Merocyclophanes A and B, antiproliferative cyclophanes from the cultured terrestrial Cyanobacterium Nostoc sp.

Phytochemistry
Hahk-Soo KangJimmy Orjala

Abstract

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 cyclophanes, named merocyclophanes A and B (1 and 2). Their structures were determined by various spectroscopic techniques including HRESIMS, and 1D and 2D NMR analyses. The stereoconfiguration was assigned on the basis of X-ray crystallographic and CD analyses. The structures of merocyclophanes A and B (1 and 2) established a hitherto unknown [7.7]paracyclophane skeleton in nature, as 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.

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Citations

Oct 6, 2015·Marine Drugs·Elena TaleroVirginia Motilva
Jan 26, 2016·Marine Drugs·Michael PreisitschSabine Mundt
Apr 9, 2015·Frontiers in Chemistry·Xuguang GaoTao Ye
Sep 4, 2014·The Journal of Antibiotics·Michael PreisitschSabine Mundt
Mar 3, 2017·Journal of Natural Products·Daniel S MayJimmy Orjala
Feb 1, 2019·Natural Product Reports·Teresa P MartinsPedro N Leão
Jun 4, 2019·Marine Drugs·Justine DemayBenjamin Marie
Oct 9, 2018·Journal of Applied Phycology·Camila M CrnkovicJimmy Orjala
Dec 26, 2018·Natural Product Research·Nguyen Van ThanhChau Van Minh
Jul 4, 2017·Nature Chemical Biology·Hitomi NakamuraEmily P Balskus
Jan 21, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hina QamarBenoît Chénais
Mar 20, 2021·Genome Biology and Evolution·Joachim Steen LarsenBrett Anthony Neilan
Aug 1, 2021·Molecular Phylogenetics and Evolution·Kirti M NitnawareGunvant B Patil

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