Piltunines A–F from the Marine-Derived Fungus <i>Penicillium piltunense</i> KMM 4668

Six new carotane sesquiterpenoids piltunines A&#8722;F (<b>1</b>&#8722;<b>6</b>) together with known compounds (<b>7</b>&#8722;<b>9</b>) were isolated from the marine-derived fungus <i>Penicillium piltunense</i> KMM 4668. Their...

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Main Authors: Shamil Sh. Afiyatullov, Olesya I. Zhuravleva, Alexandr S. Antonov, Elena V. Leshchenko, Mikhail V. Pivkin, Yuliya V. Khudyakova, Vladimir A. Denisenko, Evgeny A. Pislyagin, Natalya Yu. Kim, Dmitrii V. Berdyshev, Gunhild von Amsberg, Sergey A. Dyshlovoy
Format: Article
Language:English
Published: MDPI AG 2019-11-01
Series:Marine Drugs
Subjects:
Online Access:https://www.mdpi.com/1660-3397/17/11/647
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author Shamil Sh. Afiyatullov
Olesya I. Zhuravleva
Alexandr S. Antonov
Elena V. Leshchenko
Mikhail V. Pivkin
Yuliya V. Khudyakova
Vladimir A. Denisenko
Evgeny A. Pislyagin
Natalya Yu. Kim
Dmitrii V. Berdyshev
Gunhild von Amsberg
Sergey A. Dyshlovoy
author_facet Shamil Sh. Afiyatullov
Olesya I. Zhuravleva
Alexandr S. Antonov
Elena V. Leshchenko
Mikhail V. Pivkin
Yuliya V. Khudyakova
Vladimir A. Denisenko
Evgeny A. Pislyagin
Natalya Yu. Kim
Dmitrii V. Berdyshev
Gunhild von Amsberg
Sergey A. Dyshlovoy
author_sort Shamil Sh. Afiyatullov
collection DOAJ
description Six new carotane sesquiterpenoids piltunines A&#8722;F (<b>1</b>&#8722;<b>6</b>) together with known compounds (<b>7</b>&#8722;<b>9</b>) were isolated from the marine-derived fungus <i>Penicillium piltunense</i> KMM 4668. Their structures were established using spectroscopic methods. The absolute configurations of <b>1</b>&#8722;<b>7</b> were determined based on circular dichroism (CD) and nuclear Overhauser spectroscopy (NOESY) data as well as biogenetic considerations. The cytotoxic activity of some of the isolated compounds and their effects on regulation of reactive oxygen species (ROS) and nitric oxide (NO) production in lipopolysaccharide-stimulated macrophages were examined.
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spelling doaj.art-24d5c438906a4991a6da5ce04e03f7412022-12-22T02:20:48ZengMDPI AGMarine Drugs1660-33972019-11-01171164710.3390/md17110647md17110647Piltunines A–F from the Marine-Derived Fungus <i>Penicillium piltunense</i> KMM 4668Shamil Sh. Afiyatullov0Olesya I. Zhuravleva1Alexandr S. Antonov2Elena V. Leshchenko3Mikhail V. Pivkin4Yuliya V. Khudyakova5Vladimir A. Denisenko6Evgeny A. Pislyagin7Natalya Yu. Kim8Dmitrii V. Berdyshev9Gunhild von Amsberg10Sergey A. Dyshlovoy11G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, RussiaLaboratory of Experimental Oncology, Department of Oncology, Hematology and Bone Marrow Transplantation with Section Pneumology, Hubertus Wald-Tumorzentrum, University Medical Center Hamburg-Eppendorf, 20246 Hamburg, GermanyG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, RussiaSix new carotane sesquiterpenoids piltunines A&#8722;F (<b>1</b>&#8722;<b>6</b>) together with known compounds (<b>7</b>&#8722;<b>9</b>) were isolated from the marine-derived fungus <i>Penicillium piltunense</i> KMM 4668. Their structures were established using spectroscopic methods. The absolute configurations of <b>1</b>&#8722;<b>7</b> were determined based on circular dichroism (CD) and nuclear Overhauser spectroscopy (NOESY) data as well as biogenetic considerations. The cytotoxic activity of some of the isolated compounds and their effects on regulation of reactive oxygen species (ROS) and nitric oxide (NO) production in lipopolysaccharide-stimulated macrophages were examined.https://www.mdpi.com/1660-3397/17/11/647<i>penicillium piltunense</i>secondary metabolitescarotane sesquiterpenoidscytotoxic activity
spellingShingle Shamil Sh. Afiyatullov
Olesya I. Zhuravleva
Alexandr S. Antonov
Elena V. Leshchenko
Mikhail V. Pivkin
Yuliya V. Khudyakova
Vladimir A. Denisenko
Evgeny A. Pislyagin
Natalya Yu. Kim
Dmitrii V. Berdyshev
Gunhild von Amsberg
Sergey A. Dyshlovoy
Piltunines A–F from the Marine-Derived Fungus <i>Penicillium piltunense</i> KMM 4668
Marine Drugs
<i>penicillium piltunense</i>
secondary metabolites
carotane sesquiterpenoids
cytotoxic activity
title Piltunines A–F from the Marine-Derived Fungus <i>Penicillium piltunense</i> KMM 4668
title_full Piltunines A–F from the Marine-Derived Fungus <i>Penicillium piltunense</i> KMM 4668
title_fullStr Piltunines A–F from the Marine-Derived Fungus <i>Penicillium piltunense</i> KMM 4668
title_full_unstemmed Piltunines A–F from the Marine-Derived Fungus <i>Penicillium piltunense</i> KMM 4668
title_short Piltunines A–F from the Marine-Derived Fungus <i>Penicillium piltunense</i> KMM 4668
title_sort piltunines a f from the marine derived fungus i penicillium piltunense i kmm 4668
topic <i>penicillium piltunense</i>
secondary metabolites
carotane sesquiterpenoids
cytotoxic activity
url https://www.mdpi.com/1660-3397/17/11/647
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