Green Extraction of Alkaloids and Polyphenols from Leaves with Natural Deep Eutectic Solvents and Profiling by HPLC-PDA-IT-MS/MS and HPLC-QTOF-MS/MS.

Jeniffer Torres-Vega, Sergio Gómez-Alonso, José Pérez-Navarro, Edgar Pastene-Navarrete
Author Information
  1. Jeniffer Torres-Vega: Pharmacognosy laboratory, Department of Pharmacy, Faculty of Pharmacy, Unidad de Desarrollo Tecnológico (UDT), University of Concepción, Concepción 4191996, Chile.
  2. Sergio Gómez-Alonso: Regional Institute for Applied Scientific Research, Faculty of Chemical Sciences, University of Castilla-La Mancha, Castilla-La Mancha, 10, 1307 Ciudad Real, Spain. ORCID
  3. José Pérez-Navarro: Regional Institute for Applied Scientific Research, Faculty of Chemical Sciences, University of Castilla-La Mancha, Castilla-La Mancha, 10, 1307 Ciudad Real, Spain.
  4. Edgar Pastene-Navarrete: Pharmacognosy laboratory, Department of Pharmacy, Faculty of Pharmacy, Unidad de Desarrollo Tecnológico (UDT), University of Concepción, Concepción 4191996, Chile. ORCID

Abstract

Mol., is a Chilean medicinal tree used for gastrointestinal and liver diseases. Such medicinal properties are associated with the presence of bioactive flavonoids and aporphine alkaloids. In this study, a new green and efficient extraction method used seven natural deep eutectic solvents (NADES) as extraction media. The extraction efficiency of these NADES was assessed, determining the contents of boldine and total phenolic compounds (TPC). Chemical profiling of was done by high-performance liquid chromatography coupled to photo diode array detector and electrospray ion-trap mass spectrometry (HPLC-PDA-ESI-IT/MS) and electrospray ionization quadrupole time-of-flight high-resolution mass spectrometry (HPLC-ESI-QTOF-MS). Among the NADES tested, NADES4 (choline chloride-lactic acid) and NADES6 (proline-oxalic acid) enable better extraction of boldine with 0.427 ± 0.018 and 2.362 ± 0.055 mg of boldine g of plant, respectively. Extraction of boldine with NADES4 and NADES6 was more efficient than extractions performed with methanol and water. On the other hand, the highest TPC were obtained using NADES6, 179.442 ± 3.79 mg of gallic acid equivalents (GAE g). Moreover, TPC in extracts obtained with methanol does not show significant differences with NADES6. The HPLC-PAD-MS/MS analysis enable the tentative identification of 9 alkaloids and 22 phenolic compounds. The results of this study demonstrate that NADES are a promising green extraction media to extract bioactive compounds and could be a valuable alternative to classic organic solvents.

Keywords

References

J Chromatogr A. 2010 Jan 22;1217(4):443-9 [PMID: 20022332]
Fitoterapia. 2016 Jul;112:30-37 [PMID: 27118320]
Fitoterapia. 2012 Apr;83(3):441-60 [PMID: 22178683]
Talanta. 2017 Jun 1;168:329-335 [PMID: 28391863]
J Nat Prod. 2018 Mar 23;81(3):679-690 [PMID: 29513526]
Pharmacol Res. 1994 Jan-Feb;29(1):1-12 [PMID: 8202440]
Anal Chim Acta. 2013 Mar 5;766:61-8 [PMID: 23427801]
Phytochem Anal. 2015 Sep-Oct;26(5):339-45 [PMID: 26108161]
J Am Chem Soc. 2004 Jul 28;126(29):9142-7 [PMID: 15264850]
Fitoterapia. 2018 Jun;127:179-185 [PMID: 29454020]
Int J Mol Sci. 2013 Mar 12;14(3):5750-64 [PMID: 23481637]
Plant Physiol. 2011 Aug;156(4):1701-5 [PMID: 21677097]
J Ethnopharmacol. 2018 Dec 5;227:139-149 [PMID: 30179713]
Sci Rep. 2019 Oct 4;9(1):14327 [PMID: 31586109]
Phytother Res. 2009 Jul;23(7):1024-7 [PMID: 19145575]
Int J Anal Chem. 2017;2017:5178729 [PMID: 29348751]
Mol Med. 2012 Sep 25;18:1136-46 [PMID: 22714713]
Toxicol Appl Pharmacol. 2015 May 15;285(1):12-22 [PMID: 25771127]
J Agric Food Chem. 2017 May 10;65(18):3591-3601 [PMID: 28414232]
Int J Mol Sci. 2014 Apr 25;15(5):7183-98 [PMID: 24776762]
Int J Mol Sci. 2018 Jun 25;19(7): [PMID: 29941815]
Neurotoxicology. 2008 Nov;29(6):1136-40 [PMID: 18590764]
J Pharm Anal. 2017 Apr;7(2):77-86 [PMID: 29404021]
Talanta. 2010 Dec 15;83(2):623-30 [PMID: 21111183]
Ultrason Sonochem. 2013 Jan;20(1):287-93 [PMID: 22784641]
Chem Soc Rev. 2012 Nov 7;41(21):7108-46 [PMID: 22806597]
Planta Med. 1991 Dec;57(6):519-22 [PMID: 1818341]
Molecules. 2018 Jul 20;23(7): [PMID: 30036998]
J Chromatogr A. 2018 Sep 14;1567:99-110 [PMID: 30033169]
Chem Biol Interact. 2006 Jan 5;159(1):1-17 [PMID: 16221469]
Anal Chim Acta. 2017 Aug 1;979:1-23 [PMID: 28599704]
Free Radic Res. 2003 Apr;37(4):447-52 [PMID: 12747739]
Chem Rev. 2014 Nov 12;114(21):11060-82 [PMID: 25300631]
J Nat Prod. 2017 May 26;80(5):1387-1396 [PMID: 28414230]
Phytother Res. 2014 Nov;28(11):1637-45 [PMID: 24853276]

Grants

  1. 1150948/Fondo Nacional de Desarrollo Científico y Tecnológico
  2. FONDEQUIP EQM150025/Comisión Nacional de Investigación Científica y Tecnológica
  3. Beca Conicyt Doctorado Nacional Nº 21150990/Comisión Nacional de Investigación Científica y Tecnológica
  4. Program of Investigation Associative (PIA), project AFB170007/Comisión Nacional de Investigación Científica y Tecnológica

Word Cloud

Similar Articles

Cited By