An integrated chip-mass spectrometry and epifluorescence approach for online monitoring of bioactive metabolites from incubated Actinobacteria in picoliter droplets

2018 ◽  
Vol 410 (29) ◽  
pp. 7679-7687 ◽  
Author(s):  
Konstantin Wink ◽  
Lisa Mahler ◽  
Julia R. Beulig ◽  
Sebastian K. Piendl ◽  
Martin Roth ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Online Monitoring ◽  
Bioactive Metabolites

A new furan carboxamide and two potential precursors from a terrestrial streptomycete

2017 ◽  
Vol 72 (3) ◽  
pp. 175-182 ◽  
Author(s):  
Humaira Naureen ◽  
Michel Feussi Tala ◽  
Khaled A. Shaaban ◽  
Mohamed Shaaban ◽  
Anja Schüffler ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Density Functional ◽  
Acid Amide ◽  
Octadecenoic Acid ◽  
Gas Chromatography Mass Spectrometry ◽  
Bioactive Metabolites ◽  
Cytotoxic Activities ◽  
Tetradecanoic Acid ◽  
Vinyl Phenol ◽  
New Compounds

Abstract Three new bioactive metabolites, 1,6-dihydroxy- 2-methyl-heptan-4-one (1), 4-hydroxy-1-(2-methyl-oxiranyl)- pentan-2-one (2), and 2-(2-hydroxy-propyl)-4-methylfuran- 3-carboxylic acid amide (3) were isolated from the terrestrial Streptomyces sp. isolate ANK245, along with the new microbial constituent p-vinylanisol (4a) and the known metabolites p-vinyl-phenol (4b) and phenethyl alcohol. Analysis of the nonpolar part of the extract by gas chromatography/mass spectrometry (GC-MS) provided further evidence for tetradecanoic acid, 9-octadecenoic acid, hexadecanoic acid, 2-methoxy-4-vinylphenol (4c), 4-hydroxy-3-methoxy-benzaldehyde, o-hydroxybiphenyl, and 1,5,9-trimethyl-4,8,13-cyclotetradecatrien-1,3-diol (5). Structures 1–3 of the new compounds were elucidated by nuclear magnetic resonance (NMR) and NMR spectroscopy, but mass spectrometry (MS) techniques and their absolute configuration were determined by density functional theory (DFT) calculations and Mosher derivatisation. Their antimicrobial and cytotoxic activities were evaluated in comparison with the crude bacterial extract.

scholarly journals Use of Mass Spectrometry to Determine the Diversity of Toxins Produced by Gambierdiscus and Fukuyoa Species from Balearic Islands and Crete (Mediterranean Sea) and the Canary Islands (Northeast Atlantic)

Toxins ◽  
2020 ◽  
Vol 12 (5) ◽  
pp. 305 ◽  
Author(s):  
Pablo Estevez ◽  
Manoëlla Sibat ◽  
José Manuel Leão-Martins ◽  
Angels Tudó ◽  
Maria Rambla-Alegre ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Mediterranean Sea ◽  
Canary Islands ◽  
High Resolution Mass Spectrometry ◽  
Balearic Islands ◽  
Bioactive Metabolites ◽  
Toxic Compounds ◽  
Madeira Archipelago ◽  
Species Specific

Over the last decade, knowledge has significantly increased on the taxonomic identity and distribution of dinoflagellates of the genera Gambierdiscus and Fukuyoa. Additionally, a number of hitherto unknown bioactive metabolites have been described, while the role of these compounds in ciguatera poisoning (CP) remains to be clarified. Ciguatoxins and maitotoxins are very toxic compounds produced by these dinoflagellates and have been described since the 1980s. Ciguatoxins are generally described as the main contributors to this food intoxication. Recent reports of CP in temperate waters of the Canary Islands (Spain) and the Madeira archipelago (Portugal) triggered the need for isolation and cultivation of dinoflagellates from these areas, and their taxonomic and toxicological characterization. Maitotoxins, and specifically maitotoxin-4, has been described as one of the most toxic compounds produced by these dinoflagellates (e.g., G. excentricus) in the Canary Islands. Thus, characterization of toxin profiles of Gambierdiscus species from adjacent regions appears critical. The combination of liquid chromatography coupled to either low- or high-resolution mass spectrometry allowed for characterization of several strains of Gambierdiscus and Fukuyoa from the Mediterranean Sea and the Canary Islands. Maitotoxin-3, two analogues tentatively identified as gambieric acid C and D, a putative gambierone analogue and a putative gambieroxide were detected in all G. australes strains from Menorca and Mallorca (Balearic Islands, Spain) while only maitotoxin-3 was present in an F. paulensis strain of the same region. An unidentified Gambierdiscus species (Gambierdiscus sp.2) from Crete (Greece) showed a different toxin profile, detecting both maitotoxin-3 and gambierone, while the availability of a G. excentricus strain from the Canary Islands (Spain) confirmed the presence of maitotoxin-4 in this species. Overall, this study shows that toxin profiles not only appear to be species-specific but probably also specific to larger geographic regions.

scholarly journals Feature-Based Molecular Networking to Target the Isolation of New Caffeic Acid Esters from Yacon (Smallanthus sonchifolius, Asteraceae)

Metabolites ◽  
2020 ◽  
Vol 10 (10) ◽  
pp. 407
Author(s):  
Guillermo F. Padilla-González ◽  
Nicholas J. Sadgrove ◽  
Gari V. Ccana-Ccapatinta ◽  
Olga Leuner ◽  
Eloy Fernandez-Cusimamani
Keyword(s):  
Mass Spectrometry ◽  
Caffeic Acid ◽  
High Resolution Mass Spectrometry ◽  
Chemical Diversity ◽  
Bioactive Metabolites ◽  
Molecular Networking ◽  
Smallanthus Sonchifolius ◽  
Feature Based ◽  
Caffeic Acid Esters ◽  
Acid Esters

Smallanthus sonchifolius (yacon) is an edible tuberous Andean shrub that has been included in the diet of indigenous people since before recorded history. The nutraceutical and medicinal properties of yacon are widely recognized, especially for the improvement of hyperglycemic disorders. However, the chemical diversity of the main bioactive series of caffeic acid esters has not been explored in detail. In this metabolomics study, we applied the latest tools to facilitate the targeted isolation of new caffeic acid esters. Using liquid chromatography coupled to tandem mass spectrometry (LC-MS/MS), we analyzed extracts from different organs (roots, vascular tissues of the stems, stem epidermis, leaves, bracts, and ray flowers) and followed a feature-based molecular networking approach to characterize the structural diversity of caffeic acid esters and recognize new compounds. The analysis identified three potentially new metabolites, one of them confirmed by isolation and full spectroscopic/spectrometric assignment using nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HRMS), and MS/MS. This metabolite (5-O-caffeoyl-2,7-anhydro-d-glycero-β-d-galacto-oct-2-ulopyranosonic acid), along with eight known caffeic acid esters, was isolated from the roots and stems. Furthermore, based on detailed tandem MS analyses, we suggest that the two isomeric monocaffeoyl-2,7-anhydro-2-octulopyranosonic acids found in yacon can be reliably distinguished based on their characteristic MS2 and MS3 spectra. The outcome of the current study confirms the utility of feature-based molecular networking as a tool for targeted isolation of previously undescribed metabolites and reveals the full diversity of potentially bioactive metabolites from S. sonchifolius.

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