Rapid Characterization of Triterpene Saponins from Zornia brasiliensis by HPLC-ESI-MS/MS

Nascimento, Yuri Mangueira do; Abreu, Lucas Silva; Lima, Ramon; Costa, Vicente Carlos O.; Melo, José Iranildo Miranda de; Braz-Filho, Raimundo; Silva, Marcelo Sobral; Tavares, Josean Fechine

doi:10.3390/molecules24142519

Cited by 11 publications

(6 citation statements)

References 37 publications

(51 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Saponin 37 (T R = 29.5 min) showed the same molecular ion as saponin 30 , [M-H] − ion at m / z 793 and exhibited MS 2 fragment ions at m / z 775 (water loss), m / z 731 (water and carbone dioxide losses), and m / z 613 (hexose and water losses). Therefore, this compound was assigned according to Nascimento et al as soyasaponin βe’ [ 33 ]. In addition, soyasaponin βg’ (compound 39 , T R = 30.34 min) was also identified in the same paper with a parent ion [M-H] − ion at m / z 763 and characteristic MS 2 fragment ions at m / z 719, 701, 613, 523, and 455.…”

Section: Resultsmentioning

confidence: 99%

HESI-MS/MS Analysis of Phenolic Compounds from Calendula aegyptiaca Fruits Extracts and Evaluation of Their Antioxidant Activities

et al. 2022

View full text Add to dashboard Cite

Considering medicinal plants as an inexhaustible source of active ingredients that may be easily isolated using simple and inexpensive techniques, phytotherapy is becoming increasingly popular. Various experimental approaches and analytical methods have been used to demonstrate that the genus Calendula (Asteraceae) has a particular richness in active ingredients, especially phenolic compounds, which justifies the growing interest in scientific studies on this genus’ species. From a chemical and biological viewpoint, Calendula aegyptiaca is a little-studied plant. For the first time, high-performance liquid chromatography combined with negative electrospray ionization mass spectrometry (HPLC-HESI-MS) was used to analyze methanolic extracts of Calendula aegyptiaca (C. aegyptiaca) fruits. Thirty-five molecules were identified. Flavonoids (47.87%), phenolic acids (5.18%), and saponins (6.47%) formed the majority of these chemicals. Rutin, caffeic acid hexoside, and Soyasaponin βg’ were the most abundant molecules in the fruit methanolic extract, accounting for 17.49% of total flavonoids, 2.32 % of total phenolic acids, and 0.95% of total saponins, respectively. The antioxidant activity of the fruit extracts of C. aegyptiaca was investigated using FRAP, TAC, and DPPH as well as flavonoids and total phenols content. Because the phenolic components were more extractable using polar solvents, the antioxidant activity of the methanolic extract was found to be higher than that of the dichloromethane and hexane extracts. The IC50 value for DPPH of methanolic extract was found to be 0.041 mg·mL−1. Our findings showed that C. aegyptiaca is an important source of physiologically active compounds.

show abstract

Section: Resultsmentioning

confidence: 99%

HESI-MS/MS Analysis of Phenolic Compounds from Calendula aegyptiaca Fruits Extracts and Evaluation of Their Antioxidant Activities

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Identification of triterpene saponins by UHPLC‐UV‐MS/MS with CID in negative ion mode is a well‐established and widely employed technique 25,26,41 . Once known compounds are identified in the data set, database searches can be used as a guidance to discover the structure of new metabolites with modified core structures from a given class.…”

Section: Resultsmentioning

confidence: 99%

“…In this work we used MZmine 2 , which contains methods for all data processing stages, such as spectral filtering, peak detection, alignment, normalisation and identification 21 . Recent literature reports this tool for the structural determination of compounds from several metabolite classes such as flavonoids, 19,22 alkaloids, 17,23,24 and saponins 25,26 …”

Section: Introductionmentioning

confidence: 99%

Mass spectrometry as a tool for the dereplication of saponins from Ampelozizyphus amazonicus Ducke bark and wood

