¹H NMR-based Chemical Profiling of Retail Samples of Peumus boldus (Boldo) Leaves
DOI:
https://doi.org/10.29356/jmcs.v69i3.2336Keywords:
1H NMR, Peumus boldus M., aqueous extract, chemical profiling, multivariate analysis, HRMS-ESI, boldineAbstract
Abstract. Aqueous extracts of seven commercial samples of boldo leaves (Peumus boldus) were subjected to 1H NMR analysis to elucidate their chemical profiling. The ground leaves were extracted with ultrasound using water as a solvent at 60 °C for 15 min. The resulting extracts were then analyzed using 1H NMR spectroscopy, unveiling the presence of seven amino acids (alanine, asparagine, glutamine, phenylalanine, proline, tyrosine, and valine), three sugars (α- and β-glucose, fructose, and sucrose), and seven short-chain carboxylic acids (acetic, citric, formic, glyceric, malic, malonic, and succinic acids). Through multivariate statistical analysis of the gathered 1H NMR data, including PCA and OPLS-DA, a consistent chemical profile emerged across the examined samples. Variations were mainly due to differences in the relative concentrations of the mentioned metabolites. In addition, High Resolution Mass Spectrometry-ESI (HRMS-ESI) confirmed the presence of boldine in all samples tested, aiding in the authentication of boldo samples. Additionally, the major alkaloid N-methyllaurotetanine, a typical component of boldo leaves, was also identified.
Resumen. Los extractos acuosos de siete muestras comerciales de hojas de boldo (Peumus boldus) se sometieron a análisis de RMN 1H para dilucidar su perfil químico. Las hojas molidas se extrajeron por ultrasonido utilizando agua como disolvente a 60°C durante 15 minutos. Los extractos resultantes se sometieron a análisis por RMN 1H, revelando la presencia de siete aminoácidos (alanina, asparagina, glutamina, fenilalanina, prolina, tirosina y valina), tres azúcares (α y β-glucosa, fructosa y sacarosa) y siete ácidos carboxílicos de cadena corta (acético, cítrico, glicérico, málico, malónico y succínico). Mediante el análisis estadístico multivariante de los datos de RMN 1H reunidos, incluyendo PCA y OPLS-DA, se observó un perfil químico coherente en todas las muestras examinadas. Las variaciones se debieron principalmente a diferencias en las concentraciones relativas de los metabolitos mencionados. Además, la espectrometría de masas de alta resolución-ESI (HRMS-ESI) confirmó la presencia de boldina en todas las muestras analizadas, ayudando a la autenticación de las muestras de boldo. También se identificó el alcaloide principal N-metillaurotetanina, un componente típico de las hojas de boldo.
Downloads
References
Ravindran, P.N.; Pillai G.S.; Divakaran M. K.V. Peter.Woodhead Publishing. 2012, 2, 557-582. DOI: https://doi.org/10.1533/9780857095688.557.
Cassels, B. K. Springer, Cham. 2021, 2, 429-438. DOI: https://doi.org/10.1007/978-3-030-62818-5_33.
Vogel, H.; Razmilic, I.; Muñoz, M.; Doll, U.; San Martín, J. Planta Med. 1999, 65, 90-91. DOI: https://doi.org/10.1055/s-2006-960450.
Speisky, H.; Cassels, B.K. Pharmacol. Res. 1994, 29, 1-12. DOI: https://doi.org/10.1016/1043-6618(94)80093-6.
De Souza, P.; Vilhena da Silva, R.; Mota da Silva, L.; Steimbach, V.; Moreno, K.; Gasparotto, A. J. Evidence-Based Complementary Altern. Med. 2022, 2022, 4560607. DOI: https://doi.org/10.1155/2022/4560607.
Refaie, A.; Shalby, A. B.; Booles H. F.; Kassem, S.M.; Eshak, M. G.; Farrag, A.R.H.; Khalil W.K.B. Egypt. J. Chem. 2022, 65, 687-698. DOI: https://doi.org/10.21608/EJCHEM.2022.120306.5401.
O’Brien, P.; Carrasco-Pozo, C.; Speisky, H. Chem. Biol. Interact. 2006, 159, 1-17. DOI: https://doi.org/10.1016/j.cbi.2005.09.002.
Yang, X.; Gao, X.; Cao, Guo, Q.; Li, S.; Zhu, Z.; Zhao, Y.; Tu, P.; Chai, X. Planta Med. 2018, 84, 20-25. DOI: https://doi.org/10.1055/s-0043-113447.
Subramaniam, N.; Kannan, P.; Ashokkumar K.; Thiruvengadam, D. J. Biochem. Mol. Toxicol. 2019, 33, e22404. DOI: https://doi.org/10.1002/jbt.22404.
