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Antimicrobial isoflavans and other metabolites of Dalea nana.
Belofsky, Gil; Cruz, Caroline; Schultz, Trevor; Zapata, Maxwell; Wilcox, Dominique; Wasmund, Brendan; Salomon, Christine E; Spiegel, P Clint.
Afiliación
  • Belofsky G; Department of Chemistry, Central Washington University, Ellensburg, WA, 98926, United States. Electronic address: belofskyg@cwu.edu.
  • Cruz C; Department of Chemistry, Central Washington University, Ellensburg, WA, 98926, United States.
  • Schultz T; Department of Chemistry, Central Washington University, Ellensburg, WA, 98926, United States.
  • Zapata M; Department of Chemistry, Central Washington University, Ellensburg, WA, 98926, United States.
  • Wilcox D; Department of Chemistry, Central Washington University, Ellensburg, WA, 98926, United States.
  • Wasmund B; Department of Chemistry, Central Washington University, Ellensburg, WA, 98926, United States.
  • Salomon CE; Center for Drug Design, University of Minnesota, Minneapolis, MN, 55455, United States.
  • Spiegel PC; Department of Chemistry, Western Washington University, Bellingham, WA, 98225, United States.
Phytochemistry ; 226: 114224, 2024 Oct.
Article en En | MEDLINE | ID: mdl-39032794
ABSTRACT
The phytochemical investigation of extracts from Dalea nana roots and aerial parts led to the isolation of thirteen phenolic compounds. Three previously undescribed isoflavans, named verdeans A-C (1, 3, and 7), were characterized. Two additional isoflavans (2 and 5) were previously undescribed enantiomers of known compounds. A previously undescribed isoflavone (verdean D, 10) was found, and the known specialized metabolites, isoflavans 4, 6, 8, and 9, isoflavone 11, flavone 12, and a 2-arylbenzofuran 13, were also isolated. All but one (7) of the isoflavans were prenylated. The structures of the previously undescribed compounds were deduced by NMR spectroscopy, supported by HRESI mass spectrometry. The absolute configurations of 1-3, 5, and 7-9 were determined by ECD. Compounds 1, 3, 4, 6, and 8 exhibited in vitro antimicrobial activities, causing complete growth inhibition (MIC) at concentrations between 6.7 and 37.0 µM against Cryptococcus neoformans and between 8.9 and 25.0 µM against methicillin resistant Staphylococcus aureus (MRSA). The most broadly active previously undescribed compound was verdean A (1), with MIC values of 6.7 and 12.9 µM toward C. neoformans and MRSA, respectively, and an MIC of 10.0 µM against the often-intractable C. albicans.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Pruebas de Sensibilidad Microbiana / Cryptococcus neoformans / Staphylococcus aureus Resistente a Meticilina / Isoflavonas Idioma: En Revista: Phytochemistry Año: 2024 Tipo del documento: Article Pais de publicación: Reino Unido

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Pruebas de Sensibilidad Microbiana / Cryptococcus neoformans / Staphylococcus aureus Resistente a Meticilina / Isoflavonas Idioma: En Revista: Phytochemistry Año: 2024 Tipo del documento: Article Pais de publicación: Reino Unido