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Molecules 2017, 22(10), 1674; doi:10.3390/molecules22101674

Furanones and Anthranilic Acid Derivatives from the Endophytic Fungus Dendrothyrium variisporum

1
Department of Microbial Drugs, Helmholtz Centre for Infection Research and German Centre for Infection Research (DZIF), partner site Hannover/Braunschweig, Inhoffenstrasse 7, 38124 Braunschweig, Germany
2
Department of Chemistry, Faculty of Science, University of Dschang, P.O. Box 67, Dschang, Cameroon
3
Laboratory of Applied Microbiology, Department of Microbiology, Faculty of Natural and Life Sciences, University Sétif 1 Ferhat Abbas, 19000 Sétif, Algeria
4
Department of Microbiology-Biochemistry, Faculty of Natural and Life Sciences, University of Batna 2, 05000 Batna, Algeria
5
Department of Chemistry, Faculty of Science, Aswan University, 81528 Aswan, Egypt
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 18 September 2017 / Revised: 5 October 2017 / Accepted: 6 October 2017 / Published: 9 October 2017
(This article belongs to the Section Natural Products)
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Abstract

Extracts from an endophytic fungus isolated from the roots of the Algerian plant Globularia alypum showed prominent antimicrobial activity in a screening for novel antibiotics. The producer organism was identified as Dendrothyrium variisporum by means of morphological studies and molecular phylogenetic methods. Studies on the secondary metabolite production of this strain in various culture media revealed that the major components from shake flasks were massarilactones D (1) and H (2) as well as two new furanone derivatives for which we propose the trivial names (5S)-cis-gregatin B (3) and graminin D (4). Scale-up of the fermentation in a 10 L bioreactor yielded massarilactone D and several further metabolites. Among those were three new anthranilic acid derivatives (57), two known anthranilic acid analogues (8 and 9) and three cyclopeptides (1012). Their structures were elucidated on the basis of extensive spectroscopic analysis (1D- and 2D-NMR), high-resolution mass spectrometry (HRESIMS), and the application of the modified Mosher’s method. The isolated metabolites were tested for antimicrobial and cytotoxic activities against various bacteria, fungi, and two mammalian cell lines. The new Metabolite 5 and Compound 9 exhibited antimicrobial activity while Compound 9 showed cytotoxicity activity against KB3.1 cells. View Full-Text
Keywords: Montagnulaceae; Dendrothyrium variisporum; fermentation; furancarboxylic acid derivatives; anthranilic acid derivatives; antimicrobial activity; cytotoxicity Montagnulaceae; Dendrothyrium variisporum; fermentation; furancarboxylic acid derivatives; anthranilic acid derivatives; antimicrobial activity; cytotoxicity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Teponno, R.B.; Noumeur, S.R.; Helaly, S.E.; Hüttel, S.; Harzallah, D.; Stadler, M. Furanones and Anthranilic Acid Derivatives from the Endophytic Fungus Dendrothyrium variisporum. Molecules 2017, 22, 1674.

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