Abstract
Gossypol is a sesquiterpene that occurs naturally in seed and other parts of the cotton plant. Because of restricted rotation around the binaphthyl bond, it occurs naturally as enantiomeric mixtures with (+)-gossypol to (−)-gossypol ratios that vary between 97:3 and 31:69. Commercial cotton varieties (Gossypium hirsutum) normally exhibit an approximate 3:2 ratio. (+)-Gossypol is significantly less toxic than (−)-gossypol to nonruminant animals; thus, cottonseed containing high levels of (+)-gossypol might be safely fed to nonruminants. Gossypol, however, is an important component in the cotton plant's defense against insect herbivores, but it is not known how cotton plants that exhibit high levels of (+)-gossypol in the foliage might be affected by insect herbivory. To address this question, 1-d-old Helicoverpa zea larvae were fed diets with 0.16, 0.20, and 0.24% racemic, (+)-, and (−)-gossypol. Larval pupal weights, days-to-pupation, and survival were adversely affected by all gossypol diets compared with the control diet. Statistical differences were determined by comparing the compounds among themselves at the three levels and between the three compounds at the same level. When the compounds were compared among themselves, no large differences were observed in pupal weights or in days-to-pupation among any of the diets. Among the three compounds, at the 0.16% level, the diet containing racemic gossypol was the most effective at reducing survival. At the 0.20 and 0.24% levels of racemic (+)- and (−)-gossypol, survival was not statistically different. The overall results indicate that (+)-gossypol is as inhibitory to H. zea larvae as racemic or (−)-gossypol, and thus, cotton plants containing predominantly the (+)-enantiomer in foliage may maintain significant defense against insect herbivory.
Similar content being viewed by others
References
Agresti, A. 2002. Categorical Data Analysis, 2nd edn. John Wiley & Sons, Inc., New York.
Bailey, C. A., Stipanovic, R. D., Ziehr, M. S., Haq, A. U., Sattar, M., Kubena, L. F., Kim, H. L., and Vieira, R. D. M. 2000. Cottonseed with a high (+)- to (−)-gossypol enantiomer ratio favorable to broiler production. J. Agric. Food Chem. 48:5692–5695.
Bell, A. A., Puckhaber, L. S., Kim, H. L., Stipanovic, R. D., and Percival, E. 2000. Genetic approaches for increasing percentages of (+)-gossypol levels in cotton, pp. 218–230, in C. Benedict and G. Jividen (eds.). Genetic Control of Cotton Fiber and Seed Quality. Cotton Inc., Cary, NC.
Benz, C. C., Keniry, M. A., Ford, J. M., Townsend, A. J., Cox, F. W., Palayoor, S., Matlin, S. A., Hait, W. N., and Cowan, K. H. 1990. Biochemical correlates of the antitumor and antimitochondrial properties of gossypol enantiomers. Mol. Pharmacol. 37:840–847.
Blackstaffe, L., Shelley, M. D., and Fish, R. G. 1997. Cytotoxicity of gossypol enantiomers and its quinone metabolite gossypolone in melanoma cell lines. Melanoma Res. 7:364–372.
Cass, Q. B., Tiritan, E., Matlin, S. A., and Freire, E. C. 1991. Gossypol enantiomer ratios in cotton seeds. Phytochemistry 30:2655–2657.
Dowd, M. K. 2003. Preparation of enantiomeric gossypol by crystallization. Chirality 15:486–493.
Gonzalez-Garza, M. T., Matlin, S. A., Mata-Cardenas, B. D., and Said-Fernandez, S. 1993. Differential effects of the (+)- and (−)- gossypol enantiomers upon Entamoeba histolytica axenic cultures. J. Pharm. Pharmacol. 45:144–145.
Hedin, P. A., Parrott, W. L., and Jenkins, J. N. 1992. Relationship of glands, cotton square terpenoid aldehydes, and other allelochemicals to larval growth of Heliothis virescens (Lepidoptera: Noctuidae). J. Econ. Entomol. 85:359–364.
Hosmer, D. W., and Lemeshow, S. 2000. Applied Logistic Regression, 2nd End. John Wiley & Sons, Inc., New York.
Jenkins, J. N., Maxwell, F. G., and Lafever, H. N. 1966. The comparative preference of insects for glanded and glandless cottons. J. Econ. Entomol. 59:352–356.
Jaroszewski, J. W., Strøm-Hansen, T., and Hanson, S. H. 1992a. Optical activity of gossypol. Chirality 4:216–221.
Jaroszewski, J. W., Strøm-Hansen, T., Hanson, S. H., Thastrup, O., and Kofod, H. 1992b. On the botanical distribution of chiral forms of gossypol. Planta Med. 58:454–458.
