Allicin: Chemistry and biological properties

Borlinghaus, Jan; Albrecht, Frank; Gruhlke, Martin; Nwachukwu, Ifeanyi; Slusarenko, Alan

doi:10.3390/molecules190812591

Cited by 900Garlic and Onion StudiesGenomics, phytochemicals, and oxidative stressSulfur Compounds in Biology

Allicin: Chemistry and biological properties

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Borlinghaus, Jan, Albrecht, Frank, Gruhlke, Martin, Nwachukwu, Ifeanyi, Slusarenko, Alan·2014·Molecules

DOI 10.3390/molecules190812591PMC PMC6271412

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Abstract

Allicin (diallylthiosulfinate) is a defence molecule from garlic (Allium sativum L.) with a broad range of biological activities. Allicin is produced upon tissue damage from the non-proteinogenic amino acid alliin (S-allylcysteine sulfoxide) in a reaction that is catalyzed by the enzyme alliinase. Current understanding of the allicin biosynthetic pathway will be presented in this review. Being a thiosulfinate, allicin is a reactive sulfur species (RSS) and undergoes a redox-reaction with thiol groups in glutathione and proteins that is thought to be essential for its biological activity. Allicin is physiologically active in microbial, plant and mammalian cells. In a dose-dependent manner allicin can inhibit the proliferation of both bacteria and fungi or kill cells outright, including antibiotic-resistant strains like methicillin-resistant Staphylococcus aureus (MRSA). Furthermore, in mammalian cell lines, including cancer cells, allicin induces cell-death and inhibits cell proliferation. In plants allicin inhibits seed germination and attenuates root-development. The majority of allicin’s effects are believed to be mediated via redox-dependent mechanisms. In sub-lethal concentrations, allicin has a variety of health-promoting properties, for example cholesterol- and blood pressure-lowering effects that are advantageous for the cardio-vascular system. Clearly, allicin has wide-ranging and interesting applications in medicine and (green) agriculture, hence the detailed discussion of its enormous potential in this review. Taken together, allicin is a fascinating biologically active compound whose properties are a direct consequence of the molecule’s chemistry.

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In allicin biosynthesis, cysteine is transformed to alliin, which is hydrolyzed by the allinase enzyme.
“In the allicin biosynthesis, cysteine is transformed to alliin that is hydrolyzed by the allinase enzyme [38].”
From Chemical Constituents and Pharmacological Activities of Garlic (Allium sativum L.): A Review (2020) · cites this paper as [38]

