{"title":"Antimicrobial isoflavans and other metabolites of Dalea nana","authors":"","doi":"10.1016/j.phytochem.2024.114224","DOIUrl":null,"url":null,"abstract":"<div><p>The phytochemical investigation of extracts from <em>Dalea nana</em> roots and aerial parts led to the isolation of thirteen phenolic compounds. Three previously undescribed isoflavans, named verdeans A-C (<strong>1</strong>, <strong>3</strong>, and <strong>7</strong>), were characterized. Two additional isoflavans (<strong>2</strong> and <strong>5</strong>) were previously undescribed enantiomers of known compounds. A previously undescribed isoflavone (verdean D, <strong>10</strong>) was found, and the known specialized metabolites, isoflavans <strong>4</strong>, <strong>6</strong>, <strong>8</strong>, and <strong>9</strong>, isoflavone <strong>11</strong>, flavone <strong>12</strong>, and a 2-arylbenzofuran <strong>13</strong>, were also isolated. All but one (<strong>7</strong>) 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 <strong>1</strong>–<strong>3</strong>, <strong>5</strong>, and <strong>7</strong>–<strong>9</strong> were determined by ECD. Compounds <strong>1</strong>, <strong>3</strong>, <strong>4</strong>, <strong>6</strong>, and <strong>8</strong> exhibited <em>in vitro</em> antimicrobial activities, causing complete growth inhibition (MIC) at concentrations between 6.7 and 37.0 μM against <em>Cryptococcus neoformans</em> and between 8.9 and 25.0 μM against methicillin resistant <em>Staphylococcus aureus</em> (MRSA). The most broadly active previously undescribed compound was verdean A (<strong>1</strong>), with MIC values of 6.7 and 12.9 μM toward <em>C. neoformans</em> and MRSA, respectively, and an MIC of 10.0 μM against the often-intractable C. albicans.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phytochemistry","FirstCategoryId":"99","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0031942224002619","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 0
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.
期刊介绍:
Phytochemistry is a leading international journal publishing studies of plant chemistry, biochemistry, molecular biology and genetics, structure and bioactivities of phytochemicals, including ''-omics'' and bioinformatics/computational biology approaches. Phytochemistry is a primary source for papers dealing with phytochemicals, especially reports concerning their biosynthesis, regulation, and biological properties both in planta and as bioactive principles. Articles are published online as soon as possible as Articles-in-Press and in 12 volumes per year. Occasional topic-focussed special issues are published composed of papers from invited authors.