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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
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discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
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MetaCyc Pathway: alliin degradation

Enzyme View:

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Synonyms: thiosulfinate biosynthesis, allium thiosulfinates, garlic thiosulfinate, cysteine sulfoxide degradation

Superclasses: Degradation/Utilization/Assimilation Secondary Metabolites Degradation Nitrogen Containing Secondary Compounds Degradation

Some taxa known to possess this pathway include ? : Allioideae , Allium cepa , Allium cepa aggregatum , Allium sativum

Expected Taxonomic Range: Allioideae

Summary:
Plants belonging to the Allioideae family have been valued both for flavor and medicinal purposes throughout the world. Uncrushed whole garlic bulbs contain in equal amounts as major organosulfur compounds cysteine sulfoxides and γ-glutamylcysteines . The odorless non protein alliin is the substrate which is acted upon by the allinase enzyme [Van92]. In garlic, the enzyme and substrate are contained within a specific tissue, i.e. the bundle sheath cells of the clove [Ellmore94] and compartmentalized more specifically in the vacuole (alliinase) and cell cytoplasm (alliin) [Shimon07]. The characteristic pungent odor is emitted only when the tissue is crushed and the enzyme interacts with the substrate.

The degradation of allium organosulphur compounds occurs mainly in bulbs and the allinase enzyme has been purified from bulbs as well as leaves and also from a number of other plants including Acacia and Brassicaceae members [Van92]. Allinases are now reported from a wide variety of organisms including bacteria and fungi [Rössner02]. The variety and composition of organosulfur compounds in Allium is explained by the kinetics of cysteine sulfoxide hydrolysis and the reactivity of the initial sulfenic acids [Rose05]. The allinase of Allium sativum accumulates S-alkyl and S-2-propenyl (allyl) derivatives but not S-1-propenyl derivatives [Manabe98].

Allinases require pyridoxal 5'-phosphate as a cofactor. Following the cofactor binding allinase is able to convert alliin to allylsulfenate [Shimon07], which in turn reacts spontaneously to form allicin, a parent compound of a number of other sulfur-containing compounds such as thiosulfinates, allyl sulfides, dithiines and ajoenes [Shimon07]. The biosynthesis of the flavor precursor alliin is still not completely understood [Jones04] although, there are proposed pathways with partial experimental proof. Hence, currently only the degradation of the alliin [Hughes05] is shown here.

Superpathways: superpathway of alliin degradation

Credits:
Created 15-Nov-2007 by Pujar A , Cornell University
Revised 19-Jun-2012 by Foerster H , Boyce Thompson Institute


References

Ellmore94: Ellmore, G.S, Feldberg, R.S (1994). "Alliin lyase localization in bundle sheaths of the garlic clove (Allium sativum)." American Journal of Botany, 81, 89-94.

Hughes05: Hughes J, Tregova A, Tomsett AB, Jones MG, Cosstick R, Collin HA (2005). "Synthesis of the flavour precursor, alliin, in garlic tissue cultures." Phytochemistry 66(2);187-94. PMID: 15652575

Jones04: Jones MG, Hughes J, Tregova A, Milne J, Tomsett AB, Collin HA (2004). "Biosynthesis of the flavour precursors of onion and garlic." J Exp Bot 55(404);1903-18. PMID: 15234988

Manabe98: Manabe T, Hasumi A, Sugiyama M, Yamazaki M, Saito K (1998). "Alliinase [S-alk(en)yl-L-cysteine sulfoxide lyase] from Allium tuberosum (Chinese chive)--purification, localization, cDNA cloning and heterologous functional expression." Eur J Biochem 257(1);21-30. PMID: 9799098

Rose05: Rose P, Whiteman M, Moore PK, Zhu YZ (2005). "Bioactive S-alk(en)yl cysteine sulfoxide metabolites in the genus Allium: the chemistry of potential therapeutic agents." Nat Prod Rep 22(3);351-68. PMID: 16010345

Rössner02: Rössner, Jan, Kubec, R, Velísˇek. J, Davídek, J (2002). "Formation of aldehydes from S-alk(en)ylcysteines and their sulfoxides." Eur Food Res Technol 215:124-130.

Shimon07: Shimon LJ, Rabinkov A, Shin I, Miron T, Mirelman D, Wilchek M, Frolow F (2007). "Two structures of alliinase from Alliium sativum L.: apo form and ternary complex with aminoacrylate reaction intermediate covalently bound to the PLP cofactor." J Mol Biol 366(2);611-25. PMID: 17174334

Van92: Van Damme EJ, Smeets K, Torrekens S, Van Leuven F, Peumans WJ (1992). "Isolation and characterization of alliinase cDNA clones from garlic (Allium sativum L.) and related species." Eur J Biochem 209(2);751-7. PMID: 1385120

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Nock87: Nock LP, Mazelis M (1987). "The C-S Lyases of Higher Plants : Direct Comparison of the Physical Properties of Homogeneous Alliin Lyase of Garlic (Allium sativum) and Onion (Allium cepa)." Plant Physiol 85(4);1079-83. PMID: 16665807

Ohsumi93: Ohsumi, C, Hayashi, T, Sano, K (1993). "Formation of alliin in the culture tissues of Allium sativum. oxidation of S-Allyl-L-Cysteine." Phytochemistry, 33,1,107-111.

Rabinkov94: Rabinkov A, Zhu XZ, Grafi G, Galili G, Mirelman D (1994). "Alliin lyase (Alliinase) from garlic (Allium sativum). Biochemical characterization and cDNA cloning." Appl Biochem Biotechnol 48(3);149-71. PMID: 7979352


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Mon Dec 22, 2014, BIOCYC13A.