This study investigated the bioactivity of six pigments from the Australian Cortinarius mushroom genus, specifically targeting their influence on various fungi, viruses, and an inflammatory stimulus. It was discovered that when tested between 25-26.3 [microns], (1S,3S)-Austrocortirubin [M1], (1R,3R)-Austrocortilutein [M2], (1S,3S)-Austrocortilutein [M3] and (1S,3R)-Austrocortilutein [M4] were all equally effective at inhibiting C. albicans growth. At these same concentrations, M1 and M3 effectively prevented A. fumigatus growth. It was theorised that the identical S-configured hydroxyls on these compounds' 1st and 3rd carbons were advantageous against mould growth, specifically A. fumigatus. It was also confirmed that (3R/S)-1-deoxy-Austrocortirubin [M5] and Torosachrysone [T] were significantly less effective at preventing either yeast or mould growth compared to the other Cortinarius pigments. The compounds were deemed to have no antiviral effect against either HPIV3 or RSV. When the compounds were exposed to human peripheral macrophages, their anti-inflammatory activity was shown to be minimal. Additionally, across all in vitro assays, these compounds were highly cytotoxic against LLC-MK2, HEp-2 and Human macrophage cells. Although, during cytotoxicity screening, the Compounds M2-M5 were identified as selectively toxic to the cancerous cell line (HEp-2) over a normal cell line (LLC-MK2), which could indicate a beneficial future research path.