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6S,8α-Dihydroxy-14,15-Dihydrocarapin (Khayanone) from the Stem Bark of Khaya Senegalensis (Meliaceae): Isolation and its Crystal Structure

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Abstract

Khayanone was isolated from the stem bark of African mahogany, Khaya senegalensis (Meliaceae), and characterized as 6S,8α-dihydroxy-14,15-dihydrocarapin on the basis of spectral analysis and single crystal X-ray diffraction study. The compound crystallizes in the tetragonal space group P4 1 2 1 2 with unit cell parameters: a = 13.2315(19) Å, c = 29.118(6) Å, Z = 8. The crystal structure has been solved by direct methods and refined to R = 0.0375 for 4552 unique reflections. The six-membered rings A and B exist in boat conformations, rings C and D in chair conformations, and the furan ring is planar. The crystal structure is stabilized by O-H···O and C-H···O interactions. This is the first report about 6S configuration of mexicanolide revealed by X-ray diffraction analysis. The configuration of oxygenated C-6 in mexicanolide-group limonoids is discussed.

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Acknowledgement

The authors are grateful to the financial support from South Carolina Nutrition Research Consortium and a grant from National Institutes of Health, R21CA107138.

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Authors and Affiliations

  1. Department of Food Science & Human Nutrition, Clemson University, Clemson, SC, 29634, USA

    Huaping Zhang & Feng Chen

  2. Department of Chemistry, Clemson University, Clemson, SC, 29634, USA

    Don VanDerveer

  3. Department of Genetics and Biochemistry, Clemson University, Clemson, SC, 29634, USA

    Xi Wang

  4. Department of Pathology and Microbiology, School of Medicine, University of South Carolina, South Carolina Cancer Center, Columbia, SC, 29208, USA

    Xiao M. Androulakis & Michael J. Wargovich

Authors
  1. Huaping Zhang
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  2. Don VanDerveer
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  3. Xi Wang
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  4. Feng Chen
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  5. Xiao M. Androulakis
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  6. Michael J. Wargovich
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Correspondence to Feng Chen or Michael J. Wargovich.

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Zhang, H., VanDerveer, D., Wang, X. et al. 6S,8α-Dihydroxy-14,15-Dihydrocarapin (Khayanone) from the Stem Bark of Khaya Senegalensis (Meliaceae): Isolation and its Crystal Structure. J Chem Crystallogr 37, 463–467 (2007). https://doi.org/10.1007/s10870-007-9193-x

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  • DOI: https://doi.org/10.1007/s10870-007-9193-x

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