RF-3192C and other polyketides from the marine endophytic Aspergillus niger ASSB4: structure assignment and bioactivity investigation

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

doi:10.1007/s00044-020-02658-6

RF-3192C and other polyketides from the marine endophytic Aspergillus niger ASSB4: structure assignment and bioactivity investigation

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

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

6 Scopus citations

Abstract

Chemical investigation of the methanolic extract of endophytic Aspergillus niger SB4, isolated from the marine alga Laurencia obtuse, afforded the pentacyclic polyketide, RF-3192C (1), the dimeric coumarin orlandin (2), fonsecin B (3), TMC-256A1 (4), cyclo-(Leu-Ala) (5), and cerebroside A (6).The chemical structure of RF-3192C (1) is assigned herein for the first time using 1D/2D NMR and HRESI-MS. Additionally, the revision of the NMR assignments of orlandin (2) was reported herein as well. Investigation of the antimicrobial activities of isolated compounds revealed the high activity of RF-3192C (1) against Pseudomonas aeruginosa and Bacillus subtilis, and moderate activity against yeast. Moreover, an in vitro cytotoxic activity against liver (HEPG2), cervical (HELA), lung (A549), prostate (PC3), and breast (MCF7) cancer cell lines of the isolated compounds was evaluated. The isolation and taxonomical characterization of the producing fungus was reported as well. [Figure not available: see fulltext.]

Original language	English
Pages (from-to)	647-654
Number of pages	8
Journal	Medicinal Chemistry Research
Volume	30
Issue number	3
DOIs	https://doi.org/10.1007/s00044-020-02658-6
State	Published - Mar 2021

Bibliographical note

Funding Information:
The authors are thankful to the NMR and MS Departments in Bielefeld University for the spectral measurements. We thank Carmela Michalek for her assistance in biological activity testing; Marco Wißbrock and Anke Nieß for technical assistance. This research work has been financed by the German Academic Exchange Service (DAAD) with funds from the German Federal Foreign Office 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, the University of Kentucky Markey Cancer Center and the National Center for Advancing Translational Sciences (UL1TR000117 and UL1TR001998).

Publisher Copyright:
© 2020, Springer Science+Business Media, LLC, part of Springer Nature.

Keywords

Aspergillus niger
Biological activities
Marine-Endophyte
Polyketides
RF-3192C

ASJC Scopus subject areas

Pharmacology, Toxicology and Pharmaceutics (all)
Organic Chemistry

UN SDGs

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

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10.1007/s00044-020-02658-6

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@article{47232101ca5d4ba8bb7df946f6f54eda,

title = "RF-3192C and other polyketides from the marine endophytic Aspergillus niger ASSB4: structure assignment and bioactivity investigation",

abstract = "Chemical investigation of the methanolic extract of endophytic Aspergillus niger SB4, isolated from the marine alga Laurencia obtuse, afforded the pentacyclic polyketide, RF-3192C (1), the dimeric coumarin orlandin (2), fonsecin B (3), TMC-256A1 (4), cyclo-(Leu-Ala) (5), and cerebroside A (6).The chemical structure of RF-3192C (1) is assigned herein for the first time using 1D/2D NMR and HRESI-MS. Additionally, the revision of the NMR assignments of orlandin (2) was reported herein as well. Investigation of the antimicrobial activities of isolated compounds revealed the high activity of RF-3192C (1) against Pseudomonas aeruginosa and Bacillus subtilis, and moderate activity against yeast. Moreover, an in vitro cytotoxic activity against liver (HEPG2), cervical (HELA), lung (A549), prostate (PC3), and breast (MCF7) cancer cell lines of the isolated compounds was evaluated. The isolation and taxonomical characterization of the producing fungus was reported as well. [Figure not available: see fulltext.]",

keywords = "Aspergillus niger, Biological activities, Marine-Endophyte, Polyketides, RF-3192C",

