Methods for determining thioglucosides inCrambe abyssinica

Four methods are described for the determination of thioglucosides inCrambe abyssinica: sulfate ion, sulfur balance, silver complexing, and hot-water extraction. The analytical results of all four methods agree closely as to the thioglucoside content in dehulled, defatted meal, from 11–12%. Any one of these methods should be useful in studying new plant species because approximate thioglucoside content is obtained even though the specific thioglucosides and isothiocyanates involved may not be known. Presented in part at the AOCS Meeting, Chicago, 1964. A laboratory of the No. Utiliz. Res. & Dev. Div., ARS, USDA.     

Crambe seed processing. improved feed meal by soda ash treatment

Crambe seed, like rapeseed, is characterized by having thioglucosides and perhaps other antigrowth factors that diminish feed value and palatability. A soda ash cooking process was developed that modifies the thioglucosides in crambe meal and significantly improves its feeding value. Destruction of the undesirable thioglucoside fraction of the meal was demonstrated, not only by paper Chromatographic changes but also by negative results in tests which were based on conversion of the thioglucoside to thiooxazolidone. Sodium carbonate, added at a level of 1.4% (whole seed basis), destroys both the goitrin precursor,epi-progoitrin thioglucoside, and the ultraviolet-absorbing compounds in the meal, at least one of which is associated with bitterness. Animal-feeding tests demonstrated the improved palatability and nutritional quality of the meal. Presented in part at the AOCS Meeting, Philadelphia, October 1966. Journal Series, Nebraska Agricultural Experiment Station. No. Utiliz. Res. Dev. Div., ABS, USDA.     

Crambe seed processing: Improved feed meal by ammoniation

An improved crambe meal has been developed by using an ammonia-heat treatment to give significantly better nutritive value and acceptability. The quantity of ammonia permanently bound as nitrogen in the processed meal was from 0.5 to 1.5% of the meal weight and varied with conditions of reaction. Destruction of the undesirable thioglucoside fraction of the meal was demonstrated by paper chromatograph changes and by the absence of the thioglucoside conversion product thiooxazolidone. Ultraviolet-absorbing compounds in the meal, at least one of which is associated with bitterness, were also modified. Feeding experiments with chicks and cattle show the improved palatability and nutritional quality. Incorporation of the ammonia reaction into desolventizer-toaster operations should be possible to provide an economical means of improving the feeding value of crambe meal. Presented in part at the AOCS Meeting, Houston, April 1965. No. Utiliz. Res. Dev. Div., ARS, USDA.     

Pentacylic triterpenes ofJurinea anatolic boiss. andJurinea consanguinea DC. Fruit

Pentacyclic triterpene alcohols, together with their acetate, myristate, and palmitate esters, comprise about 40% of the petroleum ether extract of the fruit (seed and pericarp) of twoJurinea species. All the triterpene esters and a porition of the free triterpene alcohols in theJ. anatolica extract are derived from the pericarp portion of the fruit. The triterpene alcohol moieties and their approximate percentage of the hydrolyzed extract ofJ. anatolica fruit are α-amyrin, 5%; β-amyrin, 6%; lupeol, 6%; and ψ-taraxasterol plus taraxasterol, 16%.J. consanguinea fruit extract yields essentially the same amount of the same five triterpene alcohols on hydrolysis. These concentrations of triterpenoid materials are believed to be the largest found in plant tissues. No. Utiliz. Res. Dev. Div., ARS, USDA.     

Aflatoxins in hull and meats of cottonseed

We have found that when aflatoxins are a contaminant of cottonseed, they may be distributed both in the hulls and in the meats. The concentrations in hulls and meats do not appear to be correlated. Aflatoxins were found in hulls and not in meats of some seed samples, and the reverse situation also was observed. The amounts of toxins were generally much greater in meats, which contained up to 10,200 ppb, than in hulls, which contained up to 390 ppb aflatoxins. Hulls as well as meats fromAspergillus flavus-damaged seed represent a potential source of aflatoxin contamination, and both should be analyzed in order to accurately assess the total aflatoxins in seeds. Crops Research Division, ARS, USDA. So. Utiliz. Res. Dev. Div., ARS, USDA.     

