Soledad Quiroz-Carreño1, Carlos L Céspedes-Acuña1, David S Seigler2, Julio Alarcón-Enos1. 1. Laboratorio de Síntesis y Biotransformación de Productos Naturales, Grupo de Investigación Química y Biotecnología de Productos Naturales Bioactivos, Departamento Ciencias Básicas, Universidad del Bio-Bio, Chillán, Chile. 2. Department of Plant Biology, Herbarium, University of Illinois at Urbana-Champaign, Urbana-Champaign, IL, USA.
Abstract
INTRODUCTION: Talguenea quinquinervia has been used in folk medicine and to dye wool, and the main constituents are alkaloids and triterpenes. Identification of these type of compounds in this specie is a necessary step to understand the biological properties. OBJECTIVE: To evaluate the relationship between the chemical composition of root from T. quinquinervia and its insecticidal properties using liquid chromatography electrospray ionisation tandem mass spectrometry (LC-ESI-MS/MS). METHODS: Alkaloids were extracted using Soxhlet extraction with methanol. Total extract was partitioned at pH 2 and 12 to enrich alkaloid constituents and to remove interferences. The separation of alkaloids in the Talguenea extract was performed on a C18 column using gradient elution and their tandem mass spectra were obtained by quadrupole time-of-flight tandem mass spectrometry (QTOF-MS/MS) to perform accurate mass measurements of fragment ions for the alkaloid constituents. RESULTS: Several types of alkaloids were separated and identified by LC-ESI-MS/MS. The structural assignment of individual alkaloids was performed based on convergence of MS/MS spectral data, pH partitioning behaviour, LC retention behaviour, and accurate mass measurements. The pH partition of the extract provided structural information about unknown alkaloids extracted from T. quinquinervia. A total of 20 compounds were identified and tentatively characterised, and of these 15 alkaloids were reported for the first time in the investigated T. quinquinervia. CONCLUSION: The chemical profiling of alkaloids in T. quinquinervia with different origins was performed for the first time and provided diagnostic ions for diverse alkaloids in T. quinquinervia. Insecticidal activity observed can be explain by the presence of alkaloid and pentacyclic triterpenes on the fractions assayed.
INTRODUCTION: Talguenea quinquinervia has been used in folk medicine and to dye wool, and the main constituents are alkaloids and triterpenes. Identification of these type of compounds in this specie is a necessary step to understand the biological properties. OBJECTIVE: To evaluate the relationship between the chemical composition of root from T. quinquinervia and its insecticidal properties using liquid chromatography electrospray ionisation tandem mass spectrometry (LC-ESI-MS/MS). METHODS:Alkaloids were extracted using Soxhlet extraction with methanol. Total extract was partitioned at pH 2 and 12 to enrich alkaloid constituents and to remove interferences. The separation of alkaloids in the Talguenea extract was performed on a C18 column using gradient elution and their tandem mass spectra were obtained by quadrupole time-of-flight tandem mass spectrometry (QTOF-MS/MS) to perform accurate mass measurements of fragment ions for the alkaloid constituents. RESULTS: Several types of alkaloids were separated and identified by LC-ESI-MS/MS. The structural assignment of individual alkaloids was performed based on convergence of MS/MS spectral data, pH partitioning behaviour, LC retention behaviour, and accurate mass measurements. The pH partition of the extract provided structural information about unknown alkaloids extracted from T. quinquinervia. A total of 20 compounds were identified and tentatively characterised, and of these 15 alkaloids were reported for the first time in the investigated T. quinquinervia. CONCLUSION: The chemical profiling of alkaloids in T. quinquinervia with different origins was performed for the first time and provided diagnostic ions for diverse alkaloids in T. quinquinervia. Insecticidal activity observed can be explain by the presence of alkaloid and pentacyclic triterpenes on the fractions assayed.
Authors: Evelyn Muñoz-Nuñez; Soledad Quiroz-Carreño; Edgar Pastene-Navarrete; David S Seigler; Carlos Céspedes-Acuña; Ignacio Martínez Valenzuela; Martina Oppliger Muñoz; Alexis Salas-Burgos; Julio Alarcón-Enos Journal: Metabolites Date: 2022-07-20
Authors: Soledad Quiroz-Carreño; Edgar Pastene-Navarrete; Cesar Espinoza-Pinochet; Evelyn Muñoz-Núñez; Luis Devotto-Moreno; Carlos L Céspedes-Acuña; Julio Alarcón-Enos Journal: Molecules Date: 2020-11-03 Impact factor: 4.411