Cited by 81Natural Antidiabetic Agents StudiesFlavonoids in Medical ResearchProtein Interaction Studies and Fluorescence Analysis

The inhibitory effects of flavonoids and antiestrogens on the Glut1 glucose transporter in human erythrocytes

Martin, Hans-Jörg, Kornmann, Frank, Fuhrmann, Günter Fred·2003·Chemico-Biological Interactions

Abstract

Flavonoids and isoflavonoids are potent inhibitors of glucose efflux in human erythrocytes. Net changes of sugars inside the cells were measured by right angle light scattering. The inhibitory potency of hydroxylated flavonoids depends on the pH of the medium. The apparent affinity is maximal at low pH where the molecule is in the undissociated form. The following K(i)-values at pH 6.5 in microM have been obtained: phloretin 0.37+/-0.03, myricetin 0.76+/-0.42, quercetin 0.93+/-0.28, kaempferol 1.33+/-0.17, isoliquiritigenin 1.96, genistein 3.92+/-0.62, naringenin 8.88+/-1.88, 7-hydroxyflavone 17.58+/-3.15 and daidzein 18.62+/-2.85. Flavonoids carrying hydroxyl groups are weak acids and are deprotonated at high pH-values. From spectral changes pK-values between 6.80 (naringenin) and 7.73 (myricetin) have been calculated. No such pK-value could be obtained from quercetin which was rather unstable at alkaline pH. Flavone itself without a hydroxyl group does not demonstrate any absorbance changes at different pH-values and no significant change in inhibition of glucose transport with pH (K(i)-value around 35 microM). In this respect it is similar to the antiestrogens diethylstilbestrol, tamoxifen and cyclofenil with K(i)-values for glucose efflux inhibition of 2.61+/-0.30, 6.75+/-2.03 and 3.97+/-0.54 microM. Except for phloretin, the flavonoids investigated have planar structures. The inhibitory activity in glucose efflux of planar flavonoids increases exponentially with the numb…

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Crossref · 10.1016/j.cbi.2003.06.001

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Authors
Martin, H.-J., Kornmann, F., & Fuhrmann, G. F.
Affiliations
Philipps University of Marburg (DE)
Corresponding author
Fuhrmann, Günter Fred
Venue
Chemico-Biological Interactions
Publisher
Elsevier BV
Published
2003-12
Volume
146
Issue
3
Pages
225-235
ISSN
0009-2797 (ISSN-L)
OpenAlex
W2057656781
Cited by
80
References
21
Citations by year
2026: 1 · 2025: 4 · 2024: 3 · 2023: 3 · 2022: 2 · 2021: 5 · 2020: 3 · 2019: 7 · 2018: 6 · 2017: 3 · 2016: 7 · 2015: 6 · 2014: 1 · 2013: 6 · 2012: 2
FWCI
2.24
Type
journal article
Language
en
Open access
closed
Locations
  • Chemico-Biological Interactions (publishedVersion)
  • PubMed (publishedVersion)
Topics
  • Health Sciences › Medicine › Endocrinology, Diabetes and Metabolism › Natural Antidiabetic Agents Studies
  • Health Sciences › Medicine › Pharmacology › Flavonoids in Medical Research
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Protein Interaction Studies and Fluorescence Analysis
Keywords
flavonoids, isoflavonoids, antiestrogens, GLUT1 glucose transporter, human erythrocytes, phloretin, myricetin, quercetin, kaempferol, isoliquiritigenin, genistein, naringenin, daidzein, flavones, diethylstilbestrol, tamoxifen, cyclofenil, pK values, pH dependence, hydroxyl number, planar structures
MeSH terms
Erythrocytes, Flavonoids, Humans, Hydrogen-Ion Concentration, Kinetics, Monosaccharide Transport Proteins, Estrogen Receptor Modulators, Glucose Transporter Type 1, In Vitro Techniques

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