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[3H]Allicin: preparation and applications.

T Miron1, T Bercovici, A Rabinkov

  • 1Department of Biological Chemistry, The Weizmann Institute of Science, Rehovot 76100, Israel.

Analytical Biochemistry
|July 22, 2004
PubMed
Summary

Researchers developed a simple method to create tritium-labeled allicin, the active compound in garlic. This labeled allicin is useful for studying its biological activities and creating labeled derivatives for metabolic research.

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Editors' note.

Applied biochemistry and biotechnology·2013

Area of Science:

  • Biochemistry
  • Organic Chemistry
  • Pharmacology

Background:

  • Allicin, the active component of garlic, exhibits diverse biological activities.
  • Mechanistic and pharmacokinetic studies necessitate labeled allicin for research.
  • The volatile and unstable nature of allicin presents challenges for labeling.

Purpose of the Study:

  • To develop a straightforward method for preparing tritium-labeled allicin.
  • To synthesize labeled allicin derivatives for metabolic studies.
  • To investigate the interaction of labeled allicin with proteins.

Main Methods:

  • Preparation of synthetic [(3)H]alliin ([2,3-(3)H]allylcysteine sulfoxide).
  • Enzymatic conversion of [(3)H]alliin to [(3)H]allicin using immobilized alliinase.

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  • Purification of [(3)H]allicin via differential adsorption on Porapak Q resin.

    • Main Results:

    • A simple method for preparing [(3)H]labeled allicin was established.
    • [(3)H]allicin was successfully used to synthesize labeled [(3)H]allylmercapto derivatives of SH peptides and proteins, including [(3)H]S-allylmercaptoglutathione.
    • Incubation of alliinase with [(3)H]allicin resulted in the modification of 1.4 cysteine residues per enzyme subunit.

    Conclusions:

    • The developed method provides a reliable way to obtain labeled allicin.
    • Labeled allicin and its derivatives are valuable tools for metabolic and biochemical studies.
    • Allicin's reactivity with thiol groups was further confirmed through enzyme modification studies.