New azaphilones from Chaetomium globosum isolated from the built environment

• Published in: Tetrahedron letters Vol. 54; no. 6; pp. 568 - 572
• Main Authors: McMullin, David R., Sumarah, Mark W., Blackwell, Barbara A., Miller, J. David
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 06.02.2013; Elsevier
• Subjects: Antiinfectives and antibacterials; Azaphilone; Chaetomium globosum; Chaetomugilin; Chaetoviridin; Chemistry; Chemistry, Organic; Culture; Indoor; Isochromophilone; Liquids; Physical Sciences; Science & Technology; Strain; Tetrahedrons; Two dimensional; Isochromophilone; Azaphilone; Chaetomium globosum; Chaetomugilin; Chaetoviridin; FUNGI; CHAETOMUGILINS; CYTOTOXIC METABOLITES
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2012.11.084

Molecular models of 4′-epi-N-2-hydroxyethyl-azachaetoviridin A (1), N-2-butyric-azochaetoviridin E, and isochromophilone XIII (3) isolated from an indoor strain of Chaetomium globosum. A strain of Chaetomium globosum (DAOM 240359) was isolated from an indoor air sample in Ottawa, Ontario, Canada. When fermented in liquid culture, this strain produced a number of known metabolites including chaetoglobosins A (6), C, and F (7), chaetomugilin D (5), chaetoviridin A (4), and three new nitrogenous azaphilones; 4′-epi-N-2-hydroxyethyl-azachaetoviridin A (1), N-2-butyric-azochaetoviridin E (2), and isochromophilone XIII (3). The structures were elucidated by spectroscopic analysis including; HRMS, 1D and 2D NMR, UV, and ORD. Compounds 2–7 were antimicrobial when tested using quantitative growth inhibition assays.