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Stack bar graphs of flavonoid types. This figure displays the distribution of main flavonoid backbones among different Ocotea species, as annotated by MS² processing. The stacked bars represent the various flavonoid subclasses and their respective biosynthetic pathways on the right side
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We introduce a liquid chromatography – mass spectrometry with data-independent acquisition (LC-MS/DIA)-based strategy, specifically tailored to achieve comprehensive and reliable glycosylated flavonoid profiling. This approach facilitates in-depth and simultaneous exploration of all detected precursors and fragments during data processing, employin...
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Citations
... Mez has been documented to possess anti-inflammatory, [14] antimicrobial, [15] cytotoxic, [16] and acaricidal properties, [17] although its chemical composition has not been thoroughly characterized. Recent investigations suggest that O. diospyrifolia primarily produces alkaloids and glycosylated flavonoids, [18,19] but there remains a significant gap in the knowledge of specific compounds and their potential biological effects. A notable example is the recent isolation of diospirifoline, a new aporphine alkaloid, along with eight other known NPs. [14] The scarcity of detailed chemical information limits the ability to conduct robust chemophenetic analyses and hinders accurate botanical classifications. ...
... [28] In that way, for hits with available reference fragmentation spectra (MS/MS) in online databases, such as the Global Natural Products Social Molecular Networking (GNPS) and MassBank of North America (MoNA), annotations were performed by comparing these spectra. This process resulted in 27 annotations with confidence level 2 according to MSI. [24] The annotation of flavonoids was done based on aglycone distribution within the DIA data, [18] and resulted in 11 glycosylated flavonols of kaempferol and quercetin. The strategy employed enabled the annotation of both the aglycone cores and sugar moieties. ...
... [29,30] The fragmentations regarding glycosylated flavonoids were based on heterolytic and homolytic cleavage of O-glycosyl bond, with the aglycone as the main fragment and the neutral loss revealing the possible sugar units. [18,31] Other proposed fragmentations were based on well-established mechanisms in gasphase chemistry. [28] The proposed fragmentation pathways for the formation of the main diagnostic ions for the annotated NPs at confidence level 2b were shown in Figure 3. ...
Ocotea is an important genus of Lauraceae plant family that comprises over 400 species, many of which pose challenges in taxonomic differentiation due to their complex botanical characteristics. Chemosystematics, and more recently, chemophenetics, have emerged as valuable tools to address these challenges based on their natural products (NPs) composition. O. diospyrifolia (Meisn.) Mez is a poorly studied species with known pharmacological potential. Here, we applied ultra‐high performance liquid chromatography coupled with high‐resolution tandem mass spectrometry (UHPLC‐HRMS) allied to a curated in‐house database with all previous isolated NPs from the Ocotea genus (OcoteaDB), gas phase fragmentations reactions, and biosynthesis. The strategy resulted in compounds annotated in confidence levels 2 (n=27), 3 (n=231), and 4 (n=21) according to the Metabolomics Standards Initiative (MSI). Additional annotations based on fragmentation proposals (n=16) were also included. The study revealed that O. diospyrifolia is a great alkaloid producer, even though different lignoids, which also comes from the shikimate pathway, were annotated. Additionally, the flavonoid profile predominantly consists of flavonol glycosides, complementing prior reports. This study provides the first comprehensive chemical profile of O. diospyrifolia leaves, which corroborates the chemotaxonomy of the species, and also contributes to further characterization studies, as the UHPLC‐HRMS data is publicly available.
Liquid chromatography, when used in conjunction with mass spectrometry (LC/MS), is a powerful tool for conducting accurate and reproducible investigations of numerous metabolites in natural products (NPs). LC/MS has gained prominence in metabolomic research due to its high throughput, the availability of multiple ionization techniques and its ability to provide comprehensive metabolite coverage. This unique method can significantly influence various scientific domains. This review offers a comprehensive overview of the current state of LC/MS‐based metabolomics in the investigation of NPs. This review provides a thorough overview of the state of the art in LC/MS‐based metabolomics for the investigation of NPs. It covers the principles of LC/MS, various aspects of LC/MS‐based metabolomics such as sample preparation, LC modes, method development, ionization techniques and data pre‐processing. Moreover, it presents the applications of LC/MS‐based metabolomics in numerous fields of NPs research such as including biomarker discovery, the agricultural research, food analysis, the study of marine NPs and microbiological research. Additionally, this review discusses the challenges and limitations of LC/MS‐based metabolomics, as well as emerging trends and developments in this field.
Gold nanoparticles functionalized with 18-crown 6-ether (18C6-AuNPs) can be used for detection of tannic acid, epigallocatechin gallate, and epicatechin gallate by color change in the μg mL⁻¹ range. 18C6-AuNPs were insensitive to l-ascorbic acid and l-tyrosine unlike conventional detection methods, such as Folin & Ciocalteu assay, whose principle is based on the redox reaction of polyphenols. Although 18C6-AuNPs did not respond to some polyphenols, such as gallic acid and epicatechin, if the polyphenols of interest are responsive to this approach, these are expected to be effective nanomaterial for simple sensing of polyphenols.