Heidari, R.; Moezi, L.; Asadi, B.; Ommati, M.M.; Azarpira, N. PharmaNutrition. 2017, 5, 109-117. DOI: https://doi.org/10.1016/j.phanu.2017.07.001.
Park, I; Lee, H-S; Lee, S-G; Park, J-D; Ahn, V-J. J. Econ. Entomol. 2000, 93, 331-335. DOI: https://doi.org/10.1603/0022-0493-93.2.331.
Otero, C.; Miranda-Rojas, S.; Llancalahuén, F.M.; Fuentes, J.A.; Atala, C.; González-Silva, G.; Verdugo, D.; Sierra-Rosales, P., Moreno, A., Gordillo-Fuenzalida, F. Food Chem. 2022, 370, 131012. DOI: https://doi.org/10.1016/j.foodchem.2021.131012.
Passone, M.A; Etcheverry, M. Int. J. Food Microbiol. 2014, 168-169, 17-23. DOI: https://doi.org/10.1016/j.ijfoodmicro.2013.10.009.
Silva Borges de Castro, D.; Brentan da Silva, D.; Domingues-Tibúrcio, J.; Guerra-Sobral, M.E.; Ferraz, V.; Gutterres-Taranto, A.; Serrão, J.E.; Máximo de Siquiera, J.; Nunes-Alves, S. Exp. Parasitol. 2016, 171, 84-90. DOI: https://doi.org/10.1016/j.exppara.2016.10.008.
Dias-Machado, C.; Pereira dos Santos, V.L.; Schimandeiro-Novak, R., Schechtel-Koch, M., Arcaro, G., Raman, V., Cavichiolo-Franco, C.R., Farago, P.V., Manfron-Budel, J. Flora. 2021, 279, 151827. DOI: https://doi.org/10.1016/j.flora.2021.151827.
Cardoso-Correla-Teixeira, C.; Pereira de Freitas-Carbal, T.; Barreto de Sousa, J.P., Teixeira, S.P.; Kenupp-Bastos, J.; de Freitas, L.A.P. Pharmacogn. J. 2016, 8, 264-272. DOI: https://doi.org/10.5530/pj.2016.3.16.
Steenkamp, P.A; Steenkamp, L.H.; Mancama, D.T. Springer, Cham. 2018, 303-347. DOI: https://doi.org/10.1007/978-3-319-62229-3_10.
Félix-Silva, J.; Tomaz, I.M.; Silva, M.G.; Santos, K.S.C.R.; Silva-Júnior, A.A.; Carvalho, M.C.R.D.; Soares, L.A.L.; Fernandes-Pedrosa, M.F. Rev. Bras. de Plantas Medicinais. 2012, 14, 548-555. DOI: https://doi.org/10.1590/S1516-05722012000300018.
Bakiri, A.; Hubert, J.; Reynaud, R.; Lanthony, S.; Harakat, D.; Renault, J-H.; Nuzillard, J-M. J. Nat. Prod. 2017, 80, 1387-1396. DOI: https://doi.org/10.1021/acs.jnatprod.6b01063.
Simirgiotis, M.J.; Schmeda-Hirschmann, G. J. Chromatogr. A. 2010, 1217, 443-449. https://doi.org/10.1016/j.chroma.2009.11.014.
Torres-Vega, J; Gómez-Alonso, S; Pérez-Navarro, J; Pastene-Navarrete, E. Plants. 2020, 9, 242 DOI: https://doi.org/10.3390/plants9020242.
Xu, Y; Liu, Z; Liu, Z; Feng, Z; Zhang, L; Wan, X; Yang, X. Food Chem. 2020, 317,126428. DOI: http://doi.org/10.1016/j.foodchem.2020.126428.
Zhao, M.; Ma, Y; Dai, L-L; Zhang, D-L; Li, J-H; Yuan, W-X; Li, Y; Zhou, H. Food Anal. Methods. 2013, 6(1), 69–75. DOI: https://doi.org/10.1007/s12161-012-9408-4.
Alcázar, A; Ballesteros, O; Jurado, J. M; Pablos, F; Martín, M. J; Vilches, J. L; Navalón, A. J. Agric. Food Chem. 2007, 55, 5960-5965. DOI: https://doi.org/10.1021/jf070601a.
Gladden, L. B. J. Physiol. 2004, 558, 5-30. DOI: https://doi.org/10.1113/jphysiol.2003.058701.
Seigler, D.S.S. Plant Secondary Metabolism. 1998, 578–616. DOI: https://doi.org/10.1007/978-1-4615-4913-0_32.
Lea, P.J.; Sodek, L.; Parry, M.A.J.; Shewry P.R.; Halford, N.G. Ann. Appl. Biol. 2006, 150, 1-26. https://doi.org/10.1111/j.1744-7348.2006.00104.x.
