Effect of organic reducing agents and ferrous ion on thioglucosidase activity of Crambe abyssinica seed

1970 ◽  
Vol 48 (9) ◽  
pp. 1024-1028 ◽  
Author(s):  
H. L. Tookey ◽  
I. A. Wolff
Keyword(s):  
Reducing Agents ◽  
Ferrous Ion ◽  
Seed Meal ◽  
Crambe Abyssinica ◽  
Meal Pattern ◽  
Crambe Seed ◽  
Crambe Meal ◽  
Insoluble Particles

The addition of L-ascorbate or 2-mercaptoethanol to aged crambe seed meal tends to restore the fresh meal pattern of epi-progoitrin hydrolysis to nitriles instead of (R)-goitrin. Neither of these reducing agents has an effect on the breakdown of epi-progoitrin to goitrin by an insoluble particulate thioglucosidase from crambe meal. The addition of ferrous ion to the insoluble particles results in the conversion of epi-progoitrin to (2S)-1-cyano-2-hydroxy-3-butene instead of (R)-goitrin over a range from pH 3.9 to 6.7.

Solubilization and Selected Properties of Crambe Seed Thioglucosidase (Thioglucoside Glucohydrolase, EC 3.2.3.1)

1973 ◽  
Vol 51 (9) ◽  
pp. 1305-1310 ◽  
Author(s):  
H. L. Tookey
Keyword(s):  
Substrate Inhibition ◽  
Apparent Molecular Weight ◽  
Ferrous Ion ◽  
Soluble Enzyme ◽  
Ammonium Sulfate Precipitation ◽  
Michaelis Constant ◽  
Sequential Fractionation ◽  
Crambe Abyssinica ◽  
Crambe Seed ◽  
Insoluble Particles

Ultrasonic treatment releases thioglucoside glucohydrolase (thioglucosidase) from insoluble particles of Crambe abyssinica seed meal. The crude enzyme is optimally activated by 10−2 M ascorbate, requires a reducing agent for stability, and is inhibited by 10−3 M p-chloromercuribenzenesulfonate.Chromatography of a meal extract on cross-linked dextran separates two enzyme fractions. About 80% of the activity elutes at an apparent molecular weight of 110 000; the remainder elutes at the void volume. Both crude soluble enzyme and the fractions from the dextran column produce goitrin from epi-progoitrin, but in the presence of ferrous ion the chief aglucon product becomes 1-cyano-2-hydroxy-3-butene. The Michaelis constant (of the major peak) at pH 5 is 0.004 M. Ferrous ion produces substrate inhibition at high epi-progoitrin levels. Sequential fractionation of meal extract by ammonium sulfate precipitation and by chromatography on cross-linked dextran effects an 80-fold purification.

Crambe Thioglucoside Glucohydrolase (EC 3.2.3.1): Separation of a Protein Required for Epithiobutane Formation

1973 ◽  
Vol 51 (12) ◽  
pp. 1654-1660 ◽  
Author(s):  
H. L. Tookey
Keyword(s):  
Ammonium Sulfate ◽  
Ferrous Ion ◽  
Seed Meal ◽  
Proteinaceous Material ◽  
Saturated Ammonium Sulfate ◽  
Crambe Seed

Sonicated extract of crambe seed meal prepared in the presence of ferrous ion and dithiothreitol enzymatically converts epi-progoitrin to glucose, HSO4−, and a mixture of 1-cyano-2-hydroxy-3,4-epithiobutanes (50–70%) and 1-cyano-2-hydroxy-3-butene (30–50%). A fraction of the extract precipitating between 60 and 70% saturated ammonium sulfate contains thioglucosidase that converts epi-progoitrin essentially to 1-cyano-2-hydroxy-3-butene. Chromatography (on cross-linked dextran) of a 40–60% ammonium sulfate fraction leads to separation of a proteinaceous material (s20 = 2.6 S) that does not hydrolyze epi-progoitrin but, in the presence of thioglucosidase, promotes the formation of 1-cyano-2-hydroxy-3,4-epithiobutanes in amounts proportional to those from crude seed meal extract.

