X-ray, 1H/13C 2D and 3D NMR studies of the structures of davallene and adipedatol, two triterpenes isolated from American Adiantum capillus-veneris

Polish Journal of Chemistry

Volumn 78, Issue 3, 2004, Pages 389-408

  Jankowski, C K ^a   Aumelas, A ^a   Thuery P ^b   Reyes Chilpa, R ^c   Jimenez Estrada, M ^c   Barrios, H ^c   Diaz, E ^c  

^a UNIVERSITÉ DE MONCTON   (Canada)

^b CEA SACLAY   (France)

^c UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

3D NMR of triterpenes; NMR 1D and 2D of triterpenes; Triterpenes from Adiantum; X rays 2D

Indexed keywords

ADIANTUM CAPILLUS VENERIS EXTRACT; ADIPEDATOL; DAVALLENE; HERBACEOUS AGENT; PLANT EXTRACT; TRITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ADIANTUM; ADIANTUM CAPILLUS VENERIS; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; DRUG ISOLATION; DRUG STRUCTURE; MEDICINAL PLANT; NONHUMAN; PLANT ROOT; PROTON NUCLEAR MAGNETIC RESONANCE; WESTERN HEMISPHERE; X RAY DIFFRACTION;

EID: 1642542515     PISSN: 01375083     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (45)

