Pretrichodermamides D-F from a Marine Algicolous Fungus Penicillium sp. KMM 4672

Anton N Yurchenko; Olga F Smetanina; Elena V Ivanets; Anatoly I Kalinovsky; Yuliya V Khudyakova; Natalya N Kirichuk; Roman S Popov; Carsten Bokemeyer; Gunhild von Amsberg; Ekaterina A Chingizova; Shamil Sh Afiyatullov; Sergey A Dyshlovoy

doi:10.3390/md14070122

Pretrichodermamides D-F from a Marine Algicolous Fungus Penicillium sp. KMM 4672

Mar Drugs. 2016 Jun 27;14(7):122. doi: 10.3390/md14070122.

Affiliations

¹ G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, Russia. [email protected].
² G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, Russia. [email protected].
³ School of Natural Science, Far Eastern Federal University, Sukhanova St., 8, Vladivostok 690000, Russia. [email protected].
⁴ G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, Russia. [email protected].
⁵ G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, Russia. [email protected].
⁶ G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, Russia. [email protected].
⁷ G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, Russia. [email protected].
⁸ Laboratory of Experimantal Oncology, Department of Oncology, Hematology and Bone Marrow Transplantation with Section Pneumology, Hubertus Wald-Tumorzentrum, University Medical Center Hamburg-Eppendorf, Hamburg 20246, Germany. [email protected].
⁹ Laboratory of Experimantal Oncology, Department of Oncology, Hematology and Bone Marrow Transplantation with Section Pneumology, Hubertus Wald-Tumorzentrum, University Medical Center Hamburg-Eppendorf, Hamburg 20246, Germany. [email protected].
¹⁰ G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, Russia. [email protected].
¹¹ G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, Russia. [email protected].
¹² G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, Russia. [email protected].
¹³ School of Natural Science, Far Eastern Federal University, Sukhanova St., 8, Vladivostok 690000, Russia. [email protected].
¹⁴ Laboratory of Experimantal Oncology, Department of Oncology, Hematology and Bone Marrow Transplantation with Section Pneumology, Hubertus Wald-Tumorzentrum, University Medical Center Hamburg-Eppendorf, Hamburg 20246, Germany. [email protected].

Abstract

Three new epidithiodiketopiperazines pretrichodermamides D-F (1-3), together with the known N-methylpretrichodermamide B (4) and pretrichodermamide С (5), were isolated from the lipophilic extract of the marine algae-derived fungus Penicillium sp. KMM 4672. The structures of compounds 1-5 were determined based on spectroscopic methods. The absolute configuration of pretrichodermamide D (1) was established by a combination of modified Mosher's method, NOESY data, and biogenetic considerations. N-Methylpretrichodermamide B (5) showed strong cytotoxicity against 22Rv1 human prostate cancer cells resistant to androgen receptor targeted therapies.

Keywords: cytotoxicity; diketopiperazine; marine-derived fungus; oxazadecaline; secondary metabolites.

MeSH terms

Biological Products / chemistry*
Biological Products / pharmacology
Cell Line, Tumor
Diterpenes / chemistry*
Diterpenes / pharmacology
Drug Screening Assays, Antitumor
Fungi / chemistry*
Humans
Marine Biology / methods
Molecular Structure
Penicillium / chemistry*
Piperazines / chemistry*
Piperazines / pharmacology

Substances

Biological Products
Diterpenes
Piperazines
epidithiodiketopiperazine