Cyclopropenoid Fatty Acids Research Articles

Final report on the safety assessment of Hydrogenated Cottonseed Oil, Cottonseed (Gossypium) Oil, Cottonseed Acid, Cottonseed Glyceride, and Hydrogenated Cottonseed Glyceride.

Hydrogenated Cottonseed Oil, Cottonseed (Gossypium) Oil, Cottonseed Acid, Cottonseed Glyceride, and Hydrogenated Cottonseed Glyceride are cosmetic ingredients derived from Cottonseed Oil and used as skin-conditioning agents and surfactants. Nonoils known to be toxic that may be found in cottonseed oils include gossypol, aflatoxin, and cyclopropenoid fatty acids (CPFA). Toxic heavy metal and/or polychlorinated biphenyl (PCB) or other pesticide contamination is also possible. Cottonseed Oil was nontoxic in acute oral toxicity studies in rats. In a short-term study, rabbits that had been fed 2% Cottonseed Oil for 7 weeks had significantly lower blood chemistry parameters (compared to wheat bran controls) and significantly more stored hepatic vitamin A (compared to rabbits fed other fats). Cottonseed Oil controls used as vehicles in two parenteral studies produced negative results. Hydrogenated Cottonseed Oil tested in formulation did not produce dermal or ocular irritation in rabbits. An oral-dose reproductive study tested up to 30% Cottonseed Oil (with 1% CPFAs) and reported no adverse effects on sexual maturity and reproductive performance of the F0 generation; changes were noted in the F1 generation but reproductive capacity was not altered. Parenteral-dose reproductive studies reported no adverse effects. Cottonseed Oil was not mutagenic. Cottonseed Oil did not induce aberrant crypt foci when given orally to mice, but in other studies, it increased the incidence of spontaneous mammary tumors in rats and mice. Mice fed 20% Hydrogenated Cottonseed Oil during induction and promotion of photocarcinogenesis had significantly lower tumor incidence compared to mice fed 20% sunflower oil. Hydrogenated Cottonseed Oil in formulation (up to approximately 21%) was neither an irritant nor sensitizer in clinical studies. Limited clinical data indicated that Cottonseed Oil does not contain allergic protein. Based on the available data, it was concluded that these ingredients may be used safely in cosmetic formulations if established limits on gossypol, heavy metals, and pesticide concentrations are not exceeded.

Final Report on the Safety Assessment of Hydrogenated Cottonseed Oil, Cottonseed (Gossypium) Oil, Cottonseed Acid, Cottonseed Glyceride, and Hydrogenated Cottonseed Glyceride

Hydrogenated Cottonseed Oil, Cottonseed (Gossypium) Oil, Cottonseed Acid, Cottonseed Glyceride, and Hydrogenated Cottonseed Glyceride are cosmetic ingredients derived from Cottonseed Oil and used as skin-conditioning agents and surfactants. Non-oils known to be toxic that may be found in cottonseed oils include gossypol, aflatoxin, and cyclopropenoid fatty acids (CPFA). Toxic heavy metal and/or polychlorinated biphenyl (PCB) or other pesticide contamination is also possible. Cottonseed Oil was nontoxic in acute oral toxicity studies in rats. In a short-term study, rabbits that had been fed 2% Cottonseed Oil for 7 weeks had significantly lower blood chemistry parameters (compared to wheat bran controls) and significantly more stored hepatic vitamin A (compared to rabbits fed other fats). Cottonseed Oil controls used as vehicles in two parenteral studies produced negative results. Hydrogenated Cottonseed Oil tested in formulation did not produce dermal or ocular irritation in rabbits. An oral-dose reproductive study tested up to 30% Cottonseed Oil (with 1% CPFAs) and reported no adverse effects on sexual maturity and reproductive performance of the F0 generation; changes were noted in the F1 generation but reproductive capacity was not altered. Parenteral-dose reproductive studies reported no adverse effects. Cottonseed Oil was not mutagenic. Cottonseed Oil did not induce aberrant crypt foci when given orally to mice, but in other studies, it increased the incidence of spontaneous mammary tumors in rats and mice. Mice fed 20% Hydrogenated Cottonseed Oil during induction and promotion of photocarcinogenesis had significantly lower tumor incidence compared to mice fed 20 % sunflower oil. Hydrogenated Cottonseed Oil in formulation (up to 21 %) was neither an irritant nor sensitizer in clinical studies. Limited clinical data indicated that Cottonseed Oil does not contain allergic protein. Based on the available data, it was concluded that these ingredients may be used safely in cosmetic formulations if established limits on gossypol, heavy metals, and pesticide concentrations are not exceeded.