1. (a) Mickel J.T. and Beitel J.M., Pteridophites. Flora de Oaxaca, México. Mem. New York Bot. Garden, 1988, 46, 1-568;
2. (b) Moran R.C. and Riba R., Psilotaceae a Salviniaceae. Flora Mesoamericana. G. Davidse, M. Souza and S. Knapp, (Eds). Universidad Nacional Autonoma de México, 1, 470 (1995).
3. Nakane T., Maeda Y., Ebihara H., Arai Y., Masuda K., Takano A., Ageta H., Shiojima K., Cai S.Q. and Abdel-Halim O.B., Chem. Pharm. Bull., 50, 1273 (2002).
4. Nakane T., Arai Y., Masuda K., Ishizaki Y., Ageta H. and Shiojima K., Chem. Pharm. Bull., 47, 543 (1999); 42, 39 (1994); 41, 268 (1993).
5. Nakane T., Arai Y., Masuda K., Ishizaki Y., Ageta H. and Shiojima K., Chem. Pharm. Bull., 47, 543 (1999); 42, 39 (1994); 41, 268 (1993).
6. Nakane T., Arai Y., Masuda K., Ishizaki Y., Ageta H. and Shiojima K., Chem. Pharm. Bull., 47, 543 (1999); 42, 39 (1994); 41, 268 (1993).
7. Ageta H. and Iwata K., Tetrahedron Lett., 48, 6069 (1966).
8. Ageta H. and Shiojima K., J. Chem. Soc., Chem. Commun., 1372 (1968).
9. Argueta-Villamar A., Cano L.M. and Rodarte M.E. (Eds). Atlas de las Plantas de la Medicina Tradicional Mexicana. Instituto Nacional Indigenista. México., 1, 442 (1994).
10. Sengupta P., Dutt C.P., Sen M., Das K., Miyahara K. and Kawasaki T., Indian J. Chem., 228, 883 (1983).
11. (a) Derome A., in Modern Techniques for Chemistry Research, Pergamon Press. N.Y. 1987, p. 240;
12. (b) Freeman R., Spin Choreography. Basic Steps in High Resolution in NMR Spectrum. Oxford, 1997.
13. Hull W.E., in 2D NMR Spectroscopy for Chemist and Biochemist. Chapter 2, W.R. Croasmum, R.M.K. Carlson (Eds.), VCH Publishers, N.Y. 1987.
14. Martin G.E. and Sektzer A.S., Two Dimensional NMR Methods for Establishing Molecular Connectivity, VCH Publishers, N.Y. 1988, p. 219.
15. Bodenhausen G. and Reuben D.J., Chem. Phys. Lett., 69, 185 (1980).
16. (a) Wider G. and Wuthrich K., J. Magn. Reson., 102, 239 (1993);
17. (b) Muller L., J. Am. Chem. Soc., 101, 4481 (1979);
18. (c) Marek R., Kralik L. and Skelenar V., Tetrahedron Lett., 38, 665 (1997);
19. (d) Bax A., Griffey R.H. and Hawkins B.L., J. Magn. Reson., 55, 301 (1983);
20. (e) Bax A., Ikura M., Kay L., Torchia D.A. and Tschudin R., J. Magn. Reson., 86, 304 (1990).
21. (a) Bax A. and Summers M.F., J. Am. Chem. Soc., 108, 2093 (1986);
22. (b) Pearson G.A., J. Magn. Reson., 64, 487 (1985).
23. (a) Cavanagh J., Fairbrother W., Palmer III A. and Skelton N., in Protein NMR Spectroscopy. Principles and Practice. Academic Press 1996, USA Chapter 4, p. 637;
24. ( b) Griesinger C., Sorensen O.W. and Ernst R.R., J. Magn. Reson., 90, 433 (1989).
25. Lerner L. and Bax A., J. Magn. Reson., 69, 375 (1986).
26. Wehrli F.W. and Nishida T., The Use of Carbon-13 NMR Spectroscopy in Natural Products Chemistry. Progress in the Chemistry of Organic Natural Products., 1979 36, 1-216. Springer-Verlag, N.Y.
27. More terpene structure assignments via high-resolution NMR: (a) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (b) Belsner K., Büchele B., Werz U., Syrovets T. and Simmet T., Magn. Res. Chem., 41, 115 (2003); (c) Bouget-Bonnet S., Rochd M., Mutzenhardt P. and Henry M., Magn. Res. Chem., 40, 618 (2002); (d) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (e) Reynolds W.F., McLean S., Burke S.J. and Jacobs H., Magn. Res. Chem., 39, 757 (2001); (f) Soliman H.S.M., Simon A., Toth G. and Duddeck H., Magn. Res. Chem., 39, 567 (2001); (g) Salazar G.C.M., Silva G.D.F., Duarte L.P., Vieira Filho S.A. and Lula I.S., Magn. Res. Chem., 38, 977 (2000); (h) Joshi B.S., Singh K.L. and Roy R., Magn. Res. Chem., 37, 295 (1999); (i) Sahu N.P., Koike K., Jia Z., Mondal N.B., Achari B. and Nikaido T., Magn. Res. Chem.,, 37, 152 (1999); (j) Elgamal M.H.A., Soliman H.S.M., Toth G., Halasz J. and Duddeck H., Magn. Res. Chem., 34, 697 (1996); (k) Ascenso J.R. and Ferreira M.J.U., Magn. Res. Chem., 35, 643 (1997); (l) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 35, 637 (1997); (m) Toth G., Simon A., Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T. and Horvath G., Magn. Res. Chem., 36, 376 (1998); (n) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 36, 151 (1998).
