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Physiological effects and metabolism of gossypol

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Book cover Residue Reviews

Part of the book series: Residue Reviews ((RECT,volume 61))

Abstract

Gossypol1 is a yellow coloring matter which occurs in various parts of the cotton plant. Longmore (1886) first isolated it as a crude pigment from cottonseed oil “foots,” a material which results from the refinement of crude cottonseed oil with sodium hydroxide and contains free fatty acids, phospholipids, gossypol, and other pigments. Marchlewski (1899) crystallized the acetic acid derivative of a compound from the same source, which he named “gossypol” to designate its origin, genus Gossypium (family Malvaceae), and its chemical nature as a phenol. Gossypol is found in the pigment “glands” (ovispherical bodies about 100 to 400 µm long) of the seed, leaf, stem, laproot bark, and roots of the cotton plant (Royce et al. 1941, Smith 1962). Studies of changes in the gossypol content of cottonseed during different stages of development of the bolls showed that the greatest increase in gossypol occurs between the time of maturity of the boll and the time it is about to open (Adams et al. 1960). Gossypol synthesis in all tissues of the cotton plant was induced in response to such irritants as pathogens, metabolic inhibitors, and cupric and mercuric ions (Bell 1967). Gossypol constitutes 20 to 40% of the weight of the pigment glands in cottonseed (Boatner 1948). Cottonseed usually contains 0.4 to 1.7% gossypol. The total world production of cottonseed is about 25 million tons/year (containing approximately 78,000 tons of gossypol) and about three to six million tons are produced in the United States (Decossas et al. 1968). An average ton of cottonseed gives about 335 pounds of oil and 945 pounds of meal (Altschul et al. 1958). If refined 60% protein cottonseed flour is prepared for human use, 300 to 400 pounds/ton is produced; the remainder can be used for animal feed. It is estimated that only onefourth of the cottonseed flour potentially available could satisfy the present worldwide shortage of protein (Gillham 1969).

Fellow of the Environmental Health Sciences Institute of the National Institutes of Health, No. 1F22 ES01723-01.

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References

  • Abou-Donia, M. B., and J. W. Dieckert: Gossypol: Subcellular localization and stimulation of rat liver microsomal oxidases. Toxicol. Applied Pharmacol. 18, 507 (1971).

    Article  Google Scholar 

  • Abou-Donia, M. B., and J. W. Dieckert:Gossypol: Uncoupling of respiratory chain and oxidative phosphorylation. Life Sci. 14, 1955 (1974 a).

    Google Scholar 

  • Abou-Donia, M. B., and J. W. Dieckert: Urinary and biliary excretion of 14C-gossypol in swine. Nutr. 104, 754 (1974 b).

    Google Scholar 

  • Abou-Donia, M. B., and J. W. Dieckert:Metabolic fate of gossypol: The metabolism of 14C-gossypol in swine. Toxicol. Applied Pharmacol. 31, 32 (1975).

    Article  Google Scholar 

  • Abou-Donia, M. B., and J. W. Dieckert: , and C. M. Lyman: Mass spectrometry of some gossypol ethers. J. Agr. Food Chem. 18, 534 (1970 a).

    Google Scholar 

  • Abou-Donia, M. B., and J. W. Dieckert:, and C. M. Lyman: Studies on the metabolic fate of gossypol in the rat using 14C labeled gossypol. Presented 60th Ann. Meeting Amer. Oil Chem. Soc. San Francisco, Calif. (1969).

    Google Scholar 

  • Abou-Donia, M. B., and J. W. Dieckert:Metabolic fate of gossypol: The metabolism of 14C-gossypol in laying hens. Toxicol. Applied Pharmacol. 17, 4473 (1970).

    Google Scholar 

  • Abou-Donia, M. B., and J. W. Dieckert:, and J. W. Dieckert: Metabolic fate of gossypol: The metabolism of 14C-gossypol in rats. Lipids 5, 938 (1970 b).

    Google Scholar 

  • Abou-Donia, M. B., and J. W. Dieckert:, F. Taman, N. M. Bakery and A. H. EL-Sfbae: Gossypol: Antagonistic effect on toxicity of insecticides to Spodoptera littoralis. Experientia 30, 1152 (1974).

    Google Scholar 

  • Adams, R., T. A. Geissman, and S. D. Edwards: Gossypol, a pigment of cottonseed. Chem. Rev. 60, 555 (1960).

    Article  PubMed  CAS  Google Scholar 

  • Adams, R., R. C. Morris, T. A. Geissman, D. J. Butterbaugh, and E. C. Kirkpatrick: Structure of gossypol. XV. An interpretation of its reactions. J. Amer. Chem. Soc. 60, 2193 (1938).

    Article  CAS  Google Scholar 

  • Afifi, A., A. A. Abdel-Barry, S. A. Kamel, and I. Heikal: Bahtim 110 a new Egyptian cotton free of gossypol induced by radiation. Bahtim Expt. Stat. Tech. Bull. 80, 1 (1965).

    Google Scholar 

  • Ahmad, M.: Metabolism of gossypol in Sus scrofa a monogastric mammal. Ph.D. Dissertation, Texas A and M Univ., College Station, Texas (1965).

    Google Scholar 

  • Albrecht, J. E., A. J. Clawson, and F. H. Smith: Rate of depletion and route of elimination of intravenously injected gossypol in swine. J. Animal Sci. 35, 941 (1972).

    CAS  Google Scholar 

  • Albrecht, J. E., L. C. Ulberg, and F. H. Smith: Effects of high gossypol cottonseed meal on the electrocardiograms of swine. J. Animal Sci. 27, 976 (1968).

    CAS  Google Scholar 

  • Alsberg, C. L., and E. W. Schwartze: Pharmacological action of gossypol. J. Pharmacol. Expt. Ther. 13, 504 (1919).