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Enhancement of the Fungicidal Activity of Amphotericin B by Allicin: Effects on Intracellular Ergosterol Trafficking
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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 · see citing works
Enzymatic Carbon–Sulfur Bond Formation in Natural Product Biosynthesis
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Chemical composition and bioactive compounds of garlic (Allium sativum L.) as affected by pre- and post-harvest conditions: A review
Martins, N. A., Petropoulos, S. A., & Ferreira, I. C. F. R. (2016) · Food Chemistry · doi:10.1016/j.foodchem.2016.05.029 · Cited by 523 · see citing works
Plant Secondary Metabolites: The Weapons for Biotic Stress Management
Al-Khayri, J. M., Ramakrishnan, R., Toppo, V., Chole, P. B., Banadka, A., Sudheer, W. N., Nagella, P., Shehata, W. F., Al-Mssallem, M. Q., Alessa, F. M., et al. (2023) · Metabolites · doi:10.3390/metabo13060716 · Cited by 497 · see citing works
Autophagy as a molecular target for cancer treatment
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Ethnobotany and the Role of Plant Natural Products in Antibiotic Drug Discovery
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Plant nutraceuticals as antimicrobial agents in food preservation: terpenoids, polyphenols and thiols
Gutiérrez‐del‐Río, I., Fernández, J., & Lombó, F. (2018) · International Journal of Antimicrobial Agents · doi:10.1016/j.ijantimicag.2018.04.024 · Cited by 342 · see citing works
Bioactive potential of fruit and vegetable wastes
Coman, V., Teleky, B., Mitrea, L., Martău, G. A., Szabo, K., Călinoiu, L. F., & Vodnar, D. C. (2019) · Advances in food and nutrition research · doi:10.1016/bs.afnr.2019.07.001 · Cited by 328 · see citing works
Antiviral potential of garlic (Allium sativum) and its organosulfur compounds: A systematic update of pre-clinical and clinical data
Rouf, R., Uddin, S. J., Sarker, D. K., Islam, M. T., Ali, E. S., Shilpi, J. A., Nahar, L., Tiralongo, E., & Sarker, S. D. (2020) · Trends in Food Science & Technology · doi:10.1016/j.tifs.2020.08.006 · Cited by 320 · see citing works
Lipid-lowering nutraceuticals in clinical practice: position paper from an International Lipid Expert Panel
Cicero, A. F. G., Colletti, A., Bajraktari, G., Descamps, O. S., Djuric, D. M., Владиславович, Е. М., Fras, Z., Katsiki, N., Langlois, M. R., Latkovskis, G., et al. (2017) · Nutrition Reviews · doi:10.1093/nutrit/nux047 · Cited by 298 · see citing works
Lipid lowering nutraceuticals in clinical practice: position paper from an International Lipid Expert Panel
Cicero, A. F. G., Colletti, A., Bajraktari, G., Descamps, O., Djuric, D. M., Ezhov, M., Fras, Z., Katsiki, N., Langlois, M., Latkovskis, G., et al. (2017) · Archives of Medical Science · doi:10.5114/aoms.2017.69326 · Cited by 281 · see citing works
The Chemistry of Protein Oxidation in Food
Hellwig, M. (2019) · Angewandte Chemie International Edition · doi:10.1002/anie.201814144 · Cited by 259 · see citing works
Allicin and health: A comprehensive review
Salehi, B., Zucca, P., Orhan, İ. E., Azzini, E., Adetunji, C. O., Mohammed, S. A., Banerjee, S., Sharopov, F. S., Rigano, D., Sharifi‐Rad, J., et al. (2019) · Trends in Food Science & Technology · doi:10.1016/j.tifs.2019.03.003 · Cited by 249 · see citing works
Food as medicine: targeting the uraemic phenotype in chronic kidney disease
Mafra, D., Borges, N. A., Lindholm, B., Shiels, P. G., Evenepoel, P., & Stenvinkel, P. (2021) · Nature Reviews Nephrology · doi:10.1038/s41581-020-00345-8 · Cited by 238 · see citing works
More than 18,000 effectors in the Legionella genus genome provide multiple, independent combinations for replication in human cells
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A Comparison of the Antibacterial and Antifungal Activities of Thiosulfinate Analogues of Allicin
