Industrial Riboflavin Fermentation Broths Represent a Diverse Source of Natural Saturated and Unsaturated Lactones

Birk, Florian; Fraatz, Marco Alexander; Esch, Patrick van; Heiles, Sven; Pelzer, Ralf; Zorn, Holger

doi:10.1021/acs.jafc.9b01154

Cited by 11 publications

(16 citation statements)

References 46 publications

(93 reference statements)

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“…However, the discovery by Ma and Xia [114] that light-induced Paternò-Büchi (PB) reactions can aid DB position assignments with relative ease and with inexpensive equipment has sparked the interest in chemical derivatization strategies that enable structure elucidation. In particular, most recent derivatization strategies target lipid DBs or adjacent carbon atoms and are based on PB [114][115][116][117][118][119][120][121][122], epoxidation [123][124][125], ozonolysis [126], or hydroxylation reactions [127] (Scheme 2).…”

Section: Chemical Derivatization Prior To Tandem Msmentioning

confidence: 99%

“…PB reactions with acpy and other carbonyl compounds have been used not only to analyze standards but also to investigate complex lipid extracts from body fluids, cells, or tissues revealing DB positions and sometimes sn-isomers for CEs [116,130], FAs [116], GPs [121], and SLs [131]. Recently, PB methods have been extended to also target small FA metabolites [117][118][119] or have been adapted to benefit other advanced tandem MS tools such as UVPD [115] or ion/ion reactions [122].…”

Section: Chemical Derivatization Prior To Tandem Msmentioning

confidence: 99%

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Advanced tandem mass spectrometry in metabolomics and lipidomics—methods and applications

Heiles

2021

Anal Bioanal Chem

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Metabolomics and lipidomics are new drivers of the omics era as molecular signatures and selected analytes allow phenotypic characterization and serve as biomarkers, respectively. The growing capabilities of untargeted and targeted workflows, which primarily rely on mass spectrometric platforms, enable extensive charting or identification of bioactive metabolites and lipids. Structural annotation of these compounds is key in order to link specific molecular entities to defined biochemical functions or phenotypes. Tandem mass spectrometry (MS), first and foremost collision-induced dissociation (CID), is the method of choice to unveil structural details of metabolites and lipids. But CID fragment ions are often not sufficient to fully characterize analytes. Therefore, recent years have seen a surge in alternative tandem MS methodologies that aim to offer full structural characterization of metabolites and lipids. In this article, principles, capabilities, drawbacks, and first applications of these “advanced tandem mass spectrometry” strategies will be critically reviewed. This includes tandem MS methods that are based on electrons, photons, and ion/molecule, as well as ion/ion reactions, combining tandem MS with concepts from optical spectroscopy and making use of derivatization strategies. In the final sections of this review, the first applications of these methodologies in combination with liquid chromatography or mass spectrometry imaging are highlighted and future perspectives for research in metabolomics and lipidomics are discussed. Graphical abstract

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Section: Chemical Derivatization Prior To Tandem Msmentioning

confidence: 99%

Section: Chemical Derivatization Prior To Tandem Msmentioning

confidence: 99%

Advanced tandem mass spectrometry in metabolomics and lipidomics—methods and applications

Heiles

2021

Anal Bioanal Chem

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“…These compounds have low perception thresholds (e.g., γ-nonalactone 25 µg/L, γ-decalactone 0.88-1 mg/L and γ-dodecalactone 7 µg/L) [7,8] and very powerful odor descriptors that range from peach-like and coconut to creamy and floral [9]. Generally, odor perception thresholds are inversely related to the length of the side chain of the lactone [10]. In addition, some lactones present anti-microbial and anti-inflammatory properties [11][12][13].…”

Section: Introductionmentioning

confidence: 99%

“…Nonetheless, in recent years, there is a growing number of studies that are addressing this problem and exploring the production of lactones from more renewable substrates. Recent examples are the identification and engineering of the filamentous fungus Ashbya gossypii as a microorganism able to perform de novo biosynthesis of lactones [23] and biotransformation of non-hydroxy fatty acids [10], as well as the engineering of Y. lipolytica to perform biotransformation of non-hydroxy fatty acids [20].…”

