Polyneurines A-H, iboga alkaloids from Tabernaemontana polyneura

Tang SY 1 , Tan CH 2 , Sim KS 3 , Yong KT 3 , Lim KH 4 , Low YY 5 Show all authors , Lim SH 6

Affiliations 

  • 1 Department of Chemistry, Faculty of Science, Universiti Malaya, 50603, Kuala Lumpur, Malaysia
  • 2 Institute of Biological Sciences, Faculty of Science, Universiti Malaya, 50603, Kuala Lumpur, Malaysia; Department of Biotechnology, Faculty of Applied Science, Lincoln University, 47301, Petaling Jaya, Selangor, Malaysia
  • 3 Institute of Biological Sciences, Faculty of Science, Universiti Malaya, 50603, Kuala Lumpur, Malaysia
  • 4 School of Pharmacy, University of Nottingham Malaysia, Jalan Broga, 43500, Semenyih, Selangor, Malaysia
  • 5 Department of Chemistry, Faculty of Science, Universiti Malaya, 50603, Kuala Lumpur, Malaysia. Electronic address: yylow@um.edu.my
  • 6 Department of Chemistry, Faculty of Science, Universiti Malaya, 50603, Kuala Lumpur, Malaysia. Electronic address: shlim80@um.edu.my
Phytochemistry, 2023 Apr;208:113587.
PMID: 36646163 DOI: 10.1016/j.phytochem.2023.113587

Abstract

Eight undescribed iboga alkaloids, polyneurines A-H, were isolated from the bark of Tabernaemontana polyneura. The structures of these alkaloids were established by interpretation of the MS and NMR data, while the configurations were determined using GIAO NMR calculations and DP4+ probability analysis, TDDFT-ECD method, or X-ray diffraction analysis. Polyneurine A possesses a γ-lactone unit embedded within the iboga skeleton, while polyneurines D and E incorporate a formylmethyl moiety at C-3 of the iboga skeleton. Biosynthetic pathways towards the formation of polyneurines A, C, D, and E were proposed.

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

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