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Simultaneous UHPLC/DAD/( plus /-)HESI-MS/MS Analysis of Phenolic Acids and Nepetalactones in Methanol Extracts of Nepeta Species: A Possible Application in Chemotaxonomic Studies

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2015
Authors
Mišić, Danijela
Šiler, Branislav
Gašić, Uroš M.
Avramov, Stevan N.
Živković, Suzana
Nestorović Živković, Jasmina
Milutinovic, Milica
Tešić, Živoslav Lj.
Article (Published version)
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Abstract
Introduction - Nepeta species contain a variety of secondary metabolites, including iridoid monoterpenes - nepetalactones and phenolic acids - that are considered the main bioactive constituents. This work represents the first attempt to comparatively explore variations in these two major groups of secondary metabolites within the genus. Objective - To develop an efficient analytical methodology for simultaneous analysis of nepetalactones and phenolic acids in methanol extracts of selected Nepeta species, and to evaluate its potential application in chemotaxonomic studies. Material and methods - A UHPLC combined with linear-trap quadrupole (LTQ) orbitrap MS method was used to characterise chemical diversity and complexity of phenolics among 12 selected Nepeta species. A targeted metabolomic approach using UHPLC coupled to a diode array detector (DAD) and combined with (+/-) heated electrospray ionisation (HESI) MS/MS was developed and validated for quantitative analysis of six hydroxyc...innamic acid derivatives and four nepetalactones. Results - Phenolic profiling provided a valuable database of bioactive compounds in the plant group studied, including phenolic acids (hydroxybenzoic and hydroxycinnamic acids) and flavonoids (flavones, flavonols and flavanones). Principal component analysis and cluster analysis suggested the applicability of 10 targeted compounds as chemomarkers for chemotaxonomic studies. Pearson's correlation analysis revealed significant positive correlations between metabolites involved in different biosynthetic pathways (phenylpropanoid or monoterpenoid). Conclusion - The described targeted metabolomic approach proved to be highly beneficial in designing a phytochemical overview of the genus Nepeta, and might have applications in further clarification of phylogenetic relations. Furthermore, it has the potential to be implemented in a routine quality control of plant material and herbal preparations.

Keywords:
Chemotaxonomy / targeted metabolomic analysis / nepetalactone / phenolic acids / catmint / catnip / Lamiaceae / Nepeta
Source:
Phytochemical Analysis, 2015, 26, 1, 72-85
Publisher:
  • Wiley-Blackwell, Hoboken
Funding / projects:
  • Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research (EU-256716)
  • Structure-properties relationships of natural and synthetic molecules and their metal complexes (RS-172017)
  • Physiological, chemical and molecular analysis of the diversity of selected rare and endangered plant species and application of biotechnology for ex situ conservation and production of biologically active compounds (RS-173024)
Note:
  • Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3420