Sinapine and related esters in seed meal of Crambe abyssinica

1968 ◽  
Vol 16 (1) ◽  
pp. 132-135 ◽  
Author(s):  
Franklin L. Austin ◽  
Ivan A. Wolff
Keyword(s):  
Seed Meal ◽  
Crambe Abyssinica

scholarly journals THE FEEDING VALUE OF SOLVENT-EXTRACTED CAMELINA MEAL EFFECTS OF LEVELS FED, HEAT TREATMENTS AND FLAVOR SUPPLEMENTS

1967 ◽  
Vol 47 (2) ◽  
pp. 109-114 ◽  
Author(s):  
G. O. Korsrud ◽  
J. M. Bell
Keyword(s):  
Control Diet ◽  
Maximum Growth ◽  
Brassica Napus L ◽  
Growth Depression ◽  
Crambe Abyssinica ◽  
Crambe Seed ◽  
Camelina Meal ◽  
Feeding Value ◽  
Dry Heating ◽  
Camelina Seed

Camelina seed was ground, solvent-extracted, and fed at levels of 0, 5, 10, 15, 20 and 25% of the diet to weanling mice. Licorice (0 and 0.025%) was tested as a cross-treatment to modify flavor. Levels up to 10% resulted in no adverse effects on growth of mice but each increase in level beyond 10% resulted m a significant (P <.05) reduction in gains and feed intakes. Licorice was ineffective.In a second experiment 20 to 22% of camelina meal was fed m all diets. Raw meal was compared with dry-heated meal (12 hours, 135 °C), autoclaved meal (15 min, 1.2 kg/cm2), steam-stripped (2 hours, 110 °C) and a casein–methionine–supplemented control diet. In each case, four myrosinase-source supplements were added: nil, crambe seed, rapeseed, and camelina seed (Crambe abyssinica Hochst., Brassica napus L., and Cameline sativa Crantz).Destruction of myrosinase by any method of heating resulted in significantly better feeding value of camelina meal, but steam stripping was superior to dry heating or autoclaving.It was concluded that camelina meal is probably superior to rapeseed and crambe meals, in that more than 10% of raw meal is tolerated in the diet before growth depression occurs. Near maximum growth was obtained with myrosinase-free diets containing about 20% meal. Growth depression that occurred at the higher levels of intake exceeded that which could be accounted for by the content of volatile isothiocyanates.

Diastereomeric episulfides from epi-progoitrin upon autolysis of crambe seed meal

1968 ◽  
Vol 7 (6) ◽  
pp. 989-996 ◽  
Author(s):  
M.E. Daxenbichler ◽  
C.H. VanEtten ◽  
I.A. Wolff
Keyword(s):  
Seed Meal ◽  
Crambe Seed

EFFECTS OF VARIOUS HEAT AND MOISTURE TREATMENTS ON MYROSINASE ACTIVITY AND NUTRITIVE VALUE OF SOLVENT-EXTRACTED CRAMBE SEED MEAL

1967 ◽  
Vol 47 (2) ◽  
pp. 101-107 ◽  
Author(s):  
G. O. Korsrud ◽  
J. M. Bell
Keyword(s):  
Nutritive Value ◽  
Soybean Protein ◽  
Control Diet ◽  
Enzyme Treatment ◽  
Brassica Napus L ◽  
Growth Depression ◽  
Crambe Abyssinica ◽  
Crambe Meal

Solvent-extracted crambe meal, uncooked, dry-heated, autoclaved or steam-stripped, was fed as 0, 5 or 10% of the diet to weanling mice. Ground rapeseed (1% of the diet) was fed in a cross-treatment as a source of myrosinase.Uncooked crambe meal significantly depressed (P < 0.05) feed intakes and gains. Heating by any method tested resulted in significant improvement, but feeding value remained below that of the casein-soybean protein control diet. The addition of the myrosinase source had little effect.In a second experiment, ground seed of crambe, rape and camelina (Crambe abyssinica Hochst., Brassica napus L. and Camelina sativa Crantz) were compared as myrosinase sources when incorporated 1:4 into cooked crambe meal and allowed to react overnight at room temperature with 0 or 30% moisture in the mixture. After this enzyme treatment, half of each mixture was autoclaved to destroy myrosinase prior to ration mixing and feeding.Appreciable hydrolysis of thioglucosides occurred in vitro at 30% moisture, resulting in marked growth depression. The feeding of active myrosinase similarly depressed animal responses, apparently through in vivo thioglucoside hydrolysis. All sources of enzyme were effective.The failure to obtain more enzyme response in the first experiment was attributed to lower enzyme concentration and inferior enzyme-substrate proximity during the time when conditions were otherwise appropriate for thioglucoside hydrolysis.

