title: Allicin: chemistry and biological properties.
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.
authors.affiliation: Department of Plant Physiology, RWTH Aachen University, 52056 Aachen, Germany.
authors.forename: Jan
authors.initials: J
authors.lastname: Borlinghaus
authors.affiliation: Department of Plant Physiology, RWTH Aachen University, 52056 Aachen, Germany.
authors.forename: Frank
authors.initials: F
authors.lastname: Albrecht
authors.affiliation: Department of Plant Physiology, RWTH Aachen University, 52056 Aachen, Germany.
authors.forename: Martin C H
authors.initials: MC
authors.lastname: Gruhlke
authors.affiliation: Department of Human Nutritional Sciences, University of Manitoba, Winnipeg, MB R3T2N2, Canada.
authors.forename: Ifeanyi D
authors.initials: ID
authors.lastname: Nwachukwu
authors.affiliation: Department of Plant Physiology, RWTH Aachen University, 52056 Aachen, Germany. alan.slusarenko@bio3.rwth-aachen.de.
authors.forename: Alan J
authors.initials: AJ
authors.lastname: Slusarenko
mesh_terms: D000818:Animals; D000890:Anti-Infective Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D017360:Arabidopsis / Q000187:drug effects / Q000502:physiology; D004220:Disulfides; D018525:Germination / Q000187:drug effects; D006801:Humans; D010084:Oxidation-Reduction; D018517:Plant Roots / Q000187:drug effects / Q000502:physiology; D013441:Sulfinic Acids / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*
chemical_list: D000890:Anti-Infective Agents; D000972:Antineoplastic Agents, Phytogenic; D004220:Disulfides; D013441:Sulfinic Acids; C006452:allicin