Sargassopenillines A–G, 6,6-Spiroketals from the Alga-Derived Fungi Penicillium thomii and Penicillium lividum

Seven new 6,6-spiroketals, sargassopenillines A–G (1–7) were isolated from the alga-derived fungi Penicillium thomii KMM 4645 and Penicillium lividum KMM 4663. The structures of these metabolites were determined by HR-MS and 1D and 2D NMR. The absolute configurations of compounds 1, 5 and 6 were assigned by the modified Mosher’s method and by CD data. Sargassopenilline C (3) inhibited the transcriptional activity of the oncogenic nuclear factor AP-1 with an IC50 value of 15 µM

Zosteropenillines: Polyketides from the MarineDerived Fungus Penicillium thomii

Twelve new polyketides, zosteropenillines A–L (1–12), together with known polyketide pallidopenilline A (13), were isolated from the ethylacetate extract of the fungus Penicillium thomii associated with the seagrass Zostera marina. Their structures were established based on spectroscopic methods. The absolute configuration of zosteropenilline A (1) as 4R, 5S, 8S, 9R, 10R, and 13S was determined by a combination of the modified Mosher’s method, X‐ray analysis, and NOESY data. Absolute configurations of zosteropenillines B–D (2–4) were determined by timedependent density functional theory (TD‐DFT) calculations of ECD spectra. The effect of compounds 1–3, 7, 8, 10, and 11 on the viability of human drug‐resistant prostate cancer cells PC3 as well as on autophagy in these cancer cells and inhibitory effects of compounds 1, 2, and 8–10 on NO production in LPS‐induced RAW 264.7 murine macrophages were examined

Meroterpenoids from the Alga-Derived Fungi <i>Penicillium thomii</i> Maire and <i>Penicillium lividum</i> Westling

Ten new austalide meroterpenoids (<b>1</b>–<b>10</b>) were isolated from the alga-derived fungi <i>Penicillium thomii</i> KMM 4645 and <i>Penicillium lividum</i> KMM 4663. Their structures were elucidated by extensive spectroscopic analysis and by comparison with related known compounds. The absolute configurations of some of the metabolites were assigned by the modified Mosher’s method and CD data. Compounds <b>1</b>, <b>2</b>, <b>8</b>, and <b>9</b> were able to inhibit AP-1-dependent transcriptional activity in JB6 Cl41 cell lines at noncytotoxic concentrations. Austalides <b>1</b>–<b>5</b>, <b>8</b>, and <b>9</b> exhibited significant inhibitory activity against <i>endo</i>-1,3-β-d-glucanase from a crystalline stalk of the marine mollusk <i>Pseudocardium sachalinensis</i>

Pallidopenillines: Polyketides from the Alga-Derived Fungus <i>Penicillium thomii</i> Maire KMM 4675

Eleven new polyketides, pallidopenillines <b>1</b>–<b>11</b>, were isolated from the alga-derived fungus <i>Penicillium thomii</i>. The structures of these compounds were established based on spectroscopic methods. The absolute configuration of pallidopenilline A (<b>1</b>) as 4<i>R</i>, 5<i>S</i>, 8<i>S</i>, 9<i>R</i>, 10<i>R</i>, 13<i>R</i> was established using a combination of the modified Mosher’s method, X-ray analysis, and NOESY data. The absolute configurations of <b>2</b>–<b>5</b> were determined by time-dependent density functional theory calculations of the ECD spectra and ECD and NOESY data. It was shown that 1-acetylpallidopenilline A (<b>2</b>) and pallidopenilline G (<b>10</b>) inhibit the growth of colonies of 22Rv1 cells by 40% at 2 and 1 μM, respectively

Pallidopenillines: Polyketides from the Alga-Derived Fungus <i>Penicillium thomii</i> Maire KMM 4675

Eleven new polyketides, pallidopenillines <b>1</b>–<b>11</b>, were isolated from the alga-derived fungus <i>Penicillium thomii</i>. The structures of these compounds were established based on spectroscopic methods. The absolute configuration of pallidopenilline A (<b>1</b>) as 4<i>R</i>, 5<i>S</i>, 8<i>S</i>, 9<i>R</i>, 10<i>R</i>, 13<i>R</i> was established using a combination of the modified Mosher’s method, X-ray analysis, and NOESY data. The absolute configurations of <b>2</b>–<b>5</b> were determined by time-dependent density functional theory calculations of the ECD spectra and ECD and NOESY data. It was shown that 1-acetylpallidopenilline A (<b>2</b>) and pallidopenilline G (<b>10</b>) inhibit the growth of colonies of 22Rv1 cells by 40% at 2 and 1 μM, respectively