LIPIDS AND CARBOHYDRATES FROM Althaea nudiflora AND A. armeniaca ROOTS

Lipids from roots ofAlthaea nudifloraandA. Armeniacawere studied. The carbohydrate and fatty-acid compositions were found. The lipids ofA. NudifloraandA. Armeniacacontain 22.3 and 12.6%, respectively, of cyclopropenoid fatty acids, the physical chemical properties of which are presented. The optimal degree of grinding, temperature, and raw-material-to-extractant ratio for aqueous extraction of water-soluble polysaccharides from althaea roots were chosen from a single statistically significant experiment

Delta9 desaturase activity in bovine subcutaneous adipose tissue of different fatty acid composition.

Two experiments were conducted to investigate the relationship between delta9 desaturase (stearoyl-coenzyme A desaturase) activity and fatty acid composition in subcutaneous adipose tissue from cattle of different backgrounds. In Experiment 1, subcutaneous adipose tissue samples were taken from carcasses of pasture-fed cattle and feedlot cattle fed for 100, 200, or 300 d. Adipose tissue from pasture-fed cattle had significantly lower total saturated fatty acids and higher total unsaturated fatty acids than feedlot cattle. Desaturase activity correspondingly was 60-85% higher in pasture-fed cattle than in feedlot cattle. There was no difference in the fatty acid composition or desaturase activity among samples from the 100-, 200-, and 300-d feedlot cattle. In Experiment 2, adipose tissue samples were collected from carcasses of feedlot cattle fed for 180 d with either a standard feedlot ration (control group), or a ration containing rumen-protected cottonseed oil (CSO) for the last 70-80 d. Adipose tissue from the CSO-fed cattle was more saturated than that from the control group, having significantly more 18:0 and less 16:1 and 18:1. Correspondingly, adipose tissue from the CSO group had significantly lower desaturase activity. The elevated 18:2 in adipose tissue from the CSO group confirmed that unsaturated fatty acids (including cyclopropenoid fatty acids) were protected from biohydrogenation. Further studies are needed to determine whether the repression of desaturase activity results from direct inhibition by cyclopropenoic acids or by higher dietary contents of 18:2.

Effects on dietary phosphorus of treating cottonseed meal with crystalline ferrous sulphate for the prevention of brown yolk discolouration.

1. Two experiments were carried out to examine whether the adverse effects on laying hen performance of treating cottonseed meal (CSM) with crystalline ferrous sulphate heptahydrate (FSH) to prevent brown yolk discolouration, was a consequence of iron reducing the availability of dietary phosphorus. Two batches of CSM, with different free gossypol and cyclopropenoid fatty acid contents, were treated with FSH at a 4:1 weight ratio of iron to free gossypol, and incorporated into diets at 300 g/kg with or without supplementation with sodium dihydrogen phosphate (SHP), and fed to hens. 2. FSH treatment of CSM reduced food intake and egg production. Although performance was improved by supplementing the FSH-treated CSM diets with SHP, it was still poorer than that achieved by hens fed a non-CSM control diet. 3. Brown yolk discolouration was prevented by treatment of CSM with FSH. Additional phosphorus did not produce any significant effects on brown colour development in yolks, indicating that the bioavailable gossypol content of the diets had not been altered; however, chemical analyses showed an apparent increase in the free gossypol content of the diets with the inclusion of SHP, suggesting that the assay gives misleading results.

