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>

Meroantarctines A–C, Meroterpenoids with Rearranged Skeletons from the Alga-Derived Fungus <i>Penicillium antarcticum</i> KMM 4685 with Potent p‑Glycoprotein Inhibitory Activity

New meroterpenoids, meroantarctines A–C (1–3), with unique 6/5/6/6, 6/5/6/5/6, and 6/5/6/5 polycyclic systems were isolated from the alga-derived fungus Penicillium antarcticum KMM 4685. Their structures were elucidated by spectroscopic methods, X-ray diffraction, and quantum chemical calculations. A biogenetic pathway for 1–3 was proposed. Meroantarctines A–C (1–3) inhibited p-glycoprotein activity and could resensitize drug-resistant cancer cells to docetaxel

Meroantarctines A–C, Meroterpenoids with Rearranged Skeletons from the Alga-Derived Fungus <i>Penicillium antarcticum</i> KMM 4685 with Potent p‑Glycoprotein Inhibitory Activity

New meroterpenoids, meroantarctines A–C (1–3), with unique 6/5/6/6, 6/5/6/5/6, and 6/5/6/5 polycyclic systems were isolated from the alga-derived fungus Penicillium antarcticum KMM 4685. Their structures were elucidated by spectroscopic methods, X-ray diffraction, and quantum chemical calculations. A biogenetic pathway for 1–3 was proposed. Meroantarctines A–C (1–3) inhibited p-glycoprotein activity and could resensitize drug-resistant cancer cells to docetaxel

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