P-15 生合成研究を用いたブレファリズミン-Cの^<13>C NMRの帰属(ポスター発表の部)

概要

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Blepharismins (BPs) are toxic pigments of a negatively phototactic ciliate Blepharisma japonicum. This pigment was first reported in 1905, and was extensively studied by Giese. The chemical structure of BP(s) was elucidated in 1997 independently by Song, and Naoki. with analyzing HMQC and HMBC NMR spectra of BP-C or tetramethoxy derivatives of BPs. BPs (1), which consist as a mixture of five congeners, are structurally related to naturally occurring polycyclic phenanthroperylene quinones such as hypericin, a photodynamic toxin of Hypericum, and stentorin isolated from another negatively phototactic ciliate Stentor coeruleus. BPs are shown to be converted to stentorin via oxyblepharismines (OxyBPs) by UV-irradiation, whose structures were determined by Spitzner. Lensi studied OxyBP-choromoprotein association, and helical properties of OxyBP with or without the chromoprotein. The function of BPs has not been fully elucidated, but three functions have been clarified: light perception, defense against predators or UV irradiation. BPs are highly ring-condensed compound with a lot of substituted sp^2 carbons, therefore assignment of the ^<13>C NMR signals has not been completely achieved in the previous reports. Herein we like to report full assignment of the ^<13>C NMR signals of BP-C (1c) using samples obtained by feeding of ^<13>C-labeled sodium acetates to the cells of B. japonicum in the culture media.
天然有機化合物討論会の論文
2007-08-24