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Molecular structure of an ancient folk medicine: Berberine hydrogen sulfate

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Abstract

The crystal structure of the versatile folk medicine berberine hydrogen sulfate, (C20H18NO4)+HSO −4 , has been determined by the heavy-atom method and refined by blocked full-matrix least-squares refinement. The crystals are triclinic, space groupF¯1,a=20.370(5),b=7.435(2),c=27.427(6) Å,α=97.700(9),β=116.222(9),γ=85.456.(8)°,Z=8,D x =1.556 g cm−3,D m =1.549(5) g cm−3. The structure refined toR=0.070 for 1659 observed reflections withI(hkl)≧2.5σ[I(hkl)]. The ring system of the berberine molecule is approximately planar, with both −OCH3 groups twisted slightly out of the plane. Heterocyclic ringB has a half-chair conformation with a pseudo-two-fold axis bisecting the bonds C(9)-C(10) and C(7)-C(8), diagonal to the isoquinoline groupAB. The five-membered ringE has an envelope conformation, the apical atom C(1) being out of plane.

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Author notes

  1. Bijan Etemadi Abdol Abadi

    Present address: Geology Department, College of A. and S., Shiraz University, Shiraz, Iran

Authors and Affiliations

  1. Department of Crystallography, Birkbeck College, Malet Street, WC1E7HX, London, UK

    Bijan Etemadi Abdol Abadi, David S. Moss & Rex A. Palmer

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  1. Bijan Etemadi Abdol Abadi
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  2. David S. Moss
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  3. Rex A. Palmer
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Abdol Abadi, B.E., Moss, D.S. & Palmer, R.A. Molecular structure of an ancient folk medicine: Berberine hydrogen sulfate. Journal of Crystallographic and Spectroscopic Research 14, 269–281 (1984). https://doi.org/10.1007/BF01161164

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  • DOI: https://doi.org/10.1007/BF01161164

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