Mendonça

Simas

et al. 2020

Phytochemical Analysis

View full text Add to dashboard Cite

Introduction Mass spectrometry in natural products research has been used as a first step to identify possible chemical structures and to guide subsequent efforts to isolate novel compounds. Preparations of Ampelozizyphus amazonicus Ducke (AA) are known for their high content of saponins, especially dammarane‐type triterpenoid aglycones. In the Amazon, where it is known as “saracura‐mirá”, roots and bark are widely used for the treatment and prevention of malaria, while the wood is discarded. The extract prepared from the wood is also saponin‐rich, but its exact chemical composition has not been described. Objective This study provides information on the chemical profiling and tentative structural identification of the major compounds (saponins) present in aqueous and ethanol extracts of bark and wood of AA by mass spectrometry. Methods The strategy used to identify compounds present in all samples was ultra‐high‐performance liquid chromatography with an ultraviolet detector coupled to tandem mass spectrometry (UHPLC‐UV‐MS/MS) for the analysis of fragmentation patterns through product ion scan using MZmine 2 software. Also, direct sample injection and electrospray ionisation combined with high‐resolution mass spectrometry (DI‐ESI‐HRMS) measurements were performed. Results The extracts showed chemical similarity, and 95 saponins were tentatively identified in AA wood and bark, including 73 which are described for the first time as tentative structures for this plant species. Conclusion This research describes a useful method for the fast and simultaneous tentative identification of major saponins in AA, contributing to the study of the chemical properties of this genus and family. Furthermore, it demonstrates the importance of the qualitative dereplication process, allowing a straightforward way to propose the tentative identification of compounds.

show abstract

“…Since natural products are one of the most important sources of new drugs, highly integrated interdisciplinary research methods have shown great power in drug discovery of natural products [2] . However, due to the similar structure and polarity of these compounds, they are difficult to separate with ordinary technology unless some special combined detection and separation technologies, such as HPLC‐ESIMS n , HPLC‐DAD‐MS, and HPLC‐PDA‐(HRMS)‐SPE‐NMR, which are wildly used to rapidly direct the isolation and identification of target compounds from crude extracts of medicinal plants [3–5] . Among them, by analyzing retention time ( t R ), UV spectrum data, fluorescence characteristics, extracted ion current (EIC) results, molecular weight and mass fragment behavior information based on HPLC/MS technology, it is easy to infer the corresponding components in a complex mixture [6–8] .…”

Section: Introductionmentioning

confidence: 99%

Acetylated Rhamnose Triterpenoid Saponins from Glechoma longituba Analyzed by LC‐Q‐TOFMS

Ouyang

Ma²,

Xie

et al. 2021

Chemistry & Biodiversity

View full text Add to dashboard Cite

The aim of the present work is to isolate a series of triterpene derivatives with rhamnosyl linking acetyl groups from Glechoma longituba according to the structural characteristics of previously described triterpene saponins. The extract ion chromatography spectrum of the crude extract of G. longituba was detected and analyzed by HPLC‐HR‐ESI‐MS to determine possible components, and these metabolites were traced and separated by combining high‐resolution mass spectrometry and predicted liquid chromatography retention time. Three 11α, 12α‐epoxypentacyclic oleanolic acid triterpene saponins (glechomanosides H–J) and one ursane triterpene aldehyde saponin with a C‐28 aldehyde group were isolated from G. longituba. The structure of these compounds was confirmed by NMR and compared with those of previously characterized compounds. The strategy described in this report enables a rapid, reliable, and complete analysis of glycoside compounds containing different numbers of acetyl groups at different positions on the sugar.

show abstract

Rapid Characterization of Triterpene Saponins from Zornia brasiliensis by HPLC-ESI-MS/MS

Cited by 11 publications

References 37 publications

HESI-MS/MS Analysis of Phenolic Compounds from Calendula aegyptiaca Fruits Extracts and Evaluation of Their Antioxidant Activities

HESI-MS/MS Analysis of Phenolic Compounds from Calendula aegyptiaca Fruits Extracts and Evaluation of Their Antioxidant Activities

Mass spectrometry as a tool for the dereplication of saponins from Ampelozizyphus amazonicus Ducke bark and wood

Acetylated Rhamnose Triterpenoid Saponins from Glechoma longituba Analyzed by LC‐Q‐TOFMS

Contact Info

Product

Resources

About