author = "Mahmoud, {Manar M.} and Abdel-Razek, {Ahmed S.} and Abdelaaty Hamed 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. We thank Carmela Michalek for her assistance in biological activity testing; Marco Wi{\ss}brock and Anke Nie{\ss} for technical assistance. This research work has been financed by the German Academic Exchange Service (DAAD) with funds from the German Federal Foreign Office 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, the University of Kentucky Markey Cancer Center and the National Center for Advancing Translational Sciences (UL1TR000117 and UL1TR001998). Publisher Copyright: {\textcopyright} 2020, Springer Science+Business Media, LLC, part of Springer Nature.",

year = "2021",

month = mar,

doi = "10.1007/s00044-020-02658-6",

language = "English",

volume = "30",

pages = "647--654",

number = "3",

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T2 - structure assignment and bioactivity investigation

AU - Mahmoud, Manar M.

AU - Abdel-Razek, Ahmed S.

AU - Hamed, Abdelaaty

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. We thank Carmela Michalek for her assistance in biological activity testing; Marco Wißbrock and Anke Nieß for technical assistance. This research work has been financed by the German Academic Exchange Service (DAAD) with funds from the German Federal Foreign Office 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, the University of Kentucky Markey Cancer Center and the National Center for Advancing Translational Sciences (UL1TR000117 and UL1TR001998). Publisher Copyright: © 2020, Springer Science+Business Media, LLC, part of Springer Nature.

PY - 2021/3

Y1 - 2021/3

N2 - Chemical investigation of the methanolic extract of endophytic Aspergillus niger SB4, isolated from the marine alga Laurencia obtuse, afforded the pentacyclic polyketide, RF-3192C (1), the dimeric coumarin orlandin (2), fonsecin B (3), TMC-256A1 (4), cyclo-(Leu-Ala) (5), and cerebroside A (6).The chemical structure of RF-3192C (1) is assigned herein for the first time using 1D/2D NMR and HRESI-MS. Additionally, the revision of the NMR assignments of orlandin (2) was reported herein as well. Investigation of the antimicrobial activities of isolated compounds revealed the high activity of RF-3192C (1) against Pseudomonas aeruginosa and Bacillus subtilis, and moderate activity against yeast. Moreover, an in vitro cytotoxic activity against liver (HEPG2), cervical (HELA), lung (A549), prostate (PC3), and breast (MCF7) cancer cell lines of the isolated compounds was evaluated. The isolation and taxonomical characterization of the producing fungus was reported as well. [Figure not available: see fulltext.]

AB - Chemical investigation of the methanolic extract of endophytic Aspergillus niger SB4, isolated from the marine alga Laurencia obtuse, afforded the pentacyclic polyketide, RF-3192C (1), the dimeric coumarin orlandin (2), fonsecin B (3), TMC-256A1 (4), cyclo-(Leu-Ala) (5), and cerebroside A (6).The chemical structure of RF-3192C (1) is assigned herein for the first time using 1D/2D NMR and HRESI-MS. Additionally, the revision of the NMR assignments of orlandin (2) was reported herein as well. Investigation of the antimicrobial activities of isolated compounds revealed the high activity of RF-3192C (1) against Pseudomonas aeruginosa and Bacillus subtilis, and moderate activity against yeast. Moreover, an in vitro cytotoxic activity against liver (HEPG2), cervical (HELA), lung (A549), prostate (PC3), and breast (MCF7) cancer cell lines of the isolated compounds was evaluated. The isolation and taxonomical characterization of the producing fungus was reported as well. [Figure not available: see fulltext.]

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KW - Biological activities

KW - Marine-Endophyte

KW - Polyketides

KW - RF-3192C

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AN - SCOPUS:85097014728

SN - 1054-2523

VL - 30

SP - 647

EP - 654

JO - Medicinal Chemistry Research

JF - Medicinal Chemistry Research

IS - 3

ER -

RF-3192C and other polyketides from the marine endophytic Aspergillus niger ASSB4: structure assignment and bioactivity investigation

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

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