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6α,7α-epoxy-5α,17α,dihydroxy-1-oxo-22R-witha-2,24-dienolide in leaves of Withania somnifera: Isolation and its crystal structure

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6α,7α-epoxy-5α,17α,dihydroxy-1-oxo-22R-witha-2,24-dienolide (C28H38O6) was isolated from Withania somnifera leaves. The structure of the withanolide was established by spectral analysis and X-ray diffraction studies as withanone. The compound crystallizes in the orthorhombic space group P212121 with unit cell parameters: a = 9.191(10) Å, b = 12.858(6) Å, c = 21.400(16) Å, Z = 4. The crystal structure was solved by direct methods and refined to R = 0.0603 for 1742 observed reflections. There is positional disorder of the H atom in a hydroxy group (O5), resulting in two possible hydrogen-bond linkages. All the rings of the steroid skeleton are trans connected. Ring A exists in a half-chair conformation, ring B is intermediate between a half-chair and a sofa, ring C a distorted chair, and five-membered ring D is intermediate between a half-chair and an envelope. The δ-lactone ring E adopts a sofa conformation. The twist along the length of the steroid nucleus is negligible [C19–C10…C13–C18=1.8°]. Both the hydroxy groups are involved in hydrogen bonding.

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Acknowledgments

The authors are thankful to the Head, SAIF, IIT, Madras, Chennai for the use of the data collection facility. One of us (Vivek) is thankful to the University Grants Commission, Govt. of India, for research funding under DRS Programme [Project No. F-530/1/DRS/2001(SAP-I)]

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Authors and Affiliations

  1. Post-Graduate Department of Physics, University of Jammu, Jammu Tawi, 180 006, India

    Pankaj Bandhoria & Vivek K. Gupta

  2. Natural Products Chemistry Division, Regional Research Laboratory, Jammu Tawi, 180 001, India

    Musarat Amina, Naresh K. Satti, Prabhu Dutt & Krishan A. Suri

Authors
  1. Pankaj Bandhoria
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  2. Vivek K. Gupta
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  3. Musarat Amina
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  4. Naresh K. Satti
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  5. Prabhu Dutt
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  6. Krishan A. Suri
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Corresponding author

Correspondence to Vivek K. Gupta.

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Supplementary material

CCDC-272526 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data_request/cif.

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Bandhoria, P., Gupta, V.K., Amina, M. et al. 6α,7α-epoxy-5α,17α,dihydroxy-1-oxo-22R-witha-2,24-dienolide in leaves of Withania somnifera: Isolation and its crystal structure. J Chem Crystallogr 36, 153–159 (2006). https://doi.org/10.1007/s10870-005-9041-9

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