New Meroterpenoid Derivatives from the Pomegranate-Derived Endophytic Fungus <i>Talaromyces purpureogenus</i>

In this study, we report the isolation of two new meroterpenoids, miniolutelide D (<b>1</b>) and miniolutelide E (13-<i>epi</i>-miniolutelide C) (<b>2</b>), along with two meroterpenoidal analogues (<b>3</b> and <b>4</b>) and two phenolic c...

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Main Authors: Alaa Anwar, Mohamed S. Elnaggar, Ahmed M. Elissawy, Nehal Ibrahim, Attila Mándi, Tibor Kurtán, Zhen Liu, Sherweit H. El-Ahmady, Rainer Kalscheuer
Format: Article
Language:English
Published: MDPI AG 2023-11-01
Series:Molecules
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Online Access:https://www.mdpi.com/1420-3049/28/22/7650
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author Alaa Anwar
Mohamed S. Elnaggar
Ahmed M. Elissawy
Nehal Ibrahim
Attila Mándi
Tibor Kurtán
Zhen Liu
Sherweit H. El-Ahmady
Rainer Kalscheuer
author_facet Alaa Anwar
Mohamed S. Elnaggar
Ahmed M. Elissawy
Nehal Ibrahim
Attila Mándi
Tibor Kurtán
Zhen Liu
Sherweit H. El-Ahmady
Rainer Kalscheuer
author_sort Alaa Anwar
collection DOAJ
description In this study, we report the isolation of two new meroterpenoids, miniolutelide D (<b>1</b>) and miniolutelide E (13-<i>epi</i>-miniolutelide C) (<b>2</b>), along with two meroterpenoidal analogues (<b>3</b> and <b>4</b>) and two phenolic compounds (<b>5</b> and <b>6</b>) from the endophytic fungus <i>Talaromyces purpureogenus</i> derived from <i>Punica granatum</i> fruits. Their structures were elucidated using extensive MS, 1D, and 2D NMR spectroscopic analyses as well as by comparing with data in the literature. The absolute configurations of <b>1</b> and <b>2</b> were determined using TDDFT-ECD calculations. Antimicrobial activity was evaluated. Compound <b>5</b> displayed significant activity against methicillin-resistant <i>Staphylococcus aureus</i> strain ATCC 700699 and moderate activity against <i>S. aureus</i> strain ATCC 29213.
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spelling doaj.art-9fe91847e96247a3b87f22cfd312daec2023-11-24T14:58:34ZengMDPI AGMolecules1420-30492023-11-012822765010.3390/molecules28227650New Meroterpenoid Derivatives from the Pomegranate-Derived Endophytic Fungus <i>Talaromyces purpureogenus</i>Alaa Anwar0Mohamed S. Elnaggar1Ahmed M. Elissawy2Nehal Ibrahim3Attila Mándi4Tibor Kurtán5Zhen Liu6Sherweit H. El-Ahmady7Rainer Kalscheuer8Department of Pharmacognosy, Faculty of Pharmacy, Ain-Shams University, Abbassia, Cairo 11566, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, Ain-Shams University, Abbassia, Cairo 11566, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, Ain-Shams University, Abbassia, Cairo 11566, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, Ain-Shams University, Abbassia, Cairo 11566, EgyptDepartment of Organic Chemistry, University of Debrecen, P.O. Box 400, 4002 Debrecen, HungaryDepartment of Organic Chemistry, University of Debrecen, P.O. Box 400, 4002 Debrecen, HungaryKey Laboratory of Study and Discovery of Small Targeted Molecules of Hunan Province, School of Medicine, Hunan Normal University, Changsha 410013, ChinaDepartment of Pharmacognosy, Faculty of Pharmacy, Ain-Shams University, Abbassia, Cairo 11566, EgyptInstitute of Pharmaceutical Biology and Biotechnology, Heinrich Heine University, Universitätsstrasse 1, 40225 Düsseldorf, GermanyIn this study, we report the isolation of two new meroterpenoids, miniolutelide D (<b>1</b>) and miniolutelide E (13-<i>epi</i>-miniolutelide C) (<b>2</b>), along with two meroterpenoidal analogues (<b>3</b> and <b>4</b>) and two phenolic compounds (<b>5</b> and <b>6</b>) from the endophytic fungus <i>Talaromyces purpureogenus</i> derived from <i>Punica granatum</i> fruits. Their structures were elucidated using extensive MS, 1D, and 2D NMR spectroscopic analyses as well as by comparing with data in the literature. The absolute configurations of <b>1</b> and <b>2</b> were determined using TDDFT-ECD calculations. Antimicrobial activity was evaluated. Compound <b>5</b> displayed significant activity against methicillin-resistant <i>Staphylococcus aureus</i> strain ATCC 700699 and moderate activity against <i>S. aureus</i> strain ATCC 29213.https://www.mdpi.com/1420-3049/28/22/7650<i>Talaromyces purpureogenus</i>endophytesmeroterpenoidsstructural elucidationabsolute configurationantimicrobial activity
spellingShingle Alaa Anwar
Mohamed S. Elnaggar
Ahmed M. Elissawy
Nehal Ibrahim
Attila Mándi
Tibor Kurtán
Zhen Liu
Sherweit H. El-Ahmady
Rainer Kalscheuer
New Meroterpenoid Derivatives from the Pomegranate-Derived Endophytic Fungus <i>Talaromyces purpureogenus</i>
Molecules
<i>Talaromyces purpureogenus</i>
endophytes
meroterpenoids
structural elucidation
absolute configuration
antimicrobial activity
title New Meroterpenoid Derivatives from the Pomegranate-Derived Endophytic Fungus <i>Talaromyces purpureogenus</i>
title_full New Meroterpenoid Derivatives from the Pomegranate-Derived Endophytic Fungus <i>Talaromyces purpureogenus</i>
title_fullStr New Meroterpenoid Derivatives from the Pomegranate-Derived Endophytic Fungus <i>Talaromyces purpureogenus</i>
title_full_unstemmed New Meroterpenoid Derivatives from the Pomegranate-Derived Endophytic Fungus <i>Talaromyces purpureogenus</i>
title_short New Meroterpenoid Derivatives from the Pomegranate-Derived Endophytic Fungus <i>Talaromyces purpureogenus</i>
title_sort new meroterpenoid derivatives from the pomegranate derived endophytic fungus i talaromyces purpureogenus i
topic <i>Talaromyces purpureogenus</i>
endophytes
meroterpenoids
structural elucidation
absolute configuration
antimicrobial activity
url https://www.mdpi.com/1420-3049/28/22/7650
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