Leontiev, R., Hohaus, N., Jacob, C., Gruhlke, M. C. H., & Slusarenko, A. J. (2018) · Scientific Reports · doi:10.1038/s41598-018-25154-9 · Cited by 217 · see citing works
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Converting organosulfur compounds to inorganic polysulfides against resistant bacterial infections
Xu, Z., Qiu, Z., Liu, Q., Huang, Y., Li, D., Shen, X., Fan, K., Xi, J., Gu, Y., Tang, Y. M., et al. (2018) · Nature Communications · doi:10.1038/s41467-018-06164-7 · Cited by 199 · see citing works
Characteristics and Health Benefits of Phytochemicals
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Allicin Induces Thiol Stress in Bacteria through S-Allylmercapto Modification of Protein Cysteines
Müller, A., Eller, J., Albrecht, F., Prochnow, P., Kuhlmann, K., Bandow, J. E., Slusarenko, A. J., & Leichert, L. I. O. (2016) · Journal of Biological Chemistry · doi:10.1074/jbc.m115.702308 · Cited by 169 · see citing works
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Antimicrobial activity of nanoliposomes co-encapsulating nisin and garlic extract against Gram-positive and Gram-negative bacteria in milk
Pinilla, C. M. B., & Brandelli, A. (2016) · Innovative Food Science & Emerging Technologies · doi:10.1016/j.ifset.2016.07.017 · Cited by 170 · see citing works
Diallylthiosulfinate (Allicin), a Volatile Antimicrobial from Garlic (Allium sativum), Kills Human Lung Pathogenic Bacteria, Including MDR Strains, as a Vapor
Reiter, J., Levina, N., van der Linden, M., Gruhlke, M. C. H., Martin, C., & Slusarenko, A. J. (2017) · Molecules · doi:10.3390/molecules22101711 · Cited by 168 · see citing works
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Phytochemicals as modifiers of gut microbial communities
Dingeo, G., Alex Brito, O., Samouda, H., Iddir, M., Frano, M. R. L., & Bohn, T. (2020) · Food & Function · doi:10.1039/d0fo01483d · Cited by 170 · see citing works
The Effects of Allicin, a Reactive Sulfur Species from Garlic, on a Selection of Mammalian Cell Lines
Gruhlke, M., Nicco, C., Batteux, F., & Slusarenko, A. (2016) · Antioxidants · doi:10.3390/antiox6010001 · Cited by 165 · see citing works
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Therapeutic role of functional components in Alliums for preventive chronic disease in human being
Zeng, Y., Li, Y., Yang, J., Pu, X., Du, J., Yang, X., Yang, T., & Yang, S. (2017) · Evidence-Based Complementary and Alternative Medicine · doi:10.1155/2017/9402849 · Cited by 157 · see citing works
Garlic Revisited: Antimicrobial Activity of Allicin-Containing Garlic Extracts against Burkholderia cepacia Complex
Wallock-Richards, D., Doherty, C. J., Doherty, L., Clarke, D. J., Place, M., Govan, J. R. W., & Campopiano, D. J. (2014) · PLoS ONE · doi:10.1371/journal.pone.0112726 · Cited by 151 · see citing works
Stability and extraction of bioactive sulfur compounds from Allium genus processed by traditional and innovative technologies
Poojary, M. M., Putnik, P., Kovačević, D. B., Barba, F. J., Lorenzo, J. M., Dias, D. A., & Shpigelman, A. (2017) · Journal of Food Composition and Analysis · doi:10.1016/j.jfca.2017.04.007 · Cited by 145 · see citing works
Chemistry and biochemistry of cold physical plasma derived reactive species in liquids
Wende, K., von Woedtke, T., Weltmann, K., & Bekeschus, S. (2018) · Biological Chemistry · doi:10.1515/hsz-2018-0242 · Cited by 139 · see citing works
Phytogenic Bioactive Compounds Shape Fish Mucosal Immunity
Firmino, J. P., Galindo‐Villegas, J., Reyes‐López, F. E., & Gisbert, E. (2021) · Frontiers in Immunology · doi:10.3389/fimmu.2021.695973 · Cited by 144 · see citing works
Graphene-Based Materials for Inhibition of Wound Infection and Accelerating Wound Healing
Shariati, A., Hosseini, S. M., Chegini, Z., Seifalian, A., & Arabestani, M. R. (2022) · Biomedicine & Pharmacotherapy · doi:10.1016/j.biopha.2022.114184 · Cited by 132 · see citing works
