Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 1, Pages 194-202Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02569
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Funding
- National Research Foundation (NRF) grant by the Korea government (MSIP) [NRF-2015M1A5A1041808]
- Korea Basic Science Institute under the RD program [D37700]
- National Research Foundation of Korea [2015M1A5A1041808] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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Following isolation of the polyhydroxy compound, ostreol B, from cultivated cells of the toxic dinoflagellate Ostreopsis cf. ovata collected in South Korea, 1D and 2D NMR spectroscopy were employed to determine the planar chemical structure of this compound, which contained a tetrahydropyran ring, two terminal double bonds, and 21 hydroxyl groups. The absolute configurations of all stereogenic carbon centers in ostreol B were then determined through a combination of the J-based configuration analysis, rotating frame Overhauser effect correlations, and the modified Mosher method following cleavage of the 1,2-diol bonds: Ostreol B was also found to exhibit moderate cytotoxicity in HepG2, Neuro-2a and HCT-116 cells.
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