Asai, N; Nakajima, N; Tamaoki, M; Kamada, H; Kondo, N. Plant Cell Physiol. 2000, 41, 10-15. DOI: https://doi.org/10.1093/pcp/41.1.10.
Kirma, M; Araújo, W. L; Fernie, A. R; Galili, G. J. Exp. Bot. 2012, 63, 4995-5001. https://doi.org/10.1093/jxb/ers119.
Fuentes-Barros, G; Castro-Saavedra, S; Liberona, L; Acevedo-Fuentes, W; Tirapegui, C; Mattar, C; Cassels, B. K. Fitoterapia. 2018, 127, 179–185. DOI: https://doi.org/10.1016/j.fitote.2018.02.020.
Ribeiro, F. F; Da Conceicão, L.D.O; Oyama, E. M; Furlan, M. R. Visão Acadêmica. 2017, 18. DOI: https://doi.org/10.5380/acd.v18i3.54224.
Santos, R.L.; Nobre, M.S.C., Guimarães, G.P., Viera, K.V.M., Felismino, D.C., Dantas, I.C., Silva, L.A. CABI, 2011, 9781845938338.0666, 666-669. DOI: https://doi.org/10.1079/9781845938338.0666.
Mauro, C; Silva, C. de P; Missima, J; Ohnuki, T; Rinaldi, R. B; Frota, M. Rev. Brasileira de Farmacognosia. 2008, 18, 608–613. DOI: https://doi.org/10.1590/s0102-695x2008000400019.
Pereira-Dos Santos, L; Azevedo-Martins, R.C.; Kelce-Pires, C; Oliveira-Gomes, A; Larcher-De Almeida, M.F; Cruz-Da Rocha, E.D.A; Santana-Carvalho, E.L; Dolejal-Zanetti, G. Braz. J. Health Rev. 2023, 6, DOI: https://doi.org/10.34119/bjhrv6n2-059.
Milaneze-Gutierre, M. A; Famelli, M. C; Capel, L. S; Romagnolo, M. B. Acta Sci.Biol. Sci. 2007, 29, 125-130.
Ramos da Silva, L.R.; Ataide-Correia, Z; Cajueiro-Gurgel, E.S; Ribeiro, O; Gomes-Silva, S; Oliveira-Ferreira, O; Andrade, E.H.A; Santana de Oliveira, M. Molecules. 2023, 28, 6482. DOI: https://doi.org/10.3390/molecules28186482.
Duarte, M. D. R.; Lopes, J. F. Rev. Brazilian Pharmacogn. 2007, 17, 549-556. DOI: https://doi.org/10.1590/S0102-695X2007000400013.
Almeida, F. C. G.; Lemonica, I. P. J. Ethnopharmacol. 2000, 73, 53–60. DOI: https://doi.org/10.1016/s0378-8741(00)00275-0.
Machado, C. D; Pereira dos Santos, V. L; Novak, R. S; Koch, M. S; Arcaro, G; Raman, V; Budel, J. M. Flora. 2021, 279, 151827. DOI: https://doi.org/10.1016/j.flora.2021.151827.
Kazemi-Noureini, S; Tanavar, F. Chem.-Biol. Interact. 2015, 231, 27–34. DOI: https://doi.org/10.1016/j.cbi.2015.02.020.
Siiang-Lau, Y; Chih-Ling, W; Murugan, D; Mustafa, M.R. J. Cardiovasc. Pharmacol. 2015, 65, 522-531. DOI: https://doi.org/10.1097/FJC.0000000000000185.
Cassels, B.K.; Fuentes-Barros, G.; Castro-Saavedra, S. Curr. Tradit. Med. 2018, 5, 31-65. DOI: https://doi.org/10.2174/2215083804666181113112928.
Galvez-Ranilla, L.; Knon, Y.I.; Apostolidis, E.; Shetty, K. Bioresour. Technol. 2010, 10, 4676-4689. DOI: https://doi.org/10.1016/j.biortech.2010.01.093.
Mello de Souza, W.F.; Mariano, X.M.; Isnard, J.L.; Santos de Souza, G.; De Souza, A.L.; Tavares de Carvalho, R.J.; Barbosa, C.; Siqueira, C.L.; Alves, R.F. Food Int. Res. 2019, 124, 27-33. DOI: https://doi.org/10.1016/j.foodres.2018.12.059.
Simirgiotis, M.J.; Schemeda-Hirschmann, G.J. Chromatogr. A. 2010, 1217, 443-449. DOI: https://doi.org/10.1016/j.chroma.2009.11.014.

Downloads
Published
Issue
Section
License
Copyright (c) 2025 Estefanía de Jesús Terán-Sánchez, Yair Cruz-Narvaez, Erick A. Herrera-Jurado, Mabel M. Montenegro-Sustaita, Elvia Becerra-Martínez, L. Gerardo Zepeda-Vallejo

This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
