Mass Spectrometry and Its Importance for the Analysis and Discovery of Active Molecules in Natural Products

Mass spectrometry is one of the best techniques for analyzing the structure of a molecule. It usually provides information about the molecular weight of a substance, and it can present atomic mass units and up to ten thousandths of atomic mass units depending on the accuracy of the mass analyzer. In addition, it provides information on the positive ions formed in the ionization process, which is linked to the chemical structure of the molecule and the nature of the bonds. This technique is widely used for analyzing compounds from natural products. The development of the technique combined with the use of software and databases has been remarkable in recent years, improving the ionization processes and the ion analysis. Since natural products generally constitute a mixture of a complex quantity of components, mechanisms have been developed for coupling to chromatographic techniques of various kinds. This review aims to show how mass spectrometry has contributed to the qualitative quality control in natural products, as well as in the finding of new metabolites of industrial interest.

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Qualitative and Quantitative Analysis of the Major Constituents in WLJ Herbal Tea Using Multiple Chromatographic Techniques

Molecules ◽

10.3390/molecules23102623 ◽

2018 ◽

Vol 23 (10) ◽

pp. 2623 ◽

Cited By ~ 4

Author(s):

Chao-Zhan Lin ◽

Run-Jing Zhang ◽

Yu-Feng Yao ◽

Xiao-Dan Huang ◽

Rong-Bo Zheng ◽

...

Keyword(s):

Mass Spectrometry ◽

Quality Control ◽

High Performance Liquid Chromatography ◽

Liquid Chromatography ◽

Quantitative Analysis ◽

High Performance ◽

Good Precision ◽

Herbal Tea ◽

Chromatographic Techniques ◽

Flight Mass Spectrometry

Quality control of Chinese herbal tea remains a challenge due to our poor knowledge of their complex chemical profile. This study aims to investigate the chemical composition of one of the best-selling and famous brand of beverage in China, Wanglaoji Herbal Tea (WLJHT), via a full component quantitative analysis. In this paper, a total of thirty-two representative constituents were identified or tentatively characterized using ultra-high performance liquid chromatography coupled with quadrupole tandem time-of-flight mass spectrometry (UPLC-Q-TOF-MS). Moreover, the quantitative analyses of fourteen constituents were performed by high performance liquid chromatography with a triple quadruple tandem mass spectrometry (HPLC-MS/MS) method and saccharide compositions of WLJHT were also quantitatively determined by high performance liquid chromatography (HPLC) with evaporative light scattering detector (ELSD) on a Hilic column, separately. Using multiple chromatographic techniques presented a good precision, sensitivity, repeatability and stability, and was successfully applied to analyze 16 batches of WLJHT samples. Therefore, it would be a reliable and useful approach for the quality control of WLJHT.

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Recent Applications of Mass Spectrometry in the Study of Grape and Wine Polyphenols

ISRN Spectroscopy ◽

10.1155/2013/813563 ◽

2013 ◽

Vol 2013 ◽

pp. 1-45 ◽

Cited By ~ 40

Author(s):

Riccardo Flamini

Keyword(s):

Mass Spectrometry ◽

Molecular Weight ◽

Quality Control ◽

Structural Characterization ◽

Antioxidant Activities ◽

Soft Ionization ◽

Wine Consumption ◽

Highly Effective ◽

Wine Polyphenols

Polyphenols are the principal compounds associated with health benefic effects of wine consumption and in general are characterized by antioxidant activities. Mass spectrometry is shown to play a very important role in the research of polyphenols in grape and wine and for the quality control of products. The soft ionization of LC/MS makes these techniques suitable to study the structures of polyphenols and anthocyanins in grape extracts and to characterize polyphenolic derivatives formed in wines and correlated to the sensorial characteristics of the product. The coupling of the several MS techniques presented here is shown to be highly effective in structural characterization of the large number of low and high molecular weight polyphenols in grape and wine and also can be highly effective in the study of grape metabolomics.