Crambe seed processing: Decomposition of glucosinolates (thioglucosides) with chemical additives

Crambe meal was cooked with a variety of bases and metal salts to study decomposition of the undesirable glucosinolate (thioglucoside),epi-progoitrin. Salts of iron and copper were preferred because they were the most active decomposers and because they did not reduce the lysine content as did the alkalies. An unsaturated hydroxy nitrile, representing about 25 mole per cent of the decomposedepi-progoitrin, was the major reaction product left in the cooked meal. A thionamide product, representing about 7 mole per cent of the decomposedepi-progoitrin, was also observed in meals cooked with metallic salts. The thionamide was relatively unstable in moist, hot crambe meal, especially at basic pH, and may therefore be an intermediate in a complex decomposition path. Rats fed ferrous sulfate-treated crambe meal as 30% of a protein sufficient diet gained 70% compared with a basal control. Enlargement of thyroid, liver and kidneys was about 1.5 times that of the control organs. A crambe meal heated under the same conditions but without ferrous sulfate and fed at the same diet level caused 100% mortality within two weeks. Presented at AOCS Meeting, Houston, Texas, May 1971. Northern Marketing and Nutrition Research Division, ARS, USDA.     

Mustard seed processing: Simple methods for following heat damage to protein meals

Processed mustard seed contains a considerably higher content of reducing sugar than other oilseeds. During processing, the natural reducing sugar is supplmented with glucose released by enzyme hydrolysis of the thioglucoside, and this total content reaches a value of more than 3% of the defatted mustard meal. This quantity of reducing sugar in mustard seed is three times more than that in soybean meal. Consequently, the browning reaction, which degrades protein, presents a greater problem in processing oilseeds containing thioglucosides than oilseeds free of thioglucosides. In developing the processing of mustard seed, the degree of heat treatment given the protein meals had to be determined. Several indirect methods were developed for following the effects of heat treatment on protein quality. Nitrogen solubility index, optical density of aqueous extracts, and reducing sugar content correlated well with degradation of heat-labile amino acids, such as lysine, arginine, and histidine, and gave an index of protein quality. Presented at the AOCS meeting in Minneapolis, 1963. A laboratory of No. Utiliz. Res. and Dev. Div., ARS, USDA.     

Search for new industrial oils. XI. Oils of boraginaceae

Analysis of seed oils from 29 species of the family Boraginaceae revealed widespread occur-rence of 6,9,12-octadecatrienoic and C₁₈ noncon-jugated tetraenoic acids in addition to linolenic and other common C₁₆ and C₁₈ acids. The 6,9,12-octadecatrienoic acid ranged in amount from 0-27%, tetraene from 0-17%, and linolenic acid from 0.3-50%. Iodine values of the oils ranged from 88-225. A laboratory of the No. Utiliz. Res. and Dev. Div., ARS, USDA. A division of ARS, USDA.     

Pre-Ripening damage to cottonseed byaspergillus flavus is not influenced by seed coat permeability

Infection of cottonseed (Gossypium hirsutum L.) byAspergillus flavus and associated production of aflatoxins are problems in the arid portions of the United States cotton belt. The hard seed (impermeable to water) characteristic confers resistance to these problems in ripened cottonseed. Experiments were done to determine if low seed coat permeability to water or impermeability protect developing seeds from deterioration and aflatoxin formation. No differences were observed in the degree of seed deterioration in the various cotton lines that could be attributed to seed coat permeability. It is likely that, because the impermeable or low permeability phenotypes are expressed only upon seed ripening, these characteristics afford no protection to cottonseed against attack byA. flavus during seed development. To whom correspondence should be addressed at USDA/ARS, Dept. of Botany and Plant Pathology, Michigan State University, East Lansing, MI 48824-1312.     

An Apparatus for Rapid Preparation of Oil and Oil-Free Meal from Brassica Seed

An apparatus for the rapid preparation of large numbers of oil and “oil-free” meal samples from Brassica seed is described. Batches of sixty 0.2 g to 2.0 g seed samples can be ground and solvent extracted simultaneously, followed by filtration, solvent washing and vacuum drying of the meal. The oil can be recovered quantitatively for gravimetric oil content determination.     

Search for new industrial oils. XII. Fifty-eight euphorbiaceae oils,including one rich in vernolic acid

Seed oil ofEuphorbia lagascae Spreng. contains 57% ofcis-12,13-epoxy-cis-9-octadecenoic (vernolic) acid. The amt of trivernolin in the glycerides of this species indicates random or restricted random distribution of the vernolic acid. Seed from 57 additional species in the Euphorbiaceae were analyzed for oil and protein contents and also for fatty acid composition of the oils. Iodine values (I.V.) of the oils ranged from 87–221. Among these oils, samples were encountered with as much as 76% linolenic, 77% linoleic or 84% oleic acid. Presented at the AOCS in New Orleans, 1964. A laboratory of the No. Utiliz. Res. & Dev. Div., ARS, USDA. ARS, USDA.     