    Google Scholar 

  • Altschul, A. M., C. M. Lyman, and F. H. Thurber: Cottonseed meal. In A. M. Altschul (ed.): Processed plant protein foodstuffs, p. 469. New York: Academic Press (1958).

    Google Scholar 

  • Baker, K. J., and S. E. Bradley: Binding of sulfobramophthalein (Bsp) sodium by plasma albumin. Its role in hepatic Bsp extraction. J. Clin. Invest. 45, 281 (1966).

    Article  PubMed  CAS  Google Scholar 

  • Baliga, B. P., and C. M. Lyman: Preliminary report on the nutritional significance of bound gossypol in cottonseed meal. J. Amer. Oil Chem. Soc. 34, 21 (1957).

    Article  CAS  Google Scholar 

  • Baugher, W. L., and T. Campbell: Gossypol detoxification by fungi. Science 164, 1526 (1969).

    Article  PubMed  CAS  Google Scholar 

  • Bell, A. A.: Formation of gossypol in infected or chemically irritated tissues of gossypuim species. Phytopathol. 57, 759 (1967).

    CAS  Google Scholar 

  • Berardi, L. C., and L. A. Goldblatt: Gossypol. In I. E. Liener (ed.): Toxic con- stituents of plant foodstuffs, p. 211. New York: Academic Press (1969).

    Google Scholar 

  • Bickford, W. G., F. C. Pack, L. E. Castillon, and C. H. Mack: The antioxidant and antipolymerization properties of gossypol, dianilinogossypol and related materials. J. Amer. Oil. Chem. Soc. 31, 91 (1954).

    Article  CAS  Google Scholar 

  • Boatner, C. H.: Pigments of Cottonseed. In A. E. Baily (ed.): Cottonseed, p. 213. New York: Interscience (1948).

    Google Scholar 

  • Boatner, C. H., M. Carvaella, and L. Kyane: Quantitative determination of extractable gossypol in cottonseed and cottonseed meal. Ind. Eng. Chem. 16, 566 (1944).

    CAS  Google Scholar 

  • Boatner, C. H., C. S. Samuels, C. M. Hall, and M. C. Curet: The pigments of cottonseed. H. Gossycaerulin, a blue quinoid gossypol derivative occurring in cooked cottonseed. J. Amer. Chem. Soc. 69, 668 (1947).

    CAS  Google Scholar 

  • Bottger, G. T., and R. Patana: Growth, development, and survival of certain lipidoptera fed gossypol in the diet. J. Econ. Entomol. 59, 1166 (1966).

    CAS  Google Scholar 

  • Bottger, G. T., E. T. Sheehan, and M. J. Lukefahr: Relation of gossypol content of cotton plants to insect resistance. J. Econ. Entoml. 57, 283 (1964).

    CAS  Google Scholar 

  • Braham, J. E., R. Jarquin, R. Bressani, J. M. Gonzalez, and L. G. Elias: Effect of gossypol on the iron-binding capacity of serum in swine. J. Nutrition 93, 241 (1967 a).

    Google Scholar 

  • Braham, J., L. G. ELÌAS, M. Gonzalez, and R. Bressoni: Effect of calcium and gossypol on the performance of swine and on certain enzymes and other blood constituents. J. Nutrition 91, 47 (1967 b).

    Google Scholar 

  • Brauer, R. W., JR.: Mechanisms of bile secretion. J. Amer. Med. Assoc. 169, 1462 (1959).

    Article  CAS  Google Scholar 

  • Breakey, E. P., and H. S. Olcott: The non-toxicity of gossypol to certain insects. Science 87, 87 (1938).

    Article  PubMed  CAS  Google Scholar 

  • Bressani, R., A. Aguirre, and N. S. Scrimshaw: All-vegetable protein mixtures for human feeding. II. The nutritive value of corn, sorghum, rice and buckwheat substitutes for lime-treated corn in Incap Vegetable mixture eight. J. Nutrition 69, 351 (1959).

    CAS  Google Scholar 

  • Bressani, R., L. G. Elias and J. E. Braham: Studies in dogs on the absorption of gossypol from cottonseed flour containing vegetable mixture. J. Nutrition 83, 209 (1964).

    CAS  Google Scholar 

  • Buitrago, J. A., A. J. Clawson, and F. H. Smith: Effects of dietary iron on gossypol accumulation in and elimination from porcine Jiver. J. Animal Sci. 31, 554 (1970).

    CAS  Google Scholar 

  • Bydagyan, F. E., B. D. Vlodimirov, L. M. Levitskii, and K. A. Shchurov: Influences of prolonged consumption of small amounts of cottonseed meal on the human organism. Gigiena i Sanit. 7, 28 (1947).

    Google Scholar 

  • Cabell, C. A., and I. P. Earle: Relation of amount and quality of protein in the diet to free gossypol tolerance by the rat. J. Amer. Oil Chem. Soc. 33, 416 (1957).

    Article  Google Scholar 

  • Campbell, K. N., R. C. Morris, and R. Adams: The structure of gossypol I. J. Amer. Chem. Soc. 59, 1723 (1937).

    Article  CAS  Google Scholar 

  • Carruth, F. E.: Methods for approximating the relative toxicity of cottonseed products. J. Biol. Chem. 32, 87 (1917).

    CAS  Google Scholar 

  • Contribution to the chemistry of gossypol, the toxic principle of cottonseed. J. Amer. Chem. Soc. 40, 647 (1918).

    Article  Google Scholar 

  • Stability of bound gossypol to digestion. J. Amer. Oil Chem. Soc. 24, 58 (1947).

    Article  Google Scholar 

  • Castillon, L. E., and A. M. Altschul: Preparation of water-soluble combination products of gossypol and their toxicity to aquarium fish. Proc. Soc. Expt. Biol. Med. 74, 623 (1950).

