Diverse polyketides from the marine endophytic Alternaria sp. LV52: Structure determination and cytotoxic activities

Manar M. Mahmoud; Ahmed S. Abdel-Razek; Hesham S.M. Soliman; Larissa V. Ponomareva; Jon S. Thorson; Khaled A. Shaaban; Mohamed Shaaban

doi:10.1016/j.btre.2021.e00628

Diverse polyketides from the marine endophytic Alternaria sp. LV52: Structure determination and cytotoxic activities

Manar M. Mahmoud, Ahmed S. Abdel-Razek, Hesham S.M. Soliman, Larissa V. Ponomareva, Jon S. Thorson, Khaled A. Shaaban, Mohamed Shaaban

Research output: Contribution to journal › Article › peer-review

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Abstract

We report the isolation and characterization of five polyketides [alternariol (1), alternariol-9-methyl ether (2), altertoxin I (3), altertoxin II (4) and tenuazonic acid (5)] from the marine endophytic Alternaria sp. LV52 derived from Cystoseira tamariscifolia, collected from the Red Sea at Nabq-Bay, Egypt. The chemical structures of compounds 1–5 were identified by extensive 1D, 2D NMR, and HR mass measurements. Isolation and phenotypic and genotypic characterization of the producing fungus is reported. The antimicrobial activity of the produced extract and derived compounds was examined against a panel of test organisms. In addition, an in vitro cytotoxic activity of 1–5 was performed against diverse cancer cell lines: HEPG2, HELA, A549 and PC3, revealing that compounds 2 and 4 are potentially cytotoxic against A549 and PC3 with EC₅₀ of 0.73 µg/ml (2.69 µM) and 0.17 µg/ml (0.64 µM) for 2, and 0.40 µg/ml (1.15 µM) and 0.12 µg/ml (0.33 µM) for 4, respectively.

Original language	English
Article number	e00628
Journal	Biotechnology Reports
Volume	33
DOIs	https://doi.org/10.1016/j.btre.2021.e00628
State	Published - Mar 2022

Bibliographical note

Funding Information:
The authors are thankful to the NMR and MS Departments in Bielefeld University for the spectral measurements. This research work has been financed by the German Academic Exchange Service (DAAD) in the frame of the Research Training Network “Novel Cytotoxic Drugs from Extremophilic Actinomycetes” (Project ID 57166072 ). This work was also supported by National Institutes of Health grant R01 GM115261 (JST), the Center of Biomedical Research Excellence (COBRE) in Pharmaceutical Research and Innovation ( CPRI , NIH P20 GM130456 ), the University of Kentucky College of Pharmacy and the National Center for Advancing Translational Sciences ( UL1TR000117 and UL1TR001998 ).

Publisher Copyright:
© 2021 The Authors

Keywords

Alternaria sp.
Cytotoxicity
Marine endophyte
Polyketides
Taxonomy

ASJC Scopus subject areas

Biotechnology
Applied Microbiology and Biotechnology

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.btre.2021.e00628

Cite this

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title = "Diverse polyketides from the marine endophytic Alternaria sp. LV52: Structure determination and cytotoxic activities",

abstract = "We report the isolation and characterization of five polyketides [alternariol (1), alternariol-9-methyl ether (2), altertoxin I (3), altertoxin II (4) and tenuazonic acid (5)] from the marine endophytic Alternaria sp. LV52 derived from Cystoseira tamariscifolia, collected from the Red Sea at Nabq-Bay, Egypt. The chemical structures of compounds 1–5 were identified by extensive 1D, 2D NMR, and HR mass measurements. Isolation and phenotypic and genotypic characterization of the producing fungus is reported. The antimicrobial activity of the produced extract and derived compounds was examined against a panel of test organisms. In addition, an in vitro cytotoxic activity of 1–5 was performed against diverse cancer cell lines: HEPG2, HELA, A549 and PC3, revealing that compounds 2 and 4 are potentially cytotoxic against A549 and PC3 with EC50 of 0.73 µg/ml (2.69 µM) and 0.17 µg/ml (0.64 µM) for 2, and 0.40 µg/ml (1.15 µM) and 0.12 µg/ml (0.33 µM) for 4, respectively.",

keywords = "Alternaria sp., Cytotoxicity, Marine endophyte, Polyketides, Taxonomy",

