{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T17:24:32Z","timestamp":1786987472387,"version":"build-2736575974"},"reference-count":19,"publisher":"Georg Thieme Verlag KG","issue":"07","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Planta Med"],"published-print":{"date-parts":[[2023,6]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The phytochemical investigation of extracts of Dalea jamesii root and aerial portions led to the isolation of ten phenolic compounds. Six previously undescribed prenylated\n          isoflavans, summarily named ormegans A\u200a\u2013\u200aF (1\u200a\u2013\u200a6), were characterized, along with two new arylbenzofurans (7, 8), a known flavone (9), and a known chroman (10).\n          The structures of the new compounds were deduced by NMR spectroscopy, supported by HRESI mass spectrometry. The absolute configurations of 1\u200a\u2013\u200a6 were determined by circular dichroism\n          spectroscopy. Compounds 1\u200a\u2013\u200a9 exhibited in vitro antimicrobial activities, causing 98% or greater growth inhibition at concentrations as low as 2.5\u200a\u2013\u200a5.1\u2009\u00b5M against\n          methicillin-resistant Staphylococcus aureus, vancomycin-resistant Enterococcus faecalis, and Cryptococcus neoformans. Interestingly, the most active compound was the\n          dimeric arylbenzofuran 8 (&gt;\u200990% growth inhibition at 2.5\u2009\u00b5M) against both methicillin-resistant S. aureus and vancomycin-resistant E. faecalis, tenfold more active\n          than its corresponding monomer (7).<\/jats:p>","DOI":"10.1055\/a-2013-3008","type":"journal-article","created":{"date-parts":[[2023,3,2]],"date-time":"2023-03-02T23:56:10Z","timestamp":1677801370000},"page":"754-763","source":"Crossref","is-referenced-by-count":1,"title":["Antimicrobial Isoflavans and Other Metabolites of Dalea jamesii"],"prefix":"10.1055","volume":"89","author":[{"given":"Gil","family":"Belofsky","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Central Washington University, Ellensburg, Washington, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hyojin","family":"Ahn","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Central Washington University, Ellensburg, Washington, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maxwell","family":"Zapata","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Central Washington University, Ellensburg, Washington, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dominique","family":"Wilcox","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Central Washington University, Ellensburg, Washington, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christine E.","family":"Salomon","sequence":"additional","affiliation":[{"name":"Center for Drug Design, University of Minnesota, Minneapolis, Minnesota, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"P. Clint","family":"Spiegel","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Western Washington University, Bellingham, Washington, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"194","published-online":{"date-parts":[[2023,3,2]]},"reference":[{"key":"ref1","doi-asserted-by":"crossref","first-page":"112423","DOI":"10.1016\/j.phytochem.2020.112423","article-title":"Investigation of Dalea parryi (Fabaceae) metabolites for anthelmintic activity against the human pathogenic hookworm Ancylostoma ceylanicum","volume":"177","author":"G Belofsky","year":"2020","journal-title":"Phytochemistry"},{"key":"ref2","first-page":"307","volume-title":"Dalea Genus, Chemistry, and Bioactivity Studies","author":"M A Peralta","year":"2019"},{"key":"ref5","doi-asserted-by":"crossref","first-page":"232","DOI":"10.1038\/s41558-022-01290-z","article-title":"Rapid intensification of the emerging southwestern North American megadrought in 2020\u201321","volume":"12","author":"A P Williams","year":"2022","journal-title":"Nat Clim Change"},{"key":"ref6","doi-asserted-by":"crossref","first-page":"1140","DOI":"10.1021\/np401083g","article-title":"Antimicrobial and antiinsectan phenolic metabolites of Dalea searlsiae","volume":"77","author":"G Belofsky","year":"2014","journal-title":"J Nat Prod"},{"key":"ref7","doi-asserted-by":"crossref","first-page":"981","DOI":"10.1055\/s-0031-1298627","article-title":"A prenylated flavanone from Dalea elegans inhibits rhodamine 6\u2009G efflux and reverses fluconazole-resistance in Candida albicans","volume":"78","author":"M