Meroantarctines A–C, Meroterpenoids with Rearranged Skeletons from the Alga-Derived Fungus <i>Penicillium antarcticum</i> KMM 4685 with Potent p-Glycoprotein Inhibitory Activity
Elena V. Leshchenko, Alexandr S. Antonov, Sergey A. Dyshlovoy, Dmitrii V. Berdyshev, Jessica Hauschild, Olesya I. Zhuravleva, Gleb V. Borkunov, Alexander S. Menshov, Natalya N. Kirichuk, Roman S. Popov, А.В. Герасименко, А.А. Удовенко, Markus Graefen, Carsten Bokemeyer, Gunhild von Amsberg, Anton N. Yurchenko
Abstract
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.