author = "Mahmoud, {Manar M.} and Abdel-Razek, {Ahmed S.} and Soliman, {Hesham S.M.} and Ponomareva, {Larissa V.} and Thorson, {Jon S.} and Shaaban, {Khaled A.} and Mohamed Shaaban",

note = "Funding Information: The authors are thankful to the NMR and MS Departments in Bielefeld University for the spectral measurements. This research work has been financed by the German Academic Exchange Service (DAAD) in the frame of the Research Training Network “Novel Cytotoxic Drugs from Extremophilic Actinomycetes” (Project ID 57166072 ). This work was also supported by National Institutes of Health grant R01 GM115261 (JST), the Center of Biomedical Research Excellence (COBRE) in Pharmaceutical Research and Innovation ( CPRI , NIH P20 GM130456 ), the University of Kentucky College of Pharmacy and the National Center for Advancing Translational Sciences ( UL1TR000117 and UL1TR001998 ). Publisher Copyright: {\textcopyright} 2021 The Authors",

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doi = "10.1016/j.btre.2021.e00628",

language = "English",

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T1 - Diverse polyketides from the marine endophytic Alternaria sp. LV52

T2 - Structure determination and cytotoxic activities

AU - Mahmoud, Manar M.

AU - Abdel-Razek, Ahmed S.

AU - Soliman, Hesham S.M.

AU - Ponomareva, Larissa V.

AU - Thorson, Jon S.

AU - Shaaban, Khaled A.

AU - Shaaban, Mohamed

N1 - Funding Information: The authors are thankful to the NMR and MS Departments in Bielefeld University for the spectral measurements. This research work has been financed by the German Academic Exchange Service (DAAD) in the frame of the Research Training Network “Novel Cytotoxic Drugs from Extremophilic Actinomycetes” (Project ID 57166072 ). This work was also supported by National Institutes of Health grant R01 GM115261 (JST), the Center of Biomedical Research Excellence (COBRE) in Pharmaceutical Research and Innovation ( CPRI , NIH P20 GM130456 ), the University of Kentucky College of Pharmacy and the National Center for Advancing Translational Sciences ( UL1TR000117 and UL1TR001998 ). Publisher Copyright: © 2021 The Authors

PY - 2022/3

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N2 - We report the isolation and characterization of five polyketides [alternariol (1), alternariol-9-methyl ether (2), altertoxin I (3), altertoxin II (4) and tenuazonic acid (5)] from the marine endophytic Alternaria sp. LV52 derived from Cystoseira tamariscifolia, collected from the Red Sea at Nabq-Bay, Egypt. The chemical structures of compounds 1–5 were identified by extensive 1D, 2D NMR, and HR mass measurements. Isolation and phenotypic and genotypic characterization of the producing fungus is reported. The antimicrobial activity of the produced extract and derived compounds was examined against a panel of test organisms. In addition, an in vitro cytotoxic activity of 1–5 was performed against diverse cancer cell lines: HEPG2, HELA, A549 and PC3, revealing that compounds 2 and 4 are potentially cytotoxic against A549 and PC3 with EC50 of 0.73 µg/ml (2.69 µM) and 0.17 µg/ml (0.64 µM) for 2, and 0.40 µg/ml (1.15 µM) and 0.12 µg/ml (0.33 µM) for 4, respectively.

AB - We report the isolation and characterization of five polyketides [alternariol (1), alternariol-9-methyl ether (2), altertoxin I (3), altertoxin II (4) and tenuazonic acid (5)] from the marine endophytic Alternaria sp. LV52 derived from Cystoseira tamariscifolia, collected from the Red Sea at Nabq-Bay, Egypt. The chemical structures of compounds 1–5 were identified by extensive 1D, 2D NMR, and HR mass measurements. Isolation and phenotypic and genotypic characterization of the producing fungus is reported. The antimicrobial activity of the produced extract and derived compounds was examined against a panel of test organisms. In addition, an in vitro cytotoxic activity of 1–5 was performed against diverse cancer cell lines: HEPG2, HELA, A549 and PC3, revealing that compounds 2 and 4 are potentially cytotoxic against A549 and PC3 with EC50 of 0.73 µg/ml (2.69 µM) and 0.17 µg/ml (0.64 µM) for 2, and 0.40 µg/ml (1.15 µM) and 0.12 µg/ml (0.33 µM) for 4, respectively.

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KW - Polyketides

KW - Taxonomy

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ER -

Diverse polyketides from the marine endophytic Alternaria sp. LV52: Structure determination and cytotoxic activities

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

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