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Physiological effects and metabolism of gossypol

Conference paper
Part of the Residue Reviews book series (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).

Keywords

Cotton Plant Seed Meal Cottonseed Meal Free Gossypol Pigment Gland 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. Abou-Donia, M. B., and J. W. Dieckert: Gossypol: Subcellular localization and stimulation of rat liver microsomal oxidases. Toxicol. Applied Pharmacol. 18, 507 (1971).CrossRefGoogle Scholar
  2. Abou-Donia, M. B., and J. W. Dieckert:Gossypol: Uncoupling of respiratory chain and oxidative phosphorylation. Life Sci. 14, 1955 (1974 a).Google Scholar
  3. Abou-Donia, M. B., and J. W. Dieckert: Urinary and biliary excretion of 14C-gossypol in swine. Nutr. 104, 754 (1974 b).Google Scholar
  4. 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).CrossRefGoogle Scholar
  5. 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
  6. 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
  7. 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
  8. 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
  9. 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
  10. Adams, R., T. A. Geissman, and S. D. Edwards: Gossypol, a pigment of cottonseed. Chem. Rev. 60, 555 (1960).PubMedCrossRefGoogle Scholar
  11. 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).CrossRefGoogle Scholar
  12. 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
  13. 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
  14. 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).Google Scholar
  15. 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).Google Scholar
  16. Alsberg, C. L., and E. W. Schwartze: Pharmacological action of gossypol. J. Pharmacol. Expt. Ther. 13, 504 (1919).Google Scholar
  17. 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
  18. 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).PubMedCrossRefGoogle Scholar
  19. 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).CrossRefGoogle Scholar
  20. Baugher, W. L., and T. Campbell: Gossypol detoxification by fungi. Science 164, 1526 (1969).PubMedCrossRefGoogle Scholar
  21. Bell, A. A.: Formation of gossypol in infected or chemically irritated tissues of gossypuim species. Phytopathol. 57, 759 (1967).Google Scholar
  22. 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
  23. 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).CrossRefGoogle Scholar
  24. Boatner, C. H.: Pigments of Cottonseed. In A. E. Baily (ed.): Cottonseed, p. 213. New York: Interscience (1948).Google Scholar
  25. Boatner, C. H., M. Carvaella, and L. Kyane: Quantitative determination of extractable gossypol in cottonseed and cottonseed meal. Ind. Eng. Chem. 16, 566 (1944).Google Scholar
  26. 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).Google Scholar
  27. Bottger, G. T., and R. Patana: Growth, development, and survival of certain lipidoptera fed gossypol in the diet. J. Econ. Entomol. 59, 1166 (1966).Google Scholar
  28. 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).Google Scholar
  29. 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
  30. 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
  31. Brauer, R. W., JR.: Mechanisms of bile secretion. J. Amer. Med. Assoc. 169, 1462 (1959).CrossRefGoogle Scholar
  32. Breakey, E. P., and H. S. Olcott: The non-toxicity of gossypol to certain insects. Science 87, 87 (1938).PubMedCrossRefGoogle Scholar
  33. 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).Google Scholar
  34. 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).Google Scholar
  35. 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).Google Scholar
  36. 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
  37. 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).CrossRefGoogle Scholar
  38. Campbell, K. N., R. C. Morris, and R. Adams: The structure of gossypol I. J. Amer. Chem. Soc. 59, 1723 (1937).CrossRefGoogle Scholar
  39. Carruth, F. E.: Methods for approximating the relative toxicity of cottonseed products. J. Biol. Chem. 32, 87 (1917).Google Scholar
  40. Contribution to the chemistry of gossypol, the toxic principle of cottonseed. J. Amer. Chem. Soc. 40, 647 (1918).CrossRefGoogle Scholar
