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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. DOI: https://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. 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. 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. 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. 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. DOI: 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. 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. DOI: 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. 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. 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. 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. 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. 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. DOI: https://doi.org/10.4025/actascibiolsci.v29i2.445
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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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.
