Cottonseed Pigment Glands Research Articles

Assessment of uncertainty sources of free gossypol measurement in cottonseed by high-performance liquid chromatography

Gossypol is a polyphenolic component found in pigment glands of whole cottonseed, it is toxic in its free-form (FG) to livestock farm animals. It can be degraded through the preparation and extraction of the tested sample, leading to inaccurate quantification of FG content in animal diets. The primary size of the laboratory samples, the particle size of the analytical samples, and interval of time between grinding and solvent extraction were tested as uncertainties of the sample preparations. The efficiency of extraction, accuracy, linearity, matrix effects, limits of detection and quantification were assessed in the chemical analysis. The chemical analysis contributes as a minor source of uncertainty in analysis, despite the occurrence of matrix effects. Solvent soaking time can be considered as an effective uncertainty source; at least 16 h of soaking in acetone should be applied to extract FG from glands. Trueness and precision are the accuracy parameters most affected in the steps prior to the chemical analysis. The reduction of particle size as the increase of the interval of time between grinding and chemical analysis affected the trueness of results. On the other hand, precision was affected by the sample size of analytical and laboratory sample preparation. The best practices to reduce the uncertainty in FG analysis increase the confidence of cottonseed use as an animal feed source regarding its toxicity, improving animal health and the safety of animal products intended to human consumption.

Effect of Gossypol Source and Level on Chick Growth

Evidence that toxic effects of cottonseed pigment glands on young growing chickens is caused by free gossypol has been presented by Lillie and Bird (1950). Eagle and Davies (1957) have shown that at a dietary level equivalent to 0.1% free gossypol pigment glands give greater growth depression in rats than pure gossypol. However, this report contained no information on how frequently the diets were prepared in order to prevent destruction of gossypol.In this paper data are presented on the relative toxicities to young chickens of cottonseed meats (decorticated seed), cottonseed pigment glands, and pure gossypol when the materials were fed at levels to supply equal amounts of free gossypol. The diets were prepared frequently to minimize inactivation of gossypol. PROCEDUREGroups of 20 day-old New Hampshire or cross bred meat-type males were placed in separate decks of battery brooders at the start of each experiment. The first five experiments …

Comparison of Performance of Layers Fed Soybean, Glandless or Glanded Cottonseed Meals

HEYWANG (1947) reported that glanded cottonseed meals and soybean meal were of about equal value as sources of protein in diets for layers, with egg production, feed consumption, maintenance of body weight, and mortality as criteria. In a later study (Heywang et al., 1949) it was found that glanded cottonseed meal made by either the hydraulic or the solvent process, could be included at the 10% level in diets for breeders with no adverse effect on the hatchability of their eggs if the meal contained 0.12% or less free gossypol. In both reports data are given on the undesirable effect of these cottonseed meals on the color of yolks and whites in stored eggs.The results of experiments by a number of investigators show that: (1) gossypol, which is in the pigment glands of cottonseed, causes dark discolorations in egg yolks, (2) cyclopropenoid fatty acids, which are in cottonseed lipids,…

A Review of Cyclopropenoid Compounds: Biological Effects of Some Derivatives

1. INTRODUCTIONAPPROXIMATELY 40 years have passed since reports first appeared concerning discolorations in eggs laid by hens fed cottonseed products. About 1930 it was recognized that two disorders were in evidence. In one, the egg white of stored eggs developed a pink or red color, so that the condition became known as the “pink white” disorder. The other effect, which may be present at the same time, was manifested by brown or olive colors in the yolk. The latter defect is attributed to the interaction of yolk iron with gossypol from the cottonseed pigment glands, and is aggravated when the pink white disorder occurs simultaneously.It was soon found that ingestion of other plants of the botanical order Malvales could also cause the appearance of pink whites in eggs, and later work was directed towards seeking the causes of the disorder among the plant products. Pink white discoloration of…

Gossyverdurin: A newly isolated pigment from cottonseed pigment glands

AbstractThe constituents of cottonseed pigment glands were fractionated by the use of column chromatography with DEAE cellulose ion exchanger and silicic acid, and a new green pigment was isolated. The acute oral toxicity of the new pigment was determined using rats as experimental animals. The LD‐50 value obtained was 0.66 g/kg of body weight indicating that the new pigment which was named gossyverdurin is the most toxic of any cottonseed pigment so far reported. Gossyverdurin showed absorption maxima at 250, 370, and 560 mॖ. Reaction with para‐anisidine under the conditions used for the determination of gossypol gave an absorption peak similar to that obtained with gossypol indicating that the new compound is structurally related to gossypol. In addition a second peak at 342 mॖ appears on reaction with para‐anisidine indicating important structural differences between gossypol and gossyverdurin.

