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Allicin
Allicin
is an organosulfur compound obtained from garlic, a species in the family Alliaceae.[1] It was first isolated and studied in the laboratory by Chester J. Cavallito
Chester J. Cavallito
and John Hays Bailey in 1944.[2][3] When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic.[4] The allicin generated is unstable and quickly changes into a series of other sulfur-containing compounds such as diallyl disulfide.[5] Allicin
Allicin
is part of a defense mechanism against attacks by pests on the garlic plant.[6]

Contents

1 Structure and occurrence 2 Biosynthesis 3 Research 4 History 5 See also 6 References

Structure and occurrence[edit] Allicin
Allicin
features the thiosulfinate functional group, R-S(O)-S-R. The compound is not present in garlic unless tissue damage occurs,[1] and is formed by the action of the enzyme alliinase on alliin.[1] Allicin is chiral but occurs naturally only as a racemate.[3] The racemic form can also be generated by oxidation of diallyl disulfide:[7]

(SCH2CH=CH2)2 + RCO3H → CH2=CHCH2S(O)SCH2CH=CH2 + RCO2H

Alliinase
Alliinase
is irreversibly deactivated below pH 3; as such, allicin is generally not produced in the body from the consumption of fresh or powdered garlic.[8][9] Furthermore, allicin can be unstable, breaking down within 16 hours at 23 °C.[10] Biosynthesis[edit] Allicin
Allicin
is an oily, slightly yellow liquid that gives garlic its unique odor. It is a thioester of sulfenic acid and is also known as allyl thiosulfinate.[11] Its biological activity can be attributed to both its antioxidant activity and its reaction with thiol-containing proteins.[12] In the biosynthesis of allicin (thio-2-propene-1-sulfinic acid S-allyl ester), cysteine is first converted into alliin (+ S-allyl-L-cysteine sulfoxide). The enzyme alliinase, which contains pyridoxal phosphate (PLP), cleaves alliin, generating allysulfenic acid, pyruvate, and ammonium.[12] At room temperature allysulfenic acid is unstable and highly reactive, which cause two molecules of it to spontaneously combine in a dehydration reaction to form allicin.[11] Produced in garlic cells, allicin is released upon disruption, producing a potent characteristic scent when garlic is cut or cooked.[5][6]

Biosynthesis of Allicin

Research[edit] Allicin
Allicin
has been studied for its potential to treat various kinds of multiple drug resistance bacterial infections, as well as viral and fungal infections in vitro, but as of 2016, the safety and efficacy of allicin to treat infections in people was unclear.[13] In a small clinical trial, a daily high dose of extracted allicin (20 times the amount in a garlic clove) showed effectiveness to prevent the common cold.[14] A Cochrane review found this to be not sufficient to draw conclusions.[15] History[edit] Allicin
Allicin
was discovered as part of efforts to create thiamine derivatives in the 1950s, mainly in Japan. Allicin
Allicin
became a model for medicinal chemistry efforts to create other thiamine disulfides. The results included sulbutiamine, fursultiamine (thiamine tetrahydrofurfuryl disulfide) and benfothiamine. These compounds are hydrophobic, easily pass from the intestines to the bloodstream, and are reduced to thiamine by cysteine or glutathione.[16]:302 See also[edit]

Wikimedia Commons has media related to Allicin.

Allyl isothiocyanate, the active piquant chemical in mustard, radishes, horseradish and wasabi syn-Propanethial-S-oxide, the chemical found in onions List of phytochemicals in food

References[edit]