A Peralta","year":"2012","journal-title":"Planta Med"},{"key":"ref9","doi-asserted-by":"publisher","DOI":"10.15620\/cdc:82532","volume-title":"Antibiotic resistance threats in the United States, 2019","author":"Centers for Disease Control and Prevention (CDC)","year":"2019"},{"key":"ref10","first-page":"454","article-title":"Treatment strategies for cryptococcal infection: challenges, advances and future outlook","volume":"19","author":"K R Iyer","year":"2021","journal-title":"Nature"},{"key":"ref11","doi-asserted-by":"crossref","first-page":"dlaa114","DOI":"10.1093\/jacamr\/dlaa114","article-title":"Treatment of methicillin-resistant Staphylococcus aureus (MRSA): Updated guidelines from the UK","volume":"3","author":"N M Brown","year":"2021","journal-title":"JAC Antimicrob Resist"},{"key":"ref12","doi-asserted-by":"crossref","first-page":"753","DOI":"10.1016\/S0031-9422(03)00390-X","article-title":"Isoflavanoids from roots of Erythrina zeyheri","volume":"64","author":"H Tanaka","year":"2003","journal-title":"Phytochemistry"},{"key":"ref13","doi-asserted-by":"crossref","first-page":"14180","DOI":"10.1038\/s41598-021-92964-9","article-title":"Insights into the molecular properties underlying antibacterial activity of prenylated (iso) flavonoids against MRSA","volume":"11","author":"S Kalli","year":"2021","journal-title":"Sci Rep"},{"key":"ref14","doi-asserted-by":"crossref","first-page":"573","DOI":"10.1016\/S0031-9422(97)00291-4","article-title":"Phenolic metabolites from Erythrina species","volume":"46","author":"A E Nkengfack","year":"1997","journal-title":"Phytochemistry"},{"key":"ref15","doi-asserted-by":"crossref","first-page":"2177","DOI":"10.1016\/j.phytochem.2005.02.002","article-title":"Circular dichroism, a powerful tool for the assessment of absolute configuration of flavonoids","volume":"66","author":"D Slade","year":"2005","journal-title":"Phytochemistry"},{"key":"ref16","doi-asserted-by":"crossref","first-page":"415","DOI":"10.5012\/bkcs.2009.30.2.415","article-title":"Absolute configurations of (\u00b1)-glabridin enantiomers","volume":"30","author":"M Kim","year":"2009","journal-title":"Bull Korean Chem Soc"},{"key":"ref17","first-page":"1667","article-title":"Two isoprenoid-substituted isoflavans from roots of Maackia tenuifolia. Phytochemistry 1996;43: 893\u2013896 and the associated Corrigenda, Zeng JF, Li GL, Xu X, Zhu DY","volume":"47","author":"J F Zeng","year":"1998","journal-title":"Phytochemistry"},{"key":"ref18","doi-asserted-by":"crossref","first-page":"871","DOI":"10.3987\/COM-05-10321","article-title":"Two new isoflavonoids and a new 2-arylbenzofuran from the roots of Erythrina variegata","volume":"65","author":"H Tanaka","year":"2005","journal-title":"Heterocycles"},{"key":"ref19","first-page":"1060","article-title":"Studies on chemical constituents of Epimedium brevicornum","volume":"41","author":"H Guo","year":"2006","journal-title":"Zhongguo Yaoxue Zazhi"},{"key":"ref20","first-page":"012031","article-title":"Cytotoxic activity of quinoline alkaloids and acylphloroglucinol from the leaves of Melicope denhamii","volume":"1095","author":"R D Saputri","year":"2018","journal-title":"J Phys: Conf Ser"},{"key":"ref21","first-page":"DC4","article-title":"Detection of vancomycin resistance among Enterococcus faecalis and Staphylococcus aureus","volume":"10","author":"R Rengaraj","year":"2016","journal-title":"J Clin Diagn Res"},{"key":"ref22","volume-title":"Performance standards for antimicrobial susceptibility testing","author":"Clinical and Laboratory Standards Institute (CLSI)","year":"2017"}],"container-title":["Planta Medica"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/www.thieme-connect.de\/products\/ejournals\/pdf\/10.1055\/a-2013-3008.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,6,20]],"date-time":"2023-06-20T23:01:00Z","timestamp":1687302060000},"score":1,"resource":{"primary":{"URL":"http:\/\/www.thieme-connect.de\/DOI\/DOI?10.1055\/a-2013-3008"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,3,2]]},"references-count":19,"journal-issue":{"issue":"07","published-online":{"date-parts":[[2023,6,20]]},"published-print":{"date-parts":[[2023,6]]}},"URL":"https:\/\/doi.org\/10.1055\/a-2013-3008","archive":["Portico","CLOCKSS"],"relation":{},"ISSN":["0032-0943","1439-0221"],"issn-type":[{"value":"0032-0943","type":"print"},{"value":"1439-0221","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,3,2]]}}}