Research Article Bioprospecting of an Endolichenic Fungus Phanerochaete sordida Isolated from Mangrove-Associated Lichen Bactrospora myriadea Ramani H. Weerasinghe , 1 Chaitrali D. Shevkar , 2 Kasun Maduranga , 1 Komal H. Pandey , 2 Renuka N. Attanayake , 3 Abhijeet S. Kate , 2 Gothamie Weerakoon , 4 Santosh K. Behera , 2 Kiran S. Kalia , 2 and Priyani A. Paranagama 1 1 Department of Chemistry, University of Kelaniya, Kelaniya 11600, Sri Lanka 2 National Institute of Pharmaceutical Education and Research, Ahmedabad 382355, India 3 Department of Plant and Molecular Biology, University of Kelaniya, Kelaniya 11600, Sri Lanka 4 Algae, Fungi and Plants Division, Department of Life Sciences, The Natural History Museum, Cromwell Road, London SW7 5BD, UK Correspondence should be addressed to Priyani A. Paranagama; priyani@kln.ac.lk Received 21 December 2021; Revised 14 March 2022; Accepted 15 March 2022; Published 16 April 2022 Academic Editor: Josefina Pons Copyright © 2022 Ramani H. Weerasinghe et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Bioassay-guided fractionation of the ethyl acetate extract of Phanerochaete sordida, an endolichenic fungus (ELF) isolated from the host lichen Bactrospora myriadea, collected from Negombo lagoon, Sri Lanka, led to the isolation of a bioactive compound. Following the identification of the fungus using morphological and DNA barcoding techniques, the pure compound was isolated using column chromatography, preparative TLC, and semipreparative HPLC. The structure elucidation was carried out using IR, HR-ESI-MS and 1 H, 13 C & 2D NMR spectroscopic methods. The in vitro bioassays conducted revealed that compound 1 has a high antioxidant activity with ABTS •+ (IC 50 58:91 ± 1:35 μM), moderate anti-inflammatory activity (IC 50 254:79 ± 1:41 μM), comparable antibacterial activity against the oral-bacterial strain Streptococcus mutans (MIC 898.79 μM and MLC 1797.58 μM), moderate tyrosinase inhibition (IC 50 1713:69 ± 8:65 μM), and moderate cytotoxicity against oral cancer (IC 50 13:65 ± 0:02 μM), in comparison with respective positive controls. The in silico experiments conducted for tyrosinase inhibition and cytotoxicity using Schrödinger revealed results in line with the in vitro results, thus confirming the bioactivities. The molecule also satisfies the key features of drug likeliness according to pharmacokinetic studies. 1. Introduction Endolichenic fungi (ELF), asymptomatic fungal associates which live in the interior of a lichen thallus, serve as an incredible source of novel bioactive compounds. While adding evidence in proving lichens to be “cradles of fungal diversification” [1], this distinct group of fungi has been found to produce compounds with antioxidant, antibacte- rial, anti-inflammatory, antifungal, anticancer, and numer- ous other potentials [2]. Subsequent to the first report of such isolated compounds in 2007 [3], more than 172 com- pounds have been isolated and explored from ELF while more than 99 of them had been novel molecules [4]. Exper- iments conducted in Sri Lanka revealed numerous such potent compounds, which include polyketides from ELF Penicillium citrinum [5] and Curvularia trifolli [6] along with more metabolites from Daldinia eschscholtzii [7] Xylaria psidii [8], and Neurospora ugadawe [9]. The ELF used in the present study, Phanerochaete sordida, was isolated from the host lichen Bactrospora Hindawi Journal of Chemistry Volume 2022, Article ID 3193689, 11 pages https://doi.org/10.1155/2022/3193689