Antimicrobial Isoflavans and Other Metabolites of Dalea jamesii

Gil Belofsky, Hyojin Ahn, Maxwell Zapata, Dominique Wilcox, Christine E. Salomon, P. Clint Spiegel

Research output: Contribution to journalArticlepeer-review

Abstract

The phytochemical investigation of extracts of Dalea jamesii root and aerial portions led to the isolation of ten phenolic compounds. Six previously undescribed prenylated isoflavans, summarily named ormegans A-F (1-6), were characterized, along with two new arylbenzofurans (7, 8), a known flavone (9), and a known chroman (10). The structures of the new compounds were deduced by NMR spectroscopy, supported by HRESI mass spectrometry. The absolute configurations of 1-6 were determined by circular dichroism spectroscopy. Compounds 1-9 exhibited in vitro antimicrobial activities, causing 98% or greater growth inhibition at concentrations as low as 2.5-5.1 μM against methicillin-resistant Staphylococcus aureus, vancomycin-resistant Enterococcus faecalis, and Cryptococcus neoformans. Interestingly, the most active compound was the dimeric arylbenzofuran 8 (> 90% growth inhibition at 2.5 μM) against both methicillin-resistant S. aureus and vancomycin-resistant E. faecalis, tenfold more active than its corresponding monomer (7).

Original languageEnglish (US)
Pages (from-to)754-763
Number of pages10
JournalPlanta Medica
Volume89
Issue number7
DOIs
StatePublished - Oct 5 2022

Bibliographical note

Funding Information:
Plant material was originally collected with funding provided by the National Institutes of Health, National Center for Complementary and Integrative Health under award R15AT008546.

Publisher Copyright:
© 2022 Georg Thieme Verlag. All rights reserved.

Keywords

  • Cryptococcus neoformans
  • Dalea jamesii
  • Fabaceae
  • MRSA
  • VRE
  • arylbenzofuran
  • circular dichroism
  • isoflavan

PubMed: MeSH publication types

  • Journal Article

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