Induction of terata in hamsters by solanidane alkaloids derived from Solanum tuberosum

Chemical Research in Toxicology

Volumn 9, Issue 2, 1996, Pages 426-433

  Gaffield, William ^a   Keeler, Richard F ^b  

^a WESTERN REGIONAL RESEARCH CENTER   (United States)

^b AGRICULTURAL RESEARCH SERVICE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SOLANUM ALKALOID;

ANIMAL CELL; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; CRANIOFACIAL MALFORMATION; DRUG POTENCY; FEMALE; FETUS MALFORMATION; MUTAGEN TESTING; NONHUMAN; POTATO; SYRIAN HAMSTER; TERATOGENESIS; TOMATO;

ADMINISTRATION, ORAL; ANIMALS; BENZO(A)PYRENE; CRICETINAE; DOSE-RESPONSE RELATIONSHIP, DRUG; EMBRYONIC AND FETAL DEVELOPMENT; FEMALE; KINETICS; MALE; MESOCRICETUS; MODELS, BIOLOGICAL; PREGNANCY; PRENATAL EXPOSURE DELAYED EFFECTS; SACCHAROMYCES CEREVISIAE; SOLANACEOUS ALKALOIDS; SOLANUM TUBEROSUM; SPECIES SPECIFICITY; TERATOGENS;

EID: 0029877841     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx950091r     Document Type: Article

References (44)