    Article  CAS  Google Scholar 

  • Cater, C. M., and C. M. Lyman: Reactions of gossypol with amino acids and other amino compounds. J. Amer. Oil Chem. Soc. 46, 649 (1969).

    Article  CAS  Google Scholar 

  • Chance, B., G. R. Williams, and G. Hollunger: Inhibition of electron and energy transfer in mitochondria. Iii. Spectroscopic and respiratory effects of uncoupling agents. J. Biol. Chem. 238, 439 (1963).

    PubMed  CAS  Google Scholar 

  • Chang, W. Y.: The chemical characteristics of cottonseed meal as related to the biological utilization. M.S. Thesis, Texas A and M Univ. College Station, Texas (1955).

    Google Scholar 

  • Chappell, J. B.: The effects of 2,4-dinitrophenol on mitochondrial oxidations. Biochem. J. 90, 237 (1964).

    PubMed  CAS  Google Scholar 

  • Clark, E. P.: Studies on gossypol II. Concerning the nature of Carruth’s D gossypol. J. Biol. Chem. 76, 229 (1928 a).

    Google Scholar 

  • Clark, E. P.: Studies on gossypol IV. Apogossypol. J. Biol. Chem. 78, 159 (1928 b).

    Google Scholar 

  • Clawson, A. J., and F. H. Smith: Effect of dietary iron on gossypol toxicity and on residues of gossypol in porcine liver. J. Nutrition 89, 307 (1966).

    CAS  Google Scholar 

  • Clawson, A. J., and E. R. Barrick: Accumulation of gossypol in the liver and factors influencing the toxicity of injected gossypol. J. Animal Sci. 21, 911 (1962).

    Google Scholar 

  • J. C. Osborne, and E. R. Barrick: Effect of protein source, autoclaving, and lysine supplementation on gossypol toxicity. J. Animal Sci. 20, 547 (1961).

    Google Scholar 

  • Conkerton, E. J., and V. L. Frampton: Reaction of gossypol with free epsilon-amino groups of lysine in proteins. Arch. Biochem. Biophys. 81, 130 (1959).

    Article  PubMed  CAS  Google Scholar 

  • Couch, J. R., W. Y. Chang, and C. M. Lyman: The effect of free gossypol on chick growth. Poultry Sci. 34, 178 (1955).

    Article  CAS  Google Scholar 

  • Danke, R. J., and A. D. Tillman: Effect of free gossypol and supplemental dietary iron on blood constituents of rats. J. Nutrition 87, 493 (1965).

    CAS  Google Scholar 

  • Datta, S. C., V. V. S. Murti, and T. R. Seshadri: A new component of the flowers of Thespesia populnea: (-b) gossypol. Curr. Sci. 37, 135 (1968).

    CAS  Google Scholar 

  • Dechary, J. M., and L. E. Brown: Substituted arylimino derivatives of gossypol. J. Amer. Oil Chem. Soc. 33, 76 (1956).

    Article  CAS  Google Scholar 

  • Decossas, K. M., L. J. Molaison, A. DE B. Kleppinger, and V. L. Laporte: Cottonseed oil and meal utilization. J. Amer. Oil Chem. Soc. 45, 52A (1968).

    Google Scholar 

  • Dieckert, J. W., and M. B. Abou-Donia: Metabolism of gossypol in mammals. In: Swine research, 1966–70, p. 30. Texas A and M Univ., College Station, Texas (1972).

    Google Scholar 

  • Dowell, C. T., and Menaul: Effect of autoclaving upon the toxicity of cottonseed meal. J. Agr. Res. 26, 9 (1923).

    CAS  Google Scholar 

  • Eagle, E.: Detoxification of cottonseed pigment glands with ferrous sulfate. Proc. Soc. Expt. Biol. Med. 72, 444 (1949).

    Article  CAS  Google Scholar 

  • Eagle, E.: Effect of repeated doses of gossypol on the dog. Arch. Biochem. Biophys. 26, 68 (1950).

    CAS  Google Scholar 

  • Eagle, E.: A review of some physiological effects of gossypol and cottonseed pigment glands. J. Amer. Oil Chem. Soc. 37, 40 (1960).

    Article  CAS  Google Scholar 

  • Eagle, E.:, H. F. Bialek, D. L. Davies, and J. W. Brewer: Detoxification of cottonseed by salts and alkalies. J. Amer. Oil Chem. Soc. 31, 121 (1954).

    CAS  Google Scholar 

  • Eagle, E.:, L. E. Castillon, C. M. Hall, and C. H. Boatner: Acute oral toxicity of gossypol and cottonseed pigment glands for rats, mice, rabbits and guinea pigs. Arch. Biochem. 18, 271 (1948).

    CAS  Google Scholar 

  • Edwards, J. D., JR.: Total synthesis of gossypol. J. Amer. Chem. Soc. 80, 3798 (1958).

    Article  CAS  Google Scholar 

  • EL-Nockrasity, A. S., C. M. Lyman, and J. W. DoLlahite: The acute oral toxicity of cottonseed pigment glands and intraglandular pigments. J. Amer. Oil Chem. Soc. 40, 14 (1963).

    Google Scholar 

  • Ferguson, T. M., J. R. Couch, and R. H. RignoN: Histopathology of animal reactions to pigment compounds: Chickens. In: Proc. Conference on Chemical Structure and Reactions of Gossypol and Non-gossypol Pigments in Cottonseed, p. 131. S. Regional Laboratory, New Orleans, La. (1959).

    Google Scholar 

  • Finlay, T. H., E. D. Dharmgrongartama, and G. E. Perlman: Mechanism of the gossypol inactivation of pepsinogen. J. Biol. Chem. 248, 4827 (1973).

