*Article* **COX Inhibitory and Cytotoxic Naphthoketal-Bearing Polyketides from** *Sparticola junci*

**Katherine Yasmin M. Garcia 1,2 , Mark Tristan J. Quimque 1,2,3, Gian Primahana 4,5,6 , Andreas Ratzenböck <sup>7</sup> , Mark Joseph B. Cano 1,2, Jeremiah Francis A. Llaguno <sup>2</sup> , Hans-Martin Dahse <sup>8</sup> , Chayanard Phukhamsakda 9,10 , Frank Surup 4,5 , Marc Stadler 4,5 and Allan Patrick G. Macabeo 2,\***


**Abstract:** Axenic fermentation on solid rice of the saprobic fungus *Sparticola junci* afforded two new highly oxidized naphthalenoid polyketide derivatives, sparticatechol A (**1**) and sparticolin H (**2**) along with sparticolin A (**3**). The structures of **1** and **2** 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 **1–3** were evaluated for COX inhibitory, antiproliferative, cytotoxic and antimicrobial activities. Compounds **1** and **2** exhibited strong inhibitory activities against COX-1 and COX-2. Molecular docking analysis of **1** conferred favorable binding against COX-2. Sparticolin H (**2**) and A (**3**) showed a moderate antiproliferative effect against myelogenous leukemia K-562 cells and weak cytotoxicity against HeLa and mouse fibroblast cells.

**Keywords:** *Sparticola junci*; structure elucidation; ECD-TDDFT; COX inhibitory; molecular docking; antiproliferative; cytotoxic
