4.7 Article

Pyrrolizidine alkaloids and unusual millingtojanine A-B from Jacobaea vulgaris (syn. Senecio jacobaea L.)

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PHYTOCHEMISTRY
卷 190, 期 -, 页码 -

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PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.phytochem.2021.112862

关键词

Jacobaea vulgaris Gaertn; Senecio jacobaea; Tansy ragwort; Asteraceae; pyrrolizidine alkaloids; Millingtojanine; X-ray diffraction analysis; ECD calculation

资金

  1. National Natural Science Foundation of China [U1703235]
  2. Central Asia Drug Discovery and Development Centre of Chinese Academy of Science

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Four undescribed pyrrolizidine alkaloids and two enantiomeric pairs of unusual alkaloids were isolated from whole plant extracts of Jacobaea vulgaris Gaertn. The structures were determined through spectroscopic and X-ray diffraction analysis, with some confirmed by comparison of theoretical and experimental data. These compounds exhibit unique structural features and possess rare natural moieties.
Four undescribed pyrrolizidine alkaloids (seneciojanine A-D), two enantiomeric pairs of unusual alkaloids (millingtojanine A-B) with a unique tricyclic core, and nine known pyrrolizidine alkaloids were isolated from whole plant extracts of Jacobaea vulgaris Gaertn. The structures of the undescribed compounds were established by extensive spectroscopic and spectrometric analyses and comparison of theoretical and experimental ECD data. Several of the structures were also confirmed by X-ray diffraction analysis. Seneciojanine A-D possess a rare natural necine moiety with an alpha,beta-unsaturated carbonyl group located at C-3 and a hydroxyl substituent at C-8.

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