Meroantarctines A-C, Meroterpenoids with Rearranged Skeletons from the Alga-Derived Fungus Penicillium antarcticum 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; Andrey V Gerasimenko; Anatoly A Udovenko; Markus Graefen; Carsten Bokemeyer; Gunhild von Amsberg; Anton N Yurchenko

doi:10.1021/acs.jnatprod.2c00677

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 Dec 23;85(12):2746-2752. doi: 10.1021/acs.jnatprod.2c00677. Epub 2022 Nov 22.

Authors

Elena V Leshchenko^{1

2}, Alexandr S Antonov², Sergey A Dyshlovoy^{1

3

4}, Dmitrii V Berdyshev², Jessica Hauschild^{3

4}, Olesya I Zhuravleva^{1

2}, Gleb V Borkunov¹, Alexander S Menshov², Natalya N Kirichuk², Roman S Popov², Andrey V Gerasimenko⁵, Anatoly A Udovenko⁵, Markus Graefen⁴, Carsten Bokemeyer³, Gunhild von Amsberg^{3

4}, Anton N Yurchenko²

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

ATP Binding Cassette Transporter, Subfamily B
Fungi*
Molecular Structure
Penicillium* / chemistry
Terpenes / chemistry
X-Ray Diffraction

Substances

ATP Binding Cassette Transporter, Subfamily B
Terpenes

Supplementary concepts

Penicillium antarcticum