Xylochemical Synthesis and Biological Evaluation of the Orchidaceous Natural Products Isoarundinin I, Bleochrin F, Blestanol K, and Pleionol

  • J Nat Prod. 2023 Jan 27;86(1):131-137. doi: 10.1021/acs.jnatprod.2c00830.
Leander Geske  1 ,  Joris Baier  1 ,  Joelle C Boulos  2 ,  Thomas Efferth  2 ,  Till Opatz  1
Affiliations
  • 1. Department of Chemistry, Organic Chemistry Section, Johannes Gutenberg University, Duesbergweg 10-14, 55128 Mainz, Germany.
  • 2. Institute of Pharmaceutical and Biomedical Sciences, Johannes Gutenberg University, Staudingerweg 5, 55128 Mainz, Germany.
PMID: 36538372 DOI: 10.1021/acs.jnatprod.2c00830
Abstract

The first total syntheses of the orchid-derived natural products isoarundinin I (1), (±)-bleochrin F ((±)-2), (±)-blestanol K ((±)-3), and (±)-pleionol ((±)-4) from renewable starting Materials are reported, along with the evaluation of their biological activities. The total syntheses were based on regioselective aromatic bromination reactions in combination with a key acid-promoted regioselective intramolecular cyclization. The biological results suggest that isoarundinin I (1), (±)-blestanol K ((±)-3), and (±)-pleionol ((±)-4) have the potential to inhibit the growth of both sensitive and multidrug-resistant Cancer cells.