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Evidence of noncovalent complexes in some natural extracts: Ceylon tea and mate extracts.
J Mass Spectrom. 2020 Jul; 55(7):e4459.JM

Abstract

Considering the high complexity of natural extracts, because of the presence of organic molecules of different chemical nature, the possibility of formation of noncovalent complexes should be taken into account. In a previous investigation, the formation of bimolecular complexes between caffeine and catechins in green tea extracts (GTE) has been experimentally proven by means of mass spectrometric and 1 H nuclear magnetic resonance experiments. The same approaches have been employed in the present study to evaluate the presence of bimolecular complexes in Ceylon tea and mate extracts. The obtained results show that in the case of Ceylon tea extracts, protonated theaflavin is detectable, together with theaflavin/caffein complexes, while caffeine/catechin complexes, already detected in green tea, are still present but at lower concentration. This aspect is evidenced by the comparison of precursor ion scans performed on protonated caffeine for the two extracts. The spectra obtained in these conditions for GTE and Ceylon tea show that the complexes of caffeine with epigallocatechin (EGC), epicatechin gallate (ECG), and epigallocatechin gallate (EGCG), highy abundant in the case of GTE (signal-to-chemical noise ratio in the range 50-100), are negligible (signal-to-chemical noise ratio in the range 2-3) in the case of Ceylon tea. Mate extracts show the formation of bimolecular complexes involving caffeine but not catechins, and chlorogenic acid becomes responsible for other complex formation. Under positive ion and negative ion conditions, accurate mass measurements allow the identification of malealdehyde, chlorogenic acid, caffeine, two isomers of dicaffeoylquinic acid, rutin, and kaempferol-3-O-rutinoside. These data indicate that the formation of complexes in natural extracts is a common behavior, and their presence must be considered in the description of natural extracts and, consequently, in their biological activity.

Authors+Show Affiliations

Nano-Inspired Biomedicine Lab, Fondazione Istituto di Ricerca Pediatrica Città della Speranza, 35127, Padova, Italy.First Surgical Clinic Section, Department of Surgical, Oncological and Gastroenterological Sciences, University of Padova, 35122, Padova, Italy.Nano-Inspired Biomedicine Lab, Fondazione Istituto di Ricerca Pediatrica Città della Speranza, 35127, Padova, Italy.Institute of Condensed Matter Chemistry and Technologies for Energy (ICMATE), National Research Council-CNR, 35127, Padova, Italy.Institute of Condensed Matter Chemistry and Technologies for Energy (ICMATE), National Research Council-CNR, 35127, Padova, Italy.Ricerca Fitochimica, Aboca S.p.A. Società Agricola, 52037, Località Aboca 20, San Sepolcro, Arezzo, Italy.Ricerca Fitochimica, Aboca S.p.A. Società Agricola, 52037, Località Aboca 20, San Sepolcro, Arezzo, Italy.Ricerca Fitochimica, Aboca S.p.A. Società Agricola, 52037, Località Aboca 20, San Sepolcro, Arezzo, Italy.Nano-Inspired Biomedicine Lab, Fondazione Istituto di Ricerca Pediatrica Città della Speranza, 35127, Padova, Italy.Nano-Inspired Biomedicine Lab, Fondazione Istituto di Ricerca Pediatrica Città della Speranza, 35127, Padova, Italy. First Surgical Clinic Section, Department of Surgical, Oncological and Gastroenterological Sciences, University of Padova, 35122, Padova, Italy.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31663260

Citation

Crotti, Sara, et al. "Evidence of Noncovalent Complexes in some Natural Extracts: Ceylon Tea and Mate Extracts." Journal of Mass Spectrometry : JMS, vol. 55, no. 7, 2020, pp. e4459.
Crotti S, D'Aronco S, Moracci L, et al. Evidence of noncovalent complexes in some natural extracts: Ceylon tea and mate extracts. J Mass Spectrom. 2020;55(7):e4459.
Crotti, S., D'Aronco, S., Moracci, L., Tisato, F., Porchia, M., Mattoli, L., Burico, M., Bedont, S., Traldi, P., & Agostini, M. (2020). Evidence of noncovalent complexes in some natural extracts: Ceylon tea and mate extracts. Journal of Mass Spectrometry : JMS, 55(7), e4459. https://doi.org/10.1002/jms.4459
Crotti S, et al. Evidence of Noncovalent Complexes in some Natural Extracts: Ceylon Tea and Mate Extracts. J Mass Spectrom. 2020;55(7):e4459. PubMed PMID: 31663260.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Evidence of noncovalent complexes in some natural extracts: Ceylon tea and mate extracts. AU - Crotti,Sara, AU - D'Aronco,Sara, AU - Moracci,Laura, AU - Tisato,Francesco, AU - Porchia,Marina, AU - Mattoli,Luisa, AU - Burico,Michela, AU - Bedont,Stella, AU - Traldi,Pietro, AU - Agostini,Marco, Y1 - 2019/12/02/ PY - 2019/07/02/received PY - 2019/10/07/revised PY - 2019/10/14/accepted PY - 2019/10/31/pubmed PY - 2021/3/27/medline PY - 2019/10/31/entrez KW - 1H NMR KW - Ceylon tea KW - Mate KW - accurate mass measurements KW - bimolecular complexes KW - natural products KW - precursor ion scans SP - e4459 EP - e4459 JF - Journal of mass spectrometry : JMS JO - J Mass Spectrom VL - 55 IS - 7 N2 - Considering the high complexity of natural extracts, because of the presence of organic molecules of different chemical nature, the possibility of formation of noncovalent complexes should be taken into account. In a previous investigation, the formation of bimolecular complexes between caffeine and catechins in green tea extracts (GTE) has been experimentally proven by means of mass spectrometric and 1 H nuclear magnetic resonance experiments. The same approaches have been employed in the present study to evaluate the presence of bimolecular complexes in Ceylon tea and mate extracts. The obtained results show that in the case of Ceylon tea extracts, protonated theaflavin is detectable, together with theaflavin/caffein complexes, while caffeine/catechin complexes, already detected in green tea, are still present but at lower concentration. This aspect is evidenced by the comparison of precursor ion scans performed on protonated caffeine for the two extracts. The spectra obtained in these conditions for GTE and Ceylon tea show that the complexes of caffeine with epigallocatechin (EGC), epicatechin gallate (ECG), and epigallocatechin gallate (EGCG), highy abundant in the case of GTE (signal-to-chemical noise ratio in the range 50-100), are negligible (signal-to-chemical noise ratio in the range 2-3) in the case of Ceylon tea. Mate extracts show the formation of bimolecular complexes involving caffeine but not catechins, and chlorogenic acid becomes responsible for other complex formation. Under positive ion and negative ion conditions, accurate mass measurements allow the identification of malealdehyde, chlorogenic acid, caffeine, two isomers of dicaffeoylquinic acid, rutin, and kaempferol-3-O-rutinoside. These data indicate that the formation of complexes in natural extracts is a common behavior, and their presence must be considered in the description of natural extracts and, consequently, in their biological activity. SN - 1096-9888 UR - https://www.unboundmedicine.com/medline/citation/31663260/Evidence_of_noncovalent_complexes_in_some_natural_extracts:_Ceylon_tea_and_mate_extracts_ L2 - https://doi.org/10.1002/jms.4459 DB - PRIME DP - Unbound Medicine ER -