トリカブト属ジテルペンアルカロイドのLC-APCI-MSによる構造解析と末梢血流量増加作用について  [in Japanese] Studies on Structural Elucidation of Aconitum Diterpenoid Alkaloid by LC-APCI-MS and Effects of Aconitum Diterpenoid Alkaloid on Cutaneous Blood Flow  [in Japanese]

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Abstract

The chemical constituents of <i>Aconitum yesoense</i> var. <i>macroyesoense</i> and <i>Aconitum japonicum</i> were examined using high-resolution spectral analysis. Twelve novel alkaloids were isolated from <i>A. yesoense</i> var. <i>macroyesoense</i> together with 20 known alkaloids. Eight novel alkaloids were isolated from <i>A. japonicum</i> together with 15 known alkaloids. An HPLC-atmospheric pressure chemical ionization-mass spectrometry (HPLC-APCI-MS) method was useful for the simultaneous determination of 21 <i>Aconitum</i> alkaloids found in <i>A. yesoense</i> var. <i>macroyesoense</i> and A. <i>japonicum</i>. These compounds were fairly stable under the conditions used, and the protonated molecules or fragment ions characteristic of the molecule appeared as base peaks in the mass spectra and were used for selected ion monitoring. HPLC-APCI-MS is a very promising approach for structural investigations of positional isomers and stereoisomers. This method was applied successfully to stereoisomeric <i>Aconitum</i> alkaloids differing in configuration at C-1, -6, or -12. Comparison of the APCI spectra showed that the abundance of fragment ions was significantly higher for the C-1, -6, or -12 β-form alkaloid than for C-1, -6, or -12 α-form alkaloid. The main alkaloid constituents in the root of <i>A. yesoense</i> var. <i>macroyesoense</i>, <i>Aconitum</i> alkaloids of the C<sub>20</sub>-diterpenoid type, kobusine and pseudokobusine, and their acyl derivatives were examined for their peripheral vasoactivities by measuring laser-flowmetrically the cutaneous blood flow in the hind foot of mice after intravenous administration. It is thought that the hydroxyl groups of alkaloids, especially a free OH group of pseudokobusine at C-6, were important for action on the peripheral vasculature leading to dilatation, and the results indicated that esterification of the hydroxyl group at C-15 with either anisoate, veratroate, or <i>p</i>-nitrobenzoate may contribute to enhancement of the activity of the parent alkaloids.<br>

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 122(11), 929-956, 2002-11-01

    The Pharmaceutical Society of Japan

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Codes

  • NII Article ID (NAID)
    10010204168
  • NII NACSIS-CAT ID (NCID)
    AN00284903
  • Text Lang
    JPN
  • Article Type
    REV
  • ISSN
    00316903
  • NDL Article ID
    6342267
  • NDL Source Classification
    ZS51(科学技術--薬学)
  • NDL Call No.
    Z19-411
  • Data Source
    CJP  NDL  J-STAGE 
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