TESTS FOR EPI-PROGOITRIN, DERIVED NITRILES, AND GOITRIN IN BODY TISSUES FROM CATTLE FED CRAMBE MEAL

1977 ◽  
Vol 57 (1) ◽  
pp. 75-80 ◽  
Author(s):  
C. H. VANETTEN ◽  
M. E. DAXENBICHLER ◽  
W. SCHROEDER ◽  
L. H. PRINCEN ◽  
T. W. PERRY
Keyword(s):  
Rumen Fluid ◽  
The Body ◽  
Shoulder Muscle ◽  
Crambe Seed ◽  
Crambe Meal ◽  
Body Tissues ◽  
Muscle Tissues ◽  
Sheep Rumen ◽  
Kidney Liver ◽  
Unsaturated Nitrile

Beef cattle were fed a ration formulated with up to 10% processed crambe seed meal, which contained varying amounts of the glucosinolate epi-progoitrin (e-PG), unsaturated nitrile [(S) 1-cyano-2-hydroxy-3-butene], and goitrin. Taken at commercial slaughter of the animals, samples of their fat from near the kidney, the kidney, liver, and shoulder muscle tissues contained no detectable e-PG, unsaturated nitrile, episulfide nitriles [isomers 1-cyano-(S)-2-hydroxy-(R)- and (S)-3-epithiobutanes], or goitrin. Examination of gas–liquid (GLC) curves also showed absence of an isomer of goitrin, recently reported to be formed by the action of sheep rumen fluid on progoitrin. Details on the separation of the small amounts of active compounds from the body tissues and on their subsequent GLC analyses are presented. Detection was possible to levels below 1 ppm. Results from spiked body tissues show the sensitivity and the precision that can be expected.

Rapeseed meal autolysis. Formation of diastereomeric (2R)-1-cyano-2-hydroxy-3,4-epithiobutanes from progoitrin

1967 ◽  
Vol 45 (17) ◽  
pp. 1971-1974 ◽  
Author(s):  
M. E. Daxenbichler ◽  
C. H. VanEtten ◽  
W. H. Tallent ◽  
I. A. Wolff
Keyword(s):  
Brassica Napus ◽  
Rapeseed Meal ◽  
Chiral Center ◽  
Optical Rotatory Dispersion ◽  
Rotatory Dispersion ◽  
Seed Meal ◽  
Optical Rotatory ◽  
Brassica Napus L ◽  
Crambe Abyssinica ◽  
Dispersion Data

When defatted seed from Brassica napus L. var. Regina II (a rapeseed) was autolyzed, its major thioglucoside (progoitrin) underwent degradation analogous to that for epiprogoitrin in Crambe abyssinica seed meal. Depending on the conditions, (R)-1-cyano-2-hydroxy-3-butene and the diastereomeric forms of (2R)-1-cyano-2-hydroxy-3,4-epithiobutane were formed in autolyzed B. napus meal instead of (S)-goitrin. The configuration at the chiral center containing the hydroxyl is assigned on the basis of known data. The configuration at carbon 3 of the episulfides is predicted on the basis of the optical rotatory dispersion data.

Seed Meal Detoxication, Seed Meal from Crambe abyssinica

1965 ◽  
Vol 13 (1) ◽  
pp. 24-27 ◽  
Author(s):  
C. H. VanEtten ◽  
M. E. Daxenbichler ◽  
J. E. Peters ◽  
I. A. Wolff ◽  
A. N. Booth
Keyword(s):  
Seed Meal ◽  
Crambe Abyssinica

Enantiomeric 3-hydroxypent-4-enethionamides from thioglucosides of Crambe and Brassica seeds by action of ferrous salts

1968 ◽  
Vol 46 (9) ◽  
pp. 1507-1512 ◽  
Author(s):  
F. L. Austin ◽  
C. A. Gent ◽  
I. A. Wolff
Keyword(s):  
Brassica Napus ◽  
Magnetic Resonance ◽  
Proton Magnetic Resonance ◽  
Optical Rotatory Dispersion ◽  
Rotatory Dispersion ◽  
Seed Meal ◽  
Optical Rotatory ◽  
Crambe Abyssinica ◽  
Magnetic Resonance Studies ◽  
Derivatives Of

epi-Progoitrin, the major thioglucoside of Crambe abyssinica seed, is cleaved by ferrous salts to yield (S)-1-cyano-2-hydroxy-3-butene and (S)-3-hydroxypent-4-enethionamide. The products are the same whether obtained from the purified thioglucoside or from the seed meal. Identical behavior was observed for seed meal of Brassica napus, which gave corresponding derivatives of the opposite configuration. Optical rotatory dispersion and proton magnetic resonance studies suggest the existence of solvent-dependent differences in rotamer composition for the 3-hydroxypent-4-enethionamides.

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