The acute oral toxicity of cottonseed pigment glands and intraglandular pigments

AbstractAcute oral toxicity studies were carried out on cottonseed pigment glands, gossypol, diaminogossypol and gossypurpurin using rats as experimental animals. It was found that both diaminogossypol and gossypurpurin are considerably less toxic than pure gossypol. The pigment glands were more toxic than gossypol and it was concluded that the toxicity of pigments cannot be accounted for entirely on the basis of their gossypol content.Administration of gossypol with cottonseed oil orSterculia foetida oil, both of which contain cyclopropene fatty acids, increased the toxicity very slightly over that found when gossypol was administered in corn oil. In the case of corn oil andSterculia foetida oil, the difference was statistically significant.Less gossypol was also found in the feces when the test dose was given in cottonseed oil orS. foetida oil indicating a possible effect of the cyclopropene fatty acids in increasing gossypol absorption.

A review of some physiological effects of gossypol and cottonseed pigment glands

Journal of the American Oil Chemists' SocietyVolume 37, Issue 1 p. 40-43 Technical A review of some physiological effects of gossypol and cottonseed pigment glands Edward Eagle, Edward Eagle Research Laboratories, Swift and Company, Chicago, IllinoisSearch for more papers by this author Edward Eagle, Edward Eagle Research Laboratories, Swift and Company, Chicago, IllinoisSearch for more papers by this author First published: 01 January 1960 https://doi.org/10.1007/BF02630823Citations: 23 Presented at the Conference on Chemical Structure and Reactions of Gossypol and Nongoassypol Pigments of Cottonseed, Southern Utilization Research and Development Division, U.S.D.A., New Orleans, La., March 19–20, 1959. AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat Citing Literature Volume37, Issue1January 1960Pages 40-43 RelatedInformation

Effect of long‐term storage on acute oral toxicity and gossypol content of cottonseed pigment glands

SummarySix samples of cottonseed pigment glands and two samples of pure gossypol stored for more than four to nine years were re‐evaluated for their acute oral toxicity in the rat and re‐analyzed for gossypol content. There was no appreciable effect on the acute oral toxicity or gossypol content after these long storage periods.

Relationship between the Weight of Chicks and Levels of Dietary Free Gossypol Supplied by Different Cottonseed Products

THE use of cottonseed meals as sources of protein in the diets of growing chickens is increasing, at least partly because they frequently are cheaper than other protein concentrates and recent investigations have led to improvement in their nutritive value. However, because of the toxic properties of gossypol, a component of the pigment glands of cottonseed, the quantity of a cottonseed meal that can be used advantageously in the diet of growing chickens may depend on the quantity of gossypol the meal supplies to the diet.It seems unnecessary in this paper to mention more than a few pertinent references to the literature on the toxicity of gossypol. Withers and Carruth (1915) were apparently the first to report a correlation between a decrease in the amount of gossypol that could be extracted from cottonseed with diethyl ether and an improvement in the nutritive value of the cooked seed. As a …

Cottonseed Meal as a Substitute for Soybean Oil Meal in Poultry Rations ,

RINGROSE and Morgan (1938) reported that hydraulic cottonseed meal could replace one-half of the meat scraps in chick starter rations. Boatner et al. (1948) showed that chick growth was retarded by gossypol and related substances in cottonseed meal. Clark et al. (1948) found solvent cottonseed meal to be slightly superior to hydraulic cottonseed meal when fed to chicks. They also reported that equal parts of solvent or hydraulic cottonseed meal with soybean oil meal gave results similar to that obtained with soybean oil meal alone. Lillie and Bird (1950) concluded from their studies that the toxicity of cottonseed pigment glands fed to chicks daily by capsule was due entirely to the gossypol content of the glands. Richardson and Blaylock (1950a) obtained rapid growth in young chickens fed a diet which contained cottonseed meal as the only source of protein, when the diet was supplemented with vitamin B12 and synthetic lysine …

Observations on Two Components of Cottonseed that Cause Discolorations in Eggs

THERE is experimental evidence that two components of cottonseed cause egg yolk discolorations. One of these components is gossypol. The identity of the other is unknown, but it causes “pink” albumen and yolk discolorations different from those caused by gossypol.The report of Schaible, Moore and Moore (1934) is apparently the first showing conclusively that gossypol is the component of cottonseed pigment glands responsible for “olive-green” discolorations. That the yolk discolorations attributable to gossypol may range from olive-green or light chocolate brown to nearly black is indicated by the observations of Swenson, Fieger and Upp (1942), and of Heywang, Denton and Bird (1949).In his experiments, Lorenz (1939) found that gossypol gives the yolk an olive-green color, while another component of cottonseed, either responsible for or closely associated with the Halphen reaction, causes an abnormal enlargement of the yolk and a reddish brown color of yolk and albumen when eggs …

