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Axenic fermentation on solid rice of the saprobic fungus <i>Sparticola junci</i> afforded two new highly oxidized naphthalenoid polyketide derivatives, sparticatechol A (<b>1</b>) and sparticolin H (<b>2</b>) along with sparticolin A (<b>3</b>). The structures of <b>1</b> and <b>2</b> were elucidated on the basis of their NMR and HR-ESIMS spectroscopic data. Assignment of absolute configurations was performed using electronic circular dichroism (ECD) experiments and Time-Dependent Density Functional Theory (TDDFT) calculations. Compounds <b>1–3</b> were evaluated for COX inhibitory, antiproliferative, cytotoxic and antimicrobial activities. Compounds <b>1</b> and <b>2</b> exhibited strong inhibitory activities against COX-1 and COX-2. Molecular docking analysis of <b>1</b> conferred favorable binding against COX-2. Sparticolin H (<b>2</b>) and A (<b>3</b>) showed a moderate antiproliferative effect against myelogenous leukemia K-562 cells and weak cytotoxicity against HeLa and mouse fibroblast cells.