Alliin

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of Alliin
General
Surname Alliin
other names
  • (2 R , 3 S ) - S -Allylcystein- S oxide
  • S -allyl- L -cystein- S oxide
  • ( S ) -3- (Allylsulfinyl) - L -alanine
  • ( S ) -3- (2-propenylsulfinyl) - L -alanine
Molecular formula C 6 H 11 NO 3 S
Brief description

odorless, crystalline needles

External identifiers / databases
CAS number
  • 556-27-4 (+) - L -Alliine
  • 17795-26-5 (±) - L -alliine
EC number 209-118-9
ECHA InfoCard 100.008.291
PubChem 9576089
ChemSpider 7850537
Wikidata Q57741566
properties
Molar mass 177.23 g mol −1
Physical state

firmly

Melting point

163 ° C (decomposition)

solubility

soluble in water

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Alliin is a non-proteinogenic, sulfur-containing amino acid . First described in 1950 by the Swiss chemists A. Stoll and E. Seebeck, Alliin is a natural ingredient in various types of leek , such as wild garlic and especially garlic .

Occurrence

Onions of the leek family contain both alliin and the alliin-splitting enzyme alliinase (Alliin lyase, EC  4.4.1.4 , a sulfenate lyase ), but not in the same cells or cell compartments .

garlic

The alliin content in fresh garlic is 0.5 to 1% (or 5 to 14 mg / g), the enzyme reaches values ​​of up to one percent.

Alliin is stored in intact cells in the cytoplasm , whereas alliinase is stored in the vacuoles ; furthermore, in the plant alliin is mainly found in the cells of the mesophyll , while the enzyme is mainly found in the cells surrounding the vascular bundles . If the plant tissue and the cell structure are damaged - for example by eating damage or cutting up - the alliinase and its odorless substrate alliin can come into contact. A chain of chemical reactions is set in motion, during which the cytotoxic (cell-killing) allicin is produced, which is responsible for the typical odor of garlic.

Alliin ( 1 ) is transformed into allylsulfenic acid ( 2 ) and dehydroalanine ( 3 ) by alliinase . The latter component is unstable and breaks down into ammonia and pyruvic acid .
Two molecules of allylsulfenic acid then condense to form allicin .

Biological importance

The biological benefit of the alliin-alliinase reaction for the plant is to provide an antibiotic defense system against harmful parasites , microorganisms and certain predators such as insects .

properties

Alliin is chemically derived from the sulfur-containing amino acid cysteine, which is essential for humans , and is a precursor of the pharmacologically active allicin .

As a sulfoxide , the sulfur atom in the alliin is pyramidal and a center of chirality .

literature

  • GS Ellmore, RS Feldberg: Allin Lyase Localization in Bundle Sheaths of the Garlic Clove (Allium sativum). In: Am. J. Bot. Vol. 81, No. 1, 1994, pp. 89-94.
  • A. Stoll, E. Seebeck: Synthesis of natural alliin. In: Experientia. Vol. 6, No. 9, 1950, p. 330.
  • A. Stoll, E. Seebeck: Chemical investigations of alliin, and the specific principle of garlic. In: Adv. Enzymol. Vol. 11, 1951, pp. 377-400.

See also

  • Isoalliin (the double bond isomers of alliin and active ingredient of the edible onion)

Individual evidence

  1. ↑ a b c Entry on Alliin. In: Römpp Online . Georg Thieme Verlag, accessed on June 20, 2014.
  2. ↑ a b data sheet (+) - L-Alliin at Sigma-Aldrich , accessed on February 12, 2019 ( PDF ).
  3. ^ Theodor Dingermann, Rudolf Hänsel, Ilse Zündorf (eds.): Pharmaceutical Biology: Molecular Basics and Clinical Applications. 1st edition. Springer Verlag, Berlin 2002, ISBN 3-540-42844-5 , p. 61.
  4. ↑ S. Ankri, D. Mirelman: Antimicrobial properties of allicin from garlic. In: Microbes Infect. Volume 1, No. 2, 1999, pp. 125-129. PMID 10594976 .