Furanones and Anthranilic Acid Derivatives from the Endophytic Fungus Dendrothyrium variisporum.

2.50
Hdl Handle:
http://hdl.handle.net/10033/621155
Title:
Furanones and Anthranilic Acid Derivatives from the Endophytic Fungus Dendrothyrium variisporum.
Authors:
Teponno, Rémy B; Noumeur, Sara R; Helaly, Soleiman E; Hüttel, Stephan; Harzallah, Daoud; Stadler, Marc ( 0000-0002-7284-8671 )
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 (5-7), two known anthranilic acid analogues (8 and 9) and three cyclopeptides (10-12). 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.
Affiliation:
Helmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7, 38124 Braunschweig, Germany.
Citation:
Furanones and Anthranilic Acid Derivatives from the Endophytic Fungus Dendrothyrium variisporum. 2017, 22 (10) Molecules
Journal:
Molecules (Basel, Switzerland)
Issue Date:
9-Oct-2017
URI:
http://hdl.handle.net/10033/621155
DOI:
10.3390/molecules22101674
PubMed ID:
28991218
Type:
Article
Language:
en
ISSN:
1420-3049
Appears in Collections:
publications of the department of microbial drugs (MWIS)

Full metadata record

DC FieldValue Language
dc.contributor.authorTeponno, Rémy Ben
dc.contributor.authorNoumeur, Sara Ren
dc.contributor.authorHelaly, Soleiman Een
dc.contributor.authorHüttel, Stephanen
dc.contributor.authorHarzallah, Daouden
dc.contributor.authorStadler, Marcen
dc.date.accessioned2017-11-02T14:19:57Z-
dc.date.available2017-11-02T14:19:57Z-
dc.date.issued2017-10-09-
dc.identifier.citationFuranones and Anthranilic Acid Derivatives from the Endophytic Fungus Dendrothyrium variisporum. 2017, 22 (10) Moleculesen
dc.identifier.issn1420-3049-
dc.identifier.pmid28991218-
dc.identifier.doi10.3390/molecules22101674-
dc.identifier.urihttp://hdl.handle.net/10033/621155-
dc.description.abstractExtracts 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 (5-7), two known anthranilic acid analogues (8 and 9) and three cyclopeptides (10-12). 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.en
dc.language.isoenen
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/4.0/*
dc.titleFuranones and Anthranilic Acid Derivatives from the Endophytic Fungus Dendrothyrium variisporum.en
dc.typeArticleen
dc.contributor.departmentHelmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7, 38124 Braunschweig, Germany.en
dc.identifier.journalMolecules (Basel, Switzerland)en

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