    PubMed  CAS  Google Scholar 

  • Fletcher, J. L., B. T. Barrentine, L. J. Dreesen, J. E. Hill, and C. B. Shawver: The uses of ferrous sulfate to inactivate gossypol in diets of laying hens. Poultry Sci. 32, 740 (1953).

    Article  CAS  Google Scholar 

  • Frampton, V. L., J. D. Edwards, and H. R. Henze: The ultraviolet absorption spectrum of gossypol. J. Amer. Chem. Soc. 70, 3944 (1948).

    Article  CAS  Google Scholar 

  • Gallup, W. D.: The value of iron salts in countering the toxic effects of gossypol. J. Biol. Chem. 77, 437 (1928).

    CAS  Google Scholar 

  • Gallup, W. D.: Concerning the use of cottonseed meal in the diet of the rat. J. Biol. Chem. 91, 387 (1931).

    CAS  Google Scholar 

  • Gillham, F. E. M.: Cotton in a hungry world. S. Afr. J. Sci. 65, 173 (1969).

    CAS  Google Scholar 

  • Grau, C. R., E. Allen, M. Nagumo, C. L. Wornick, and P. A. Zweigast: Cotton-seed meal in poultry feed. A distinctive yolk component in the fresh eggs of hens fed gossypol. J. Agr. Food Chem. 2, 982 (1954).

    Article  CAS  Google Scholar 

  • Haddock, E. P., E. J. Zapolsky, M. Robin, and J. V. Princiotto: Biliary excretion of chelated iron. Proc. Soc. Expt. Biol. Med. 120, 663 (1965).

    Article  CAS  Google Scholar 

  • Hagen-Smit, A. J., and C. C. Nimmo: Comprehensive biochemistry, vol. 9, p. 129. New York: Elsevier (1962).

    Google Scholar 

  • Hale, F., and C. M. Lyman: Effect of protein level in the ration on gossypol tolerance in growing-fattening pig. J. Animal Sci. 16, 364 (1957).

    CAS  Google Scholar 

  • Hale, F., and C. M. Lyman: Lysine supplementation of sorghum grain-cottonseed meal rations for growing-fattening pigs. J. Animal Sci. 20, 734 (1961).

    CAS  Google Scholar 

  • Hale, F., and C. M. Lyman:, and H. A. Smith: Use of cottonseed meal in swine rations. Texas Agr. Expt. Sta. Bull. 898, 1 (1958).

    Google Scholar 

  • Halverson, J. O., and F. W. Sherwood: Investigations in the feeding of a cottonseed meal to cattle. N. Carolina Agr. Expt. Sta. Bul. 898, 1 (1930).

    Google Scholar 

  • Halverson, J. O., and F. H. Smith: Estimation of gossypol in cottonseed meal. A modified method. Ind. Eng. Chem. 5, 29 (1933).

    CAS  Google Scholar 

  • Harms, W. S., and K. T. Holley: Hypoprothrombinemia induced by gossypol. Proc. Soc. Expt. Biol. Med. 71, 297 (1951).

    Article  Google Scholar 

  • Harper, G. A., and K. J. Smith: Status of cottonseed protein. Econ. Bot. 22, 63 (1968).

    Article  CAS  Google Scholar 

  • Heinstein, P. F., D. L. Herman, S. B. Tove, and F. H. Smith: Biosynthesis of gossypol: Incorporation of Mevalonate-2–14C and isoprenyl pyrophosphates. J. Biol. Chem. 245, 4658 (1970).

    PubMed  CAS  Google Scholar 

  • Heinstein, P. F., F. H. Smith, and S. B. TovE: Biosynthesis of 14C-labeled gossypol. J. Biol. Chem. 237, 2643 (1962).

    PubMed  CAS  Google Scholar 

  • Hester, H. R., H. E. Essex, and F. C. Mann: Secretion of urine in the chicken. Amer. J. Physiol. 128, 592 (1940).

    CAS  Google Scholar 

  • Heywang, B. W., and H. R. Bird: Egg production diet, consumption and live weight in relation to the free gossypol content of the diet. Poultry Sci. 33, 851 (1954).

    Article  CAS  Google Scholar 

  • Heywang, B. W., and A. M. Altschul: Relationship between discoloration in eggs and dietary free gossypol supplied by different cottonseed products. Poultry Sci. 34, 81 (1955).

    Article  CAS  Google Scholar 

  • Hill, F. W., and K. Tatsuka: Studies of the metabolizable energy of cottonseed meals for chicks, with particular reference to the effect of gossypol. Poultry Sci. 43, 362 (1964).

    Article  Google Scholar 

  • Hogben, C. A. M., L. S. Schanker, D. J. Tocco, and B. B. Brodie: Absorption of drugs from the stomach. II. The human. J. Pharmacol. 120, 540 (1957).

    CAS  Google Scholar 

  • Hove, E. L., and Z. Hove: A method for estimating total fat soluble antioxidants based on the relation between fat peroxides and carotene destruction. J. Biol. Chem. 156, 611 (1944).

    CAS  Google Scholar 

  • Hunter, F. E.: In W. D. McElroy and B. Glass (eds.): Phosphorus metabolism, p. 297. Baltimore: Johns Hopkins (1951).

    Google Scholar 

  • Jonassen, H. B., and R. J. Demint: Interaction of gossypol with ferrous iron. J. Amer. Chem. Soc. 32, 424 (1955).

    CAS  Google Scholar 

  • Jones, D. B., and H. C. Waterman: Studies on the digestibility of proteins in vitro. IV. On the digestability of the cottonseed globulin and the effect of gossypol upon peptic-tryptic digestion of proteins. J. Biol. Chem. 56, 501 (1923).