S-Alk(en)ylcysteine sulfoxides in the genus Allium: proposed biosynthesis, chemical conversion, and bioactivities
Yoshimoto, N., & Saito, K. (2019) · Journal of Experimental Botany · doi:10.1093/jxb/erz243 · Cited by 127 · see citing works
Chemical composition and antimicrobial activity of garlic essential oils evaluated in organic solvent, emulsifying, and self-microemulsifying water based delivery systems
El-Sayed, H. S., Chizzola, R., Ramadan, A., & Edris, A. E. (2016) · Food Chemistry · doi:10.1016/j.foodchem.2016.10.052 · Cited by 126 · see citing works
Allicin, an Antioxidant and Neuroprotective Agent, Ameliorates Cognitive Impairment
Nadeem, M. S., Kazmi, I. A., Ullah, I., Muhammad, K., & Anwar, F. (2021) · Antioxidants · doi:10.3390/antiox11010087 · Cited by 129 · see citing works
Antibacterial properties of Allium sativum L. against the most emerging multidrug-resistant bacteria and its synergy with antibiotics
Magryś, A., Olender, A., & Tchórzewska, D. (2021) · Archives of Microbiology · doi:10.1007/s00203-021-02248-z · Cited by 146 · see citing works
Antifungal properties of phosphatidylcholine-oleic acid liposomes encapsulating garlic against environmental fungal in wheat bread.
Pinilla, C. M. B., Thys, R., & Brandelli, A. (2019) · Journal of food microbiology · doi:10.1016/j.ijfoodmicro.2019.01.006 · Cited by 92 · see citing works
Cysteine protecting groups: applications in peptide and protein science
Spears, R. J., McMahon, C., & Chudasama, V. (2021) · Chemical Society Reviews · doi:10.1039/d1cs00271f · Cited by 120 · see citing works
Combination Anticancer Therapies Using Selected Phytochemicals
Talib, W. H., Awajan, D., Hamed, R. A., Azzam, A. O., Mahmod, A. I., & Al-Yasari, I. H. (2022) · Molecules · doi:10.3390/molecules27175452 · Cited by 120 · see citing works
Functional relationship of vegetable colors and bioactive compounds: Implications in human health
Sharma, S., Katoch, V., Kumar, S., & Chatterjee, S. (2021) · The Journal of Nutritional Biochemistry · doi:10.1016/j.jnutbio.2021.108615 · Cited by 122 · see citing works
Functional Foods: Exploring the Health Benefits of Bioactive Compounds from Plant and Animal Sources
Dixit, V., Kamal, S. W. J., Chole, P. B., Dayal, D., Chaubey, K. K., Pal, A. K., Xavier, J., Manjunath, B. T., & Bachheti, R. K. (2023) · Journal of Food Quality · doi:10.1155/2023/5546753 · Cited by 115 · see citing works
The Reactive Sulfur Species Concept: 15 Years On
Giles, G. I., Nasim, M. J., Ali, W., & Jacob, C. (2017) · Antioxidants · doi:10.3390/antiox6020038 · Cited by 113 · see citing works
Allicin, a natural antimicrobial defence substance from garlic, inhibits DNA gyrase activity in bacteria
Reiter, J., Hübbers, A., Albrecht, F., Leichert, L. I. O., & Slusarenko, A. J. (2019) · International Journal of Medical Microbiology · doi:10.1016/j.ijmm.2019.151359 · Cited by 112 · see citing works
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Anticancer potential of allicin: A review
Catanzaro, E., Canistro, D., Pellicioni, V., Vivarelli, F., & Fimognari, C. (2022) · Pharmacological Research · doi:10.1016/j.phrs.2022.106118 · Cited by 115 · see citing works
Biological properties and therapeutic applications of garlic and its components
Melguizo‐Rodríguez, L., García‐Recio, E., Ruíz, C., Luna‐Bertos, E. D., Montes, R. I., & Costela-Ruiz, V. J. (2022) · Food & Function · doi:10.1039/d1fo03180e · Cited by 112 · see citing works
Nutraceuticals in the Management of Dyslipidemia: Which, When, and for Whom? Could Nutraceuticals Help Low-Risk Individuals with Non-optimal Lipid Levels?
Cicero, A. F. G., Fogacci, F., Stoian, A. P., Vrablik, M., Al Rasadi, K., Banach, M., Toth, P. P., & Rizzo, M. (2021) · Current Atherosclerosis Reports · doi:10.1007/s11883-021-00955-y · Cited by 110 · see citing works
