Cited by 358Garlic and Onion StudiesLipid Membrane Structure and BehaviorSulfur Compounds in Biology

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The mode of action of allicin: its ready permeability through phospholipid membranes may contribute to its biological activity

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Miron, Talia, Rabinkov, Aharon, Mirelman, David, Wilchek, Meir, Weiner, Lev·2000·Biochimica et Biophysica Acta (BBA) - Biomembranes

DOI 10.1016/s0005-2736(99)00174-1

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Abstract

Allicin (diallyl thiosulfinate) is the main biologically active component of the freshly crushed garlic extracts. In the present work the ability of allicin to cross through membranes (artificial and biological) was studied. Partition coefficients of allicin in water/octanol, water/hexadecane and water/phospholipids mixtures were determined. Using phospholipid vesicles loaded with hydrophilic thiols (reduced glutathione or 2-nitro-5-thiobenzoate), we observed that allicin freely permeates through phospholipid bilayers and interacts with the SH groups. The reaction rate of allicin with SH containing molecules after crossing the membrane was the same as in solution. Fast diffusion and permeation of allicin across human red blood cell membranes was also demonstrated. Allicin does not induce leakage, fusion or aggregation of membrane. The high permeability of allicin through membranes may greatly enhance the intracellular interaction with thiols.

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Authors: Miron, T., Rabinkov, A., Mirelman, D., Wilchek, M., & Weiner, L.
Affiliations: Weizmann Institute of Science (IL)
ORCID: Weiner, Lev
Venue: Biochimica et Biophysica Acta (BBA) - Biomembranes
Publisher: Elsevier BV
Published: 2000-01
Volume: 1463
Issue: 1
Pages: 20-30
ISSN: 0005-2736 (ISSN-L)
DOI: 10.1016/s0005-2736(99)00174-1
OpenAlex: W2037680251
Cited by: 353
References: 47
Citations by year: 2026: 9 · 2025: 11 · 2024: 12 · 2023: 17 · 2022: 16 · 2021: 28 · 2020: 28 · 2019: 17 · 2018: 16 · 2017: 11 · 2016: 10 · 2015: 16 · 2014: 16 · 2013: 13 · 2012: 18
FWCI: 10.05
Type: journal article
Language: en
Open access: bronze
doi.org
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
www.elsevier.com/open-access/userlicense/1.0/ (vor, 4947 d)
Locations: Biochimica et Biophysica Acta (BBA) - Biomembranes (publishedVersion)
PubMed (publishedVersion)
Topics: Life Sciences › Agricultural and Biological Sciences › Plant Science › Garlic and Onion Studies
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Lipid Membrane Structure and Behavior
Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Sulfur Compounds in Biology
Keywords: allicin, garlic, membrane permeability, phospholipid bilayers, partition coefficient, reduced glutathione, thiols, mechanism of action
MeSH terms: Cell Membrane Permeability, Disulfides, Electron Spin Resonance Spectroscopy, Erythrocyte Membrane, Garlic, Glutathione, Humans, Kinetics, Liposomes, Membrane Lipids, Nitrobenzoates, Magnetic Resonance Spectroscopy, Permeability, Phospholipids, Plants, Medicinal, Sulfhydryl Compounds, Sulfinic Acids, In Vitro Techniques

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The mode of action of allicin: its ready permeability through phospholipid membranes may contribute to its biological activity

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