    Google Scholar 

  • Karnegay, E. T., R. F. Kelly, T. C. Campbell, K. G. Libke, F. W. Sandrock, and J. E. Blair: Fungal-treated cottonseed meal from Swine. J. Nutrition 102, 1471 (1972).

    Google Scholar 

  • Kilburn, K. H., A. R. Hudson, G. M. Halprin, W. N. Mckenzie, and J. A. Merchant: Two patterns for bronchial damage from inhaled materials. Chest 65 (Suppl.), 61 S (1974).

    Google Scholar 

  • Killion, D. D., G. Shirley, and R. E. Frans: Oxidative and phosphorylatine activities of mitochondria isolated from cotton hypocotyls. Plant Physiol. 43, 1996 (1968).

    Google Scholar 

  • King, J. J., and L. B. DE Silva: Optically active gossypol from Thespesia populnea. Tetrahedron Letters 3, 261 (1968).

    Article  Google Scholar 

  • Kingsbury, J. M.: In: Poisonous plants of the United States and Canada. Englewood Cliffs, N.J.: Prentice-Hall (1964).

    Google Scholar 

  • Kuiken, K. A., C. M. Lyman, and F. Hale: The effect of feeding isopropanol extracted from cottonseed meal on storage quality of eggs. Poultry Sci. 27, 742 (1948).

    Article  CAS  Google Scholar 

  • Lamon, H. M., and A. R. Lee: Feed cost of egg production. Results of three years experiments at the government poultry farm. U.S. Department of Agriculture Bull. 561, 13 (1917).

    Google Scholar 

  • Lardy, H. A., D. JoHNsoN, and W. C. Mcmurray: Antibiotics as tools for metabolic sutides. I. A survey of toxic antibiotics in respiratory, phosphorylative and glycolytic systems. Arch. Biochem. Biophys. 78, 587 (1958).

    Google Scholar 

  • Lillie, R. T., and H. R. Bird: Effect of oral administration of pure gossypol and of pigments glands of cottonseed on mortality and growth of chickens. Poultry Sci. 29, 390 (1950).

    Article  CAS  Google Scholar 

  • Longmore, J.: Cottonseed oil: Its coloring matter mucilage, and description of a new method of recovering the loss occurring in the refining process. J. Soc. Chem. Ind. 5, 200 (1886).

    Google Scholar 

  • Loomis, W. D., and J. Battaile: Plant phenolic compounds and the isolation of plant enzymes. Phytochem. 5, 423 (1966).

    Article  CAS  Google Scholar 

  • Lornez, F. W.: Egg deterioration due to ingestion by hens of malvaceous materials. Poultry Sci. 18, 295 (1939).

    Article  Google Scholar 

  • Lukefahr, M. J., and D. F. Martin: Cotton plant pigments as a source of resistance to the bollworm and tobacco budworm. J. Econ. Entomol. 59, 176 (1966).

    CAS  Google Scholar 

  • Lyman, C. M., B. P. Baliga, and M. Slay: Reactions of proteins with gossypol. Arch. Biochem. Biophys. 84, 486 (1959).

    Article  PubMed  CAS  Google Scholar 

  • Lyman, C. M., J. T. Cronin, M. M. Trant, and G. V. Odell: Metabolism of gossypol in the chick. J. Amer. Oil Soc. 46, 100 (1969).

    Article  CAS  Google Scholar 

  • Lyman, C. M., A. S. EL-Nockrasity, and J. W. Dollahite: Gossyverdurin: A newly isolated pigment from cottonseed pigment glands. J. A.er. Oil Chem. Soc. 40, 571 (1963).

    CAS  Google Scholar 

  • Marchlewski, L.: Gossypol, ein Bestandtheil der Baumwollsamen. J. prakt. Chem. 60, 84 (1899).

    Article  CAS  Google Scholar 

  • Mattil, H. A.: Antioxidants and the autooxidation of fats. J. Biol. Chem. 90, 141 (1931).

    Google Scholar 

  • Maxwell, F. G., H. N. Lafever, and J. N. Jenkins: Blister beetles on glandless cotton. J. Econ. Entomol. 58, 792 (1965).

    Google Scholar 

  • Mcmichael, S. C.: Combined effect of glandless genes gl2 and gl, on pigment glands in cotton plant. Agron. J. 52, 385 (1960).

    Article  Google Scholar 

  • Meksongsee, L. A., A. J. Clawson, and F. H. Smith: The in vivo effect of gossypol on cytochrome oxidase, succinoxidase, and succinic dehydrogenase in animal tissues. J. Agr. Food Chem. 18, 917 (1970).

    Article  CAS  Google Scholar 

  • Menaul, P.: The physiological effect of gossypol. J. Agr. Res. 26, 233 (1923).

    CAS  Google Scholar 

  • Millburn, P., R. L. Smith, and R. T. Williams: Biliary excretion of foreign com-pounds, biphenyl, stilbestrol, and phenolphthalein in the rat; molecular weight, polarity, and metabolism as factors in biliary excretion, Biochem. J. 104, 1275 (1967).

    Google Scholar 

  • Milne, M. D., B. N. Schribner, and M. A. Crawford: Non-ionic diffusion and excretion of weak acids and bases. Amer. J. Med. 24, 709 (1958).

    Article  PubMed  CAS  Google Scholar 

  • Miravalle, R. J.: Action of the genes controlling the character of glandless seed in cotton. Crop Sci. 2, 447 (1962).

    Article  Google Scholar 

  • Morris, R. C., and R. Adams: The structure of gossypol. IV. Gossypol ethers. J. Amer. Chem. Soc. 59, 1731 (1937).

    Article  CAS  Google Scholar 

  • Mudge, G. H.: Renal pharmacology. Ann. Rev. Pharmacol. 7, 163 (1967).

