Glucosides, mustard oil

Glucobrassicin is a mustard oil glucoside found in various Bras-sica spp. (50). 3-Indoleacetonitrile (IAN) is released from glucobrassicin by the action of the enzyme myrosinase at pH 4.0. How-... 

GMELIN, R., VIRTANEN, A.I., A new type of en2ymatic cleavage of mustard oil glucosides. Formation of allylthiocyanate in Thlaspi arvense L. and benzylthiocyanate in Lepidium ruderale L. and Lepidium sativum L., Acta Chem. Scand., 1959, 13, 1474-1475. 

Ettlinger, M.G. and Dateo, G.P (1961) Studies of mustard oil glucosides. Final Report Contract DA19-129-QM-1059, US Army Natick Laboratories, Natick, MA. 

Underhill, E.W., Chisholm, M.D. and Wetter, L.R. (1962) Biosynthesis of mustard oil glucosides administration of C-labelled compounds to horseradish, nasturtium and watercress. Can.. Biochem. Physiol., 40,1505-14. 

Mathys, W., 1977, The role of malate, oxalate, and mustard oil glucosides in the evolution of zinc-resistance in herbage plants, Physiol. Plant. 40 130-136. 

The extensive investigations of Kjser and coworkers have revealed many new mustard-oil glucosides (see Table I) the findings of this group... 

Structural investigations on mustard-oil glucosides may be further comphcated by secondary reactions following the Lessen rearrangement for example, Kjaer and Christensen isolated (-l-)-4-ethyl-2-oxazolidine-... 

Intramolecular enantiosituselectivity is exemplified by the biosynthetic formation of the mustard oil glucoside sinigrin (60) in horseradish, " the deprotonation of N-Boc-pyrrolidine (62) with sec-butyllithium (s-BuLi)/(-)-sparteine, followed by methylation, "" and, the oxidation of enol 64. Intermolecular enantiosituselective transformations are exemplified by the hydrolysis of racemic N-dodecanoylphenylalanine p-nitrophenyl esters (( )-67) in the presence of tripeptide catalyst (Z)-L-Phe-L-His-L-Leu (68) in each of the latter two cases, only one (externally) enantiotopic carbonyl reacts preferentially. It should be pointed out parenthetically, that as a result of the enantiosituselectivity in these transformations, one has, in effect, kinetic resolution of ( )-67. The electron-impact induced elimination in acetate 71, and the oxidation of 73 exemplify intramolecular diastereosituselective transformations. The epoxidation of the mixture 76/77 is an example of an intermolecular diastereosituselective process at the same time that each substrate is subject to enantiositunonselectivity of the carbonyl sub-sites. 

CHISHOLM, M.D., WETTER, L.R., Biosynthesis of mustard oil glucosides 4. Administration of methionine-C14 + related compormds to horseradish.. Can. J. Biochem. Physiol, 1964,42, 1033-1040. 

David, W. A. L. and B. O. C. Gardiner, Mustard oil glucosides as feeding stimulants for Pieris brassicae larvae in a semi-synthetic diet, Entomol. Exp. Appl., 9. 247-255 (1966). 

Glucosinolate, mustard oil thioglucoside, mustard oil glucoside a natural plant product with the structure shown in Fig. 1. G. are particularly abundant... 

The above-mentioned plants, as Brassicacea, contain mustard oil glucosides (glucosinolates, cf. 17.1.2.6.5) which, immediately after seed crushing, are hydrolyzed to esters of isothio-cyanic acid. The hydrolysis is dependent on seed moisture and is catalyzed by a thioglucosidase enzyme called myrosinase (EC 3.2.3.1). In the presence of the enzyme, some of the isocyanates are isomerized into thiocyanates (esters of normal thiocyanic acid or rhodanides) and, in part, are decomposed into nitrile compounds which do not contain sulfur. All these compounds are volatile and, when dissolved in oil, are hazardous to health and detrimental to oil flavor. Moreover, they interfere with hydrogenation of the oil by acting as Ni-catalyst poisons (cf. 14.4.2.2). Therefore, in the production of rapeseed oil, a dry conditioning step is used (without live steam) to... 

Two small but distinctive groups of natural products found in higher plants which show a clear and definite relationship to their biosynthetic precursors, the a-L-amino acids, are the cyanogenic glycosides (128)162,163 jjjg mustard oil glucosides or glucosinolates... 

Mustard oil glucosides (139) are found primarily in the plant family Cruciferae and they readily undergo enzymic hydrolysis... 

Matsuo, M. and Underhill, E.W. (1969) Biosynthesis of mustard oil glucosides XII. A UDP-glucose thiohydroxamate glycosyltransferase from Tropaeolum majtts. Biochem., Biophys. Res. Commun., 36, 18-23. 

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