| Summary: | During the course of a screening for novel biologically active secondary metabolites produced by the Sordariomycetes (Ascomycota, Fungi), the ex-type strain of <i>Jugulospora vestita</i> was found to produce seven novel xanthone-anthraquinone heterodimers, xanthoquinodin A11 (<b>1</b>) and xanthoquinodins B10–15 (<b>2</b>–<b>7</b>), together with the already known compound xanthoquinodin B4 (<b>8</b>). The structures of the xanthoquinodins were determined by analysis of the nuclear magnetic resonance (NMR) spectroscopic and mass spectrometric data. Moreover, the absolute configurations of these metabolites were established by analysis of the <sup>1</sup>H−<sup>1</sup>H coupling constants, nuclear Overhauser effect spectroscopy (NOESY) correlations, and Electronic Circular Dichroism (ECD) spectroscopic data. Antifungal and antibacterial activities as well as cytotoxicity of all compounds were tested. Xanthoquinodin B11 showed fungicidal activities against <i>Mucor hiemalis</i> [minimum inhibitory concentration (MIC) 2.1 µg/mL], <i>Rhodotorula glutinis</i> (MIC 2.1 µg/mL), and <i>Pichia anomala</i> (MIC 8.3 µg/mL). All the compounds <b>1</b>–<b>8</b> displayed anti-Gram-positive bacteria activity (MIC 0.2–8.3 µg/mL). In addition, all these eight compounds showed cytotoxicity against KB 3.1, L929, A549, SK-OV-3, PC-3, A431, and MCF-7 mammalian cell lines. The six novel compounds (<b>1</b>–<b>3</b>, <b>5</b>–<b>7</b>), together with xanthoquinodin B4, were also found in the screening of other strains belonging to <i>Jugulospora rotula</i>, revealing the potential chemotaxonomic significance of the compound class for the genus.
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