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

1 Scopus citations

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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