| Summary: | New anthraquinone derivatives acruciquinones A–C (<b>1</b>–<b>3</b>), together with ten known metabolites, were isolated from the obligate marine fungus <i>Asteromyces cruciatus</i> KMM 4696. Acruciquinone C is the first member of anthraquinone derivatives with a 6/6/5 backbone. The structures of isolated compounds were established based on NMR and MS data. The absolute stereoconfigurations of new acruciquinones A–C were determined using ECD and quantum chemical calculations (TDDFT approach). A plausible biosynthetic pathway of the novel acruciquinone C was proposed. Compounds <b>1</b>–<b>4</b> and <b>6</b>–<b>13</b> showed a significant antimicrobial effects against <i>Staphylococcus aureus</i> growth, and acruciquinone A (<b>1</b>), dendryol B (<b>4</b>), coniothyrinone B (<b>7</b>), and ω-hydroxypachybasin (<b>9</b>) reduced the activity of a key staphylococcal enzyme, sortase A. Moreover, the compounds, excluding <b>4</b>, inhibited urease activity. We studied the effects of anthraquinones <b>1</b>, <b>4</b>, <b>7</b>, and <b>9</b> and coniothyrinone D (<b>6</b>) in an in vitro model of skin infection when HaCaT keratinocytes were cocultivated with <i>S. aureus</i>. Anthraquinones significantly reduce the negative impact of <i>S. aureus</i> on the viability, migration, and proliferation of infected HaCaT keratinocytes, and acruciquinone A (<b>1</b>) revealed the most pronounced effect.
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