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Planta Med 2023; 89(07): 754-763
DOI: 10.1055/a-2013-3008
Biological and Pharmacological Activity
Original Papers

Antimicrobial Isoflavans and Other Metabolites of Dalea jamesii

Gil Belofsky
1   Department of Chemistry, Central Washington University, Ellensburg, Washington, USA
,
Hyojin Ahn
1   Department of Chemistry, Central Washington University, Ellensburg, Washington, USA
,
Maxwell Zapata
1   Department of Chemistry, Central Washington University, Ellensburg, Washington, USA
,
Dominique Wilcox
1   Department of Chemistry, Central Washington University, Ellensburg, Washington, USA
,
Christine E. Salomon
2   Center for Drug Design, University of Minnesota, Minneapolis, Minnesota, USA
,
P. Clint Spiegel
3   Department of Chemistry, Western Washington University, Bellingham, Washington, USA
› Author AffiliationsNational Institutes of Health, National Center for Complementary and Integrative Health under award R15AT008546
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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).

Key words

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

Supporting Information

    Detailed NMR spectroscopic data and HRESI mass spectra of all compounds, CD spectra of 1 – 6, and HMBC NMR interpretive figures for compounds 1 and 7 are available as Supporting Information.

  • Supporting Information


Publication History

Received: 05 October 2022

Accepted after revision: 01 January 2023

Article published online:
02 March 2023

© 2023. Thieme. All rights reserved.

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