Toxicarioside B and toxicarioside C. New cardenolides isolated from Antiaris toxicaria latex-derived poison

Tetrahedron

Volumn 53, Issue 50, 1997, Pages 16959-16968

  Carter, Christine A ^d   Gray, Elizabeth A ^d   Schneider, Tanya L ^d   Lovett Jr , Charles M ^a   Scott, Lincoln ^b   Messer, Adam C ^c   Richardson, David P ^a  

^a WILLIAMS COLLEGE   (United States)

^b Boston University ^*  (United States)

^c U S DEPARTMENT OF STATE   (United States)

^d NONE

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE TRIPHOSPHATASE (POTASSIUM SODIUM); CARDENOLIDE; LATEX; POISON; TOXICARIOSIDE B; TOXICARIOSIDE C; UNCLASSIFIED DRUG;

ARTICLE; BIOASSAY; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG STRUCTURE; DRUG TOXICITY; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOISOMERISM; THIN LAYER CHROMATOGRAPHY; ULTRAVIOLET SPECTROPHOTOMETRY;

ANTIARIS TOXICARIA;

EID: 0030777044     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10174-0     Document Type: Article

References (43)

1. Bisset, N.G. Lloydia, 1966, 29, 1-18.
2. Bisset, N.G. and Woods, M.C. Lloydia, 1966, 29, 172-195.
3. a) Doebel, K., Schittler, E. and Reichstein, T. Helv. Chim. Acta, 1948, 31, 688-709;
4. b) Dolder, F., Tamm, Ch. and Reichstein, T. Helv. Chim. Acta, 1955, 38, 1364-1396;
5. c) Juslen, C., Wehrli, W and Reichstein, T. Helv. Chim. Acta, 1962, 45, 2285-2296;
6. d) Muhlradt, P., Weiss, Ek. and Reichstein, T. Helv. Chim. Acta, 1964, 47, 2164-2186;
7. e) Brandt, R., Kaufmann, H., and Reichstein, T. Helv. Chim. Acta, 1966, 49, 2469-2481;
8. f) Wehrli, W., Schindler, O. and Reichstein, T. Helv. Chim. Acta, 1962, 45, 1183-1205..
9. Kopp, B., Bauer, W.P. and Bernkop-Shnurch, A. Journal of Ethnopharmacology, 1992, 36, 57-62;
10. Shrestha, T., Kopp, B. and Bisset, N.G. Journal of Ethnopharmacology, 1992, 37, 129-143..
11. For an example of a common cardiotonic cardiac glycoside (i.e. digoxin), see: Foss, P.R.B. and Benezra, S.A. Anal. Profiles Drug Subst., 1980, 9, 207-243; Martindale. The Extra Pharmacopoeia, 28th/29th Ed., Pharmaceutical Press, London, 1984/1989, pp. 5801-5804.
12. For an example of a common cardiotonic cardiac glycoside (i.e. digoxin), see: Foss, P.R.B. and Benezra, S.A. Anal. Profiles Drug Subst., 1980, 9, 207-243; Martindale. The Extra Pharmacopoeia, 28th/29th Ed., Pharmaceutical Press, London, 1984/1989, pp. 5801-5804.
13. Robinson, J.A. and Ling, H.W. Brit. J. Pharmacol., 1953, 8, 79-82; Fujimoto, Y., Suzuki, Y., Kanaiwa, T., Amiya, T., Hoshi, K., Fujino, S. J. Pharm. Dyn., 1983, 6, 128-135.
14. Robinson, J.A. and Ling, H.W. Brit. J. Pharmacol., 1953, 8, 79-82; Fujimoto, Y., Suzuki, Y., Kanaiwa, T., Amiya, T., Hoshi, K., Fujino, S. J. Pharm. Dyn., 1983, 6, 128-135.
15. Carter, C.A., Gray, E.A., Schneider, T.L., Lovett, C.M, Jr., Scott, L., Messer, A.C., and Richardson, D.P Tetrahedron, 1997, 53, 13557-13566.
16. For a recent review of the chemistry and pharmacology of cardiac glycosides, see: Venkateswara Rao, R. and Vaidyanathan, C.S. J. Indian Inst. Sci., 1991, 71, 329-364.
17. Mühlradt, P. Weiss, E. and Reichstein, T. Ann. Chem., 1965, 655, 253-261; Brimacombe, J.S. and Husain, A. J. Chem. Soc., C, 1961, 16 1503-1506..
18. Mühlradt, P. Weiss, E. and Reichstein, T. Ann. Chem., 1965, 655, 253-261; Brimacombe, J.S. and Husain, A. J. Chem. Soc., C, 1961, 16 1503-1506..
19. Avron, M. Biochim. Biophys. Acta, 1960, 40, 257-272. Specific details for the bioassay will be reported elsewhere.
20. Jacobs, W.A. and Bigelow, N.M. J. Biol. Chem., 1932, 96, 647-658; Reichstein, T. and Reich, H. Ann. Rev. Biochem., 1946, 15, 155-192; Turner, R.B. and Meschino, J.A. J. Am. Chem. Soc., 1958, 80, 4862-4865; Volpp, G. and Tamm, Ch. Helv. Chim. Acta, 1959, 42, 1408-1418; Martindale, E. The Extra Pharmacopoeia, 28th/29th Ed., Pharmaceutical Press, London, 1982/1989, p. 5823.
