3‐amino‐1‐propanol as a complexing agent in the determination of total gossypol

Pons, Walter A.; Pittman, Robert A.; Hoffpauir, Carroll L.

doi:10.1007/bf02672661

Cited by 37 publications

(26 citation statements)

References 12 publications

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“…A shoulder (Fig. 4B) shown around 430-440 nm is characteristic of a Schiff base (3,4). The same shoulder peak at 430-440 nm was observed from the spectra of Schiff bases produced from reactions with aniline-G (or GA) and isopropylamine-G (or GA) (Fig.…”

Section: Resultsmentioning

confidence: 57%

Effect of pH on a gossypol complex with phospholipids: Gossypol‐PE

Kuk

Bland

2002

J Americ Oil Chem Soc

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PE, one of the major phospholipids in oilseed soapstock, may react with gossypol to form Schiff bases. PE amounts to 20-30% of the phosphorus compounds in soapstock. In this report, the dependence on pH of the Schiff base products between PE and gossypol was investigated using a spectrophotometer, an HPLC equipped with an ELSD, and an LC-MS system. We observed that at pH 7 the Schiff reaction product and reactants were clearly detected by ELSD, absorption, and LC-MS spectra. The absorption spectra displayed the characteristic peak for the Schiff bases around 430-440 nm. The absorption spectra also indicated that the reaction was pH dependent. The reaction temperatures were 60 and 90°C. The LC-MS spectra supported the formation of Schiff bases as well as methyl ether derivatives of gossypol in alcohol at the elevated temperatures. The implications of these experimental findings are presented in this paper.Gossypol and phosphatides are extracted with TG when cottonseed meal and oil are produced by solvent extraction (1). By adding caustics to extracted oil, FFA, phosphatides, and gossypol are separated from oil, producing soapstock as a byproduct. Soapstock, separated from oil by centrifugation, is usually added back to animal feed (1). Cottonseed meal is one of the most popular feeds for ruminant animals.Gossypol reacts with protein [ε-amino groups of lysine (2)], and with alkyl-and phenylamines (3,4) to form bound gossypol. Because of its toxicity problem, the amount of free gossypol allowed in animal feed is lower than that of bound gossypol (3). Although gossypol reactions with phosphatides are believed to form a class of bound gossypol (5,6), experimental investigations to confirm the reaction in detail are scarce. In particular, the reversibility of the reaction and the effect of pH on the reaction have not been reported thus far. It is extremely important to investigate the reappearance of free gossypol by reversion of the reaction from the Schiff product, gossypol-phosphatide, because of the animals' physiological sensitivity to free gossypol (7). In general, PE amounts to up to 20-30% of phosphatides in oilseed soapstock (1). The dependence on pH of the Schiff product between PE and gossypol was investigated in this paper using a spectrophotometer, a highperformance liquid chromatograph equipped with an ELSD, and an LC-MS system. The reaction temperatures were room temperature (RT), 60 and 90°C. The formation of the Schiff base product was confirmed by mass spectra obtained from an atmospheric pressure chemical ionization (APCI) source. MATERIALS and METHODS Materials.A typical oilseed PE (1,2-di-9-octadecenoyl-snglycero-3-phosphatidylethanolamine; 99% pure with formula weight 716) extracted from soy (Avanti Lipids, Alabaster, AL), gossypol-acetic acid (GA) from cottonseed (89.61% gossypol by weight; SRRC, ARS, USDA, New Orleans, LA), and reagent-grade amines (isopropyl amine and aniline), HPLC solvents and reagents, and gossypol (G) (reagent grade; Sigma-Aldrich, St. Louis, MO) were used.Gossypol reaction...

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Section: Resultsmentioning

confidence: 57%

Effect of pH on a gossypol complex with phospholipids: Gossypol‐PE

Kuk

Bland

2002

J Americ Oil Chem Soc

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“…The seeds also contain abundant amounts of the elements Na, Mg, Ca, Fe, Zn, Mn, and Ni. Gossypol, the phenolic compound found in cotton seed and known to cause undesirable physiological effects on nonruminants such as poultry and swine (Pons, 1977), was found in okra seed only as traces. Finally, since most cereals are very deficient in some elements, in particular calcium; therefore, fortification of cera1 flours with okra seed flour may improve the dietary saturation.…”

