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Mar. Drugs 2017, 15(2), 46; doi:10.3390/md15020046

Zosteropenillines: Polyketides from the Marine-Derived Fungus Penicillium thomii

1
Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, Russia
2
School of Natural Science, Far Eastern Federal University, 8 Sukhanova St., Vladivostok 690090, Russia
3
Institute of Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, Russia
4
Laboratory of Experimental Oncology, Department of Oncology, Hematology and Bone Marrow Transplantation with Section Pneumology, Hubertus Wald‐Tumorzentrum, University Medical Center, 20246 Hamburg, Germany
*
Authors to whom correspondence should be addressed.
Received: 28 December 2016 / Accepted: 13 February 2017 / Published: 17 February 2017
(This article belongs to the Special Issue Marine Fungal Natural Products)
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Abstract

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. View Full-Text
Keywords: marine fungi; Penicillium thomii; polyketide decalin derivative; X‐ray; ECD spectra marine fungi; Penicillium thomii; polyketide decalin derivative; X‐ray; ECD spectra
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Afiyatullov, S.S.; Leshchenko, E.V.; Berdyshev, D.V.; Sobolevskaya, M.P.; Antonov, A.S.; Denisenko, V.A.; Popov, R.S.; Pivkin, M.V.; Udovenko, A.A.; Pislyagin, E.A.; von Amsberg, G.; Dyshlovoy, S.A. Zosteropenillines: Polyketides from the Marine-Derived Fungus Penicillium thomii. Mar. Drugs 2017, 15, 46.

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