  41. Stability of bound gossypol to digestion. J. Amer. Oil Chem. Soc. 24, 58 (1947).CrossRefGoogle Scholar
  42. 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).CrossRefGoogle Scholar
  43. 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).CrossRefGoogle Scholar
  44. 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).PubMedGoogle Scholar
  45. 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
  46. Chappell, J. B.: The effects of 2,4-dinitrophenol on mitochondrial oxidations. Biochem. J. 90, 237 (1964).PubMedGoogle Scholar
  47. Clark, E. P.: Studies on gossypol II. Concerning the nature of Carruth’s D gossypol. J. Biol. Chem. 76, 229 (1928 a).Google Scholar
  48. Clark, E. P.: Studies on gossypol IV. Apogossypol. J. Biol. Chem. 78, 159 (1928 b).Google Scholar
  49. 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).Google Scholar
  50. 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
  51. 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
  52. 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).PubMedCrossRefGoogle Scholar
  53. Couch, J. R., W. Y. Chang, and C. M. Lyman: The effect of free gossypol on chick growth. Poultry Sci. 34, 178 (1955).CrossRefGoogle Scholar
  54. 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).Google Scholar
  55. 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).Google Scholar
  56. Dechary, J. M., and L. E. Brown: Substituted arylimino derivatives of gossypol. J. Amer. Oil Chem. Soc. 33, 76 (1956).CrossRefGoogle Scholar
  57. 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
  58. 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
  59. Dowell, C. T., and Menaul: Effect of autoclaving upon the toxicity of cottonseed meal. J. Agr. Res. 26, 9 (1923).Google Scholar
  60. Eagle, E.: Detoxification of cottonseed pigment glands with ferrous sulfate. Proc. Soc. Expt. Biol. Med. 72, 444 (1949).CrossRefGoogle Scholar
  61. Eagle, E.: Effect of repeated doses of gossypol on the dog. Arch. Biochem. Biophys. 26, 68 (1950).Google Scholar
  62. Eagle, E.: A review of some physiological effects of gossypol and cottonseed pigment glands. J. Amer. Oil Chem. Soc. 37, 40 (1960).CrossRefGoogle Scholar
  63. 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).Google Scholar
  64. 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).Google Scholar
  65. Edwards, J. D., JR.: Total synthesis of gossypol. J. Amer. Chem. Soc. 80, 3798 (1958).CrossRefGoogle Scholar
  66. 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
  67. 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
  68. Finlay, T. H., E. D. Dharmgrongartama, and G. E. Perlman: Mechanism of the gossypol inactivation of pepsinogen. J. Biol. Chem. 248, 4827 (1973).PubMedGoogle Scholar
  69. 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).CrossRefGoogle Scholar
  70. Frampton, V. L., J. D. Edwards, and H. R. Henze: The ultraviolet absorption spectrum of gossypol. J. Amer. Chem. Soc. 70, 3944 (1948).CrossRefGoogle Scholar
  71. Gallup, W. D.: The value of iron salts in countering the toxic effects of gossypol. J. Biol. Chem. 77, 437 (1928).Google Scholar
  72. Gallup, W. D.: Concerning the use of cottonseed meal in the diet of the rat. J. Biol. Chem. 91, 387 (1931).Google Scholar
  73. Gillham, F. E. M.: Cotton in a hungry world. S. Afr. J. Sci. 65, 173 (1969).Google Scholar
  74. 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).CrossRefGoogle Scholar
  75. 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).CrossRefGoogle Scholar
  76. Hagen-Smit, A. J., and C. C. Nimmo: Comprehensive biochemistry, vol. 9, p. 129. New York: Elsevier (1962).Google Scholar
  77. 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).Google Scholar
  78. Hale, F., and C. M. Lyman: Lysine supplementation of sorghum grain-cottonseed meal rations for growing-fattening pigs. J. Animal Sci. 20, 734 (1961).Google Scholar
  79. 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
  80. 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
  81. Halverson, J. O., and F. H. Smith: Estimation of gossypol in cottonseed meal. A modified method. Ind. Eng. Chem. 5, 29 (1933).Google Scholar
  82. Harms, W. S., and K. T. Holley: Hypoprothrombinemia induced by gossypol. Proc. Soc. Expt. Biol. Med. 71, 297 (1951).CrossRefGoogle Scholar
  83. Harper, G. A., and K. J. Smith: Status of cottonseed protein. Econ. Bot. 22, 63 (1968).CrossRefGoogle Scholar