Pigments of cottonseed. IV. Gossypurpurin, a purple pigment related to gossypol

SummaryGossypurpurin was prepared from gossypol via diaminogossypol, and its properties compared with gossypurpurin isolated from cottonseed pigment glands. A tentative molecular formula for synthetic gossypurpurin, C30H32O7N, has been proposed on the basis of its elementary composition. The native pigment could not be obtained in the same degree of purity as the synthetic product and the analytical data could therefore not be brought into exact agreement for the two products. However solutions of both pigments in chloroform exhibit almost identical absorption spectra and identical antimony trichloride tests. Qualitative reactions seem to indicate that the functional groups of both native and synthetic gossypurpurin are identical, and the ready conversion of both products to gossypol upon contact with acid seems to indicate that their basic structures are similar.

Studies on the Chronic Oral Toxicity of Cottonseed Meal and Cottonseed Pigment Glands

The results of these experiments point to the conclusion that cottonseed meal free of pigment glands is devoid of any toxic principle as judged by the growth of rats and histopathological examination of visceral organs. Our results would indicate that hexane-extracted meal is not completely devoid of toxic principles or appetite-depressing factors, as judged by inhibition in the growth of rats on a diet containing 15% or more of the meal. This inhibition in growth cannot be accounted for completely by the slight difference in food consumed between rats on this diet and the controls or rats on a lower dietary intake of hexane-extracted meal. It would appear at first sight that the toxicity of hexane-extracted meal (15% level) may be due to the gossypol present in the meal, since 0.256% of pigment glands (equivalent to 0.096% gossypol) in the diet of rats produced an inhibition in growth comparable to that produced by the diet containing 15% of hexane-extracted meal. However, it is doubtful if gossypol is the chief responsible constituent, since rats on the 0.256% pigment gland diet processed from seeds stored for approximately 6 months were not similarly affected. This difference in toxicity of the two samples of pigment glands used may be accounted for on the basis of storage time before processing for removal of the pigment glands. The gossypol content of the two pigment-gland diets was extremely small, 0.096 and 0.0934%, respectively, as compared to 0.16% for the diet containing 15% of hexane-extracted meal. Comparable chronic toxicity studies of gossypol were not made, because of the unavailability of enough gossypol at the time the studies with cottonseed meal and pigment glands were being carried out. Paired feeding experiments with cottonseed pigment glands and gossypol would tend to confirm the above observations that decrease in growth is not entirely due to reduced food intake, but that gossypol plays an important role in depressing growth. From the acute and subacute oral toxicological data obtained, it is concluded that the toxicity of cottonseed pigment glands and gossypol is low. Single oral doses of pigment glands of up to 3,000 mg/kg, or gossypol in doses of up to 800 mg/kg each, did not appear to produce any toxic symptoms. The repeated administration of cottonseed pigment glands in doses of 2,000 mg/kg three times at 7-day intervals caused the rats to lose weight, depressed appetite, and produced diarrhea. Similarly, the repeated oral administration of gossypol in doses of 500 mg/kg at 5-day intervals had an effect similar to that of the pigment glands except that it did not produce diarrhea. Lower doses of pigment glands or gossypol were without effect. The experimental data raise the question of whether or not chemical assay of cottonseed pigment glands for gossypol is a reliable index, since a difference has been observed in the toxicity of pigment glands processed at different times, while the gossypol content was approximately the same. Since the completion of this work a paper by Lillie and Bird (’50) on chicks has appeared in which our findings on the toxicity of cottonseed pigment glands and gossypol are confirmed.

Effect of fractionation and treatment on the acute oral toxicity and on the gossypol and gossypurpurin content of cottonseed pigment glands

