Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on the Agalwood (Jinko). IV. : Structures of 2-(2-Phenylethyl)chromone Derivatives, Agarotetrol and Isoagarotetrol
YASUO SHIMADATENJI KONISHISHIU KIYOSAWAMASATOSHI NISHIKAZUMOTO MIYAHARATOSHI KAWASAKI
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Keywords: X-ray analysis
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1986 Volume 34 Issue 7 Pages 2766-2773

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Abstract

The structures of two compounds, AH1 and AH2, isolated from agalwood "Jinko" were studied. AH1 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 (13C-NMR) data and [α]D values of the two compounds were identical, and AH1 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.AH2 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.

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© The Pharmaceutical Society of Japan
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