Glucosinolate

Soybean meal is the most frequently used source of supplemental protein in the United States (5). Cottonseed meal is another important protein supplement. Both meals are by-products from oil extraction of the seeds. Canola meal is derived from rapeseed low in emcic acid [112-86-7] and glucosinolates. Linseed (derived from flax seed), peanut, sunflower, safflower, sesame, coconut, and palm kernel meals are other sources of supplemental protein that are by-products of oil extraction (4). 

Functional properties of canola protein products can be improved by succinylation (130,131). Controlled acetylation can reduce undesirable phenoHc constituents as well (132). However, antinutrients in canola and other vegetable protein products such as glucosinolates, phytic acid, and phenoHc compounds have severely limited food appHcations of these products. 

On treatment of trialkylsilyl nitronates 1043 with MeLi, LiBr, or BuLi in THF the resulting nitrile oxide intermediates 1044 afford, in dilute THF solution (R=Me) the ketoximes 1045 in ca 50-60% yield, whereas in concentrated THF solution the O-silylated hydroxamic acids 1046 are obtained as major products [144] (Scheme 7.35). Analogously, the silyl nitronate 1047 reacts with the 2,3,4,6-tetra-O-acetyl-/ -D-glucopyranosyl thiol/triethylamine mixture to afford, via the thiohydroxi-mate 1048, in high yield, a mixture of oximes 1049 which are intermediates in the synthesis of glucosinolate [145] (Scheme 7.35). 

Table 4.1 Glucosinolates in seeds of Cakile maritima and C. arabica (from Rodman, 1976)...

Unique among the collections reported in this study was the chemistry of subsp. euxima whose glucosinolate profile consisted essentially of a single compound, allyl glucosinolate. 

Louda, S. M. and Rodman, J. E. 1983a. Ecological patterns in the glucosinolate content of a native mustard, Cardamine cordifolia, in the Rocky Mountains. J. Chem. Ecol. 9 397-422. 

Differentiation and migration of Cakile (Cruciferae) seed glucosinolate evidence. 

FENWICK G R, KEANEY R K and MULLiN w J (1983) Glucosinolates and their breakdown products in food and food plants , Crit Rev Food Sci Nutr, 18, 123-201. 

GiAMOUSTARis A and MITHEN R (1995) The effect of modifying the glucosinolate content of leaves of oilseed rape (Brassica-napus ssp oleifera) on its interaction with specialist and generalist pests . Annals Appl Bio, 126, 347-63. 

SMITH T K, LUND E K and JOHNSON I T (1998) Inhibition of dimethylhydrazine-induced aberrant crypt foci an induction of apoptosis in rat colon following oral administration of the glucosinolate sinigrin , Carcinogenesis, 19, 267-73. 

The actual level of glucosinolates in the human diet depends upon many... 

Fig. 4.1 Sinigrin is an aliphatic glucosinolate that occurs at significant levels in the human diet, notably in mustard and Brussels sprouts. When brought into contact with myrosinase, derived either from plant cells or from colonic bacteria, it is broken down to yield a variety of products including the acrid, volatile, biologically active compoimd...

Table 4.1 Glucosinolates that have been studied in relation to their anti-carcinogenic characteristics and their common dietary sources...

---