    Article  PubMed  CAS  Google Scholar 

  • Murty, K. S., and T. R. Seshadri: Chemistry of gossypol V. Products of acetylation of gossypol. Proc. Indian Acad. Sci. A34, 272 (1951).

    Google Scholar 

  • Muzaffaruddin, M., and E. R. Saxena: Physiochemical studies on the composition and stability of metal-gossypol complexes. I. Fe’ gossypol complex. J. Amer. Oil Chem. Soc. 43, 429 (1966).

    Article  CAS  Google Scholar 

  • Myers, B. D., and G. O. Throneberry: Effect of gossypol on some oxidative respiratory enzymes. Plant Physiol. 41, 787 (1966).

    Article  PubMed  CAS  Google Scholar 

  • Narain, R. C., C. M. Lyman, and J. R. CoucH: Effect of increased protein level in the hen diet on the transfer of gossypol cephalen to the egg. Poultry Sci. 37, 893 (1958).

    Article  CAS  Google Scholar 

  • Narain, R. C., C. W. Deyoe, and J. R. Couch: Effect of protein level of the diet on free gossypol tolerance in chicks. Poultry Sci. 39, 1556 (1960).

    Article  CAS  Google Scholar 

  • Narain, R. C., C. W. Deyoe, and J. R. Couch: Paper electrophoresis and albumin/globulin ratios of the serum of normal chickens and chickens fed free gossypol in the diet. Poultry Sci. 40, 21 (1961).

    Article  CAS  Google Scholar 

  • Nassar, M. A.: Inheritance of glandless seed in Egyptian cotton crosses. M.S. Thesis. Azhar Univ., Cairo, Egypt (1969).

    Google Scholar 

  • O’Conner, R. T., P. Von Der Haar, E. F. Dupre, L. E. Brown, and C. H. PoMinski: The infrared spectra of gossypol. J. Amer. Chem. Soc. 76, 2368 (1954).

    Google Scholar 

  • Olcott, H. S.: Solvent extraction of cottonseed oil. Ind. Eng. Chem. 33, 611 (1941).

    Article  CAS  Google Scholar 

  • Phelps, R. A.: Cottonseed meal for poultry. World’s Poultry Sci. J. 22, 86 (1966).

    Article  Google Scholar 

  • Podol’Skaya M. Z.: Estimation of gossypol in cottonseed meal and cottonseed meats. J. Applied Chem. (Ussr) 17, 657 (1944).

    Google Scholar 

  • Pons, W. A., JR., C. L. Hoffpauir, and R. T. O’Connor: Determination of total gossypol pigments in cottonseed materials. J. Amer. Oil Chem. Soc. 27, 390 (1950).

    CAS  Google Scholar 

  • Pons, W. A., J. Pominski, W. H. King, J. A. Harris, and T. H. Hopper: Recovery of gossypol from cottonseed gums. J. Amer. Oil Chem. Soc. 36, 328 (1959).

    Article  CAS  Google Scholar 

  • Pressman, B. C.: The effect of guanidine and alkylguanidine on the energy transfer reactions of mitochondria. J. Biol. Chem. 238, 401 (1963).

    CAS  Google Scholar 

  • Ramaswamy, H. N., and R. T. O’Connor: Metal complexes of gossypol. J. Agr. Food Chem. 17, 1406 (1969).

    Article  CAS  Google Scholar 

  • Ramaswamy, H. N., and R. T. O’Connor: Spectroscopic properties of some metal complexes of gossypol. Applied Spectrosc. 24, 50 (1970).

    Article  CAS  Google Scholar 

  • Ragu, P. K., and C. M. Cater: Gas-liquid chromatographic determination of gossypol as the trimethylsilyl ether derivative. J. Amer. Oil Chem. Soc. 44, 465 (1967).

    Article  Google Scholar 

  • Reiser, R., and H. C. Fu: The mechanism of gossypol detoxification by ruminant animals. J. Nutrition 76, 215 (1962).

    CAS  Google Scholar 

  • Ridgon, R. H., T. M. Ferguson, V. S. Mohan, and J. R. Couch: In vivo production of a ceriod-like pigment in chickens given gossypol. Amer. Med. Assoc. Arch. Pathol. 67, 94 (1959).

    Google Scholar 

  • Ridgon, R. H., G. Crass, T. M. Ferguson, and J. R. CoucH: Effects of gossypol in young chickens with the production of a ceriod-like pigment. Amer. Med. Assoc. Arch. Pathol. 65, 228 (1958).

    Google Scholar 

  • Robison, W. L.: Making cottonseed meal safe and effective when fed as the only protein concentrate to pigs in dry lot. Proc. Amer. Soc. Animal Prod. 29, 87 (1936).

    Google Scholar 

  • Roehm, J. N., D. J. Lee, and R. O. Sinnhurer: Accumulation and elimination of dietary gossypol in the organs of rainbow trout. J. Nutrition 92, 425 (1967).

    CAS  Google Scholar 

  • RoJas, S. W., and W. L. Scott: Factors affecting the nutritive value of cottonseed meal as a protein source in chick diets. Poultry Sci. 48, 819 (1969).

    Article  Google Scholar 

  • Royals, E. E.: Advanced organic chemistry, p. 592. Englewood Cliffs, N.J.: Prentiss-Hall (1961).

    Google Scholar 

  • Royce, H. D., J. R. Harrison, and E. R. Hahn: Cotton root bark as a source of gossypol. Oil and Soap. 18, 27 (1941).

    Article  CAS  Google Scholar 

  • Schanker, L. S.: Passage of drugs across body membranes. Pharmacol. Rev. 14, 501 (1962).

    PubMed  CAS  Google Scholar 

  • Schramm, G., and J. H. Benedict: Quantitative determination of traces of free gossypol in fats, oils and fatty acids by paper chromatography. J. Amer. Oil Chem. Soc. 35, 371 (1958).