DOI: 10.1002/pca.2538

ISSN: 0958-0344

PubMed: 25431035

WoS: 000349963000010

Scopus: 2-s2.0-84917691460
[ Google Scholar ]
62
51
URI
https://cherry.chem.bg.ac.rs/handle/123456789/1663
Collections
  • Publikacije
Institution/Community
Hemijski fakultet
TY  - JOUR
AU  - Mišić, Danijela
AU  - Šiler, Branislav
AU  - Gašić, Uroš M.
AU  - Avramov, Stevan N.
AU  - Živković, Suzana
AU  - Nestorović Živković, Jasmina
AU  - Milutinovic, Milica
AU  - Tešić, Živoslav Lj.
PY  - 2015
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1663
AB  - Introduction - Nepeta species contain a variety of secondary metabolites, including iridoid monoterpenes - nepetalactones and phenolic acids - that are considered the main bioactive constituents. This work represents the first attempt to comparatively explore variations in these two major groups of secondary metabolites within the genus. Objective - To develop an efficient analytical methodology for simultaneous analysis of nepetalactones and phenolic acids in methanol extracts of selected Nepeta species, and to evaluate its potential application in chemotaxonomic studies. Material and methods - A UHPLC combined with linear-trap quadrupole (LTQ) orbitrap MS method was used to characterise chemical diversity and complexity of phenolics among 12 selected Nepeta species. A targeted metabolomic approach using UHPLC coupled to a diode array detector (DAD) and combined with (+/-) heated electrospray ionisation (HESI) MS/MS was developed and validated for quantitative analysis of six hydroxycinnamic acid derivatives and four nepetalactones. Results - Phenolic profiling provided a valuable database of bioactive compounds in the plant group studied, including phenolic acids (hydroxybenzoic and hydroxycinnamic acids) and flavonoids (flavones, flavonols and flavanones). Principal component analysis and cluster analysis suggested the applicability of 10 targeted compounds as chemomarkers for chemotaxonomic studies. Pearson's correlation analysis revealed significant positive correlations between metabolites involved in different biosynthetic pathways (phenylpropanoid or monoterpenoid). Conclusion - The described targeted metabolomic approach proved to be highly beneficial in designing a phytochemical overview of the genus Nepeta, and might have applications in further clarification of phylogenetic relations. Furthermore, it has the potential to be implemented in a routine quality control of plant material and herbal preparations.
PB  - Wiley-Blackwell, Hoboken
T2  - Phytochemical Analysis
T1  - Simultaneous UHPLC/DAD/( plus /-)HESI-MS/MS Analysis of Phenolic Acids and Nepetalactones in Methanol Extracts of Nepeta Species: A Possible Application in Chemotaxonomic Studies
VL  - 26
IS  - 1
SP  - 72
EP  - 85
DO  - 10.1002/pca.2538
ER  - 
@article{
author = "Mišić, Danijela and Šiler, Branislav and Gašić, Uroš M. and Avramov, Stevan N. and Živković, Suzana and Nestorović Živković, Jasmina and Milutinovic, Milica and Tešić, Živoslav Lj.",
year = "2015",
abstract = "Introduction - Nepeta species contain a variety of secondary metabolites, including iridoid monoterpenes - nepetalactones and phenolic acids - that are considered the main bioactive constituents. This work represents the first attempt to comparatively explore variations in these two major groups of secondary metabolites within the genus. Objective - To develop an efficient analytical methodology for simultaneous analysis of nepetalactones and phenolic acids in methanol extracts of selected Nepeta species, and to evaluate its potential application in chemotaxonomic studies. Material and methods - A UHPLC combined with linear-trap quadrupole (LTQ) orbitrap MS method was used to characterise chemical diversity and complexity of phenolics among 12 selected Nepeta species. A targeted metabolomic approach using UHPLC coupled to a diode array detector (DAD) and combined with (+/-) heated electrospray ionisation (HESI) MS/MS was developed and validated for quantitative analysis of six hydroxycinnamic acid derivatives and four nepetalactones. Results - Phenolic profiling provided a valuable database of bioactive compounds in the plant group studied, including phenolic acids (hydroxybenzoic and hydroxycinnamic acids) and flavonoids (flavones, flavonols and flavanones). Principal component analysis and cluster analysis suggested the applicability of 10 targeted compounds as chemomarkers for chemotaxonomic studies. Pearson's correlation analysis revealed significant positive correlations between metabolites involved in different biosynthetic pathways (phenylpropanoid or monoterpenoid). Conclusion - The described targeted metabolomic approach proved to be highly beneficial in designing a phytochemical overview of the genus Nepeta, and might have applications in further clarification of phylogenetic relations. Furthermore, it has the potential to be implemented in a routine quality control of plant material and herbal preparations.",
publisher = "Wiley-Blackwell, Hoboken",
journal = "Phytochemical Analysis",
title = "Simultaneous UHPLC/DAD/( plus /-)HESI-MS/MS Analysis of Phenolic Acids and Nepetalactones in Methanol Extracts of Nepeta Species: A Possible Application in Chemotaxonomic Studies",
volume = "26",
number = "1",
pages = "72-85",
doi = "10.1002/pca.2538"
}
Mišić, D., Šiler, B., Gašić, U. M., Avramov, S. N., Živković, S., Nestorović Živković, J., Milutinovic, M.,& Tešić, Ž. Lj.. (2015). Simultaneous UHPLC/DAD/( plus /-)HESI-MS/MS Analysis of Phenolic Acids and Nepetalactones in Methanol Extracts of Nepeta Species: A Possible Application in Chemotaxonomic Studies. in Phytochemical Analysis
Wiley-Blackwell, Hoboken., 26(1), 72-85.
https://doi.org/10.1002/pca.2538
Mišić D, Šiler B, Gašić UM, Avramov SN, Živković S, Nestorović Živković J, Milutinovic M, Tešić ŽL. Simultaneous UHPLC/DAD/( plus /-)HESI-MS/MS Analysis of Phenolic Acids and Nepetalactones in Methanol Extracts of Nepeta Species: A Possible Application in Chemotaxonomic Studies. in Phytochemical Analysis. 2015;26(1):72-85.
doi:10.1002/pca.2538 .
Mišić, Danijela, Šiler, Branislav, Gašić, Uroš M., Avramov, Stevan N., Živković, Suzana, Nestorović Živković, Jasmina, Milutinovic, Milica, Tešić, Živoslav Lj., "Simultaneous UHPLC/DAD/( plus /-)HESI-MS/MS Analysis of Phenolic Acids and Nepetalactones in Methanol Extracts of Nepeta Species: A Possible Application in Chemotaxonomic Studies" in Phytochemical Analysis, 26, no. 1 (2015):72-85,
https://doi.org/10.1002/pca.2538 . .

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