EFFECTS OF CYCLOPROPENOID FATTY ACIDS (BAOBAB SEED OIL) ON THE FATTY ACID PROFILE OF LIPIDS FROM DIFFERENT TISSUES IN THE RAT

ABSTRACTRats were fed for 8 weeks a diet containing either Baobab seed oil (FBO) rich in cyclopropenoid fatty acids (CPFA) or heated oil (HBO) devoid of CPFA. In FBO rats, compared to controls (CO), the monounsaturated fatty acid content of adipose tissue lipids, liver triacylglycerols, liver and adrenal cholesteryl esters and liver, kidney, adrenal phospholipids were highly decreased to the benefit of saturated fatty acid content. In cholesteryl esters and phospholipids, the arachidonic acid (20:4 n‐6) content was markedly decreased, especially in adrenals. In adrenal cholesteryl esters, adrenic acid (22:4 n‐6) content was decreased more than its precursor. The effects of HBO on the tissue lipid fatty acid profile were practically absent. It is concluded that inhibition of fatty acid desaturation by CPFA previously demonstrated in vitro, was reflected in vivo in tissue lipid fatty acid composition.

The Composition of Insect-Protected Cottonseed Is Equivalent to That of Conventional Cottonseed

Cotton plants have been developed that control the major lepidopteran insect pests of cotton by the stable introduction of a gene encoding an insecticidal protein from Bacillus thuringiensis subsp. kurstaki. These plants provide season-long protection against cotton bollworm, tobacco budworm, and pink bollworm. An important component of the safety and product assessment of these lines was the comparison of the nutrient and antinutrient levels in the seed both to the parental variety and to published values for other commercial cotton varieties. Compositional equivalence confirms the appropriateness of these cotton lines for use in food and feed products. The insect-protected lines and the parental control were shown to contain levels of nutrients comparable to those of other commercial varieties. Nutrients included protein, fat, carbohydrate, moisture, ash, amino acids, and fatty acids. The levels of the antinutrients gossypol, cyclopropenoid fatty acids, and aflatoxin in the seed from the insect-protecte...

Glyphosate-Tolerant Cotton: The Composition of the Cottonseed Is Equivalent to That of Conventional Cottonseed

An important aspect of the safety assessment of genetically modified crops to be used for human food and animal feed is the product composition, including nutrients and antinutrients. Cotton lines have been developed that are tolerant to glyphosate, the active ingredient in the herbicide Roundup. The glyphosate-tolerant lines were generated by the stable insertion of a glyphosate tolerance gene in a common variety of cotton. The glyphosate tolerance gene encodes for 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS) from Agrobacterium sp. strain CP4 (CP4 EPSPS). The composition of the cottonseed and oil from two glyphosate-tolerant lines (GTCot), 1445 and 1698, was compared to that of the parental variety Coker 312 and to published values for other commercial cotton varieties. The nutrients measured in the cottonseed were protein, fat, fiber, carbohydrate, calories, moisture, ash, amino acids, and fatty acids. The antinutrients measured in the cottonseed included gossypol, cyclopropenoid fatty acids, and...

Unique Occurrence of Unusual Fatty Acids and Their Industrial Utilization

Ebenaceae plant family consists of 7 genera and more than 320 species. The present investigation describes the unique occurrence of hitherto unknown 9-keto-cis-13-octadecenoic acid (29.0%) and the cyclopropenoid fatty acids (malvalic acid 12.7% and sterculic acid 8.7%) in the seed oil of Diospyros melanoxylon as well as in the Ebenaceae plant family. Other normal fatty acids are also detected. The identification and characterization were based on FTIR, 1H NMR, 13C NMR, MS, and GLC techniques and chemical degradations.