Allicin, the Odor of Freshly Crushed Garlic: A Review of Recent Progress in Understanding Allicin’s Effects on Cells
Borlinghaus, J., Foerster, J., Kappler, U., Antelmann, H., Noll, U., Gruhlke, M. C. H., & Slusarenko, A. J. (2021) · Molecules · doi:10.3390/molecules26061505 · Cited by 117 · see citing works
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Tissue-Specific Accumulation of Sulfur Compounds and Saponins in Different Parts of Garlic Cloves from Purple and White Ecotypes
Diretto, G., Rubio‐Moraga, Á., Argandoña, J., Castillo, P., Gómez‐Gómez, L., & Ahrazem, O. (2017) · Molecules · doi:10.3390/molecules22081359 · Cited by 108 · see citing works
Enhanced antimicrobial activity and pH-responsive sustained release of chitosan/poly (vinyl alcohol)/graphene oxide nanofibrous membrane loading with allicin
Liu, Y., Song, R., Zhang, X., & Zhang, D. (2020) · International Journal of Biological Macromolecules · doi:10.1016/j.ijbiomac.2020.08.051 · Cited by 108 · see citing works
The Versatile Roles of Sulfur-Containing Biomolecules in Plant Defense—A Road to Disease Resistance
Künstler, A., Gullner, G., Ádám, A. L., Nagy, J. K., & Király, L. (2020) · Plants · doi:10.3390/plants9121705 · Cited by 108 · see citing works
Oxidative Stress-Generating Antimicrobials, a Novel Strategy to Overcome Antibacterial Resistance
Mourenza, Á., Gil, J. A., Mateos, L. M., & Letek, M. (2020) · Antioxidants · doi:10.3390/antiox9050361 · Cited by 108 · see citing works
Chemoprevention of Colorectal Cancer by Dietary Compounds
Costea, T., Hudiță, A., Ciolac, O.-A., Gălățeanu, B., Ginghină, O., Costache, M., Ganea, C., & Mocanu, M. (2018) · International Journal of Molecular Sciences · doi:10.3390/ijms19123787 · Cited by 105 · see citing works
Allicin Improves Metabolism in High-Fat Diet-Induced Obese Mice by Modulating the Gut Microbiota
Shi, X., Zhou, X., Chu, X., Wang, J., Xie, B., Ge, J., Guo, Y., Li, X., & Yang, G. (2019) · Nutrients · doi:10.3390/nu11122909 · Cited by 106 · see citing works
Analytical methods for bioactive sulfur compounds in Allium: An integrated review and future directions
Ramírez, D. A., Locatelli, D. A., González, R. E., Cavagnaro, P. F., & Camargo, A. B. (2016) · Journal of Food Composition and Analysis · doi:10.1016/j.jfca.2016.09.012 · Cited by 102 · see citing works
Calming the Storm: Natural Immunosuppressants as Adjuvants to Target the Cytokine Storm in COVID-19
Peter, A. E., Sandeep, B. V., Rao, B. G., & Kalpana, V. L. (2021) · Frontiers in Pharmacology · doi:10.3389/fphar.2020.583777 · Cited by 99 · see citing works
Chemical and Biological Properties of S-1-Propenyl-ʟ-Cysteine in Aged Garlic Extract
Kodera, Y., Ushijima, M., Amano, H., Suzuki, J., & Matsutomo, T. (2017) · Molecules · doi:10.3390/molecules22040570 · Cited by 99 · see citing works
A Comprehensive Review on Pharmacotherapeutics of Three Phytochemicals, Curcumin, Quercetin, and Allicin, in the Treatment of Gastric Cancer
Haghi, A., Azimi, H., & Rahimi, R. (2017) · Journal of Gastrointestinal Cancer · doi:10.1007/s12029-017-9997-7 · Cited by 98 · see citing works
Garlic, from Remedy to Stimulant: Evaluation of Antifungal Potential Reveals Diversity in Phytoalexin Allicin Content among Garlic Cultivars; Allicin Containing Aqueous Garlic Extracts Trigger Antioxidants in Cucumber
Hayat, S., Cheng, Z., Ahmad, H., Ali, M., Chen, X., & Wang, M. (2016) · Frontiers in Plant Science · doi:10.3389/fpls.2016.01235 · Cited by 104 · see citing works
Hydrogen Sulfide: A Novel Player in Airway Development, Pathophysiology of Respiratory Diseases, and Antiviral Defenses
Bazhanov, N., Ansar, M., Ivanciuc, T., Garofalo, R. P., & Casola, A. (2017) · American Journal of Respiratory Cell and Molecular Biology · doi:10.1165/rcmb.2017-0114tr · Cited by 97 · see citing works
Escaping mechanisms of ESKAPE pathogens from antibiotics and their targeting by natural compounds
