4.7 Article

Prorocentrol, a Polyoxy Linear Carbon Chain Compound Isolated from the Toxic Dinoflagellate Prorocentrum hoffmannianum

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 9, Pages 3131-3138

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo102585k

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Funding

  1. KAKENHI [22404006]
  2. Global COE Program for Chemistry Innovation
  3. University of Tokyo
  4. Circle for the promotion of science and Engineering
  5. Grants-in-Aid for Scientific Research [22404006] Funding Source: KAKEN

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A polyoxy linear carbon chain compound, prorocentrol (1), was isolated from cultured cells of the dinoflagellate Prorocentrum hoffmannianum, which produces a polyether carboxylic acid, okadaic acid. The structure of 1 was elucidated by detailed analyses of 2D NMR spectra. Compound 1 possesses 30 hydroxy groups, 1 ketone, and 8 double bonds on the C65-linear carbon chain. Its partial relative configuration was deduced by the proton-proton and long-range carbon - proton coupling constants, and compound 1 showed moderate cytotoxicity and antidiatom activity.

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