Modifications of hepatic drug metabolizing enzyme activities in rats fed baobab seed oil containing cyclopropenoid fatty acids

The effects on drug metabolizing enzymes of cyclopropenoid fatty acids present in baobab seed oil were evaluated in rats fed either a diet with baobab seed oil (1.27% cyclopropenoid fatty acids in the diet) or a diet with heated baobab seed oil (0.046% cyclopropenoid fatty acids in the diet). Comparison was made with rats fed a mixture of oils that contained no cyclopropenoid fatty acid. Rats fed baobab oil showed retarded growth. In comparison with the other groups, the relative liver weights were markedly increased whereas cytochrome P-450 content and NADPH cytochrome c reductase and NADH cytochrome c reductase activities were decreased. In rats fed the heated baobab oil the relative liver weight was decreased and the cytochrome P-450 level and reductase activities were increased relative to levels in rats fed the unheated oil. Ethoxycoumarin deethylase, ethoxyresorufin deethylase and pentoxyresorufin depentylase activities, expressed on the basis of cytochrome P-450, were greater in the group fed unheated baobab seed oil. Cytosolic glutathione transferase activity was markedly decreased in rats fed fresh baobab seed oil and heating the oil, which reduced the content of cyclopropenoid fatty acids, led to a considerable increase of this activity. UDP-glucuronyl transferase activities were not modified by the type of oil included in the diet. It is possible that the mechanisms of action of cyclopropenoid fatty acids are related to alterations of membrane lipid composition or microsomal proteins.

The mass spectra of the 4,4‐dimethyloxazoline derivatives of the methoxymethyl olefins of malvalic and sterculic acids

AbstractA new approach to the gas chromatographymass spectrometry analysis of cyclopropenoid fatty acids is described. The method is based on the “on‐site”‐modification of the cyclopropenoid ring with AgNO3‐saturated methanol to the methoxymethyl olefin and a subsequent “remote‐site”‐derivatization of the carboxyl group to its 4,4‐dimethyloxazoline. The mass spectra of the isomeric reaction products obtained from malvalic and sterculic acid were found to be useful for locating the original cyclopropenoid ring in the fatty acid chain.

Action of a cyclopropenoid fatty acid on the corpus luteum of pregnant and nonpregnant ewes.

The effects of a cyclopropenoid fatty acid on luteal cell function were studied. In experiment 1, pregnant ewes were laparotomized on Day 18 of gestation and ewes with CL in both ovaries were unilaterally ovariectomized. Either 1.09 mg of an extract of Sterculia foetida seeds, containing 750 micrograms sterculic acid methyl ester (SA, n = 6), or 1.09 mg oleic acid methyl ester (OA, n = 6) was injected into the artery supplying the ovary bearing CL. Jugular blood was collected on Day 18 before surgery and daily thereafter until Day 30 of gestation or until detection of estrus, whichever occurred first. Serum was assayed for progesterone (P4) by RIA. In experiment 2, CL were removed from ewes on Day 10 of the estrous cycle and slices of luteal tissue were incubated in medium containing 145 ng/ml of S. foetida extract (100 ng/ml SA) or 145 ng/ml OA (control) for 90 min. Then tissue was washed and reincubated in medium containing 25 micrograms 22(R)-hydroxycholesterol/ml or 25 micrograms pregnenolone/ml for 120 min. Tissue plus medium was analyzed for P4. Injection of SA or OA on Day 18 of gestation reduced (p < 0.01) serum levels of P4 within 24 h; concentrations of P4 then remained low, and relatively constant, in six OA control ewes that were pregnant until Day 30 of gestation and in three SA-treated ewes that had nonviable fetuses on Day 30. Serum concentrations of P4 in SA-treated ewes were lower than those of control ewes (p = 0.009). The remaining three ewes injected with SA exhibited estrus within 3 to 5 days after treatment.(ABSTRACT TRUNCATED AT 250 WORDS)

Effect of Corn Contaminated With Velvetweed Seeds on Eggs

An experiment was conducted to determine whether corn contaminated with velvetweed seeds and fed to hens was the reason for the formation of eggs with pasty and rubbery yolks observed on a commercial poultry farm in New York State. The eggs from hens fed 20% contaminated corn screenings with velvetweed seed (3% velvetweed seeds in the finished feed) appear3ed normal when broken fresh. However, egg yolks became pasty and rubbery within 24 hours of cold storage; this result occurred within one week of when the hens were fed the contaminated feed. The viscosity of yolks appeared to increase when the period of cold storage was increased. It took approximately one week after removing contaminated corn screenings from the diet for the egg yolks to return to their normal structure. The information obtained indicated that the presence of cyclopropenoid fatty acids (sterculic and malvelic acids) in the velvetweed seeds was the reason for the formation of eggs with an abnormal yolk structure and the discoloration of yolks and albumen.

