The mode of action of allicin: Its ready permeability through phospholipid membranes may contribute to its biological activity
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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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This information is mainly the basis of fungal death.
“This information is mainly the basis of fungal death19–20.”
From Bioactivities of Allium longicuspis Regel against anthracnose of mango caused by Colletotrichum gloeosporioides (Penz.) (2020) · cites this paper as [19]
Allicin is a sulfenic acid thioester and its pharmacological effect is attributed to its antioxidant activity and its interaction with thiol-containing proteins.
“Allicin (allyl thiosulfinate), is a sulfenic acid thioester and its pharmacological effect is attributed to its antioxidant activity as well as its interaction with thiol-containing proteins [37].”
From Chemical Constituents and Pharmacological Activities of Garlic (Allium sativum L.): A Review (2020) · cites this paper as [37]
Allinase enzyme, composed of pyridoxal phosphate (PLP), splits alliin and produces ammonium, pyruvate, and allyl sulfenic acid, which are highly reactive and unstable at room temperature, and two molecules combine to form allicin.
“This enzyme composed of pyridoxal phosphate (PLP) which splits alliin and produces ammonium, pyruvate, and allyl sulfenic acid that are highly reactive and unstable at room temperature, where two molecules were combined to form allicin [37,39].”
From Chemical Constituents and Pharmacological Activities of Garlic (Allium sativum L.): A Review (2020) · cites this paper as [37]
Allicin is a membrane-permeable compound that can enter cells easily and interact with cellular thiols such as glutathione or cysteine residues in proteins as well as enzymes containing reactive cysteine, and this may be the potential interpretation of allicin's toxicity.
“Allicin is a membrane-permeable compound that can enter cells easily and interact with cellular thiols such as glutathione or cysteine residues in proteins [37,89,90] as well as enzymes containing reactive cysteine and this may be the potential interpretation of allicin’s toxicity [63].”
From Chemical Constituents and Pharmacological Activities of Garlic (Allium sativum L.): A Review (2020) · cites this paper as [37]
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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)
- 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
- 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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