The DOI matches its Crossref record; 47 of the 47 references it cites were found in a registry or an index.
The mode of action of allicin: its ready permeability through phospholipid membranes may contribute to its biological activity
Open accessAbstract
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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In the citing paper
“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]
In the citing paper
“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]
In the citing paper
“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]
In the citing paper
“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]
Citations
Cites
Oxidized Redox State of Glutathione in the Endoplasmic Reticulum
Hwang, C., Sinskey, A. J., & Lodish, H. F. (1992) · Science · doi:10.1126/science.1523409 · Cited by 1,968
Vist, M., & Davis, J. H. (1990) · Biochemistry · doi:10.1021/bi00454a021 · Cited by 1,121
Transport and Diffusion Across Cell Membranes
Stein, W. D., & Lieb, W. R. (1986) · Elsevier eBooks · doi:10.1016/b978-0-12-664660-3.x5001-7 · Cited by 1,029
Ellman's reagent: 5,5′-dithiobis(2-nitrobenzoic acid)—a reexamination
Riddles, P. W., Blakeley, R. L., & Zerner, B. (1979) · Analytical Biochemistry · doi:10.1016/0003-2697(79)90792-9 · Cited by 1,027
The Organosulfur Chemistry of the Genus Allium – Implications for the Organic Chemistry of Sulfur
Block, E. (1992) · Angewandte Chemie International Edition in English · doi:10.1002/anie.199211351 · Cited by 997
Cavallito, C. J., & Bailey, J. H. (1944) · Journal of the American Chemical Society · doi:10.1021/ja01239a048 · Cited by 770
Permeability of small nonelectrolytes through lipid bilayer membranes
Walter, A., & Gutknecht, J. (1986) · The Journal of Membrane Biology · doi:10.1007/bf01870127 · Cited by 502
Garlic: The Science and Therapeutic Application of Allium Sativum L. and Related Species
Heinrich, P., & Larry, D. L. (1996) · Cited by 494
The mode of action of allicin: trapping of radicals and interaction with thiol containing proteins
Rabinkov, A., Miron, T., Konstantinovski, L., Wilchek, M., Mirelman, D., & Weiner, L. (1998) · Biochimica et Biophysica Acta (BBA) - General Subjects · doi:10.1016/s0304-4165(97)00104-9 · Cited by 426
Self-citationGarlic: A Review of Its Medicinal Effects and Indicated Active Compounds
Lawson, L. D. (1998) · ACS symposium series · doi:10.1021/bk-1998-0691.ch014 · Cited by 362
Research works printed but not linked: 2
- Stoll, 1951, Chemical investigation on alliin, the specific pinciple of garlic, Adv. Enzymol., 11, 377
- Overton, 1899, Vierteljahresschr. Naturforsch. Ges. Zurich, 44, 88
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Hyldgaard, M., Mygind, T., & Meyer, R. L. (2012) · Frontiers in Microbiology · doi:10.3389/fmicb.2012.00012 · Cited by 2,191
Physiological Implications of Hydrogen Sulfide: A Whiff Exploration That Blossomed
Wang, R. (2012) · Physiological Reviews · doi:10.1152/physrev.00017.2011 · Cited by 1,962
Chemical Constituents and Pharmacological Activities of Garlic (Allium sativum L.): A Review
El-Saber Batiha, G., Magdy Beshbishy, A., G. Wasef, L., Elewa, Y. H. A., A. Al-Sagan, A., Abd El-Hack, M. E., Taha, A. E., M. Abd-Elhakim, Y., & Prasad Devkota, H. (2020) · Nutrients · doi:10.3390/nu12030872 · Cited by 931
Allicin: Chemistry and biological properties
Borlinghaus, J., Albrecht, F., Gruhlke, M., Nwachukwu, I., & Slusarenko, A. (2014) · Molecules · doi:10.3390/molecules190812591 · Cited by 893
Hydrogen sulfide mediates the vasoactivity of garlic
Benavides, G. A., Squadrito, G. L., Mills, R. W., Patel, H. D., Isbell, T. S., Patel, R. P., Darley-Usmar, V. M., Doeller, J. E., & Kraus, D. W. (2007) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0705710104 · Cited by 902
Metadata
- 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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