Determination of cyclopropenoid fatty acids inSterculia seed oils from senegal

Seed oils ofSterculia tomentosa andS. tragacantha (Sterculiaceae) were found to contain malvalic (5.8 and 5.1%), sterculic (11.3 and 30.2%) and dihydrosterculic (0.9 and 0.5%) acids. The total amount of these two cyclopropenoid fatty acids was established by1H nuclear magnetic resonance and their cooccurrence by gas chromatography. Besides these unusual compounds, the main common fatty acids were palmitic (20 and 24%), oleic (21 and 15%) and linoleic (30 and 16%) acids.

Novel fatty acids in azima tetracantha seed oil

Azima tetracantha Lam, belonging to the Salvadoraceae plant family, was found to contain ricinoleic acid (9.8%) and cyclopropenoid fatty acids (9.6%) along with normal fatty acids.

GC‐MS characterization (Chemical lonization and electron impact modes) of the methyl esters and oxazoline derivatives of cyclopropenoid fatty acids

The CI‐(CH4) mass spectra of the methyl esters and the EI mass spectra of the oxazoline derivatives of three cyclopropenoid fatty acids (malvalic, sterculic and α‐ hydroxy‐sterculic acid) from the seed oil ofPachira aquatica were found to be useful for structure elucidation of such compounds. Furthermore, some hitherto unknown minor fatty acids were identified and the nuclear magnetic resonance data of the oil and α‐hydroxysterculic acid methyl ester are presented.

Cyclopropenoid fatty acids of six seed oils from malvaceae

AbstractThe seeds ofAlyogine hakeifolia, Alyogine huegelii,Gossypium australe, Hibiscus coatesii, Lawrencia viridigrisea andRadyera farragei (Malvaceae) contained 13.5‐18.6% oil. Linoleic acid predominated (60.0‐68.2%) in the component fatty acids of all the oils, followed by palmitic (9.9‐18.1%) and oleic acids (7.8‐15.8%). Cyclopropene fatty acids, malvalic and sterculic, were present in small concentrations (1.0‐4.4%, 0.1‐1.5% respectively). Dihydrosterculic acid was present in small quantities (trace‐2.1%).

Effects of dietary cottonseed meal and iron‐treated cottonseed meal in different laying hen genotypes

The effects of dietary screw-pressed cottonseed meal (CSM) and iron-treated CSM on laying performance and discolourations in eggs were examined in a range of hen genotypes. In experiment 1, six genotypes, obtained at point-of-lay from various sources, were fed on a non-CSM diet, a diet with 300 g CSM/kg, and a diet containing iron-treated CSM at 300 g/kg. In experiment 2, two of these genotypes were reared together from day-old and were fed from 10 to 18 weeks on a non-CSM diet or a diet containing iron-treated CSM at 250 g/kg. They were then fed on a non-CSM layer diet or a diet containing iron-treated CSM at 300 g/kg, in a 2 x 2 x 2 factorial design that also examined the effects of the rearing diet. 2. The effects on food intakes and egg production of including CSM and iron-treated CSM in layer diets depended on the genotype of the hens. The strongest interaction between breed and diet was on food intake, the breed Hubbard Golden Comet (HGC) being the least tolerant of CSM and iron-treated CSM. 3. Inclusion of iron-treated CSM in the rearer diet to supply approximately 70% of the dietary protein had no adverse effects on growth or age at first egg. Food intake and egg production between 18 and 26 weeks were affected by the iron-treated CSM layer diet, but there were no carry-over effects attributable to the rearing diets. 4. Genotype was not a factor in the development of the gossypol-related brown yolk discolouration in fresh or warm-stored eggs of hens fed on a CSM-based diet containing 197 mg free gossypol/kg and 52 mg cyclopropenoid fatty acids (CPFA)/kg (experiment 1). 5. In both experiments, the susceptibility of eggs to the CPFA-related cold storage effects depended on the genotype of the hen, eggs from hens of the HCG breed being more affected than those of ISA hens. 6. Treatment of CSM with crystalline ferrous sulphate heptahydrate, at a 4:1 weight ratio of iron to free gossypol, prevented brown yolk discolourations in all genotypes tested, as assessed by subjecting egg yolks to atmospheres of ammonia, and cold storage of eggs.

