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

Producción científica: Article › revisión exhaustiva

11 Citas (Scopus)

Resumen

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.]

Idioma original	English
Páginas (desde-hasta)	647-654
Número de páginas	8
Publicación	Medicinal Chemistry Research
Volumen	30
N.º	3
DOI	https://doi.org/10.1007/s00044-020-02658-6
Estado	Published - mar 2021

Nota bibliográfica

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

Financiación

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).

Financiadores	Número del financiador
Center of Biomedical Research Excellence
German Federal Foreign Office	57166072
University of Kentucky College of Pharmacy
National Institutes of Health (NIH)	P20 GM130456, R01 GM115261
National Center for Advancing Translational Sciences (NCATS)	UL1TR001998, UL1TR000117
University of Kentucky Markey Comprehensive Cancer Center
Deutscher Akademischer Austauschdienst France
Japan Science and Technology Agency

ODS de las Naciones Unidas

Este resultado contribuye a los siguientes Objetivos de Desarrollo Sostenible

Good health and well being
Life below water

ASJC Scopus subject areas

General Pharmacology, Toxicology and Pharmaceutics
Organic Chemistry

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10.1007/s00044-020-02658-6

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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.]",

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AU - Hamed, Abdelaaty

AU - Soliman, Hesham S.M.

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

Resumen

Nota bibliográfica

Financiación

ODS de las Naciones Unidas

ASJC Scopus subject areas

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