Citriperazines A-D produced by a marine algae-derived fungus Penicillium sp. KMM 4672

Anton Nikolaevich Yurchenko; Dmitry V Berdyshev; Olga F Smetanina; Elena V Ivanets; Olesya I Zhuravleva; Anton B Rasin; Yuliya V Khudyakova; Roman S Popov; Sergey A Dyshlovoy; Gunhild von Amsberg; Shamil Sh Afiyatullov

doi:10.1080/14786419.2018.1552696

Citriperazines A-D produced by a marine algae-derived fungus Penicillium sp. KMM 4672

Nat Prod Res. 2020 Apr;34(8):1118-1123. doi: 10.1080/14786419.2018.1552696. Epub 2019 Jan 19.

Affiliations

¹ G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Vladivostok, Russia.
² Laboratory of Biologically Active Compounds, Far Eastern Federal University, Vladivostok, Russia.
³ Laboratory of Experimental Oncology, Department of Oncology, Haematology and Bone Marrow Transplantation, Section Pneumology, Hubertus Wald-Tumorzentrum, University Medical Center Hamburg-Eppendorf, Hamburg, Germany.

PMID: 30663353
DOI: 10.1080/14786419.2018.1552696

Abstract

Four new diketopiperazine alkaloids, citriperazines A-D were isolated from algae-derived Penicillium sp. KMM 4672. The structures of compounds 1-4 were determined using spectroscopic methods. The absolute configurations of compounds 1 and 4 were established by comparison of calculated and experimental ECD spectra. The cytotoxicity of compounds 1-4 against several human prostate cell lines was evaluated.

Keywords: secondary metabolites; ECD; Penicillium sp.; TDDFT; diketopiperazines.

MeSH terms

Alkaloids / chemistry
Alkaloids / isolation & purification
Cell Line, Tumor
Cytotoxins / chemistry
Cytotoxins / isolation & purification
Cytotoxins / pharmacology
Diketopiperazines / chemistry
Diketopiperazines / isolation & purification*
Humans
Molecular Conformation
Molecular Structure
Penicillium / chemistry*
Spectrum Analysis

Substances

Alkaloids
Cytotoxins
Diketopiperazines