    Article  CAS  Google Scholar 

  • Schwartz, E. W.: Gossypol and cottonseed meal poisoning. J. Oil and Fat Ind. 3, 173 (1926).

    Article  Google Scholar 

  • Schwartz, E. W., and C. L. Alsberg: Quantitative variation of gossypol and its relation to the oil content of cottonseed. J. Agr. Res. 25, 285 (1923).

    Google Scholar 

  • Schwartz, E. W., and C. L. Alsberg: Pharmacology of gossypol. J. Agr. Res. 28, 191 (1924).

    Google Scholar 

  • Sharma, M. P., F. H. Smith, and A. J. Clawson: Effects of levels of protein and gossypol, and length of feeding period on the accumulation of gossypol in tissues of swine. J. Nutrition 88, 434 (1966).

    CAS  Google Scholar 

  • Shaver, T. N., and M. J. Lukefahr: Effect of flavonoid pigments and gossypol on growth and development of the bollworm, tobacco budworm, and pink bollworm. J. Econ. Entomol. 62, 643 (1969).

    CAS  Google Scholar 

  • Sherwood, T. W.: Studies on gossypol: The gossypol and D gossypol content of some North Carolina cottonseed meals. J. Agr. Res. 32, 793 (1926).

    CAS  Google Scholar 

  • Shier, T. R., E. M Athews, R. J. Wodzinski, and J. H. Ware: Effect of calcium and phosphate ions on the formation of soluble ion-gossypol complex. J. Agr. Food Chem. 16, 208 (1968).

    Google Scholar 

  • Shirley, D. A.: Nuclear magnetic resonance of gossypol. Proc. Conf. Inactivation of Gossypol with Mineral Salts, p. 11. New Orleans, La. (1966).

    Google Scholar 

  • Shirley, D. A.:, and W. C. Sheehan: The structure and reactions of gossypol. Iii. Alphatic anil derivatives of gossypol. J. Org. Chem. 21, 251 (1956).

    Google Scholar 

  • Singleton, V. L., and F. H. Kratzer: Toxicity and related physiological activity of phenolic substances of plant origin. J. Agr. Food Chem. 17, 497 (1969). Plant phenolics. In: Toxicants occurring naturally in foods. Washington, D.C. Nat. Acad. Sci. (1973).

    Google Scholar 

  • Skutches, C. L., D. L. Herman, and F. H. Smith: Effect of intravenous gossypol injection on iron utilization in swine. J. Nutrition 103, 851 (1973).

    CAS  Google Scholar 

  • Skutches, C. L., D. L. Herman, and F. H. Smith: Effect of dietary free gossypol on blood components and tissue iron in swine and rats. J. Nutrition 104, 415 (1974).

    CAS  Google Scholar 

  • Skutches, C. L., D. L. Herman, and F. H. Smith: Metabolism of gossypol, biosynthesized from methyl-14C- and carboxyl-14C-labeled sodium acetate in rat. J. Amer. Oil Chem. Soc. 51, 413 (1974).

    Article  CAS  Google Scholar 

  • Smith, F. H.: Spectrophotometric method for estimating gossypol in crude cottonseed oil. Ind. Eng. Chem. 18, 41 (1946 a).

    Google Scholar 

  • Smith, F. H.:SEstimation of gossypol in cottonseed meal and cottonseed meat. Ind. Eng. Chem. 18, 43 (1946 b).

    Google Scholar 

  • Smith, F. H.: Spectrophotometric determination of total gossypol in cottonseed meal and cottonseed meats. J. Amer. Oil Chem. Soc. 35, 261 (1958).

    Article  CAS  Google Scholar 

  • Smith, F. H.: Biosynthesis of gossypol by exised cotton roots. Nature 192, 261 (1961).

    Google Scholar 

  • Smith, F. H.: Synthesis and translocation of gossypol by cotton plants. Proc. Cottonseed Research Conf., p. 7 (1962).

    Google Scholar 

  • Smith, F. H.: Isolation of gossypol from tissue of porcine livers. J. Amer. Oil Chem. Soc. 40, 60 (1963).

    Article  CAS  Google Scholar 

  • Smith, F. H.: Effect of gossypol bound to cottonseed protein on growth of weanling rats. J. Agr. Food Chem. 20, 803 (1972).

    Article  CAS  Google Scholar 

  • Smith, F. H.: Preparation of 14C-gossypol by incorporation of acetate-1–14C and acetate 2–14C by biosynthesis. J. Amer. Oil Chem. Soc. 51, 410 (1974).

    Article  CAS  Google Scholar 

  • Smith, F. H.:, and J. A. Clawson: Effect of diet on accumulation of gossypol in the organs of swine. J. Nutrition 87, 317 (1965).

    CAS  Google Scholar 

  • Smith, F. H.: The effects of dietary gossypol on animals. J. Amer. Oil Chem. Soc. 47, 443 (1970).

    Article  CAS  Google Scholar 

  • Smith, F. H.:, C. L. Rhyne, and V. W. Smart: Dietary evaluation of cottonseed protein from cotton bred for low gossypol content. J. Agr. Food Chem. 9, 82 (1961).

    Article  CAS  Google Scholar 

  • Smith, H. A.: The pathology of gossypol poisoning. Amer. J. Pathol. 33, 353 (1957).

    CAS  Google Scholar 

  • StansaUrry, M. F., W. A. Pons, JR., and G. T. Den Hartog: Relations between oil nitrogen and gossypol in cottonseed kernels. J. Amer. Oil Chem. Soc. 33, 282 (1956).

    Article  Google Scholar 

  • Stowe, C. M., and G. L. Plaa: External excretion of drugs and chemicals. Ann. Rev. Pharmacol. 8, 337 (1968).