^ a b c Eric Block (1985). "The chemistry of garlic and onions". Scientific American. 252 (March): 114–9. doi:10.1038/scientificamerican0385-114. PMID 3975593.  ^ Cavallito, Chester J.; Bailey, John Hays (1944). "Allicin, the Antibacterial Principle of Allium
Allium
sativum. I. Isolation, Physical Properties and Antibacterial Action". Journal of the American Chemical Society. 66 (11): 1950. doi:10.1021/ja01239a048.  ^ a b Eric Block (2010). Garlic
Garlic
and Other Alliums: The Lore and the Science. Cambridge: Royal Society of Chemistry.  ^ Kourounakis, PN; Rekka, EA (November 1991). "Effect on active oxygen species of alliin and Allium
Allium
sativum (garlic) powder". Res Commun Chem Pathol Pharmacol. 74 (2): 249–252. PMID 1667340.  ^ a b Ilic, Dusica; Nikolic, Vesna; Nikolic, Ljubisa; Stankovic, Mihajlo; Stanojevic, Ljiljana; Cakic, Milorad (2011). " Allicin
Allicin
and related compounds: Biosynthesis, synthesis and pharmacological activity" (PDF). Facta Universitatis. 9 (1): 9–20. doi:10.2298/FUPCT1101009I.  ^ a b Borlinghaus, J; Albrecht, F; Gruhlke, M. C.; Nwachukwu, I. D.; Slusarenko, A. J. (2014). "Allicin: Chemistry and biological properties". Molecules. 19 (8): 12591–618. doi:10.3390/molecules190812591. PMID 25153873.  ^ Cremlyn, R. J. W. (1996). An introduction to organosulfur chemistry. Wiley. ISBN 0-471-95512-4.  ^ Brodnitz, M.H.; Pascale, J.V.; Derslice, L.V. (1971). "Flavor components of garlic extract". Journal of Agricultural and Food Chemistry. 19 (2): 273–5. doi:10.1021/jf60174a007.  ^ Yu, Tung-HSI; Wu, Chung-MAY (1989). "Stability of Allicin
Allicin
in Garlic Juice". Journal of Food Science. 54 (4): 977. doi:10.1111/j.1365-2621.1989.tb07926.x.  ^ Hahn, G (1996). Koch, HP; Lawson, LD, eds. Garlic: the science and therapeutic application of Allium
Allium
sativum L and related species (2nd ed.). Baltimore: Williams and Wilkins. pp. 1–24. ISBN 0-683-18147-5.  ^ a b Nikolic, V; Stankovic, M; Nikolic, Lj; Cvetkovic, D (Jan 2004). "Mechanism and kinetics of synthesis of allicin". Pharmazie. 59 (1): 10–4. PMID 14964414.  ^ a b Rabinkov, A; Miron, T; Konstantinovski, L; Wilchek, M; Mirelman, D; Weiner, L (Feb 1998). "The mode of action of allicin: trapping of radicals and interaction with thiol containing proteins". Biochim Biophys Acta. 1379 (2): 233–44. doi:10.1016/s0304-4165(97)00104-9. PMID 9528659.  ^ Marchese, Anna; Barbieri, Ramona; Sanches-Silva, Ana; Daglia, Maria; Nabavi, Seyed Fazel; Jafari, Nematollah Jonaidi; Izadi, Morteza; Ajami, Marjan; Nabavi, Seyed Mohammad (2016). "Antifungal and antibacterial activities of allicin: A review". Trends in Food Science and Technology. 52: 49. doi:10.1016/j.tifs.2016.03.010.  ^ Nahas, R; Balla, A (January 2011). "Complementary and alternative medicine for prevention and treatment of the common cold". Canadian Family Physician. 57 (1): 31–6. PMC 3024156 . PMID 21322286.  ^ Lissiman, E; Bhasale, AL; Cohen, M (11 November 2014). " Garlic
Garlic
for the common cold". The Cochrane Database of Systematic Reviews (11): CD006206. doi:10.1002/14651858.CD006206.pub4. PMID 25386977.  ^ Bettendorff, Lucien (2014). "Chapter 7 - Thiamine". In Zempleni, Janos; Suttie, John W.; Gregory, Jesse F.; Stover, Patrick J. Handbook of vitamins (Fifth edition ed.). Hoboken: CRC Press. pp. 267–324. ISBN 9781466515574. CS1 maint: Extra text (link)

v t e

Allium

Allium
Allium
species Chives Garlic Leek Onion

Onion
Onion
cultivars

Calçot Cocktail Common / Bulb

Yellow Red White

Pearl Potato Scallion Shallot Sweet Tree Vidalia Welsh

Onion
Onion
species

Allium…

…abramsii …acuminatum …aflatunense …ampeloprasum …amplectens …anceps …atrorubens …bisceptrum …bolanderi …burlewii …caeruleum …campanulatum …cernuum …chinense …cratericola …crispum …cristophii …koreanum …monanthum …platycaule …praecox …punctum …sanbornii …shevockii …siskiyouense …sphaerocephalon …stellatum …stipitatum …textile …tribracteatum …tricoccum …triquetrum …tuolumnense …unifolium …validum …victorialis …yosemitense

