Biologically Active Metabolites from the Marine Sediment-Derived Fungus <em>Aspergillus flocculosus</em>

Four new compounds were isolated from the Vietnamese marine sediment-derived fungus <i>Aspergillus flocculosus</i>, one aspyrone-related polyketide aspilactonol G (<b>2</b>), one meroterpenoid 12-epi-aspertetranone D (<b>4</b>), two drimane derivatives (<b>7...

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Main Authors: Anton N. Yurchenko, Phan Thi Hoai Trinh, Elena V. Girich (Ivanets), Olga F. Smetanina, Anton B. Rasin, Roman S. Popov, Sergey A. Dyshlovoy, Gunhild von Amsberg, Ekaterina S. Menchinskaya, Tran Thi Thanh Van, Shamil Sh. Afiyatullov
Format: Article
Language:English
Published: MDPI AG 2019-10-01
Series:Marine Drugs
Subjects:
Online Access:https://www.mdpi.com/1660-3397/17/10/579
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author Anton N. Yurchenko
Phan Thi Hoai Trinh
Elena V. Girich (Ivanets)
Olga F. Smetanina
Anton B. Rasin
Roman S. Popov
Sergey A. Dyshlovoy
Gunhild von Amsberg
Ekaterina S. Menchinskaya
Tran Thi Thanh Van
Shamil Sh. Afiyatullov
author_facet Anton N. Yurchenko
Phan Thi Hoai Trinh
Elena V. Girich (Ivanets)
Olga F. Smetanina
Anton B. Rasin
Roman S. Popov
Sergey A. Dyshlovoy
Gunhild von Amsberg
Ekaterina S. Menchinskaya
Tran Thi Thanh Van
Shamil Sh. Afiyatullov
author_sort Anton N. Yurchenko
collection DOAJ
description Four new compounds were isolated from the Vietnamese marine sediment-derived fungus <i>Aspergillus flocculosus</i>, one aspyrone-related polyketide aspilactonol G (<b>2</b>), one meroterpenoid 12-epi-aspertetranone D (<b>4</b>), two drimane derivatives (<b>7</b>,<b>9</b>), together with five known metabolites (<b>1</b>,<b>3</b>,<b>5</b>,<b>6</b>,<b>8</b>,<b>10</b>). The structures of compounds <b>1</b>–<b>10</b> were established by NMR and MS techniques. The absolute stereoconfigurations of compounds <b>1</b> and <b>2</b> were determined by a modified Mosher’s method. The absolute configurations of compounds <b>4</b> and <b>7</b> were established by a combination of analysis of ROESY data and coupling constants as well as biogenetic considerations. Compounds <b>7</b> and <b>8</b> exhibited cytotoxic activity toward human prostate cancer 22Rv1, human breast cancer MCF-7, and murine neuroblastoma Neuro-2a cells.
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spelling doaj.art-482ade90ca1347d385fcee91284f13202022-12-22T04:21:16ZengMDPI AGMarine Drugs1660-33972019-10-01171057910.3390/md17100579md17100579Biologically Active Metabolites from the Marine Sediment-Derived Fungus <em>Aspergillus flocculosus</em>Anton N. Yurchenko0Phan Thi Hoai Trinh1Elena V. Girich (Ivanets)2Olga F. Smetanina3Anton B. Rasin4Roman S. Popov5Sergey A. Dyshlovoy6Gunhild von Amsberg7Ekaterina S. Menchinskaya8Tran Thi Thanh Van9Shamil Sh. Afiyatullov10G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, RussiaDepartment of Marine Biotechnology, Nhatrang Institute of Technology Research and Application, Vietnam Academy of Science and Technology, 650000 Nha Trang, VietnamG.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, RussiaDepartment of Marine Biotechnology, Nhatrang Institute of Technology Research and Application, Vietnam Academy of Science and Technology, 650000 Nha Trang, VietnamG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, RussiaFour new compounds were isolated from the Vietnamese marine sediment-derived fungus <i>Aspergillus flocculosus</i>, one aspyrone-related polyketide aspilactonol G (<b>2</b>), one meroterpenoid 12-epi-aspertetranone D (<b>4</b>), two drimane derivatives (<b>7</b>,<b>9</b>), together with five known metabolites (<b>1</b>,<b>3</b>,<b>5</b>,<b>6</b>,<b>8</b>,<b>10</b>). The structures of compounds <b>1</b>–<b>10</b> were established by NMR and MS techniques. The absolute stereoconfigurations of compounds <b>1</b> and <b>2</b> were determined by a modified Mosher’s method. The absolute configurations of compounds <b>4</b> and <b>7</b> were established by a combination of analysis of ROESY data and coupling constants as well as biogenetic considerations. Compounds <b>7</b> and <b>8</b> exhibited cytotoxic activity toward human prostate cancer 22Rv1, human breast cancer MCF-7, and murine neuroblastoma Neuro-2a cells.https://www.mdpi.com/1660-3397/17/10/579marine-derived fungisecondary metabolitespolyketidesdrimanesmeroterpenoidscytotoxicity
spellingShingle Anton N. Yurchenko
Phan Thi Hoai Trinh
Elena V. Girich (Ivanets)
Olga F. Smetanina
Anton B. Rasin
Roman S. Popov
Sergey A. Dyshlovoy
Gunhild von Amsberg
Ekaterina S. Menchinskaya
Tran Thi Thanh Van
Shamil Sh. Afiyatullov
Biologically Active Metabolites from the Marine Sediment-Derived Fungus <em>Aspergillus flocculosus</em>
Marine Drugs
marine-derived fungi
secondary metabolites
polyketides
drimanes
meroterpenoids
cytotoxicity
title Biologically Active Metabolites from the Marine Sediment-Derived Fungus <em>Aspergillus flocculosus</em>
title_full Biologically Active Metabolites from the Marine Sediment-Derived Fungus <em>Aspergillus flocculosus</em>
title_fullStr Biologically Active Metabolites from the Marine Sediment-Derived Fungus <em>Aspergillus flocculosus</em>
title_full_unstemmed Biologically Active Metabolites from the Marine Sediment-Derived Fungus <em>Aspergillus flocculosus</em>
title_short Biologically Active Metabolites from the Marine Sediment-Derived Fungus <em>Aspergillus flocculosus</em>
title_sort biologically active metabolites from the marine sediment derived fungus em aspergillus flocculosus em
topic marine-derived fungi
secondary metabolites
polyketides
drimanes
meroterpenoids
cytotoxicity
url https://www.mdpi.com/1660-3397/17/10/579
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