Studies on the Agalwood (Jinko). IV. : Structures of 2-(2-Phenylethyl)chromone Derivatives, Agarotetrol and Isoagarotetrol

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The structures of two compounds, AH_1 and AH_2,isolated from agalwood "Jinko" were studied. AH_1 was obtained as needles having a melting point different from that of agarotetrol (powder) isolated and characterized by Yoshii et al. However, the carbon-13 nuclear magnetic resonance (^<13>C-NMR) data and [α]_D values of the two compounds were identical, and AH_1 was concluded to have the same structure, including stereochemistry, as agarotetrol. The half-chair conformation of the hexenyl ring moiety assumed by Yoshii et al. was confirmed by detailed analyses of the proton nuclear magnetic resonance (^1H-NMR) and 2D-COSY spectra.AH_2 was assigned the structure (5S, 6R, 7R, 8S)-2-(2-phenylethyl)-5e', 6e, 7e, 8'e-tetrahydroxy-5,6,7,8-tetrahydrochromone, a stereo-isomer of agarotetrol (7S, 8R), on the basis of the ^1H-NMR, X-ray analysis and circular dichroism (CD) spectral data. It was named isoagarotetrol. The hexenyl ring moiety of isoagarotetrol was found to have a half-chair conformation identical to that of agarotetrol in the crystalline state as well as in solution.
公益社団法人日本薬学会の論文
1986-07-25