Meroterpenoid and Diphenyl Ether Derivatives from <i>Penicillium</i> sp. MA-37, a Fungus Isolated from Marine Mangrove Rhizospheric Soil

<i>Penicillium</i> sp. MA-37, which was obtained from the rhizospheric soil of the mangrove plant <i>Bruguiera gymnorrhiza</i>, exhibited different chemical profiles in static and shaken fermentation modes. Three new meroterpenoid derivatives, 4,25-dehydrominiolutelide B (<b>1</b>), 4,25-dehydro-22-deoxyminiolutelide B (<b>2</b>), and isominiolutelide A (<b>3</b>), together with three known ones were characterized from its static fermentation, while three new diphenyl ether derivatives, namely, Δ^{1^′,3^′}-1′-dehydroxypenicillide (<b>4</b>), 7-<i>O</i>-acetylsecopenicillide C (<b>5</b>), and hydroxytenellic acid B (<b>6</b>), along with five related metabolites were isolated from the shaken culture. The structures of these compounds were elucidated on the basis of spectroscopic analysis, and the structure of compound <b>2</b> was confirmed by X-ray crystallographic analysis. The absolute configurations of <b>1</b>–<b>3</b> and <b>6</b> were determined by ECD and modified Mosher’s method, respectively. All isolated compounds were evaluated for brine shrimp lethality and antibacterial activity