Jadimurthy, R., Mayegowda, S. B., Nayak, S. C., Mohan, C. D., & Rangappa, K. S. (2022) · Biotechnology Reports · doi:10.1016/j.btre.2022.e00728 · Cited by 99 · see citing works
Allicin Alleviates Dextran Sodium Sulfate- (DSS-) Induced Ulcerative Colitis in BALB/c Mice
Pandurangan, A. K., Ismail, S., Saadatdoust, Z., & Esa, N. M. (2015) · Oxidative Medicine and Cellular Longevity · doi:10.1155/2015/605208 · Cited by 94 · see citing works
Review: antimicrobial properties of allicin used alone or in combination with other medications
Choo, S., Chin, V. K., Wong, E. H., Madhavan, P., Tay, S. T., Yong, P. V. C., & Chong, P. P. (2020) · Folia Microbiologica · doi:10.1007/s12223-020-00786-5 · Cited by 99 · see citing works
Aqueous garlic extract stimulates growth and antioxidant enzymes activity of tomato (Solanum lycopersicum)
Hayat, S., Ahmad, H., Ali, M., Ren, K., & Cheng, Z. (2018) · Scientia Horticulturae · doi:10.1016/j.scienta.2018.06.011 · Cited by 89 · see citing works
Vegetable Organosulfur Compounds and their Health Promoting Effects
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Untersuchungen zu zellulären Effekten von Allicin, einem physiologisch aktiven Vertreter Reaktiver Schwefelspezies, aus Knoblauch (Allium sativum L.), in verschiedenen biologischen Systemen
Gruhlke, M. C. H., & Slusarenko, A. J. (2014) · RWTH Publications (RWTH Aachen)
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Allicin and health: A comprehensive review
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Allicin from Garlic, Effective in Controlling Several Plant Diseases, is a Reactive Sulfur Species (RSS) that Pushes Cells into Apoptosis. Proceedings of the 16th International Reinhardsbrunn Symposium
Gruhlke, M. C. H., Noll, U., Arbach, M., Nwachukwu, I. D., Anwar, A., & Slusarenko, A. J. (2011) · RWTH Publications (RWTH Aachen) · Cited by 1 · see citing works
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Authors: Borlinghaus, J., Albrecht, F., Gruhlke, M., Nwachukwu, I., & Slusarenko, A.
Affiliations: RWTH Aachen University (DE)
University of Manitoba (CA)
Corresponding author: Slusarenko, Alan
ORCID: Borlinghaus, Jan
Gruhlke, Martin
Nwachukwu, Ifeanyi
Slusarenko, Alan
Venue: Molecules
Publisher: MDPI AG
Published: 2014-08-19
Volume: 19
Issue: 8
Pages: 12591-12618
ISSN: 1420-3049 (ISSN-L)
DOI: 10.3390/molecules190812591
PMC: PMC6271412
OpenAlex: W2078757278
Cited by: 893
References: 113
Citations by year: 2026: 102 · 2025: 102 · 2024: 91 · 2023: 99 · 2022: 105 · 2021: 92 · 2020: 80 · 2019: 67 · 2018: 42 · 2017: 47 · 2016: 46 · 2015: 17 · 2014: 2
FWCI: 4.21
Type: journal article
Language: en
Open access: gold
doi.org
Licence: cc-by
creativecommons.org/licenses/by/3.0/ (vor)
Locations: Molecules (publishedVersion, cc-by)
Europe PMC (PubMed Central) (publishedVersion, cc-by)
PubMed Central (publishedVersion, cc-by)
PubMed (publishedVersion)
DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
RWTH Publications (RWTH Aachen) (submittedVersion, cc-by)
RWTH Publications (RWTH Aachen)
Topics: Life Sciences › Agricultural and Biological Sciences › Plant Science › Garlic and Onion Studies
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Genomics, phytochemicals, and oxidative stress
Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Sulfur Compounds in Biology
Keywords: allicin, garlic, alliin, alliinase, thiosulfinates, reactive sulfur species, glutathione, redox signaling, antibacterial activity, antifungal activity, methicillin-resistant Staphylococcus aureus, anticancer activity, seed germination inhibition, root development, cardiovascular health, plant defense compounds
MeSH terms: Animals, Anti-Infective Agents, Antineoplastic Agents, Phytogenic, Disulfides, Humans, Oxidation-Reduction, Sulfinic Acids, Apoptosis, Arabidopsis, Plant Roots, Germination

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