Search for new industrial oils. XIII. Oils from 102 species of cruciferae

Seed from additional species of Cruciferae have been analyzed for crude protein, oil and fatty acids in the oil. Oils were like those reported earlier from other crucifers, except forCardamine impatiens which is unique among known seed oils because it contains some 25% dihydroxy acids. Erucic acid is present (0.3–55%) in about three-fourths of the 102 samples. Eicosenoic acid is a major constituent (32–53%) in four species and monohydroxy acids (45–72%) in another four. Linolenic acid occurs (2–66%) in oil of all species. Presented at the AOCS meeting in Chicago, Ill., October 11–14, 1964. A laboratory of the No. Utiliz. Res. and Dev. Div., ARS, USDA. ARS, USDA.     

The composition of safflower seed

Safflower has some interesting variations in composition. Current commercial seed types have about 40% hull, 37% oil, and 23% meal. Varities also exist with from 59-18% hull and inversely varying oil and meal percentages. The fatty acid composition of the linoleic acid type oils is quite constant at about 78% linoleic, 11% oleic, 3% stearic, 6% palmitic. Experimental types have been described with about 45% oleic: 45% linoleic, 80% oleic: 10% linoleic, and with 10% stearic. Compositional data are reviewed with particular attention to major and minor constituents (especially linolenic acid) that influence safflower use. W. Utiliz. Res. Dev. Div., ARS, USDA.     

OxygenatedTrans-3-olefinic acids in aStenachaenium seed oil

Interesting differences were found in oils from two samples ofStenachaenium macrocephalum (Compositae) seed with dissimilar storage histories. One contained significant amounts of epoxy acids (6.5%) and hydroxy conjugated dienoic acids (5.6%), but the other contained no more than 1% of these oxygenated acids. Characterization of components in the former oil established that the principal epoxy acid (4.0%) is the previously unknowncis-9, 10-epoxy-trans-3,cis-12-octadecadienoic acid. The conjugated dienols include two additional new acids with Δ3 unsaturation (2.5%): 9-hydroxy-trans-3,-trans-10,cis-12-octadecatrienoic and 13-hydroxy-trans-3,cis-9,trans-11-octadecatrienoic acoids. The nonoxygenated acids, except for the large amount (40%) oftrans-3,cis-9,cis-12-octadecatrienoic, are those that commonly occur in seed oils. Presented at the AOCS Meeting, San Francisco, April 1969. No. Utiliz. Res. Dev. Div., ARS, USDA.     

Nutritional effects of mustard seed protein detoxified with aqueous isopropanol in young rats

The effect of removing anti‐nutritional factors from n‐hexane‐extracted mustard meal using 80% isopropanol (to reduce thioglucosides, phenolics, etc.) on growth, food efficiency ratio, serum and liver lipid profiles and protein content of young rats was examined. For this n‐hexane‐extracted mustard meal was extracted with 80% isopropanol giving a fraction with 68% protein and low residual thioglucoside (0.5%) as well as phenolic (0.3%) content. This isopropanol‐extracted mustard seed protein fraction reduced the growth of young rats slightly when compared with casein. The food efficiency ratio between rats fed isopropanol‐extracted mustard seed protein or casein did not differ, nor did the protein composition affect serum total cholesterol, triglyceride, HDL‐cholesterol, LDL‐cholesterol, VLDL‐cholesterol and LDL‐C/HDL‐C ratio. However, rats fed isopropanol‐extracted mustard seed protein showed a significantly lower (p<0.05) liver cholesterol concentration than rats fed casein. Liver triglyceride and phospholipid concentrations did not differ between rats fed the two proteins, nor was serum protein affected. This study indicates that extraction of hexane‐extracted mustard meal with 80% isopropanol reduced a number of anti‐nutritional factors like thioglucoside and phenolics. Furthermore the nutritional quality of mustard seed protein fraction is comparable to casein in respect to growth, food efficiency ratio, serum lipid and protein concentrations and organ weights.     

