Macroline, talpinine, and sarpagine alkaloids from Alstonia penangiana. An NMR-based method for differentiating between A. penangiana and A. macrophylla

Yeap JS 1 , Tan CH 2 , Yong KT 2 , Lim KH 3 , Lim SH 1 , Low YY 4 Show all authors , Kam TS 5

Affiliations 

  • 1 Department of Chemistry, Faculty of Science, University of Malaya, 50603, Kuala Lumpur, Malaysia
  • 2 Institute of Biological Sciences, Faculty of Science, University of Malaya, 50603, Kuala Lumpur, Malaysia
  • 3 School of Pharmacy, University of Nottingham Malaysia Campus, Jalan Broga, 43500, Semenyih, Selangor, Malaysia
  • 4 Department of Chemistry, Faculty of Science, University of Malaya, 50603, Kuala Lumpur, Malaysia. Electronic address: yylow@um.edu.my
  • 5 Department of Chemistry, Faculty of Science, University of Malaya, 50603, Kuala Lumpur, Malaysia. Electronic address: tskam@um.edu.my
Phytochemistry, 2020 Aug;176:112391.
PMID: 32387883 DOI: 10.1016/j.phytochem.2020.112391

Abstract

Fourteen previously undescribed alkaloids comprising two N-1-hydroxymethylmacroline alkaloids, one talpinine-type oxindole acetal, a pair of equilibrating talpinine-type oxindole hemiacetals, eight oxidized derivatives of sarpagine- and akuammiline-type indole alkaloids, in addition to alstochalotine a diastereomer of gelsochalotine recently isolated from Gelsemium elegans, were isolated from the leaf and stem-bark extracts of Alstonia penangiana. The structures and relative configurations of these alkaloids were established using NMR, MS, and in one instance, confirmed by X-ray diffraction analysis. An NMR-based method is described as a useful chemotaxonomic tool for differentiating between A. penangiana and A. macrophylla. Several of the alkaloids isolated showed appreciable growth inhibitory effects when tested against a number of human cancer cell lines.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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