Zosteropenillines: Polyketides from the MarineDerived Fungus Penicillium thomii
Shamil Sh. Afiyatullov,
Elena V. Leshchenko,
Dmitrii V. Berdyshev,
Maria P. Sobolevskaya,
Alexandr S. Antonov,
Vladimir A. Denisenko,
Roman S. Popov,
Mikhail V. Pivkin,
Anatoly A. Udovenko,
Evgeny A. Pislyagin,
Gunhild von Amsberg,
Sergey A. Dyshlovoy
Affiliations
Shamil Sh. Afiyatullov
Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, Russia
Elena V. Leshchenko
Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, Russia
Dmitrii V. Berdyshev
Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, Russia
Maria P. Sobolevskaya
Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, Russia
Alexandr S. Antonov
Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, Russia
Vladimir A. Denisenko
Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, Russia
Roman S. Popov
Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, Russia
Mikhail V. Pivkin
Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, Russia
Anatoly A. Udovenko
Institute of Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, Russia
Evgeny A. Pislyagin
Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, Russia
Gunhild von Amsberg
Laboratory of Experimental Oncology, Department of Oncology, Hematology and Bone Marrow Transplantation with Section Pneumology, Hubertus Wald‐Tumorzentrum, University Medical Center, 20246 Hamburg, Germany
Sergey A. Dyshlovoy
Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, Russia
Twelve new polyketides, zosteropenillines A–L (1–12), together with known polyketide pallidopenilline A (13), were isolated from the ethylacetate extract of the fungus Penicillium thomii associated with the seagrass Zostera marina. Their structures were established based on spectroscopic methods. The absolute configuration of zosteropenilline A (1) as 4R, 5S, 8S, 9R, 10R, and 13S was determined by a combination of the modified Mosher’s method, X‐ray analysis, and NOESY data. Absolute configurations of zosteropenillines B–D (2–4) were determined by timedependent density functional theory (TD‐DFT) calculations of ECD spectra. The effect of compounds 1–3, 7, 8, 10, and 11 on the viability of human drug‐resistant prostate cancer cells PC3 as well as on autophagy in these cancer cells and inhibitory effects of compounds 1, 2, and 8–10 on NO production in LPS‐induced RAW 264.7 murine macrophages were examined.
