Cited by 64Mangiferin and Mango ExtractsMolecular spectroscopy and chiralityChemical Reaction Mechanisms

UV/vis, 1H, and 13C NMR spectroscopic studies to determine mangiferin pKa values

Gómez-Zaleta, Berenice, Ramírez-Silva, María Teresa, Gutiérrez, Atilano, González-Vergara, Enrique, Güizado-Rodríguez, Marisol, Rojas-Hernández, Alberto·2006·Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy

Abstract

The acid constants of mangiferin (a natural xanthonoid) in aqueous solution were determined through an UV/vis spectroscopic study employing the SQUAD program as a computational tool. A NMR study complements the pK(a) values assignment and evidences a H-bridge presence on 1-C. The chemical model used was consistent with the experimental data obtained. The pK(a) values determined with this procedure were as follows: H(4)(MGF)=H(3)(MGF)(-)+H(+), pKa1 (6-H)=6.52+/-0.06; H(3)(MGF)(-)=H(2)(MGF)(2-)+H(+), pKa2 (3-H)=7.97+/-0.06; H(2)(MGF)(2-)=H(MGF)(3-)+H(+), pKa3 (7-H)=9.44+/-0.04; H(MGF)(3-)=(MGF)(4-)+H(+), pKa4 (1-H)=12.10+/-0.01; where it has been considered mangiferin C(19)H(18)O(11) as H(4)(MGF). Mangiferin UV/vis spectral behavior, stability study in aqueous solution as well as NMR spectroscopy studies: one-dimensional (1)H,(13)C, 2D correlated (1)H/(13)C performed by (g)-HSQC and (g)-HMBC methods; are also presented. pK(a) values determination of H(4)(MGF) in aqueous solution is a necessary contribution to subsequent pharmacokinetic study, and a step towards the understanding of its biological effects.

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Crossref · 10.1016/j.saa.2005.09.009

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  • 1-OH and 3-OH of MGN are likely to suffer oxidation.

    “It is also worth remembering that even though the 6-OH and 7-OH are the most important groups concerning the antioxidant activity of MGN, 1-OH and 3-OH (out of the cavity) are also likely to suffer the oxidation process (Gómez-Zaleta et al., 2006).”

    From Antioxidant activity of the mangiferin inclusion complex with β-cyclodextrin (2013) · cites this paper as Gómez-Zaleta et al., 2006

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Authors
Gómez-Zaleta, B., Ramírez-Silva, M. T., Gutiérrez, A., González-Vergara, E., Güizado-Rodríguez, M., & Rojas-Hernández, A.
Affiliations
Universidad Autónoma Metropolitana (MX)
Venue
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy
Publisher
Elsevier BV
Published
2006-07
Volume
64
Issue
4
Pages
1002-1009
ISSN
1386-1425 (ISSN-L)
OpenAlex
W2009348679
Cited by
64
References
34
Citations by year
2026: 3 · 2025: 2 · 2024: 4 · 2023: 4 · 2022: 3 · 2021: 2 · 2020: 1 · 2019: 6 · 2018: 3 · 2017: 5 · 2016: 5 · 2014: 4 · 2013: 3 · 2012: 5
FWCI
7.59
Type
journal article
Language
en
Open access
closed
Locations
  • Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy (publishedVersion)
  • PubMed (publishedVersion)
Topics
  • Health Sciences › Medicine › Complementary and alternative medicine › Mangiferin and Mango Extracts
  • Physical Sciences › Chemistry › Spectroscopy › Molecular spectroscopy and chirality
  • Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
Keywords
mangiferin, pKa determination, acid dissociation constants, protonation states, aqueous stability, 1H NMR, 13C NMR, pharmacokinetics
MeSH terms
Carbon Isotopes, Hydrogen-Ion Concentration, Magnetic Resonance Imaging, Models, Chemical, Magnetic Resonance Spectroscopy, Protons, Sodium Hydroxide, Spectrophotometry, Ultraviolet, Ultraviolet Rays, Xanthones

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