    Article  PubMed  CAS  Google Scholar 

  • Sturkie, P. D.: Avian physiology, 2ed., p. 474. Ithaca, New York: Comstock (1965).

    Google Scholar 

  • Swenson, A. D., E. A. Fieger, and C. W. UPr: The nature of egg yolk discoloration produced by cottonseed meal. Poultry Sci. 21, 374 (1942).

    Article  Google Scholar 

  • Tanksley, T. D.: The effect of gossypol on some enzyme systems. Ph.D. Dissertation. Texas A and M Univ., College Station, Texas (1968).

    Google Scholar 

  • H. Neumann, C. M. Lyman, C. N. Pace, and J. M. Prescott: Inhibition of pepsinogen activation by gossypol. J. Biol. Chem. 245, 6456 (1970).

    PubMed  Google Scholar 

  • Throneberry, G. O.: Isolation of metabolically-active subcellular particles from etiolated cotton seedling hypocotyls using bovine serum albumin in preparative medium. Plant Physiol. 36, 302 (1961).

    Article  PubMed  CAS  Google Scholar 

  • Throneberry, G. O.: Factors affecting oxidative phosphorylation by subcellular particles isolated from cotton seedling hypocotyls. Plant Physiol. 37, 781 (1962).

    Article  PubMed  CAS  Google Scholar 

  • Tillman, A. D., and K. Kruse: Effect of gossypol and heat on the digestibility and utilization of soybean protein by sheep. J. Animal Sci. 21, 290 (1962).

    Google Scholar 

  • Tone, J. N., and D. R. Jensen: Effect of ingested gossypol on the growth per-formances of rats. Experientia 26, 970 (1970).

    Article  PubMed  CAS  Google Scholar 

  • Tone, J. N., and D. R. Jensen: Hematological effects of injected gossypol and iron in rats. J. Agr. Food Chem. 22, 140 (1974).

    Article  CAS  Google Scholar 

  • Vermel’, E. M., and S. A. Kruglyak: Antitumor activity of gossypol in experiments on transplantable tumors. Voprosy Onkologii (Russian) 9, 39 (1963).

    Google Scholar 

  • Von Der Harr, P., and C. H. Pominski: Pigments of cottonseed. V. Methylation of gossypurpurin. J. Org. Chem. 17, 177 (1952).

    Google Scholar 

  • Weinbach, E. C., and J. Garbus: The inhibition of uncoupling phenols with mito-chondria and with mitochondrial protein. J. Biol. Chem. 240, 1811 (1965).

    CAS  Google Scholar 

  • Weiner, I. M.: Mechanism of drug absorption and excretion: The renal excreation of drugs and related compounds. Ann. Rev. Pharmacol. 7, 39 (1967).

    Article  PubMed  CAS  Google Scholar 

  • Williams, R. T., P. Millburn, and R. L. Smith: The influence of entrohepatic circulation on toxicity of drugs. Ann. N.Y. Acad. Sci. 123, 110 (1965).

    Article  PubMed  CAS  Google Scholar 

  • Wintrobe, M. M.: Clinical hematology, ed. 2, p. 292. Philadelphia: Lea and Febiger (1947).

    Google Scholar 

  • Withers, W. A., and J. F. Brewster: Studies on cottonseed meal toxicity. II. Iron as an antidote. J. Biol. Chem. 15, 161 (1913).

    CAS  Google Scholar 

  • Withers, W. A.and F. E. Carruth: Gossypol—A toxic substance in cottonseed meal. A preliminary note. Science 41, 324 (1915 a).

    Google Scholar 

  • Withers, W. A.and F. E. Carruth: Gossypol, the toxic substance in cottonseed meal. J. Agr. Res. 7, 261 (1915 b).

    Google Scholar 

  • Withers, W. A.and F. E. Carruth: Iron as an antidote to cottonseed meal injury. J. Biol. Chem. 32, 245 (1917).

    CAS  Google Scholar 

  • Withers, W. A.and F. E. Carruth: Gossypol, the toxic substance of cottonseed. J. A.r. Res. 12, 83 (1918).

    CAS  Google Scholar 

  • Witkop, B., and T. W. Beiler: Studies on Schiff bases in connection with the mechanism of transamination. J. Amer. Chem. Soc. 76, 5589 (1954).

    Article  CAS  Google Scholar 

  • Wong, R. C., Y. Nakagawa, and G. E. Perlmann: Studies on the nature of the inhibition by gossypol of the transformation of pepsinogen to pepsin. J. Biol. Chem. 247, 1625 (1972).

    Google Scholar 

  • Woronick, C. L., and C. R. Grau: Gossypol—Cephalen compound from fresh eggs of hens fed cottonseed meal. J. Agr. Food Chem. 3, 706 (1955).

    Article  CAS  Google Scholar 

  • Young, C. T.: Relationship of protein quality to bound gossypol in oil seed meals. M.S. Thesis. N. Carolina St. Univ., Department of Animal Science, Raleigh, N.C. (1955).

    Google Scholar 

  • Young, C. T.: Manuscript received February 26, 1975; accepted May 15, 1975.

    Google Scholar 

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  1. Department of Physiology and Pharmacology, Duke University Medical Center, Durham, North Carolina, 27710, USA

    Mohamed B. Abou-Donia

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  1. Department of Entomology, University of California, 92502, Riverside, California, USA

    Francis A. Gunther

  2. Riverside, California, USA

    Jane Davies Gunther

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Abou-Donia, M.B. (1976). Physiological effects and metabolism of gossypol. In: Gunther, F.A., Gunther, J.D. (eds) Residue Reviews. Residue Reviews, vol 61. Springer, New York, NY. https://doi.org/10.1007/978-1-4613-9401-3_5

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