Isolation, Structure Elucidation, and Biological Activity of Virgineone from <i>Lachnum virgineum</i> Using the Genome-Wide <i>Candida albicans</i> Fitness Test
John G. OndeykaNatural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A., Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, New Jersey 07065, and Center of Fungal Genetics, Merck Frosst Canada Ltd., Montrel, Quebec, CanadaGuy H. HarrisNatural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A., Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, New Jersey 07065, and Center of Fungal Genetics, Merck Frosst Canada Ltd., Montrel, Quebec, CanadaDeborah L. ZinkNatural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A., Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, New Jersey 07065, and Center of Fungal Genetics, Merck Frosst Canada Ltd., Montrel, Quebec, CanadaÁngela BasilioNatural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A., Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, New Jersey 07065, and Center of Fungal Genetics, Merck Frosst Canada Ltd., Montrel, Quebec, CanadaFrancisca VicenteNatural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A., Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, New Jersey 07065, and Center of Fungal Genetics, Merck Frosst Canada Ltd., Montrel, Quebec, CanadaGerald F. BillsNatural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A., Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, New Jersey 07065, and Center of Fungal Genetics, Merck Frosst Canada Ltd., Montrel, Quebec, CanadaGonzalo PlatasNatural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A., Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, New Jersey 07065, and Center of Fungal Genetics, Merck Frosst Canada Ltd., Montrel, Quebec, CanadaJavier ColladoNatural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A., Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, New Jersey 07065, and Center of Fungal Genetics, Merck Frosst Canada Ltd., Montrel, Quebec, CanadaAntonio GonzálezNatural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A., Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, New Jersey 07065, and Center of Fungal Genetics, Merck Frosst Canada Ltd., Montrel, Quebec, CanadaMercedes de la CruzNatural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A., Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, New Jersey 07065, and Center of Fungal Genetics, Merck Frosst Canada Ltd., Montrel, Quebec, CanadaJesús Martı́nNatural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A., Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, New Jersey 07065, and Center of Fungal Genetics, Merck Frosst Canada Ltd., Montrel, Quebec, CanadaJennifer Nielsen KahnNatural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A., Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, New Jersey 07065, and Center of Fungal Genetics, Merck Frosst Canada Ltd., Montrel, Quebec, CanadaStefan GaluskaNatural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A., Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, New Jersey 07065, and Center of Fungal Genetics, Merck Frosst Canada Ltd., Montrel, Quebec, CanadaR.A. GiacobbeNatural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A., Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, New Jersey 07065, and Center of Fungal Genetics, Merck Frosst Canada Ltd., Montrel, Quebec, CanadaGeorge K. AbruzzoNatural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A., Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, New Jersey 07065, and Center of Fungal Genetics, Merck Frosst Canada Ltd., Montrel, Quebec, CanadaEmily HickeyNatural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A., Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, New Jersey 07065, and Center of Fungal Genetics, Merck Frosst Canada Ltd., Montrel, Quebec, CanadaPaul LiberatorNatural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A., Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, New Jersey 07065, and Center of Fungal Genetics, Merck Frosst Canada Ltd., Montrel, Quebec, CanadaBo JiangNatural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A., Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, New Jersey 07065, and Center of Fungal Genetics, Merck Frosst Canada Ltd., Montrel, Quebec, CanadaDeming XuNatural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A., Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, New Jersey 07065, and Center of Fungal Genetics, Merck Frosst Canada Ltd., Montrel, Quebec, CanadaTerry RoemerNatural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A., Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, New Jersey 07065, and Center of Fungal Genetics, Merck Frosst Canada Ltd., Montrel, Quebec, CanadaSheo B. SinghNatural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A., Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, New Jersey 07065, and Center of Fungal Genetics, Merck Frosst Canada Ltd., Montrel, Quebec, Canada
2008en
ABI
Аннотация
A glycosylated tetramic acid, virgineone (1), was isolated from saprotrophic Lachnum virgineum. The antifungal activity of the fermentation extract of L. virgineum was characterized in the Candida albicans fitness test as distinguishable from other natural products tested. Bioassay-guided fractionation yielded 1, a tyrosine-derived tetramic acid with a C-22 oxygenated chain and a beta-mannose. It displayed broad-spectrum antifungal activity against Candida spp. and Aspergillus fumigatus with a MIC of 4 and 16 microg/mL, respectively. Virgineone was also identified in a number of Lachnum strains collected from diverse geographies and habitats.
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