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Analysis of minor low molecular weight carbohydrates in cocoa beans by chromatographic techniques coupled to mass spectrometry

Journal of Chromatography A ◽

10.1016/j.chroma.2018.11.033 ◽

2019 ◽

Vol 1584 ◽

pp. 135-143 ◽

Cited By ~ 5

Author(s):

Roberto Megías-Pérez ◽

Ana Isabel Ruiz-Matute ◽

Marcello Corno ◽

Nikolai Kuhnert

Keyword(s):

Mass Spectrometry ◽

Molecular Weight ◽

Low Molecular Weight ◽

Cocoa Beans ◽

Chromatographic Techniques

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Systematic isolation of microbial metabolites for natural products depository (NPDepo)

Pure and Applied Chemistry ◽

10.1351/pac-con-11-08-11 ◽

2011 ◽

Vol 84 (6) ◽

pp. 1407-1420 ◽

Cited By ~ 18

Author(s):

Hiroyuki Osada ◽

Toshihiko Nogawa

Keyword(s):

Mass Spectrometry ◽

Natural Products ◽

Biological Activity ◽

Microbial Metabolites ◽

Liquid Chromatography Mass Spectrometry ◽

Chromatographic Techniques ◽

New Type ◽

Metabolite Database ◽

Microbial Products ◽

Microbial Sources

A microbial fraction library has been constructed as a part of RIKEN Natural Products Depository (NPDepo) to discover and isolate novel metabolites with unique biological activity from microbial sources efficiently and rapidly. The fraction library was made by a systematic separation method based on basic chromatographic techniques. Each fraction in the library was analyzed by liquid chromatography/mass spectrometry (LC/MS) to reveal physicochemical properties of each metabolite within the fraction, and the results were applied to construct a database for rapid discovery of novel and structurally unique compounds. We developed a new type of metabolite database called MP (microbial products) plot to visualize each metabolite on a 2D area. The combination of the fraction library and the database led to the discovery and isolation of novel metabolites, verticilactam, which was a 16-membered macrolactam with an unprecedented β-keto-amide moiety, and spirotoamides A and B, which had a highly substituted 6,6-spiroaccetal moiety and a carboxamide moiety. Moreover, based on the utilization of the MP plot, the new capacity of a streptomycete to produce specific metabolites was discovered.

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Dimethyl Sulfide in Cigarette Smoke - On the Origin of the Sulfur Compounds of Cigarette Smoke and on Their Possible Contribution to its Overall Flavor and Aroma

Beiträge zur Tabakforschung International/Contributions to Tobacco Research ◽

10.2478/cttr-2013-0156 ◽

1966 ◽

Vol 3 (9) ◽

pp. 577-582

Author(s):

R.J. Philippe

Keyword(s):

Mass Spectrometry ◽

Natural Products ◽

Cigarette Smoke ◽

Mass Spectra ◽

Dimethyl Sulfide ◽

Sulfur Compounds ◽

Chromatographic Retention ◽

Positive Identification ◽

Chromatographic Techniques ◽

Infra Red

Abstract Dimethyl sulfide has been isolated from cigarette smoke by a combination of adsorption and partition gas chromatographic techniques. Positive identification of dimethyl sulfide was obtained by infra-red spectrophotometry, mass spectrometry and gas chromatographic retention times. Both infra-red and mass spectra are presented and their most important features are discussed. Based on gas chromatographic measurements, a semiquantitative estimation of the amount of dimethyl sulfide in cigarette smoke is given. A list of the sulfur compounds identified up to now in cigarette smoke is presented as well as some discussion about their possible origin. After some evidence given on the importance of sulfur compounds on the flavour of several natural products and of some synthetic compositions, the question is raised as to the possible effect of these sulfur compounds on the overall flavour and aroma of cigarette smoke.