Onion
Onion
food

List of onion dishes Blooming Fried Onion
Onion
cake Onion
Onion
ring Pickled Sogan-dolma

Garlic
Garlic
cultivars

Elephant Garlic
Garlic
chives Snow Mountain Solo

Garlic
Garlic
species

Allium…

…canadense …drummondii …moly …neapolitanum …nigrum …roseum …sphaerocephalon …triquetrum …ursinum …vineale

Garlic
Garlic
food

List of garlic dishes Black garlic Persillade Pistou Garlic
Garlic
oil Garlic
Garlic
press Garlic
Garlic
bread Garlic
Garlic
chutney Beurre à la bourguignonne (garlic butter) Garlic
Garlic
soup

Garlic
Garlic
and onion constituents

Allicin Diallyl disulfide Diallyl trisulfide Allyl mercaptan

Related

Garlic
Garlic
Is as Good as Ten Mothers (1980 documentary)

Category Commons

v t e

TRP channel modulators

TRPA

Activators

4-Hydroxynonenal 4-Oxo-2-nonenal 4,5-EET 12S-HpETE 15-Deoxy-Δ12,14-prostaglandin J2 α- Sanshool
Sanshool
(ginger, Sichuan and melegueta peppers) Acrolein Allicin
Allicin
(garlic) Allyl isothiocyanate
Allyl isothiocyanate
(mustard, radish, horseradish, wasabi) AM404 Bradykinin Cannabichromene
Cannabichromene
(cannabis) Cannabidiol
Cannabidiol
(cannabis) Cannabigerol
Cannabigerol
(cannabis) Cinnamaldehyde
Cinnamaldehyde
(cinnamon) CR gas
CR gas
(dibenzoxazepine; DBO) CS gas
CS gas
(2-chlorobenzal malononitrile) Curcumin
Curcumin
(turmeric) Dehydroligustilide (celery) Diallyl disulfide Dicentrine
Dicentrine
( Lindera
Lindera
spp.) Farnesyl thiosalicylic acid Formalin Gingerols (ginger) Hepoxilin A3 Hepoxilin B3 Hydrogen peroxide Icilin Isothiocyanate Ligustilide (celery, Angelica acutiloba) Linalool
Linalool
(Sichuan pepper, thyme) Methylglyoxal Methyl salicylate
Methyl salicylate
(wintergreen) N-Methylmaleimide Nicotine
Nicotine
(tobacco) Oleocanthal
Oleocanthal
(olive oil) Paclitaxel
Paclitaxel
(Pacific yew) Paracetamol
Paracetamol
(acetaminophen) PF-4840154 Phenacyl chloride Polygodial
Polygodial
(Dorrigo pepper) Shogaols (ginger, Sichuan and melegueta peppers) Tear gases Tetrahydrocannabinol
Tetrahydrocannabinol
(cannabis) Thiopropanal S-oxide
Thiopropanal S-oxide
(onion) Umbellulone
Umbellulone
(Umbellularia californica) WIN 55,212-2

Blockers

Dehydroligustilide (celery) Nicotine
Nicotine
(tobacco) Ruthenium red

TRPC

Activators

Adhyperforin
Adhyperforin
(St John's wort) Diacyl glycerol GSK1702934A Hyperforin
Hyperforin
(St John's wort) Substance P

Blockers

DCDPC DHEA-S Flufenamic acid GSK417651A GSK2293017A Meclofenamic acid N-(p-amylcinnamoyl)anthranilic acid Niflumic acid Pregnenolone sulfate Progesterone Pyr3 Tolfenamic acid

