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Isolation and Crystal Structure of 6α,7α-Epoxy-5α,17α,27-trihydroxy-1-oxo-22R-witha-2,24-dienolide monohydrate-A Withasteroid from Withania somnifera Leaves

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Abstract

(5R,6S,7S,8S,9S,10R,13S,14S,17S,20R,22R)-6α,7α-epoxy-5α,17α,27-trihydroxy-1-oxo-22R-witha-2,24-dienolide has been isolated from Withania somnifera leaves. Three-dimensional X-ray intensity data were collected at 293 K on Bruker CCD area-detector diffractometer equipped with graphite-monochromated MoKα radiation (λ = 0.71073 Å). The compound crystallizes in monoclinic space group P21 with unit cell parameters: a = 6.4540(2), b = 11.3656(4), c = 17.4982(5) Å, β = 90.730 o(2), Z = 2. The crystal structure was refined to a final R-value of 0.0419 for 6122 observed reflections. One water solvent molecule was observed. All the rings of the steroid skeleton are trans connected. Rings A and B exists in a half-chair conformation, ring C a chair, and five membered ring D is intermediate between half-chair and envelope. The δ-lactone ring E adopts a distorted sofa conformation. The characteristic pattern observed in the packing diagram is the appearance of twisted chains of molecules. The packing of the molecules in the crystal is stabilized by intra- and intermolecular O–H···O and C–H···O interactions.

Graphical Abstract

The isolation and crystal structure analysis of a withasteroid isolated from Withania somnifera leaves

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Acknowledgment

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 & Madhvi M. Lal

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

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

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  1. Vivek K. Gupta
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  2. Madhvi M. Lal
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  3. Naresh K. Satti
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Correspondence to Vivek K. Gupta.

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Gupta, V.K., Lal, M.M., Satti, N.K. et al. Isolation and Crystal Structure of 6α,7α-Epoxy-5α,17α,27-trihydroxy-1-oxo-22R-witha-2,24-dienolide monohydrate-A Withasteroid from Withania somnifera Leaves. J Chem Crystallogr 41, 1064–1070 (2011). https://doi.org/10.1007/s10870-011-0047-1

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