Phenalenones and Polyesters from <i>Talaromyces stipitatus</i> and Structure Revision of Talaromycesone A

Investigation of the secondary metabolites of the filamentous fungus <i>Talaromyces stipitatus</i> led to the isolation of two new phenalenone dimers, talarohemiketal A (<b>1</b>) and talaroazasone A (<b>2</b>), and one new macrolide polyester, talaromacrolactone A (<b>3</b>), along with the reported oxyphenalenone dimers talaromycesone A (<b>4</b>), bacillisporin A (<b>5</b>), bacillisporin B (<b>6</b>), bacillisporin C (<b>7</b>), <i>epi</i>-bacillisporin F (<b>8</b>), and bacillisporin J (<b>9</b>), the phenalenone monomer funalenone (<b>10</b>), the polyesters 15G256α (<b>11</b>) and 15G256ν (<b>12</b>), and 6-hydroxymellein (<b>13</b>). Detailed analysis of 2D NMR correlations, supported by TDDFT calculations, led to the structural revision of talaromycesone A as <b>4</b> from previously reported structure <b>14</b>. In addition, the previously misassigned NMR spectra of compound <b>8</b> have been corrected.