TRPM

Activators

ADP-ribose BCTC Calcium
Calcium
(intracellular) Cold Coolact P Cooling Agent 10 CPS-369 Eucalyptol
Eucalyptol
(eucalyptus) Frescolat MGA Frescolat ML Geraniol Hydroxycitronellal Icilin Linalool Menthol
Menthol
(mint) PMD 38 Pregnenolone sulfate Rutamarin (Ruta graveolens) Steviol glycosides (e.g., stevioside) (Stevia rebaudiana) Sweet tastants (e.g., glucose, fructose, sucrose; indirectly) Thio-BCTC WS-3 WS-12 WS-23

Blockers

Capsazepine Clotrimazole DCDPC Flufenamic acid Meclofenamic acid Mefenamic acid N-(p-amylcinnamoyl)anthranilic acid Nicotine
Nicotine
(tobacco) Niflumic acid Ruthenium red Rutamarin (Ruta graveolens) Tolfenamic acid TPPO

TRPML

Activators

MK6-83 PI(3,5)P2 SF-22

TRPP

Activators

Triptolide
Triptolide
(Tripterygium wilfordii)

Blockers

Ruthenium red

TRPV

Activators

2-APB 5',6'-EET 9-HODE 9-oxoODE 12S-HETE 12S-HpETE 13-HODE 13-oxoODE 20-HETE α- Sanshool
Sanshool
(ginger, Sichuan and melegueta peppers) Allicin
Allicin
(garlic) AM404 Anandamide Bisandrographolide (Andrographis paniculata) Camphor
Camphor
(camphor laurel, rosemary, camphorweed, African blue basil, camphor basil) Cannabidiol
Cannabidiol
(cannabis) Cannabidivarin
Cannabidivarin
(cannabis) Capsaicin
Capsaicin
(chili pepper) Carvacrol
Carvacrol
(oregano, thyme, pepperwort, wild bergamot, others) DHEA Diacyl glycerol Dihydrocapsaicin
Dihydrocapsaicin
(chili pepper) Estradiol Eugenol
Eugenol
(basil, clove) Evodiamine
Evodiamine
(Euodia ruticarpa) Gingerols (ginger) GSK1016790A Heat Hepoxilin A3 Hepoxilin B3 Homocapsaicin
Homocapsaicin
(chili pepper) Homodihydrocapsaicin
Homodihydrocapsaicin
(chili pepper) Incensole
Incensole
(incense) Lysophosphatidic acid Low pH (acidic conditions) Menthol
Menthol
(mint) N-Arachidonoyl dopamine N-Oleoyldopamine N-Oleoylethanolamide Nonivamide
Nonivamide
(PAVA) (PAVA spray) Nordihydrocapsaicin
Nordihydrocapsaicin
(chili pepper) Paclitaxel
Paclitaxel
(Pacific yew) Paracetamol
Paracetamol
(acetaminophen) Phorbol esters
Phorbol esters
(e.g., 4α-PDD) Piperine
Piperine
(black pepper, long pepper) Polygodial
Polygodial
(Dorrigo pepper) Probenecid Protons RhTx Rutamarin (Ruta graveolens) Resiniferatoxin
Resiniferatoxin
(RTX) (Euphorbia resinifera/pooissonii) Shogaols (ginger, Sichuan and melegueta peppers) Tetrahydrocannabivarin
Tetrahydrocannabivarin
(cannabis) Thymol
Thymol
(thyme, oregano) Tinyatoxin
Tinyatoxin
(Euphorbia resinifera/pooissonii) Tramadol Vanillin
Vanillin
(vanilla) Zucapsaicin

Blockers

α- Spinasterol
Spinasterol
( Vernonia
Vernonia
tweediana) AMG-517 Asivatrep BCTC Cannabigerol
Cannabigerol
(cannabis) Cannabigerolic acid (cannabis) Cannabigerovarin (cannabis) Cannabinol
Cannabinol
(cannabis) Capsazepine DCDPC DHEA DHEA-S Flufenamic acid GRC-6211 HC-067047 Lanthanum Meclofenamic acid N-(p-amylcinnamoyl)anthranilic acid NGD-8243 Niflumic acid Pregnenolone sulfate RN-1734 RN-9893 Ruthenium red SB-705498 Tivanisiran Tolfenamic acid

See also: Receptor/signaling modulators • Ion channel modulators

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