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1H NMR spectral analysis of physalin A, a 13,14-seco-16,24-cyclosteroid, based on crystal structure of (25R)-2,3,25,27-tetrahydrophysalin a dimethanol solvate

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Abstract

(25R)-2,3,25,27-Tetrahydrophysalin A dimethanol solvate, C30H42O12, a derivative of 13,14-seco-16,24-cyclosteroid physalin A, crystallizes in the orthorhombic space groupP212121, witha=15.486(5),b=14.794(4), 12.248(6) Å andZ=4. The crystal structure has been solved by direct methods, and refined to an R-value of 0.053 for 2345 observed reflections.1H NMR spectral data of physalin A and its hydrogenated derivatives measured in dimethylsulfoxide-d6 solutions have been elucidated, based on the crystal structure of the tetrahydrophysalin A, enabling the assignment of all the proton signals of physalin A. Theβ-proton of C(11)-methylene has been shown to resonate at remarkably higher field due to anisotropic shielding effect of carbonyl group at C(15).

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Authors and Affiliations

  1. Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, 466, Nagoya, Japan

    Masao Kawai & Yasuo Butsugan

  2. Faculty of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, 606, Kyoto, Japan

    Tooru Taga & Yoshihisa Miwa

Authors
  1. Masao Kawai
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  2. Tooru Taga
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  3. Yoshihisa Miwa
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  4. Yasuo Butsugan
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Kawai, M., Taga, T., Miwa, Y. et al. 1H NMR spectral analysis of physalin A, a 13,14-seco-16,24-cyclosteroid, based on crystal structure of (25R)-2,3,25,27-tetrahydrophysalin a dimethanol solvate. Journal of Crystallographic and Spectroscopic Research 22, 131–137 (1992). https://doi.org/10.1007/BF01186247

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  • DOI: https://doi.org/10.1007/BF01186247

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