  84. 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).PubMedGoogle Scholar
  85. Heinstein, P. F., F. H. Smith, and S. B. TovE: Biosynthesis of 14C-labeled gossypol. J. Biol. Chem. 237, 2643 (1962).PubMedGoogle Scholar
  86. Hester, H. R., H. E. Essex, and F. C. Mann: Secretion of urine in the chicken. Amer. J. Physiol. 128, 592 (1940).Google Scholar
  87. 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).CrossRefGoogle Scholar
  88. 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).CrossRefGoogle Scholar
  89. 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).CrossRefGoogle Scholar
  90. 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).Google Scholar
  91. 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).Google Scholar
  92. Hunter, F. E.: In W. D. McElroy and B. Glass (eds.): Phosphorus metabolism, p. 297. Baltimore: Johns Hopkins (1951).Google Scholar
  93. Jonassen, H. B., and R. J. Demint: Interaction of gossypol with ferrous iron. J. Amer. Chem. Soc. 32, 424 (1955).Google Scholar
  94. 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
  95. 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
  96. 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
  97. 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
  98. King, J. J., and L. B. DE Silva: Optically active gossypol from Thespesia populnea. Tetrahedron Letters 3, 261 (1968).CrossRefGoogle Scholar
  99. Kingsbury, J. M.: In: Poisonous plants of the United States and Canada. Englewood Cliffs, N.J.: Prentice-Hall (1964).Google Scholar
  100. 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).CrossRefGoogle Scholar
  101. 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
  102. 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
  103. 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).CrossRefGoogle Scholar
  104. 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
  105. Loomis, W. D., and J. Battaile: Plant phenolic compounds and the isolation of plant enzymes. Phytochem. 5, 423 (1966).CrossRefGoogle Scholar
  106. Lornez, F. W.: Egg deterioration due to ingestion by hens of malvaceous materials. Poultry Sci. 18, 295 (1939).CrossRefGoogle Scholar
  107. 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).Google Scholar
  108. Lyman, C. M., B. P. Baliga, and M. Slay: Reactions of proteins with gossypol. Arch. Biochem. Biophys. 84, 486 (1959).PubMedCrossRefGoogle Scholar
  109. 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).CrossRefGoogle Scholar
  110. 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).Google Scholar
  111. Marchlewski, L.: Gossypol, ein Bestandtheil der Baumwollsamen. J. prakt. Chem. 60, 84 (1899).CrossRefGoogle Scholar
  112. Mattil, H. A.: Antioxidants and the autooxidation of fats. J. Biol. Chem. 90, 141 (1931).Google Scholar
  113. Maxwell, F. G., H. N. Lafever, and J. N. Jenkins: Blister beetles on glandless cotton. J. Econ. Entomol. 58, 792 (1965).Google Scholar
  114. Mcmichael, S. C.: Combined effect of glandless genes gl2 and gl, on pigment glands in cotton plant. Agron. J. 52, 385 (1960).CrossRefGoogle Scholar
  115. 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).CrossRefGoogle Scholar
  116. Menaul, P.: The physiological effect of gossypol. J. Agr. Res. 26, 233 (1923).Google Scholar
  117. 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
  118. 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).PubMedCrossRefGoogle Scholar
  119. Miravalle, R. J.: Action of the genes controlling the character of glandless seed in cotton. Crop Sci. 2, 447 (1962).CrossRefGoogle Scholar
  120. Morris, R. C., and R. Adams: The structure of gossypol. IV. Gossypol ethers. J. Amer. Chem. Soc. 59, 1731 (1937).CrossRefGoogle Scholar
  121. Mudge, G. H.: Renal pharmacology. Ann. Rev. Pharmacol. 7, 163 (1967).PubMedCrossRefGoogle Scholar
  122. 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
  123. 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).CrossRefGoogle Scholar
  124. Myers, B. D., and G. O. Throneberry: Effect of gossypol on some oxidative respiratory enzymes. Plant Physiol. 41, 787 (1966).PubMedCrossRefGoogle Scholar
  125. 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).CrossRefGoogle Scholar
  126. 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).CrossRefGoogle Scholar