Oxygenated fatty acids of oil from sunflower seeds after prolonged storage

Chemical analysis of a number of sunflower (Helianthus annuus) seed oil samples revealed a low and variable percentage of hydrogen bromide-reactive material. To characterize the compounds responsible for this reactivity, oil was extracted from selected introductions from Uruguay, Turkey, and Yugoslavia that had been subjected to prolonged storage. Two epoxy fatty acids and two conjugated dienolic acids were isolated from the methyl esters derived from these sunflower seed oils by using a combination of column chromatography and countercurrent distribution. The epoxy acids arecis-9,10-epoxystearic acid (0.5%) andcis-9,10-epoxy-cis-12-octadecenoic (coronaric) acid (2.2%). Characterization of the dienols revealed that they are 9-hydroxy-trans-10,cis-12-octadecadienoic acid (1.2%) and 13-hydroxy-cis-9,trans-11-octadecadienoic acid (1.3%). Fresher seed of some of these introductions contained less of the oxygenated components. Oil from recently produced seed of selected high-oil Russian sunflower varieties, including some currently grown in the United States, contained no more than trace amounts of oxygenated acids. Though the relative contributions of genetic and environmental factors toward genesis of oxygenated acids are not established, increase of those acids in some sunflower lines as a result of storage has been demonstrated. Presented at the AOCS-AACC Joint Meeting, Washington, D. C., April 1968. No. Utiliz. Res. Dev. Div., ARS, USDA.     

Search for new industrial oils. X. Seed oils of the calenduleae

Seed oils from 29 species in five genera of the tribe Calenduleae, family Compositae, have been examined to determine the distribution of dimorphecolic acid (9-hydroxyl-trans-10,trans-12-octadecadienoic acid) among the close relatives ofDimorphotheca. Dimorphecolic acid occurs in all five of theDimorphotheca species ofOsteospermum in amounts ranging from 34–75% of the oil. In all other species of the tribe analyzed to date, including 14 species ofOsteospermum, two ofCalendula, and two ofChrysanthemoides, the oil contained conjugated trienoic acids ranging from 14–60%. No. Util. Res. and Dev. Div., ARS, USDA. ARS, USDA     

Prepress-solvent extraction of crambe: First commercial trial run of new oilseed

Commercial-scale equipment was used to process experimentally 36 tons ofCrambe abyssinica seed grown in the western part of the United States to obtain information on the processing of this new oilseed and to determine characteristics of the oil and meal products. The run was carried out for USDA at the Pacific Vegetable Oil Corporation plant at Sidney, Nebraska, February 1964. Process objectives in the study included dehulling, primary oil removal by expeller prepress, secondary oil removal by solvent extraction and control of thioglucosides to obtain good oil quality. A continuous plant operation yielded crude oils and toasted meal that will be compared with similar products from other commercial oilseed processes. Characteristics of the crude oils that have been determined are composition, refining losses and hydrogenation ability. Organoleptic data on the refined, bleached and deodorized oils have been obtained, as well as compositional data on the desolventized-toasted meals. More than 13 tons of meal and 10 tons of oil were prepared. Presented at the AOCS Meeting, Chicago, October 1964. A laboratory of the No. Utiliz. Res. & Dev. Div., ARS, USDA.     

Vernonia anthelmintica (L.) willd. The effect of storage on the epoxy content of the seed oil and trivernolin

Accessions ofVernonia anthelmintica (L.) Willd. seed from India and Pakistan varied somewhat in the amt of oil that they contained, but the oils did not vary significantly in their epoxy content. Storage of the whole seed for periods up to three years did not affect the quality of the oil, but the activity of the seed enzyme system seemed to increase with time. The data also show a rapid development of free fatty acid once the seed is ground. The epoxy content of low FFAVernonia oil and trivernolin changed only slightly when these products were stored at room temp for six months. However, the viscosity of the samples that were exposed to light increased greatly indicating changes in the physical nature of the products. Similar behavior was exhibited by both products when they were stored under nitrogen at 100C and by trivernolin at 4C. Presented at the AOCS Meeting, Minneapolis, 1963. A laboratory of E. Utiliz. Res. & Dev. Div., ARS, USDA.     

Cyanolipids of kusum (schleichera trijuga) seed oil

A cyanolipid, consisting of two fatty acid moieties esterified with 1-cyano-2-hydroxymethylprop-2-ene-1-ol, constitutes 58% ofSchleichera trijuga (Kusum) seed oil. No Utiliz. Res. Dev. Div., ARS, USDA.