TY - JOUR
T1 - Identification of structurally diverse alkaloids in Talguenea quinquinervia (gill. Et hook) by liquid chromatography/electrospray ionisation tandem mass spectroscopy and insecticidal activity
AU - Quiroz-Carreño, Soledad
AU - Céspedes-Acuña, Carlos L.
AU - Seigler, David S.
AU - Alarcón-Enos, Julio
N1 - Funding Information:
To CONICYT FONDECYT N?1130463 and CONICYT FONDECYT N? 1161157. The authors are grateful for an internal grant from the Direcci?n de Investigaci?n, Universidad del Bio Bio, Chillan, Chile: DIUBB # 083009-2R, # 122509 and # 132209 GI/C.
Publisher Copyright:
© 2019 John Wiley & Sons, Ltd.
PY - 2019/11/1
Y1 - 2019/11/1
N2 - 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.
AB - 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.
KW - benzylisoquinoline alkaloid
KW - cyclopeptide alkaloid
KW - HPLC-MS analysis
KW - insecticidal activity
KW - Talguenea quinquinervia
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U2 - 10.1002/pca.2836
DO - 10.1002/pca.2836
M3 - Article
C2 - 31059202
AN - SCOPUS:85065308420
SN - 0958-0344
VL - 30
SP - 635
EP - 643
JO - Phytochemical Analysis
JF - Phytochemical Analysis
IS - 6
ER -