Cited by 426Garlic and Onion StudiesFree Radicals and AntioxidantsRedox biology and oxidative stress

The mode of action of allicin: trapping of radicals and interaction with thiol containing proteins

Rabinkov, Aharon, Miron, Talia, Konstantinovski, Leonid, Wilchek, Meir, Mirelman, David, Weiner, Lev·1998·Biochimica et Biophysica Acta (BBA) - General Subjects

Abstract

Allicin (thio-2-propene-1-sulfinic acid S-allyl ester) is the main biologically active component of garlic clove extracts. Its biological activity was attributed to either antioxidant activity or thiol disulfide exchange. Antioxidant properties of both allicin and its precursor, alliin (+S-allyl-L-cysteine sulfoxide), were investigated in the Fenton oxygen-radical generating system [H2O2-Fe(II)]. Using the spin trapping technique and ESR, it was found that both compounds possessed significant antioxidant activity. The reaction between allicin and L-cysteine was studied by 1H and 13C-NMR, and a S-thiolation product, S-allylmercaptocysteine, was identified. Allicin irreversibly inhibited SH-protease papain, NADP(+)-dependent alcohol dehydrogenase from Thermoanaerobium brockii (TBAD), and the NAD(+)-dependent alcohol dehydrogenase from horse liver (HLAD). All the three enzymes could be reactivated with thiol containing compounds. Papain could be reactivated with glutathione, TBAD with dithiothreitol or 2-mercaptoethanol (2-ME) but not by glutathione, while HLAD could be reactivated only with 2-ME. This study demonstrates that in addition to its antioxidant activity, the major biological effect of allicin should be attributed to its rapid reaction with thiol containing proteins.

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Crossref · 10.1016/s0304-4165(97)00104-9

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Authors
Rabinkov, A., Miron, T., Konstantinovski, L., Wilchek, M., Mirelman, D., & Weiner, L.
Affiliations
Weizmann Institute of Science (IL)
Corresponding author
Rabinkov, Aharon
Venue
Biochimica et Biophysica Acta (BBA) - General Subjects
Publisher
Elsevier BV
Published
1998-02
Volume
1379
Issue
2
Pages
233-244
ISSN
0304-4165 (ISSN-L)
OpenAlex
W1975378692
Cited by
426
References
39
Citations by year
2026: 5 · 2025: 18 · 2024: 12 · 2023: 8 · 2022: 14 · 2021: 16 · 2020: 25 · 2019: 22 · 2018: 12 · 2017: 17 · 2016: 26 · 2015: 20 · 2014: 18 · 2013: 15 · 2012: 15
FWCI
11.12
Type
journal article
Language
en
Open access
closed
Locations
  • Biochimica et Biophysica Acta (BBA) - General Subjects (publishedVersion)
  • PubMed (publishedVersion)
Topics
  • Life Sciences › Agricultural and Biological Sciences › Plant Science › Garlic and Onion Studies
  • Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
Keywords
allicin, garlic, antioxidant activity, thiol-disulfide exchange, radical trapping, Fenton reaction, alliin, S-allylmercaptocysteine, papain, alcohol dehydrogenase, enzyme reactivation, thiol-containing proteins, spin trapping
MeSH terms
Alcohol Dehydrogenase, Alcohol Oxidoreductases, Animals, Antioxidants, Cysteine, Disulfides, Enzyme Reactivators, Garlic, Horses, Liver, Magnetic Resonance Spectroscopy, Papain, Plants, Medicinal, Proteins, Sulfinic Acids, Free Radical Scavengers, Gram-Positive Asporogenous Rods, Irregular, In Vitro Techniques

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