New Meroterpenoid Derivatives from the Pomegranate-Derived Endophytic Fungus Talaromyces purpureogenus

Alaa Anwar; Mohamed S Elnaggar; Ahmed M Elissawy; Nehal Ibrahim; Attila Mándi; Tibor Kurtán; Zhen Liu; Sherweit H El-Ahmady; Rainer Kalscheuer

doi:10.3390/molecules28227650

New Meroterpenoid Derivatives from the Pomegranate-Derived Endophytic Fungus Talaromyces purpureogenus

Molecules. 2023 Nov 18;28(22):7650. doi: 10.3390/molecules28227650.

Authors

Alaa Anwar¹, Mohamed S Elnaggar^{1

2}, Ahmed M Elissawy^{1

3}, Nehal Ibrahim¹, Attila Mándi⁴, Tibor Kurtán⁴, Zhen Liu⁵, Sherweit H El-Ahmady¹, Rainer Kalscheuer²

Affiliations

¹ Department of Pharmacognosy, Faculty of Pharmacy, Ain-Shams University, Abbassia, Cairo 11566, Egypt.
² Institute of Pharmaceutical Biology and Biotechnology, Heinrich Heine University, Universitätsstrasse 1, 40225 Düsseldorf, Germany.
³ Center for Drug Discovery Research and Development, Faculty of Pharmacy, Ain-Shams University, Abbassia, Cairo 11566, Egypt.
⁴ Department of Organic Chemistry, University of Debrecen, P.O. Box 400, 4002 Debrecen, Hungary.
⁵ Key Laboratory of Study and Discovery of Small Targeted Molecules of Hunan Province, School of Medicine, Hunan Normal University, Changsha 410013, China.

Abstract

In this study, we report the isolation of two new meroterpenoids, miniolutelide D (1) and miniolutelide E (13-epi-miniolutelide C) (2), along with two meroterpenoidal analogues (3 and 4) and two phenolic compounds (5 and 6) from the endophytic fungus Talaromyces purpureogenus derived from Punica granatum 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 1 and 2 were determined using TDDFT-ECD calculations. Antimicrobial activity was evaluated. Compound 5 displayed significant activity against methicillin-resistant Staphylococcus aureus strain ATCC 700699 and moderate activity against S. aureus strain ATCC 29213.

Keywords: Talaromyces purpureogenus; absolute configuration; antimicrobial activity; endophytes; meroterpenoids; structural elucidation.

MeSH terms

Fruit
Methicillin-Resistant Staphylococcus aureus*
Molecular Structure
Pomegranate*
Staphylococcus aureus
Talaromyces* / chemistry

Supplementary concepts

Talaromyces purpureogenus

Grants and funding

M.S.E. is fully funded by a post-doc scholarship from the Ministry of Higher Education of the Arab Republic of Egypt. The authors would like to thank the Center of Drug Discovery, Ain-Shams University, for providing the chromatography instruments and recording the NMR spectroscopic data. We thank the CeMSA@HHU (Center for Molecular and Structural Analytics, Heinrich Heine University) for recording the mass-spectrometric data. The Hungarian authors were funded by the National Research Development and Innovation Office (Grant numbers: K-138672, FK-134725). The CPU time from the Governmental Information Technology Development Agency (KIFÜ) is gratefully acknowledged.