1. Schardein, J. L. (1993) Chemically Induced Birth Defects, Dekker, New York.
2. Renwick, J. H. (1972) Hypothesis: Anencephaly and spina bifida are usually preventable by avoidance of a specific but unidentified substance present in certain potato tubers. Br. J. Prev. Soc Med. 26, 67-88.
3. Poswillo, D. E., Sopher, D., and Mitchell, S. (1972) Experimental induction of foetal malformation with "blighted potato": a preliminary report. Nature 239, 462-464.
4. Keeler, R. F., Douglas, D. R., and Stallknecht, G. F. (1974) Failure of blighted russet Burbank potatoes to produce congenital deformities in rats. Proc. Soc. Exp. Biol. Med. 146, 284-286.
5. Clarke, C. A , McKendrick, O. M., and Sheppard, P. M (1973) Spina bifida and potatoes. Br. Med J. 3, 251-254.
6. Spiers, P. S., Pietrzyk, J. J., Piper, J. M., and Glebatis, D. M. (1974) Human potato consumption and neural-tube malformation. Teratology 10, 125-128.
7. Higgins, I T. T. (1975) Importance of epidemiological studies relating to hazards of food and environment. Br. Med. Bull. 31, 230-235.
8. Nevin, N. C., and Merrett, J D. (1975) Potato avoidance during pregnancy in women with a previous infant with either anencephaly and/or spina bifida. Br. J. Prev. Soc. Med. 29, 111-115
9. Scott, J. M., Kirke, P. N., and Weir, D. G. (1990) The role of nutrition in neural tube defects. Annu. Rev. Nutr. 10, 277-295
10. Keeler, R. F , Baker, D. C., and Gaffield, W. (1991) Teratogenic Solanum species and the responsible teratogens. In Handbook of Natural Toxins, Vol. 6, Toxicology of Plant and Fungal Compounds (Keeler, R. F., and Tu, A. T., Eds.) pp 83-99, Dekker, New York.
11. Keeler, R. F., Young, S., Brown, D., Stallknecht, G. F., and Douglas, D. (1978) Congenital deformities produced in hamsters by potato sprouts. Teratology 17, 327-334.
12. Brown, D., and Keeler, R F. (1978) Structure-activity relation of steroid teratogens. 3. Solanidan epimers. J. Agric Food Chem. 26, 566-569.
13. Keeler, R. F., and Binns, W. (1968) Teratogenic compounds of Veratrum californicum (Durand) V. Comparison of cyclopian effects of steroidal alkaloids from the plant and structurally related compounds from other sources. Teratology 1, 5-10.
14. Keeler, R. F. (1970) Teratogenic compounds in Veratrum californicum. IX. Structure-activity relation Teratology 3, 169-173.
15. Gaffield, W. (1990) Chirality as manifested in the biological activity of natural products In Studies in Natural Products Chemistry (Atta-ur-Rahman, Ed.) Vol 7, pp 3-28, Elsevier, Amsterdam
16. Hauck, R -S., Wegner, C., Blumtritt, P., Fuhrhop, J -H., and Nau, H. (1990) Asymmetric synthesis and teratogenic activity of (R) and (S)-2-ethylhexanoic acid, a metabolite of the plasticizer, di-(2-ethylhexyl)-phthalate. Life Sci 46, 513-518.
17. Renwick, J. H., Claringbold, W. D. B., Earthy, M. E., Few, J D , and MeLean, C. S. (1984) Neural-tube defects produced in Syrian hamsters by potato glycoalkaloids. Teratology 30, 371-381
18. Gaffield, W , Keeler, R. F., and Baker, D. C. (1991) Solanum glycoalkaloids: Plant toxins possessing disparate physiologically active structural entities. In Handbook of Natural Toxins, Vol. 6, Toxicology of Plant and Fungal Compounds ( Keeler, R. F , and Tu, A. T., Eds.) pp 135-158, Dekker, New York.
19. van Gelder, W. M. J., and Scheffer, J. J. C. (1991) Transmission of steroidal glycoalkaloids from Solanum vernei to the cultivated potato. Photochemistry 30, 165-168.
20. Maga, J A (1994) Glycoalkaloids in Solanaceae. Food Rev Int. 10, 385-418.
21. Hlywka, J. J., Stephenson, G. R., Sears, M K., and Yada, R. Y (1994) Effects of insect damage on glycoalkaloid content in potatoes (Solanum tuberosum). J. Agric. Food Chem. 42, 2545-2550.
22. Keeler, R. F. (1975) Teratogenic effects of cyclopamine and jervine in rats, mice and hamsters. Proc. Soc. Exp. Biol. Med. 149, 302-306.
23. Gaffield, W., and Keeler, R. F. (1993) Implication of C-5, C-6 unsaturation as a key structural factor in steroidal alkaloid-induced mammalian teratogenesis. Experientia 49, 922-924.
24. Keeler, R. F., Baker, D. C., and Gaffield, W. (1990) Spirosolane-containing Solanum species and induction of congenital craniofacial malformations. Toxicon 28, 873-884.
25. Keeler, R. F. (1984) Mammalian teratogenicity of steroidal alkaloids. In Isopentenoids in Plants: Biochemistry and Function (Nes, W. D., Fuller, G., and Tsai, L.-S., Eds.) pp 531-562, Dekker, New York.
26. Keeler, R. F. (1986) Teratology of steroidal alkaloids. In Alkaloids. Chemical and Biological Perspectives (Pelletier, S. W., Ed.) Vol. 4, pp 389-425, Wiley-Interscience, New York.
27. Little, T. M., and Hills, F. J. (1972) Statistical Methods in Agricultural Research, pp 193-205, Davis, CA.
28. Baker, D. C., Keeler, R. F., and Gaffield, W. (1987) Lesions of potato sprout and extracted potato sprout alkaloid toxicity in Syrian hamsters. J. Toxicol., Clin. Toxicol. 25, 199-208.
29. Agrawal, P. K., Srivastava, S. K., and Gaffield, W (1991) Carbon-13 NMR spectroscopy of steroidal alkaloids. In Alkaloids: Chemical and Biological Perspectives (Pelletier, S. W., Ed.) Vol. 7, pp 43-295, Springer Verlag, New York.
30. Budzikiewicz, H. (1964) Mass spectral fragmentation of steroidal alkaloids. Tetrahedron 20, 2267-2278.
31. Prelog, V., and Jeger, O. (1953) The chemistry of Solanum and Veratrum alkaloids. In The Alkaloids (Manske, R. H. F., and Holmes, H. L., Eds.) Vol. 3, pp 247-312, Academic Press, New York.
32. Szpilfogel, S. (1951) Steroids and sex hormones (CLXXV). N-oxides in the solanidine series. Helv. Chim. Acta 34, 843-846.
33. Gaffield, W., and Keeler, R. F. (1994) Structure-activity relations of teratogenic natural products. Pure Appl. Chem. 66, 2407-2410.
34. Gottlieb, H. E., Belic, I., Komel, R., and Mervic, M. (1981) N-Methylated products of the Solanum steroidal alkaloids tomatidine and solasodine J. Chem. Soc., Perkin Trans. 1, 1888-1890.
35. Gaffield, W., Benson, M., Haddon, W. F., and Lundin, R. E. (1983) Evidence for the structure, and for a non-chair conformation in ring F of two isomeric N-formylsolasodines. Aust. J. Chem. 36, 325-337.
36. Kusano, G., Sekimoto, C., Abe, M., In, Y., Ohishi, H., Ishida, T., and Aimi, N. (1992) The structures of two isomeric N-formates from 3-O-acetylsolasodine. Heterocycles 34, 1957-1964.
37. Gaffield, W., and Keeler, R. F. (1996) Craniofacial malformations induced in hamsters by steroidal alkaloids. J. Nat. Toxins (in press).
38. Khera, K. S. (1984) Maternal toxicity - a possible factor in fetal malformations in mice. Teratology 29, 411-416.
39. Morris, S. C., and Lee, T. H. (1984) The toxicity and teratogenicity of Solanaceae glycoalkaloids, particularly those of the potato (Solanum tuberosum): a review. Food Technol. Austral. 36, 118-124.
40. Keeler, R. F., Baker, D. C., and Gaffield, W. (1991) Solanum alkaloids. In Mycotoxins and Phytoalexins (Sharma, R. P., and Salunkhe, D. K., Eds.) pp 607-636, CRC Press, Boca Raton, FL.
41. Baker, D. C , Keeler, R F., and Gaffield, W. (1991) Toxicosis from steroidal alkaloids of Solanum species. In Handbook of Natural Toxins, Vol. 6, Toxicology of Plant and Fungal Compounds (Keeler, R. F., and Tu, A. T., Eds.)pp 71-82, Dekker, New York.
42. Juchau, M. R. (1989) Bioactivation in chemical teratogenesis. Annu. Rev. Pharmacol. Toxicol. 29, 165-187.
43. Kingsbury, J. M. (1964) Poisonous Plants of the United States and Canada, Prentice-Hall, Englewood Cliffs, NJ.
44. Ronsch, H., and Schreiber, K. (1966) Solanum alkaloids LXV. Four new 15α-hydroxyspirosolane alkaloids from the roots of Solanum dulcamara. Liebigs Ann. Chem. 694, 169-182.