Phytochemical analysis for ten Peruvian <i>Mentheae</i> ( <i>Lamiaceae</i>) by liquid chromatography associated with high resolution mass spectrometry

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Abstract

The profile of secondary metabolites in ten members of tribe Mentheae ( Nepetoideae, Lamiaceae) from Peru by liquid chromatography associated with high resolution mass spectrometry, is presented. Salvianolic acids and their precursors were found, particularly rosmarinic acid, caffeic acid ester derivatives, as well as a diversity of free and glycosylated flavonoids as main substances. At all, 111 structures were tentatively identified.

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Most cited references 67

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PubChem 2023 update

Sunghwan Kim, Jie Chen, Tiejun Cheng … (2023)

PubChem (https://pubchem.ncbi.nlm.nih.gov) is a popular chemical information resource that serves a wide range of use cases. In the past two years, a number of changes were made to PubChem. Data from more than 120 data sources was added to PubChem. Some major highlights include: the integration of Google Patents data into PubChem, which greatly expanded the coverage of the PubChem Patent data collection; the creation of the Cell Line and Taxonomy data collections, which provide quick and easy access to chemical information for a given cell line and taxon, respectively; and the update of the bioassay data model. In addition, new functionalities were added to the PubChem programmatic access protocols, PUG-REST and PUG-View, including support for target-centric data download for a given protein, gene, pathway, cell line, and taxon and the addition of the ‘standardize’ option to PUG-REST, which returns the standardized form of an input chemical structure. A significant update was also made to PubChemRDF. The present paper provides an overview of these changes.

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Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective.

Michael Wink (2003)

Secondary metabolites, at least the major ones present in a plant, apparently function as defence (against herbivores, microbes, viruses or competing plants) and signal compounds (to attract pollinating or seed dispersing animals). They are thus important for the plant's survival and reproductive fitness. Secondary metabolites therefore represent adaptive characters that have been subjected to natural selection during evolution. Molecular phylogenies of the Fabaceae, Solanaceae and Lamiaceae were reconstructed and employed as a framework to map and to interpret the distribution of some major defence compounds that are typical for the respective plant families; quinolizidine alkaloids and non-protein amino acids for legumes; tropane and steroidal alkaloids for Solanaceae, and iridoids and essential oils for labiates. The distribution of the respective compounds appears to be almost mutually exclusive in the families studied, implying a strong phylogenetic and ecological component. However, on a closer look, remarkable exceptions can be observed, in that certain metabolites are absent (or present) in a given taxon, although all the neighbouring and ancestral taxa express (or do not express, respectively) the particular trait. It is argued that these patterns might reflect differential expression of the corresponding genes that have evolved earlier in plant evolution. The inconsistent secondary metabolite profiles mean that the systematic value of chemical characters becomes a matter of interpretation in the same way as traditional morphological markers. Thus, the distribution of secondary metabolites has some value for taxonomy but their occurrence apparently reflects adaptations and particular life strategies embedded in a given phylogenetic framework.

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Determination of flavone, flavonol, and flavanone aglycones by negative ion liquid chromatography electrospray ion trap mass spectrometry.

Nicolas Fabre, Isabelle Rustan, Edmond Hoffmann … (2001)

Eleven naturally occurring flavonoid aglycones, belonging to the representative flavone, flavonol, and flavanone types were separated by high performance liquid chromatography and analyzed on-line with negative ion electrospray ionization tandem mass spectrometry (ESI-MS/MS). In order to resolve the MS/MS spectra obtained, each compound was reinvestigated by direct loop injections using an ion trap mass spectrometer. The MSn spectra obtained allowed us to propose plausible schemes for their fragmentation supported by the analysis of five complementary synthetic flavonoid aglycones. The negative ion ESI-MS/MS behavior of the different aglycones investigated in this study revealed interesting differences when compared with the previously described patterns obtained using various ionization techniques in positive ion. Thus, concerning the retro Diels-Alder (RDA) fragmentation pathways, several structurally informative anions appeared highly specific of the negative ion mode. In addition, a new lactone-type structure, instead of a ketene, was proposed for a classic RDA diagnostic ion. We also observed unusual CO, CO2, and C3O2 losses which appear to be characteristic of the negative ion mode. All these results and these unusual neutral losses show that the negative ion mode was a powerful complementary tool of the positive ion mode for the structural characterization of flavonoid aglycones by ESI-MS/MS.

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Author and article information

Contributors

Carlos A. Serrano: carlos.serrano@unsaac.edu.pe

Journal

Journal ID (nlm-ta): Sci Rep

Journal ID (iso-abbrev): Sci Rep

Title: Scientific Reports

Publisher: Nature Publishing Group UK (London )

ISSN (Electronic): 2045-2322

Publication date (Electronic): 3 July 2023

Publication date PMC-release: 3 July 2023

Publication date Collection: 2023

Volume: 13

Electronic Location Identifier: 10714

Affiliations

[1 ]GRID grid.449379.4, ISNI 0000 0001 2198 6786, Laboratorio de Química Orgánica, , Universidad Nacional de San Antonio Abad del Cusco, ; Cusco, Peru

[2 ]GRID grid.10599.34, ISNI 0000 0001 2168 6564, Laboratorio de Micología y Biotecnología, , Universidad Nacional Agraria La Molina, ; Lima, Peru

[3 ]GRID grid.12525.31, ISNI 0000 0001 2223 9184, Herbarium Truxillense (HUT), , Universidad Nacional de Trujillo, ; Trujillo, Peru

[4 ]Centro de Salud MINSA de Pisaq, Cusco, Peru

[5 ]Farmacia Magistral Solidaridad, Cusco, Peru

Article

Publisher ID: 37830

DOI: 10.1038/s41598-023-37830-6

PMC ID: 10318056

PubMed ID: 37400603

SO-VID: eb98cde8-6c52-4b23-992c-8487d704f7eb

License:

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.

History

Date received : 13 January 2023

Date accepted : 28 June 2023

Funding

Funded by: Vicerrectorado de Investigación Universidad Nacional de San Antonio Abad del Cusco

Award ID: CIPCU 003-2021-UNSAAC

Award Recipient : Carlos A. Serrano

Custom metadata

ScienceOpen disciplines: Uncategorized

Keywords: drug discovery,plant sciences

Data availability:

ScienceOpen disciplines: Uncategorized

Keywords: drug discovery, plant sciences

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Phytochemical analysis for ten Peruvian Mentheae ( Lamiaceae) by liquid chromatography associated with high resolution mass spectrometry

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