Li, H. and He, X. 1993. The effects of optical isomers of gossypol on Sertoli cells in vitro. Zhongguo Yixue Kexueyuan Xuebao 15:98–101.
Lin, T. S., Schinazi, R. F., Zhu, J., Birks, E., Carbone, R., Si, Y., WU, K., Huang, L., and Prusoff, W. H. 1993. Anti-HIV-1 activity and cellular pharmacology of various analogs of gossypol. Biochem. Pharmacol. 46:251–255.
Lindberg, M. C., Naqvi, R. H., Matlin, S. A., Zhou, R. H., Bialy, G., and Blye, R. P. 1987. Comparative anti-fertility effects of gossypol enantiomers in male hamsters. Int. J. Androl. 10:619–623.
Lordelo, M. M., Davis, A. J., Calhoun, M. C., Dowd, M. K., and Dale, N. M. 2005. Relative toxicity of gossypol enantiomers in broilers. Poultry Sci. 84:1376–1382.
Lukefahr, M. J., Noble, L. W., and Houghtaling, J. E. 1966. Growth and infestation of bollworms and other insects on glanded and glandless strains of cotton. J. Econ. Entomol. 59:817–820.
Matlin, S. A., Zhou, R., Bialy, G., Blye, R. P., Naqvi, R. H., Lindberg, M. C., and Matlin, S. A. 1985. (−)-Gossypol: an active male antifertility agent. Contraception 31:141–149.
Meisner, J., Ascher, K. R. S., and Zur, M. 1977. Phagodeterrency induced by pure gossypol and leaf extracts of a cotton strain with high gossypol content in the larva of Spodoptera littoralis. J. Econ. Entomol. 70:149–150.
Oliver, B. F., Maxwell, F. G., and Jenkins, J. N. 1971. Growth of the bollworm on glanded and glandless cottons. J. Econ. Entomol. 64:396–398.
Percy, R. G., Calhoun, M. C., and Kim, H. L. 1996. Seed gossypol variation within Gossypium barbadense L. cotton. Crop Sci. 36:193–197.
Puckhaber, L. S., Dowd, M. K., Stipanovic, R. D., and Howell, C. R. 2002. Toxicity of (+)- and (−)-gossypol to the plant pathogen, Rhizoctonia solani. J. Agric. Food Chem. 50:7017–7021.
Sang, G., Lorenzo, B., and Reidenberg, M. M. 1991. Inhibitory effects of gossypol on corticosteroid 11-β-hydroxysteroid dehydrogenase from guinea pig kidney: A possible mechanism for causing hypokalemia. J. Steroid Biochem. Mol. Biol. 39:169–176.
Shelley, M. D., Hartley, L., Fish, R. G., Groundwater, P., Morgan, J. J. G., Mort, D., Mason, M., and Evans, A. 1999. Stereo-specific cytotoxic effects of gossypol enantiomers and gossypolone in tumor cell lines. Cancer Lett. 135:171–180.
Stipanovic, R. D., Altman, D. W., Begin, D. L., Greenblatt, G. A., and Benedict, J. H. 1988. Terpenoid aldehydes in Upland cottons: analysis by aniline and HPLC methods. J. Agric. Food Chem. 36:509–515.
Stipanovic, R. D., Bailey, C. A., Kubena, L. F., and Kim, H. L. 2001. Cottonseed containing high levels of (+)-gossypol: Potential as a feed/food source, pp. 231–243, in C. Benedict and G. Jividen (eds.). Genetic Control of Cotton Fiber and Seed Quality. Cotton, Inc., Cary, NC.
Yang W.-H., Ma L.-H., Zhu H.-Q., and Xiang S.-K. 1999. Effects of different gossypol enantiomers on growth and development of cotton bollworm (Helicoverpa armigera) and Fusarium wilt. Acta Gossypii Sin. 11:31–34.
Zur, M., Meisner, J., Kabonci, E., and Ascher, K. R. S. 1979. Gossypol content of cotton leaves during the growing season, and growth suppression of Spodoptera littoralis (Boisduval) larvae on some high-gossypol (HG) cotton strains. Z. Angew. Entomol. 87:435–439.
Acknowledgment
This research was supported by the Cotton Foundation. We thank Michael O'Neil and Brittany Fuchs for excellent technical assistance.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Stipanovic, R.D., Lopez, J.D., Dowd, M.K. et al. Effect of Racemic and (+)- and (−)-Gossypol on the Survival and Development of Helicoverpa zea Larvae. J Chem Ecol 32, 959–968 (2006). https://doi.org/10.1007/s10886-006-9052-9
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10886-006-9052-9