliferative activity against the HT-29 human colon cancer cell line. Bioactivity-guided fractionation of the cell extract, combined with LC-MS analysis, led to the isolation of two new cyclophanes, named merocyclophanes A and B (1 and 2). The planar structures were determined by various spectroscopic techniques including HRESIMS, and 1D and 2D NMR experiments. The stereoconfiguration was assigned on the basis of X-ray crystallographic and CD analyses. The structures of merocyclophanes A and B (1 and 2) revealed a new natural [7.7]paracyclophane skeleton characterized by α-branched methyls at C-1/14. Merocyclophanes A and B (1 and 2) displayed antiproliferative activity against the HT-29 human colon cancer cell line with IC50 values of 3.3 and 1.7 μM, respectively.
Subject
CyanobacteriumAntiproliferative activity
HT-29 human colon cancer cells