Section: Introductionmentioning

confidence: 99%

Microbial Biosynthesis of Lactones: Gaps and Opportunities towards Sustainable Production

et al. 2021

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Lactones are volatile organic compounds widely present in foods. These chemicals are applied as flavors and fragrances in the food, cosmetics and pharmaceutical industries. Recently, the potential of lactones as green solvents and fuel precursors reinforced their role as platform compounds of future bio-based economies. However, their current mode of production needs to change. Lactones are mainly obtained through chemical synthesis or microbial biotransformation of hydroxy fatty acids. The latter approach is preferred but still needs to use more sustainable substrates. Hydroxy fatty acids are non-abundant and non-sustainable substrates from environmental, health and economic points of view. Therefore, it is urgent to identify and engineer microorganisms with the rare ability to biosynthesize lactones from carbohydrates or renewable lipids. Here, we firstly address the variety and importance of lactones. Then, the current understanding of the biosynthetic pathways involved in lactone biosynthesis is presented, making use of the knowledge acquired in microorganisms and fruits. From there, we present and make the distinction between biotransformation processes and de novo biosynthesis of lactones. Finally, the opportunities and challenges towards more sustainable production in addition to the relevance of two well-known industrial microbes, the filamentous fungus Ashbya gossypii and the yeast Yarrowia lipolytica, are discussed.

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“…Soon after its potential for riboflavin overproduction was recognized, which led to the establishment of Ashbya as a platform producer of vitamin B 2 on an industrial scale [2][3][4]. Such a platform strain has expanded uses e.g., in the production of other vitamins, flavor compounds or lipids [5][6][7][8][9]. Metabolic engineering and metabolic flux studies in Ashbya have been used to determine and improve key enzymatic reactions in pathways required for riboflavin or gamma-lactone production [9].…”

Section: Introductionmentioning

confidence: 99%

Sporulation in Ashbya gossypii

Wendland

2020

JoF

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Ashbya gossypii is a filamentous ascomycete belonging to the yeast family of Saccharomycetaceae. At the end of its growth phase Ashbya generates abundant amounts of riboflavin and spores that form within sporangia derived from fragmented cellular compartments of hyphae. The length of spores differs within species of the genus. Needle-shaped Ashbya spores aggregate via terminal filaments. A. gossypii is a homothallic fungus which may possess a and α mating types. However, the solo-MATa type strain is self-fertile and sporulates abundantly apparently without the need of prior mating. The central components required for the regulation of sporulation, encoded by IME1, IME2, IME4, KAR4, are conserved with Saccharomyces cerevisiae. Nutrient depletion generates a strong positive signal for sporulation via the cAMP-PKA pathway and SOK2, which is also essential for sporulation. Strong inhibitors of sporulation besides mutations in the central regulatory genes are the addition of exogenous cAMP or the overexpression of the mating type gene MATα2. Sporulation has been dissected using gene-function analyses and global RNA-seq transcriptomics. This revealed a role of Msn2/4, another potential PKA-target, for spore wall formation and a key dual role of the protein A kinase Tpk2 at the onset of sporulation as well as for breaking the dormancy of spores to initiate germination. Recent work has provided an overview of ascus development, regulation of sporulation and spore maturation. This will be summarized in the current review with a focus on the central regulatory genes. Current research and open questions will also be discussed.

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Industrial Riboflavin Fermentation Broths Represent a Diverse Source of Natural Saturated and Unsaturated Lactones

Cited by 11 publications

References 46 publications

Advanced tandem mass spectrometry in metabolomics and lipidomics—methods and applications

Advanced tandem mass spectrometry in metabolomics and lipidomics—methods and applications

Microbial Biosynthesis of Lactones: Gaps and Opportunities towards Sustainable Production

Sporulation in Ashbya gossypii

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