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(20R,22R)-6α,7α-Epoxy-5α,27-dihydroxy-1-oxowitha-2,24-dienolide in Leaves of Withania somnifera: Isolation and its Crystal Structure

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Abstract

(20R,22R)-6α,7α-Epoxy-5α,27-dihydroxy-1-oxowitha-2,24-dienolide (27-hydroxy-withanolide B) was isolated from Withania somnifera. The structure of the withanolide was established by spectral analysis and X-ray diffraction studies. The compound crystallizes in the orthorhombic space group P212121 with unit cell parameters: a = 9.2163(3), b = 11.1828(4), c = 23.6146(9) Å, Z = 4. The crystal structure was refined to R = 0.0495 for 3,284 observed reflections. All the rings of the steroid skeleton are trans connected. Rings A and B exist in a half-chair conformation, ring C a chair, and five membered ring D is intermediate between a half-chair and an envelope. The δ-lactone ring E adopts a distorted sofa conformation. The twist along the length of the steroid nucleus is −6.5°. The characteristic pattern observed in the packing diagram is the appearance of twisted chains of molecules packed together to form layers.

Index Abstract

Isolation and crystal structure analysis of (20R,22R)-6α,7α-epoxy-5α,27-dihydroxy-1-oxowitha-2,24-dienolide.

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Acknowledgement

The authors are thankful to the Head, SAIF, IIT, Madras, Chennai for the use of the data collection facility.

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Authors and Affiliations

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

    Vivek K. Gupta & Shaveta Mahajan

  2. Natural Products Chemistry Division, Indian Institute of Integrative Medicine, Jammu Tawi, 180 001, India

    Naresh K. Satti, Krishan A. Suri & G. N. Qazi

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  1. Vivek K. Gupta
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  2. Shaveta Mahajan
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  3. Naresh K. Satti
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Correspondence to Vivek K. Gupta.

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Gupta, V.K., Mahajan, S., Satti, N.K. et al. (20R,22R)-6α,7α-Epoxy-5α,27-dihydroxy-1-oxowitha-2,24-dienolide in Leaves of Withania somnifera: Isolation and its Crystal Structure. J Chem Crystallogr 38, 769–773 (2008). https://doi.org/10.1007/s10870-008-9388-9

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  • DOI: https://doi.org/10.1007/s10870-008-9388-9

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