Substituted arylimino derivatives of gossypol

Dechary, J. M.; Brown, L. E.

doi:10.1007/bf02612554

Cited by 14 publications

(13 citation statements)

References 7 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: 56%

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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: 56%

“…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).…”

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confidence: 99%

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

Kuk

Bland

2002

J Americ Oil Chem Soc

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“…A yellow pigment (hexaphenolic dicarbonyldinaphthalene derivative) is the main constituent of these glands, accounting for 30 to 50% of their weight (7). This pigment is quite reactive and forms complexes with reagents such as aniline, p-toluidine, and various ureas and esters (3,17,18).…”

Section: Resultsmentioning

confidence: 99%

A Microradioautographic Study of ¹⁴C-Diuron Absorption by Cotton

Strang

Rogers

1971

Weed sci.

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The techniques of cryostat sectioning, freeze-drying, and microradioautography were adapted to study the absorption and translocation of radio-labeled 3-(3,4-dichlorophenyl)-1,1-dimethylurea (14C-diuron) in root-treated cotton (Gossypium hirsutum L., var. Coker 201) plants. Diuron appeared to move primarily in the apoplast and to be transported acropetally and laterally in the transpiration stream. Radioactivity was observed to accumulate in striking concentrations in the lysigenous, or pigment, glands and the trichomes of the cotton plant. This accumulation is postulated to be a major factor in lowering the effective concentration of the herbicide in the leaves of cotton as compared to leaves of more susceptible plants, and thus may be a significant factor in the tolerance of cotton to diuron.

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“…XXV: X = H or OH Many amine derivatives of gossypol have been synthesized (22,60,213), because it was found that treatment with aniline served to decrease the toxicity of cottonseed meal. Although gossypol generally reacts with two moles of primary aromatic amines, Dechary and Brown (60) reported that it reacts with either one or two moles of o-nitroaniline and with only one mole of p,p'-diaminodiphenylmethane.…”

Section: Other Studies Of Gossypolmentioning

confidence: 99%