Zosteropenillines: Polyketides from the MarineDerived Fungus Penicillium thomii

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...

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Main Authors:	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
Format:	Article
Language:	English
Published:	MDPI AG 2017-02-01
Series:	Marine Drugs
Subjects:	marine fungi Penicillium thomii polyketide decalin derivative X‐ray ECD spectra
Online Access:	http://www.mdpi.com/1660-3397/15/2/46

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spelling	doaj-627c0b5bc5ba453faea5ffcc82bd7c802020-11-24T23:45:21ZengMDPI AGMarine Drugs1660-33972017-02-011524610.3390/md15020046md15020046Zosteropenillines: Polyketides from the MarineDerived Fungus Penicillium thomiiShamil Sh. Afiyatullov0Elena V. Leshchenko1Dmitrii V. Berdyshev2Maria P. Sobolevskaya3Alexandr S. Antonov4Vladimir A. Denisenko5Roman S. Popov6Mikhail V. Pivkin7Anatoly A. Udovenko8Evgeny A. Pislyagin9Gunhild von Amsberg10Sergey A. Dyshlovoy11Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, RussiaElyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, RussiaElyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, RussiaElyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, RussiaElyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, RussiaElyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, RussiaElyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, RussiaElyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, RussiaInstitute of Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, RussiaElyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, RussiaLaboratory of Experimental Oncology, Department of Oncology, Hematology and Bone Marrow Transplantation with Section Pneumology, Hubertus Wald‐Tumorzentrum, University Medical Center, 20246 Hamburg, GermanyElyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100‐letiya Vladivostoka, Vladivostok 690022, RussiaTwelve 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.http://www.mdpi.com/1660-3397/15/2/46marine fungi Penicillium thomii polyketide decalin derivative X‐ray ECD spectra
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	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
spellingShingle	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 Zosteropenillines: Polyketides from the MarineDerived Fungus Penicillium thomii Marine Drugs marine fungi Penicillium thomii polyketide decalin derivative X‐ray ECD spectra
author_facet	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
author_sort	Shamil Sh. Afiyatullov
title	Zosteropenillines: Polyketides from the MarineDerived Fungus Penicillium thomii
title_short	Zosteropenillines: Polyketides from the MarineDerived Fungus Penicillium thomii
title_full	Zosteropenillines: Polyketides from the MarineDerived Fungus Penicillium thomii
title_fullStr	Zosteropenillines: Polyketides from the MarineDerived Fungus Penicillium thomii
title_full_unstemmed	Zosteropenillines: Polyketides from the MarineDerived Fungus Penicillium thomii
title_sort	zosteropenillines: polyketides from the marinederived fungus penicillium thomii
publisher	MDPI AG
series	Marine Drugs
issn	1660-3397
publishDate	2017-02-01
description	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.
topic	marine fungi Penicillium thomii polyketide decalin derivative X‐ray ECD spectra
url	http://www.mdpi.com/1660-3397/15/2/46
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Zosteropenillines: Polyketides from the MarineDerived Fungus Penicillium thomii

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