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Characterization and identification of steroidal alkaloids in the Chinese herb Veratrum nigrum L. by high-performance liquid chromatography/electrospray ionization with multi-stage mass spectrometry

Authors

  • Hui-liang Li,

    1. Department of Natural Medicinal Chemistry, School of Pharmacy, The Second Military Medical University, Shanghai 200433, China
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  • Jian Tang,

    1. Department of Natural Medicinal Chemistry, School of Pharmacy, The Second Military Medical University, Shanghai 200433, China
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  • Run-hui Liu,

    1. Department of Natural Medicinal Chemistry, School of Pharmacy, The Second Military Medical University, Shanghai 200433, China
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  • Min Lin,

    1. Department of Natural Medicinal Chemistry, School of Pharmacy, The Second Military Medical University, Shanghai 200433, China
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  • Bin Wang,

    1. Department of Natural Medicinal Chemistry, School of Pharmacy, The Second Military Medical University, Shanghai 200433, China
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  • Yi-feng Lv,

    1. Department of Natural Medicinal Chemistry, School of Pharmacy, The Second Military Medical University, Shanghai 200433, China
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  • Hai-qiang Huang,

    1. Department of Natural Medicinal Chemistry, School of Pharmacy, The Second Military Medical University, Shanghai 200433, China
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  • Chuan Zhang,

    1. Department of Natural Medicinal Chemistry, School of Pharmacy, The Second Military Medical University, Shanghai 200433, China
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  • Wei-dong Zhang

    Corresponding author
    1. Department of Natural Medicinal Chemistry, School of Pharmacy, The Second Military Medical University, Shanghai 200433, China
    2. School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240, China
    • The Second Military Medical University, 325 Guohe Rd., Shanghai 200433, China.
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Abstract

Electrospray ionization multi-stage mass spectrometry (ESI-MSn) was performed to study the fragmentation behaviour of seventeen steroidal alkaloids (4 protoverine-type alkaloids, 10 germine-type alkaloids and 3 zygadenin-type alkaloids) from the Chinese herb Veratrum nigrum L. The MSn spectra of the [M+H]+ ions for steroidal alkaloids provided a wealth of structural information on the substituted groups. In positive ion mode, the three types of alkaloids showed very different characteristic ions: m/z 436 or 418 for protoverine-type alkaloids; m/z 438, 420 or 402 for germine-type alkaloids; m/z 440 or 422 for zygadenin-type alkaloids. These fragments were used to deduce their mass spectral fragmentation mechanisms. Furthermore, the primary compounds in methanolic extracts of the herb of Veratrum nigrum L. were investigated by using liquid chromatography (LC)/ESI-MSn. As a result, 21 steroidal alkaloids (5 protoverine-type alkaloids, 14 germine-type alkaloids and 2 zygadenin-type alkaloids) were selectively identified from 27 determined peaks. Eleven compounds were unambiguously identified by comparing with standard compounds and ten compounds were tentatively identified or deduced according to their MSn data. Two of these compounds (xingangermine and deacetyl xinganveratrine) were found to be novel steroidal alkaloids. In addition, the chemical structures of two pairs of steroidal alkaloid isomers were deduced by comparing their fragment ions. Given the important structural information of known and unknown steroidal alkaloids in crude herbal extracts, this study is useful for identifying these types of steroidal alkaloids in crude materials rapidly and selectively. Copyright © 2007 John Wiley & Sons, Ltd.

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