SummaryTwenty‐one preparations from cottonseed pigment glands were tested for their acute oral toxicity in 1,208 fasted rats and for their content of extractable gossypol and gossypurpurin. LD50 studies on six samples of pure gossypol were performed on 167 fasted rats. There was no correlation between the toxicity of the various samples of cottonseed pigment glands and their extractable gossypol or gossypurpurin content. Samples containing very large amounts of extractable gossypol were less toxic than many samples with considerably lower extractable gossypol content.Various fractionation procedures carried out on the same lot of cottonseed pigment glands caused wide alterations in their toxicity, from the extreme of very marked toxicity for the water‐soluble, acetone‐soluble fraction (LD50 ca. 700 mg./kg.) to no detectable toxicity for the acetone‐insoluble residue (LD50<6,000 mg./kg.).There was a decreased toxicity of subsequently prepared pigment glands with increased time of storage of the cottonseed in a silo. Storage of the pigment glands themselves at 7°C. however had little effect on their toxicity even after 26 and 32 months.The procedures causing greatest detoxification of cottonseed pigment glands, given in the order of increasing effectiveness, were: heating in the presence of water < extraction with ethanol < extraction with acetone.In the fasted rat the acute oral toxicity of pure gossypol was less than that of 17 preparations from cottonseed pigment glands having extractable gossypol contents ranging from as little as 24 to as much as 90%.

Detoxification of cottonseed pigment glands with ferrous sulfate.

Detoxification of cottonseed pigment glands with ferrous sulfate.

Preparation of gossypol from cottonseed pigment glands

SummaryCottonseed pigment glands, produced from whole cottonseed meal and defatted cottonseed meal by the gland flotation process, have been investigated as a raw material for the production of gossypol.Methods based on the previously reported properties of gossypol and cottonseed pigment glands have been developed for the relatively rapid isolation of gossypol from pigment glands.Extraction of gossypol from pigment glands with acetone followed by precipitation of gossypol acetic acid from the extract was found to be the preferable method for obtaining pure gossypol in good yields.The precautions which must be applied in order to produce gossypol on a large scale by the acetone‐acetic acid method are discussed together with methods for the purification and preservation of gossypol.

Pigment Glands of Cottonseed. III. Distribution and Some Properties of Cottonseed Pigments

1. All the gossypol and gossypurpurin of the cottonseed kernel are segregated in the pigment glands, and they constitute the only detectable pigments in the glands of four varieties of seed of Gossypium hirsutum which were examined. 2. The gossypol content of the glands is relatively constant, this pigment constituting up to approximately 50% of the weight of the glands, whereas the gossypurpurin content is relatively low and variable. 3. On the basis of the direct correlation observed between the amounts of glands and of gossypol in the kernels, it is suggested that the gland content is the principal factor which determines the gossypol content of the cottonseed kernel. 4. A yellow pigment has been detected in solution in the oil of the extraglandular tissue of the kernel. This pigment has been obtained free of gossypol, gossypurpurin, and the yellow decomposition product of gossypurpurin. Partial characterization of the extraglandular pigment has shown it to be relatively stable and to differ from every pigment previously detected in cottonseed. 5. On the basis of the distribution and properties of the pigments of cottonseed, methods for their extraction and estimation have been developed.

Pigment Glands of Cottonseed. II. Nature and Properties of Gland Walls

1. The cottonseed pigment gland has been shown to possess a rigid, thick wall inclosing a gelatinous suspension of the gland pigments. 2. The gland wall consists of five to eight irregularly shaped, curved plates,which appear to be composed of cellulose impregnated with pectin, hemicellulose, and other unidentified uronic acid derivatives. The glands are heavily incrusted with cutin. 3. The pigment glands have been shown to be resistant to the action of most reagents except water and polar organic liquids of low molecular weight. Their reaction to water consists in the immediate rupture of the wall along one or more of the seams between the plates, followed by expulsion of the gland contents as finely divided suspended particles. Water-miscible, polar organic liquids of low molecular weight affect the glands very much more slowly than water; and the extremely slow action of other organic liquids has been shown to be attributable to their slight moisture content. 4. The existence of a highly resistant pigment gland wall has been proposed to explain the anomaly of the relative stability of reactive polyphenolic pigments in cottonseed. The sensitivity of the glands to moisture has been proposed to explain various changes observed during maturation of cottonseed as well as changes which occur during the storage of moist cottonseed.

The pigment glands of cottonseed

1. The efficacy of a given solvent for the extraction of the gland pigments of cottonseed has been shown to be determined not only by its solvent power for the pigments but also by its ability to attack the pigment glands and the extent to which these glands are exposed to its action, which in turn depends upon the degree of subdivision of the seed being extracted. 2. The properties of the pigment glands have been utilized for the development of a method for mechanically fractionating cottonseed into pigment glands, embryo tissue (meal), and hull tissue. The process consists in the treatment of finely divided cottonseed with mixtures of inert liquids having densities intermediate between those of the seed parts being separated. 3. The fractionation method has been shown to be applicable to the preparation of pigment glands, and pigment-free oil and meal from flaked cottonseed. 4. The method has also been shown to be applicable to the separation of pigment glands from defatted cottonseed. *** DIRECT SUPPORT *** A02O2172 00002