Austalides V and W, new meroterpenoids from the fungus Aspergillus ustus and their antitumor activities

Tatiana V Antipova; Kirill V Zaitsev; Yuri F Oprunenko; Alexander Ya Zherebker; Gleb K Rystsov; Marina Y Zemskova; Valentina P Zhelifonova; Natalya E Ivanushkina; Anatoly G Kozlovsky

doi:10.1016/j.bmcl.2019.126708

Austalides V and W, new meroterpenoids from the fungus Aspergillus ustus and their antitumor activities

Bioorg Med Chem Lett. 2019 Nov 15;29(22):126708. doi: 10.1016/j.bmcl.2019.126708. Epub 2019 Oct 4.

Authors

Tatiana V Antipova¹, Kirill V Zaitsev², Yuri F Oprunenko³, Alexander Ya Zherebker⁴, Gleb K Rystsov⁵, Marina Y Zemskova⁵, Valentina P Zhelifonova⁶, Natalya E Ivanushkina⁶, Anatoly G Kozlovsky⁶

Affiliations

¹ G.K. Skryabin Institute of Biochemistry and Physiology of Microorganisms RAS, FSBIS FRC Pushchino Scientific Centre of Biological Research, Russian Academy of Sciences, Pushchino 142290, Russian Federation. Electronic address: tantipova@ibpm.pushchino.ru.
² Department of Chemistry, Moscow State University, Moscow 119991, Russian Federation. Electronic address: zaitsev@org.chem.msu.ru.
³ Department of Chemistry, Moscow State University, Moscow 119991, Russian Federation.
⁴ Skolkovo Institute of Science and Technology, Skolkovo 143025, Russian Federation.
⁵ G.K. Skryabin Institute of Biochemistry and Physiology of Microorganisms RAS, FSBIS FRC Pushchino Scientific Centre of Biological Research, Russian Academy of Sciences, Pushchino 142290, Russian Federation; Moscow State Regional University, Moscow 141014, Russian Federation.
⁶ G.K. Skryabin Institute of Biochemistry and Physiology of Microorganisms RAS, FSBIS FRC Pushchino Scientific Centre of Biological Research, Russian Academy of Sciences, Pushchino 142290, Russian Federation.

PMID: 31607610
DOI: 10.1016/j.bmcl.2019.126708

Abstract

Two new austalide meroterpenoids, named austalides V and W (1 and 2), were isolated from the fungus Aspergillus ustus VKM F-4692. Their structures were elucidated by extensive spectroscopic analysis and by comparison with related known compounds. The main structural feature of both compounds is a tetrahydrofuranyl ring (G), a structural fragment, first found in austalides. Austalides V (1) and W (2) were able to inhibit the propagation of prostate and bladder cancer cells; this biologic activity is possibly related to the inhibition of a number of key pathways regulating cell growth and migration.

Keywords: AKT-mTORC1 signaling pathway; Aspergillus ustus; Austalide; Fungus; Prostate and bladder cancer cells.

Publication types

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

MeSH terms

Antineoplastic Agents / chemistry
Antineoplastic Agents / isolation & purification
Antineoplastic Agents / pharmacology*
Aspergillus / chemistry*
Cell Line, Tumor
Cell Proliferation / drug effects
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Humans
Molecular Structure
Structure-Activity Relationship
Terpenes / chemistry
Terpenes / isolation & purification
Terpenes / pharmacology*

Substances

Antineoplastic Agents
Terpenes