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Glucosinolates hydrolysis

Figure 13.1 Degradation of glucosinolates. Hydrolysis is catalyzed by myrosinases and gives rise to different degradation products dependent on the structure of the glucosinolate side chain and the hydrolysis conditions. (I) isothiocyanates, the major product at pH >7 (II) nitriles, the major product at pH <4 (ID) thiocyanates, produced from 2-propenyl-, benzyl-, and 4-methylthiobutylglucosinolates (IV) oxazolidine-2-thiones, produced from glucosinolates with P-hydroxylated side chains, (V) epithionitriles, produced in the presence of epithiospecifier proteins. Figure 13.1 Degradation of glucosinolates. Hydrolysis is catalyzed by myrosinases and gives rise to different degradation products dependent on the structure of the glucosinolate side chain and the hydrolysis conditions. (I) isothiocyanates, the major product at pH >7 (II) nitriles, the major product at pH <4 (ID) thiocyanates, produced from 2-propenyl-, benzyl-, and 4-methylthiobutylglucosinolates (IV) oxazolidine-2-thiones, produced from glucosinolates with P-hydroxylated side chains, (V) epithionitriles, produced in the presence of epithiospecifier proteins.
Kissen R, Bones AM (2009) Nitrile-specifier proteins involved in glucosinolate hydrolysis in Arabidopsis thaliana. J Biolog Chem 284 12057-12070... [Pg.155]

Protein-rich rape seed residues from biodiesel production plants are rich in phenolic compounds, glucocinolates and phytic acid. Phenolic compounds and phytic acid could be used as potent antioxidants in cosmetic and pharmaceutical formulations (Shamsuddin, 1995 Amarowicz and Shahidi, 1994 Wanasundara et al., 1996 Oatway et al., 2001). Derivatives from glucosinolate hydrolysis, including isothiocyanates, thiocyanates and nitriles, could be used as anticarcinogenic agents, biopesticides and flavour compounds (Halkier and Gershenzon, 2006). [Pg.93]

GLUCOSINOLATE HYDROLYSIS AND ITS IMPACT ON GENERALIST AND SPECIALIST INSECT HERBIVORES... [Pg.101]

Effects of Isolated Glucosinolate Hydrolysis Products on Insects. 105... [Pg.101]

Natural Variation in Glucosinolate Hydrolysis Products among A. thaliana... [Pg.101]

A major proportion of the glucosinolate hydrolysis products formed upon myrosinase cleavage in some plants are nitriles. In vitro, nitrile formation associated with myrosinase-catalyzed hydrolysis is enhanced at low pH (pH<3) and in the presence of ferrous ions. In vivo, protein factors in addition to myrosinase may be responsible for nitrile formation. If the glucosinolate side chain has a terminal double bond, the sulfur released from the thioglucosidic bond may be captured by the double bond and an epithionitrile is formed.9 This reaction takes place only in plants that possess a protein factor known as epithiospecifier protein (ESP). ESP activities have been identified in several species of the Brassicaceae and shown to influence the outcome of the myrosinase-catalvzed hydrolysis reaction although they have no hydrolytic activity by themselves.10 12 The mechanism by which ESPs promote epithionitrile formation is not known. [Pg.104]

EFFECTS OF ISOLATED GLUCOSINOLATE HYDROLYSIS PRODUCTS ON INSECTS... [Pg.105]

The glucosinolate hydrolysis products most frequently demonstrated to be toxic to insects are the isothiocyanates (Table 5.1). In fact, isothiocyanates have been... [Pg.105]

Table 5.1 Examples of studies showing toxic effects of isolated glucosinolate-hydrolysis products on insects. NCS, isothiocyanate SCN, thiocyanate CN, cyanide (= nitrile). Table 5.1 Examples of studies showing toxic effects of isolated glucosinolate-hydrolysis products on insects. NCS, isothiocyanate SCN, thiocyanate CN, cyanide (= nitrile).
AN ARABIDOPSIS THALIANA EPITHIOSPECIFIER PROTEIN (ESP) ALTERS GLUCOSINOLATE HYDROLYSIS... [Pg.109]

See other pages where Glucosinolates hydrolysis is mentioned: [Pg.303]    [Pg.217]    [Pg.91]    [Pg.92]    [Pg.101]    [Pg.102]    [Pg.103]    [Pg.103]    [Pg.104]    [Pg.104]    [Pg.104]    [Pg.105]    [Pg.105]    [Pg.105]    [Pg.107]    [Pg.108]    [Pg.108]    [Pg.108]    [Pg.109]    [Pg.109]    [Pg.111]    [Pg.113]    [Pg.113]    [Pg.114]    [Pg.115]    [Pg.115]    [Pg.116]    [Pg.117]    [Pg.117]    [Pg.118]    [Pg.118]    [Pg.119]    [Pg.119]    [Pg.119]    [Pg.119]    [Pg.120]    [Pg.123]   
See also in sourсe #XX -- [ Pg.13 , Pg.91 , Pg.103 , Pg.104 , Pg.111 , Pg.113 , Pg.113 , Pg.117 , Pg.117 , Pg.118 , Pg.118 , Pg.119 , Pg.119 , Pg.128 , Pg.128 , Pg.131 ]

See also in sourсe #XX -- [ Pg.109 ]



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