  127. 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).CrossRefGoogle Scholar
  128. Nassar, M. A.: Inheritance of glandless seed in Egyptian cotton crosses. M.S. Thesis. Azhar Univ., Cairo, Egypt (1969).Google Scholar
  129. 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
  130. Olcott, H. S.: Solvent extraction of cottonseed oil. Ind. Eng. Chem. 33, 611 (1941).CrossRefGoogle Scholar
  131. Phelps, R. A.: Cottonseed meal for poultry. World’s Poultry Sci. J. 22, 86 (1966).CrossRefGoogle Scholar
  132. PodolSkaya M. Z.: Estimation of gossypol in cottonseed meal and cottonseed meats. J. Applied Chem. (Ussr) 17, 657 (1944).Google Scholar
  133. 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).Google Scholar
  134. 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).CrossRefGoogle Scholar
  135. Pressman, B. C.: The effect of guanidine and alkylguanidine on the energy transfer reactions of mitochondria. J. Biol. Chem. 238, 401 (1963).Google Scholar
  136. Ramaswamy, H. N., and R. T. O’Connor: Metal complexes of gossypol. J. Agr. Food Chem. 17, 1406 (1969).CrossRefGoogle Scholar
  137. Ramaswamy, H. N., and R. T. O’Connor: Spectroscopic properties of some metal complexes of gossypol. Applied Spectrosc. 24, 50 (1970).CrossRefGoogle Scholar
  138. 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).CrossRefGoogle Scholar
  139. Reiser, R., and H. C. Fu: The mechanism of gossypol detoxification by ruminant animals. J. Nutrition 76, 215 (1962).Google Scholar
  140. 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
  141. 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
  142. 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
  143. 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).Google Scholar
  144. 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).CrossRefGoogle Scholar
  145. Royals, E. E.: Advanced organic chemistry, p. 592. Englewood Cliffs, N.J.: Prentiss-Hall (1961).Google Scholar
  146. Royce, H. D., J. R. Harrison, and E. R. Hahn: Cotton root bark as a source of gossypol. Oil and Soap. 18, 27 (1941).CrossRefGoogle Scholar
  147. Schanker, L. S.: Passage of drugs across body membranes. Pharmacol. Rev. 14, 501 (1962).PubMedGoogle Scholar
  148. 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).CrossRefGoogle Scholar
  149. Schwartz, E. W.: Gossypol and cottonseed meal poisoning. J. Oil and Fat Ind. 3, 173 (1926).CrossRefGoogle Scholar
  150. 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
  151. Schwartz, E. W., and C. L. Alsberg: Pharmacology of gossypol. J. Agr. Res. 28, 191 (1924).Google Scholar
  152. 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).Google Scholar
  153. 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).Google Scholar
  154. Sherwood, T. W.: Studies on gossypol: The gossypol and D gossypol content of some North Carolina cottonseed meals. J. Agr. Res. 32, 793 (1926).Google Scholar
  155. 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
  156. Shirley, D. A.: Nuclear magnetic resonance of gossypol. Proc. Conf. Inactivation of Gossypol with Mineral Salts, p. 11. New Orleans, La. (1966).Google Scholar
  157. 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
  158. 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
  159. 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).Google Scholar
  160. 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).Google Scholar
  161. 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).CrossRefGoogle Scholar
  162. Smith, F. H.: Spectrophotometric method for estimating gossypol in crude cottonseed oil. Ind. Eng. Chem. 18, 41 (1946 a).Google Scholar
  163. Smith, F. H.:SEstimation of gossypol in cottonseed meal and cottonseed meat. Ind. Eng. Chem. 18, 43 (1946 b).Google Scholar
  164. Smith, F. H.: Spectrophotometric determination of total gossypol in cottonseed meal and cottonseed meats. J. Amer. Oil Chem. Soc. 35, 261 (1958).CrossRefGoogle Scholar
  165. Smith, F. H.: Biosynthesis of gossypol by exised cotton roots. Nature 192, 261 (1961).Google Scholar
  166. Smith, F. H.: Synthesis and translocation of gossypol by cotton plants. Proc. Cottonseed Research Conf., p. 7 (1962).Google Scholar
  167. Smith, F. H.: Isolation of gossypol from tissue of porcine livers. J. Amer. Oil Chem. Soc. 40, 60 (1963).CrossRefGoogle Scholar