In Vivoandin VitroEffects of a Cyclopropenoid Fatty Acid on Ovine Corpus Luteum Function*

Experiments were conducted to examine the effect of a cyclopropenoid fatty acid (CPFA) on progesterone (P4) production by the ovine corpus luteum (CL) during the estrous cycle. Ewes in Exp 1 and 2 were laparotomized on day 2 of the estrous cycle, and animals with CL in both ovaries were subjected to unilateral ovariectomy. Ewes with CL in one ovary only were not ovariectomized. During surgery, ewes were injected with a mixture of fatty acids (sterculic acid, 39%; palmitic, 29%; linoleic, 12%; malvalic acid, 9%; oleic, 8%; stearic, 3%) containing 500 micrograms sterculic acid (SA; Exp 1), 750 micrograms SA, or 750 micrograms oleic acid (Exp 2) via the artery supplying the ovary bearing the CL. Control ewes were similarly injected with vehicle only (0.1-0.2 ml dimethylsulfoxide; Exp 1 and 2, respectively). Sera from blood samples collected at 15-min intervals for 1 h after injection or once daily on alternate days of the cycle after surgery were analyzed for LH and P4, respectively. In Exp 3, slices of CL removed from five ewes on day 10 of the cycle were incubated for 90 min in medium containing 100 ng/ml SA or vehicle (10 microliters dimethylsulfoxide). Slices were then reincubated for 90 min in medium containing 10 ng/ml oLH or saline (10 microliters). Tissue and medium were analyzed for P4. Injection of 500 micrograms SA suppressed serum levels of P4 (P less than 0.01), but did not alter mean cycle length. Injection of 750 micrograms SA reduced serum concentrations of P4 and shortened estrous cycle duration (P less than 0.005). Oleic acid (750 micrograms) or as much as 1.9 mg of a mixture of fatty acids devoid of CPFA had no effect on cycle length or serum levels of P4, suggesting that altered luteal function was due to the type and not the quantity of fatty acid injected. Treatments had no effect on serum concentrations of LH. Preincubation with SA interfered with the ability of luteal slices to synthesize P4 when subsequently incubated alone or with ovine LH (P less than 0.01). It is concluded that SA acts on the CL to impair steroidogenesis and ultimately cause luteal regression.

Control of acyl lipid desaturation in the yeast Rhodotorula gracilis via the use of the cyclopropenoid fatty acid, sterculate

The effect of the cyclopropene fatty acid, sterculic acid, on fatty acid metabolism in the oleaginous yeast Rhodotorula gracilis (CBS 3043) has been studied. Sterculate caused approximately 90% inhibition of [1-14C]sterate desaturation but only about 25% inhibition when [1-14C]acetate was used as precursor. Measurement of acyl-coenzyme A (CoA) pool labelling and the pattern of distribution of radioactivity within lipid classes suggested that the high rate of inhibition of stearate desaturation was due to sterculate reducing the formation of stearoyl-CoA. In agreement with previous suggestions for plant and animal systems, experiments with a post-mitochondrial (20 000 g × 30 min) supernatant suggested that sterculoyl-CoA was the active inhibitor. The action of sterculate on endogenous lipid composition was most marked in stationary-phase cells. In such cells an increase in stearate was seen especially in the triacylglycerol pools, while α-linolenate was increased predominantly in the phospholipid fractions. The increased flux of carbon to α-linolenate at the same time that stearate desaturation appeared to be inhibited by sterculate, indicated that that two separate pathways for desaturation, employing different substrates, may operate in R. gracilis. We suggest that sterculate inhibits the stearoyl-(acyl-)CoA-dependent pathway but has little effect when phospholipids are used as substrates for acyl chain desaturation.