Effect of racemic and (+)- and (-)-gossypol on the survival and development of Helicoverpa zea larvae

Journal of Chemical Ecology

Volumn 32, Issue 5, 2006, Pages 959-968

  Stipanovic, Robert D ^a   Lopez Jr , Juan D ^a   Dowd, Michael K ^b   Puckhaber, Lorraine S ^a   Duke, Sara E ^a  

^a SOUTHERN PLAINS AGRICULTURAL RESEARCH CENTER   (United States)

^b SOUTHERN REGIONAL RESEARCH CENTER   (United States)

Author keywords

(+) Gossypol; ( ) Gossypol; Bollworm; Cotton; Cottonseed; Gossypium hirsutum; Helicoverpa zea; Host defense

Indexed keywords

GOSSYPOL;

ANTIHERBIVORE DEFENSE; COTTON; LARVAL DEVELOPMENT; SURVIVAL;

ANIMAL; ANIMAL FOOD; ARTICLE; CHEMISTRY; ECOSYSTEM; ISOMERISM; LARVA; MOTH; PHYSIOLOGY; PLANT SEED;

ANIMAL FEED; ANIMALS; ECOSYSTEM; GOSSYPOL; ISOMERISM; LARVA; MOTHS; SEEDS;

ANIMALIA; GOSSYPIUM HIRSUTUM; HELICOVERPA ZEA; INSECTA; MICROPUS;

EID: 33744732810     PISSN: 00980331     EISSN: 15731561     Source Type: Journal    
DOI: 10.1007/s10886-006-9052-9     Document Type: Article

References (29)

1. AGRESTI, A. 2002. Categorical Data Analysis, 2nd edn. John Wiley & Sons, Inc., New York.
2. 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.
3. 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.
4. 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.
5. 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.
6. CASS, Q. B., TIRITAN, E., MATLIN, S. A., and FREIRE, E. C. 1991. Gossypol enantiomer ratios in cotton seeds. Phytochemistry 30:2655-2657.
7. DOWD, M. K. 2003. Preparation of enantiomeric gossypol by crystallization. Chirality 15:486-493.
8. 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.
9. 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.
10. HOSMER, D. W., and LEMESHOW, S. 2000. Applied Logistic Regression, 2nd End. John Wiley & Sons, Inc., New York.
11. 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.
12. JAROSZEWSKI, J. W., STRØM-HANSEN, T., and HANSON, S. H. 1992a. Optical activity of gossypol. Chirality 4:216-221.
13. 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.
14. 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.
15. 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.
16. 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.
17. 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.
18. 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.
19. 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.
20. 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.
21. 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.
22. PERCY, R. G., CALHOUN, M. C., and KIM, H. L. 1996. Seed gossypol variation within Gossypium barbadense L. cotton. Crop Sci. 36:193-197.
23. 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.
24. 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.
25. 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.
26. 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.
27. 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.
28. 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.
29. 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.