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.
References
Aug 1, 1995·Planta medica·B S FalchH Bachmann
Aug 1, 1997·Applied and Environmental Microbiology·U NübelG Muyzer
Nov 23, 2000·Journal of Natural Products·A Ploutno, S Carmeli
Nov 27, 2001·Journal of Natural Products·E K SeoA D Kinghorn
Feb 19, 2002·Chemical Reviews·Howard E. Smith
Aug 12, 2004·Chemical & Pharmaceutical Bulletin·Ken-Ichi Harada
Jan 18, 2005·International Journal of Systematic and Evolutionary Microbiology·Pirjo RajaniemiKaarina Sivonen
Feb 22, 2007·Journal of Natural Products·Ha T N BuiSabine Mundt
Mar 6, 2007·Phytochemistry·Lik Tong Tan
Apr 24, 2007·Advances in Applied Microbiology·Ryan M Van WagonerJeffrey L C Wright
Aug 27, 2009·Organic & Biomolecular Chemistry·Hiroyuki YamakoshiYoshiharu Iwabuchi
May 6, 2010·Natural Product Reports·Adam C JonesWilliam H Gerwick
Sep 10, 2010·Journal of Natural Products·George E ChlipalaJimmy Orjala
Jan 1, 2009·Pharmaceutical Biology·George ChlipalaJimmy Orjala
May 7, 2011·Molecular Biology and Evolution·Koichiro TamuraSudhir Kumar
Citations
Oct 6, 2015·Marine Drugs·Elena TaleroVirginia Motilva
Jan 26, 2016·Marine Drugs·Michael PreisitschSabine Mundt
Dec 20, 2015·Journal of Natural Products·Michael PreisitschSabine Mundt
Apr 9, 2015·Frontiers in Chemistry·Xuguang GaoTao Ye
Sep 17, 2014·Tetrahedron Letters·Shangwen LuoJimmy Orjala
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
Jun 9, 2018·Marine Drugs·Vivek K BajpaiYoung-Kyu Han
Dec 26, 2018·Natural Product Research·Nguyen Van ThanhChau Van Minh
Jul 4, 2017·Nature Chemical Biology·Hitomi NakamuraEmily P Balskus
Sep 26, 2019·Frontiers in Chemistry·Nguyen Huy ThuanDipesh Dhakal
Oct 9, 2020·Phytochemistry·Víctor Tena PérezÁngel Rumbero Sánchez
May 20, 2020·ChemMedChem·Julien J FreudenreichDavid R Spring
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
Jan 31, 2018·Journal of Natural Products·Daniel S MayJimmy Orjala