A series of C14-hydroxy derivatives of dehydroabietic acid were synthesised from commercial abietic acid and evaluated for their cytotoxic, antimycotic, and antiviral activities. From these C14-hydroxy derivatives, triptoquinone C-4 epimers were obtained and their immunomodulatory activity was additionally evaluated. None of the tested compounds showed antiviral activity against herpes simplex virus type 1 (HHV-1), and nor did they display antimycotic activity against certain Aspergillus, spp. except for one compound, abieta-8,11,13-trien-14,18-diol. Interestingly, two triptoquinone epimers showed cytotoxic activity, and one of them induced mitochondrial potential loss, DNA damage and cell cycle distribution alterations in Jurkat cells, but not in human peripheral blood mononuclear cells. In addition, these compounds inhibited monocyte's differentiation and production of pro-inflammatory cytokines, IL-1β and TNF-α, and the anti-inflammatory cytokine IL-10 in the presence of LPS. In conclusion, one of the triptoquinone molecules could be a promising scaffold for the development of novel anti-cancer agents, and two of them could be potential anti-inflammatory agents.