  168. Smith, F. H.: Effect of gossypol bound to cottonseed protein on growth of weanling rats. J. Agr. Food Chem. 20, 803 (1972).CrossRefGoogle Scholar
  169. 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).CrossRefGoogle Scholar
  170. Smith, F. H.:, and J. A. Clawson: Effect of diet on accumulation of gossypol in the organs of swine. J. Nutrition 87, 317 (1965).Google Scholar
  171. Smith, F. H.: The effects of dietary gossypol on animals. J. Amer. Oil Chem. Soc. 47, 443 (1970).CrossRefGoogle Scholar
  172. 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).CrossRefGoogle Scholar
  173. Smith, H. A.: The pathology of gossypol poisoning. Amer. J. Pathol. 33, 353 (1957).Google Scholar
  174. 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).CrossRefGoogle Scholar
  175. Stowe, C. M., and G. L. Plaa: External excretion of drugs and chemicals. Ann. Rev. Pharmacol. 8, 337 (1968).PubMedCrossRefGoogle Scholar
  176. Sturkie, P. D.: Avian physiology, 2ed., p. 474. Ithaca, New York: Comstock (1965).Google Scholar
  177. 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).CrossRefGoogle Scholar
  178. 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
  179. H. Neumann, C. M. Lyman, C. N. Pace, and J. M. Prescott: Inhibition of pepsinogen activation by gossypol. J. Biol. Chem. 245, 6456 (1970).PubMedGoogle Scholar
  180. 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).PubMedCrossRefGoogle Scholar
  181. Throneberry, G. O.: Factors affecting oxidative phosphorylation by subcellular particles isolated from cotton seedling hypocotyls. Plant Physiol. 37, 781 (1962).PubMedCrossRefGoogle Scholar
  182. 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
  183. Tone, J. N., and D. R. Jensen: Effect of ingested gossypol on the growth per-formances of rats. Experientia 26, 970 (1970).PubMedCrossRefGoogle Scholar
  184. Tone, J. N., and D. R. Jensen: Hematological effects of injected gossypol and iron in rats. J. Agr. Food Chem. 22, 140 (1974).CrossRefGoogle Scholar
  185. Vermel’, E. M., and S. A. Kruglyak: Antitumor activity of gossypol in experiments on transplantable tumors. Voprosy Onkologii (Russian) 9, 39 (1963).Google Scholar
  186. Von Der Harr, P., and C. H. Pominski: Pigments of cottonseed. V. Methylation of gossypurpurin. J. Org. Chem. 17, 177 (1952).Google Scholar
  187. Weinbach, E. C., and J. Garbus: The inhibition of uncoupling phenols with mito-chondria and with mitochondrial protein. J. Biol. Chem. 240, 1811 (1965).Google Scholar
  188. Weiner, I. M.: Mechanism of drug absorption and excretion: The renal excreation of drugs and related compounds. Ann. Rev. Pharmacol. 7, 39 (1967).PubMedCrossRefGoogle Scholar
  189. 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).PubMedCrossRefGoogle Scholar
  190. Wintrobe, M. M.: Clinical hematology, ed. 2, p. 292. Philadelphia: Lea and Febiger (1947).Google Scholar
  191. Withers, W. A., and J. F. Brewster: Studies on cottonseed meal toxicity. II. Iron as an antidote. J. Biol. Chem. 15, 161 (1913).Google Scholar
  192. Withers, W. A.and F. E. Carruth: Gossypol—A toxic substance in cottonseed meal. A preliminary note. Science 41, 324 (1915 a).Google Scholar
  193. Withers, W. A.and F. E. Carruth: Gossypol, the toxic substance in cottonseed meal. J. Agr. Res. 7, 261 (1915 b).Google Scholar
  194. Withers, W. A.and F. E. Carruth: Iron as an antidote to cottonseed meal injury. J. Biol. Chem. 32, 245 (1917).Google Scholar
  195. Withers, W. A.and F. E. Carruth: Gossypol, the toxic substance of cottonseed. J. A.r. Res. 12, 83 (1918).Google Scholar
  196. Witkop, B., and T. W. Beiler: Studies on Schiff bases in connection with the mechanism of transamination. J. Amer. Chem. Soc. 76, 5589 (1954).CrossRefGoogle Scholar
  197. 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
  198. 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).CrossRefGoogle Scholar
  199. 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
  200. Young, C. T.: Manuscript received February 26, 1975; accepted May 15, 1975.Google Scholar

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© Springer Science+Business Media New York 1976

Authors and Affiliations

  1. 1.Department of Physiology and PharmacologyDuke University Medical CenterDurhamUSA

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