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Using GC-MS for natural product analysis in Nigeria: Problems and prospects

Journal of Chemical Society of Nigeria ◽

10.46602/jcsn.v45i5.532 ◽

2020 ◽

Vol 45 (5) ◽

Author(s):

B. O. Odjobo ◽

N. Ichoron ◽

N. P. Igoli ◽

J. O. Igoli

Keyword(s):

Mass Spectrometry ◽

Nuclear Magnetic Resonance ◽

Natural Products ◽

Gas Chromatography Mass Spectrometry ◽

Resonance Spectroscopy ◽

Product Analysis ◽

Mass Spectrometers ◽

Idle State ◽

Chromatographic Techniques ◽

Analytical Equipment

The absence or idle state of analytical equipment such as nuclear magnetic resonance spectroscopy, mass spectrometers and chromatographic techniques has constrained natural products research in Nigeria. Presently, gas chromatography-mass spectrometry has become the more easily available method in Nigeria for the identification of natural products in extracts. This method is sometimes fraught with non-reproducible results and the identification of non-natural or biosynthesized compounds. Several of the extracts analyzed are not volatile, some of the analysts are not competent and certified reference standards are hardly used. These coupled with poor library or database matches and data processing among others lead to the identification of compounds not recognizable from the extract or plants materials under study. This review discusses some of the problems involved in the use of this method for dereplication studies of plant extracts in Nigeria and makes some suggestions for improvement.

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Field Desorption and Fast Atom Bombardment Mass Spectrometry of Spirostanol and Furostanol Saponins from Paris polyphylla

Zeitschrift für Naturforschung C ◽

10.1515/znc-1984-3-401 ◽

1984 ◽

Vol 39 (3-4) ◽

pp. 201-211 ◽

Cited By ~ 14

Author(s):

H.-R. Schulten ◽

S. B. Singh ◽

R. S. Thakur

Keyword(s):

Mass Spectrometry ◽

Molecular Weight ◽

Natural Products ◽

Fast Atom Bombardment ◽

Structural Elucidation ◽

Molecular Weight Determination ◽

Field Desorption ◽

Furostanol Saponins ◽

Paris Polyphylla ◽

Purity Control

The application of field desorption and fast atom bombardm ent mass spectrometry for molecular weight determination and structural elucidation of spirostanol and furostanol saponins isolated from Paris Polyphylla Sm. (Liliaceae) is reported. The capacity and limitations of these methods for sugar sequencing, differentiation of isomers and purity control of oligoglycosidic natural products are discussed

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Semiautomated glycoproteomics data analysis workflow for maximized glycopeptide identification and reliable quantification

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.16.253 ◽

2020 ◽

Vol 16 ◽

pp. 3038-3051

Author(s):

Steffen Lippold ◽

Arnoud H de Ru ◽

Jan Nouta ◽

Peter A van Veelen ◽

Magnus Palmblad ◽

...

Keyword(s):

Mass Spectrometry ◽

Quality Control ◽

Data Analysis ◽

Structural Diversity ◽

Reversed Phase ◽

Mass Analyzer ◽

Data Quality Control ◽

Cysteine Oxidation ◽

Research Areas ◽

Peptide Modification

Glycoproteomic data are often very complex, reflecting the high structural diversity of peptide and glycan portions. The use of glycopeptide-centered glycoproteomics by mass spectrometry is rapidly evolving in many research areas, leading to a demand in reliable data analysis tools. In recent years, several bioinformatic tools were developed to facilitate and improve both the identification and quantification of glycopeptides. Here, a selection of these tools was combined and evaluated with the aim of establishing a robust glycopeptide detection and quantification workflow targeting enriched glycoproteins. For this purpose, a tryptic digest from affinity-purified immunoglobulins G and A was analyzed on a nano-reversed-phase liquid chromatography–tandem mass spectrometry platform with a high-resolution mass analyzer and higher-energy collisional dissociation fragmentation. Initial glycopeptide identification based on MS/MS data was aided by the Byonic software. Additional MS1-based glycopeptide identification relying on accurate mass and retention time differences using GlycopeptideGraphMS considerably expanded the set of confidently annotated glycopeptides. For glycopeptide quantification, the performance of LaCyTools was compared to Skyline, and GlycopeptideGraphMS. All quantification packages resulted in comparable glycosylation profiles but featured differences in terms of robustness and data quality control. Partial cysteine oxidation was identified as an unexpectedly abundant peptide modification and impaired the automated processing of several IgA glycopeptides. Finally, this study presents a semiautomated workflow for reliable glycoproteomic data analysis by the combination of software packages for MS/MS- and MS1-based glycopeptide identification as well as the integration of analyte quality control and quantification.

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