Section: Resultsmentioning

confidence: 99%

“…Total gossypol was determined by using a procedure developed by Pons et al (1958), while free gossypol was determined by using two different procedures Values expressed as percent of defatted and sugar-free flour. Total gossypol was determined by using a procedure developed by Pons et al (1958), while free gossypol was determined by using two different procedures Values expressed as percent of defatted and sugar-free flour.…”

Section: Methodsmentioning

confidence: 99%

Chemical composition of seeds of two okra cultivars

Al–Wandawi¹

1983

J. Agric. Food Chem.

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These findings support the hypothesis that the principal cause for the observed vigor and higher yield in fresh weight of the tobacco plants that were treated with aldicarb is its effect on the carbohydrate (increase) and protein (decrease) content of the plant. Other things being equal, the higher concentration of water-soluble sugars in the treated plants may have developed a higher osmotic pressure that increases the absorption and/or retention of water in the plant tissue. This is reflected in the whole plant as an apparently higher yield and enhanced plant vigor.In a biological system, such as the tobacco plant, the presence of a bioactive compound like aldicarb in its tissue could result in complex phenomena of interactions. Investigations regarding such interactions are very complicated and the interpretation is difficult. Further research would be necessary to elucidate the mechanisms involved in such complex phenomena.Chemical compositions of the whole mature seeds of two okra varieties were investigated. The results of amino acid analyses indicated okra seed as a potential high-protein source which due to its high lysine level may serve as a supplement to cereal-based diets in which lysine is generally the first limiting amino acid. The most limiting amino acids in the Emerald variety were found to be valine (chemical score, 54.05), isoleucine (54.31), and threonine (60.0), while in the Ibtaira variety, tryptophan, isoleucine, and valine were the most limiting amino acids with chemical scores of 56.67, 57.41, and 67.03, respectively. The results of fatty acid analyses indicaed okra seed oil is akin to other high oleic acid oils and thus is of low essential fatty acid content. The most predominant elements in okra seed were found to be K, Na, Mg, and Ca. The elements Fe, Zn, Mn, and Ni were also present in abundant amounts. Gossypol was found only as traces, while Halphen-positive cyclopropenoid compounds were detected in an amount equal to 2.5 times less than that present in crude cotton oil.In response to the present deficit and the predicted world shortage of foods, considerable research is being directed toward expanding present supplies and exploring new sources. Okra [Abelmoschus esculentus (L) Moench], appears to have potential as a high-protein crop when

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“…Available lysine was determined by (7). Free and total gossypol determinations was carried according to the method of Pons et al (8).…”

Section: Methods Of Analysismentioning

confidence: 99%

Effect of some degossypolisation treatments of cottonseed meal on its functional properties

Mohamed¹

1993

Grasas y Aceites

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RESUMENEfecto de algunos tratamientos de desgosiposilación de harina de semilla de algodón sobre sus propiedades funcionales.La presencia de gosipol es un factor limitante en el uso de harina de semilla de algodón para la alimentación animal y humana. El gosipol, en forma libre, ha sido encontrado tóxico para animales monogástricos, y el Grupo Asesor en Proteína de Naciones Unidas ha limitado su contenido en productos proteínicos de semilla de algodón al 0,06%. En el presente trabajo se ha estudiado el efecto de algunas técnicas de desgosiposilación sobre las propiedades funcionales de harinas de semillas de algodón. Los mejores resultados se obtuvieron con el método del ácido acético ya que mejoró la solubilidad de nitrógeno y lisina disponible, redujo el gosipol libre al 0,03% y aumentó la capacidad de absorción de agua, humectabilidad y fluidez. El producto proteínico resultante de este tratamiento puede ser incorporado en productos alimenticios instantáneos y horneados. El tratamiento azeótropo:amonio produjo efectos similares. El tratamiento con etanolamina está recomendado para la preparación de productos proteínicos para alimentos instantáneos. PALABRAS-CLAVE: Gosipol (eliminación) -Harina -Propiedades funcionales -Semilla de algodón. SUMMARYEffect of some degossypolisation treatments of cottonsed meal on its functional properties.

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3‐amino‐1‐propanol as a complexing agent in the determination of total gossypol

Cited by 37 publications

References 12 publications

Effect of pH on a gossypol complex with phospholipids: Gossypol‐PE

Effect of pH on a gossypol complex with phospholipids: Gossypol‐PE

Chemical composition of seeds of two okra cultivars

Effect of some degossypolisation treatments of cottonseed meal on its functional properties

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