21. Jacobs, W.A. and Bigelow, N.M. J. Biol. Chem., 1932, 96, 647-658; Reichstein, T. and Reich, H. Ann. Rev. Biochem., 1946, 15, 155-192; Turner, R.B. and Meschino, J.A. J. Am. Chem. Soc., 1958, 80, 4862-4865; Volpp, G. and Tamm, Ch. Helv. Chim. Acta, 1959, 42, 1408-1418; Martindale, E. The Extra Pharmacopoeia, 28th/29th Ed., Pharmaceutical Press, London, 1982/1989, p. 5823.
22. Jacobs, W.A. and Bigelow, N.M. J. Biol. Chem., 1932, 96, 647-658; Reichstein, T. and Reich, H. Ann. Rev. Biochem., 1946, 15, 155-192; Turner, R.B. and Meschino, J.A. J. Am. Chem. Soc., 1958, 80, 4862-4865; Volpp, G. and Tamm, Ch. Helv. Chim. Acta, 1959, 42, 1408-1418; Martindale, E. The Extra Pharmacopoeia, 28th/29th Ed., Pharmaceutical Press, London, 1982/1989, p. 5823.
23. Jacobs, W.A. and Bigelow, N.M. J. Biol. Chem., 1932, 96, 647-658; Reichstein, T. and Reich, H. Ann. Rev. Biochem., 1946, 15, 155-192; Turner, R.B. and Meschino, J.A. J. Am. Chem. Soc., 1958, 80, 4862-4865; Volpp, G. and Tamm, Ch. Helv. Chim. Acta, 1959, 42, 1408-1418; Martindale, E. The Extra Pharmacopoeia, 28th/29th Ed., Pharmaceutical Press, London, 1982/1989, p. 5823.
24. Jacobs, W.A. and Bigelow, N.M. J. Biol. Chem., 1932, 96, 647-658; Reichstein, T. and Reich, H. Ann. Rev. Biochem., 1946, 15, 155-192; Turner, R.B. and Meschino, J.A. J. Am. Chem. Soc., 1958, 80, 4862-4865; Volpp, G. and Tamm, Ch. Helv. Chim. Acta, 1959, 42, 1408-1418; Martindale, E. The Extra Pharmacopoeia, 28th/29th Ed., Pharmaceutical Press, London, 1982/1989, p. 5823.
25. Verpoorte, R. and Baerheim Svendsen, A. Pharm. Weekbl., 1976, 111(34), 833-836.
26. The Sigma-Aldrich Library of Rare Chemicals, Cmpd: S96159-0.
27. 13C-NMR data for cardiac glycosides see: Robien, W., Kopp, B., Schabl, D., and Schwarz, H. Progress in NMR Spectroscopy, 1987, 19, 131-178.
28. Dabrowski, J. in Two-Dimensional NMR Spectroscopy. Applications for Chemists and Biochemists, 2nd ed., Croasmun, W.R. and Carlson, R.M., Eds; VCH Publishers, Inc., New York, 1994, Chapter 8, p. 757.
29. Nagata, W., Tamm, Ch. and Reichstein, T. Festschr. Arthur Stoll, 1957, 715-27.
30. Kimura, M., Thoma, M. and Kikuchi, T. Yakugaku Zasshi, 1962, 82, 1320-1323.
31. Smith, C.R., Niece, L.H., Zobel, H.F., and Wolff, I.A. Phytochemistry, 1964, 3, 289-299.
32. Votocek, E. and Rac, F. Chem. Listy, 1932, 25, 465-468.
33. Weiss, E., Schindler, O. and Reichstein, T. Helv. Chim. Acta, 1958, 41, 736-762, Kopp, B., Jurenitsch, J. and Kubelka, W. J. Chromatogr, 1981, 210, 291-299.
34. Weiss, E., Schindler, O. and Reichstein, T. Helv. Chim. Acta, 1958, 41, 736-762, Kopp, B., Jurenitsch, J. and Kubelka, W. J. Chromatogr, 1981, 210, 291-299.
35. Helfenberger, H. and Reichstein, T. Helv. Chim. Acta, 1948, 31, 1470-1482; 2097-2140.
36. Muhr, H. and Reichstein, T. Helv. Chim. Acta, 1955, 38, 499-504.
37. Tamm, Ch. Helv. Chim. Acta, 1949, 32, 163-172.
38. Hauser, D. and Sigg H.P. Helv. Chim. Acta, 1971, 54, 1178-1190.
39. Kaufmann, H. Helv. Chim. Acta, 1965, 48, 83-93.
40. Euw, J.v. and Reichstein, T. Helv. Chim. Acta, 1950, 33, 485-502.
41. Khare, M.P., Schindler, O. and Reichstein, T. Helv. Chim. Acta, 1962, 45, 1547-1551.
42. Tittel, G., Habermeier, H., Wagner, H. Planta med., 1982, 45, 207-215.
43. "Gradient shape" refers to the rate of change of the solvent composition in a given program step. Thus, a linear gradient (i.e. 1.0) varies linearly with time; a negative gradient (i.e. -9.0) involves a solvent program that changes very quickly initially but then changes slowly towards the end of that program step; a positive gradient (i.e. > 1.0) is the opposite of a negative gradient.