Meroantarctines A-C, Meroterpenoids with Rearranged Skeletons from the Alga-Derived Fungus Penicillium antarcticum KMM 4685 with Potent p-Glycoprotein Inhibitory Activity

  • J Nat Prod. 2022 Nov 22. doi: 10.1021/acs.jnatprod.2c00677.
Elena V Leshchenko  1  2 ,  Alexandr S Antonov  2 ,  Sergey A Dyshlovoy  1  3  4 ,  Dmitrii V Berdyshev  2 ,  Jessica Hauschild  3  4 ,  Olesya I Zhuravleva  1  2 ,  Gleb V Borkunov  1 ,  Alexander S Menshov  2 ,  Natalya N Kirichuk  2 ,  Roman S Popov  2 ,  Andrey V Gerasimenko  5 ,  Anatoly A Udovenko  5 ,  Markus Graefen  4 ,  Carsten Bokemeyer  3 ,  Gunhild von Amsberg  3  4 ,  Anton N Yurchenko  2
Affiliations
  • 1. Institute of High Technologies and Advanced Materials, Far Eastern Federal University, Vladivostok 690922, Russian Federation.
  • 2. G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Vladivostok 690022, Russian Federation.
  • 3. Department of Oncology, Hematology and Bone Marrow Transplantation with Section Pneumology, Hubertus Wald Tumorzentrum - University Cancer Center Hamburg (UCCH), University Medical Center Hamburg-Eppendorf, 20251 Hamburg, Germany.
  • 4. Martini-Klinik, Prostate Cancer Center, University Hospital Hamburg-Eppendorf, 20251 Hamburg, Germany.
  • 5. Institute of Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Vladivostok 690022, Russian Federation.
PMID: 36413729 DOI: 10.1021/acs.jnatprod.2c00677
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.

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