28. More terpene structure assignments via high-resolution NMR: (a) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (b) Belsner K., Büchele B., Werz U., Syrovets T. and Simmet T., Magn. Res. Chem., 41, 115 (2003); (c) Bouget-Bonnet S., Rochd M., Mutzenhardt P. and Henry M., Magn. Res. Chem., 40, 618 (2002); (d) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (e) Reynolds W.F., McLean S., Burke S.J. and Jacobs H., Magn. Res. Chem., 39, 757 (2001); (f) Soliman H.S.M., Simon A., Toth G. and Duddeck H., Magn. Res. Chem., 39, 567 (2001); (g) Salazar G.C.M., Silva G.D.F., Duarte L.P., Vieira Filho S.A. and Lula I.S., Magn. Res. Chem., 38, 977 (2000); (h) Joshi B.S., Singh K.L. and Roy R., Magn. Res. Chem., 37, 295 (1999); (i) Sahu N.P., Koike K., Jia Z., Mondal N.B., Achari B. and Nikaido T., Magn. Res. Chem.,, 37, 152 (1999); (j) Elgamal M.H.A., Soliman H.S.M., Toth G., Halasz J. and Duddeck H., Magn. Res. Chem., 34, 697 (1996); (k) Ascenso J.R. and Ferreira M.J.U., Magn. Res. Chem., 35, 643 (1997); (l) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 35, 637 (1997); (m) Toth G., Simon A., Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T. and Horvath G., Magn. Res. Chem., 36, 376 (1998); (n) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 36, 151 (1998).
29. More terpene structure assignments via high-resolution NMR: (a) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (b) Belsner K., Büchele B., Werz U., Syrovets T. and Simmet T., Magn. Res. Chem., 41, 115 (2003); (c) Bouget-Bonnet S., Rochd M., Mutzenhardt P. and Henry M., Magn. Res. Chem., 40, 618 (2002); (d) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (e) Reynolds W.F., McLean S., Burke S.J. and Jacobs H., Magn. Res. Chem., 39, 757 (2001); (f) Soliman H.S.M., Simon A., Toth G. and Duddeck H., Magn. Res. Chem., 39, 567 (2001); (g) Salazar G.C.M., Silva G.D.F., Duarte L.P., Vieira Filho S.A. and Lula I.S., Magn. Res. Chem., 38, 977 (2000); (h) Joshi B.S., Singh K.L. and Roy R., Magn. Res. Chem., 37, 295 (1999); (i) Sahu N.P., Koike K., Jia Z., Mondal N.B., Achari B. and Nikaido T., Magn. Res. Chem.,, 37, 152 (1999); (j) Elgamal M.H.A., Soliman H.S.M., Toth G., Halasz J. and Duddeck H., Magn. Res. Chem., 34, 697 (1996); (k) Ascenso J.R. and Ferreira M.J.U., Magn. Res. Chem., 35, 643 (1997); (l) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 35, 637 (1997); (m) Toth G., Simon A., Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T. and Horvath G., Magn. Res. Chem., 36, 376 (1998); (n) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 36, 151 (1998).
30. More terpene structure assignments via high-resolution NMR: (a) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (b) Belsner K., Büchele B., Werz U., Syrovets T. and Simmet T., Magn. Res. Chem., 41, 115 (2003); (c) Bouget-Bonnet S., Rochd M., Mutzenhardt P. and Henry M., Magn. Res. Chem., 40, 618 (2002); (d) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (e) Reynolds W.F., McLean S., Burke S.J. and Jacobs H., Magn. Res. Chem., 39, 757 (2001); (f) Soliman H.S.M., Simon A., Toth G. and Duddeck H., Magn. Res. Chem., 39, 567 (2001); (g) Salazar G.C.M., Silva G.D.F., Duarte L.P., Vieira Filho S.A. and Lula I.S., Magn. Res. Chem., 38, 977 (2000); (h) Joshi B.S., Singh K.L. and Roy R., Magn. Res. Chem., 37, 295 (1999); (i) Sahu N.P., Koike K., Jia Z., Mondal N.B., Achari B. and Nikaido T., Magn. Res. Chem.,, 37, 152 (1999); (j) Elgamal M.H.A., Soliman H.S.M., Toth G., Halasz J. and Duddeck H., Magn. Res. Chem., 34, 697 (1996); (k) Ascenso J.R. and Ferreira M.J.U., Magn. Res. Chem., 35, 643 (1997); (l) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 35, 637 (1997); (m) Toth G., Simon A., Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T. and Horvath G., Magn. Res. Chem., 36, 376 (1998); (n) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 36, 151 (1998).
31. More terpene structure assignments via high-resolution NMR: (a) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (b) Belsner K., Büchele B., Werz U., Syrovets T. and Simmet T., Magn. Res. Chem., 41, 115 (2003); (c) Bouget-Bonnet S., Rochd M., Mutzenhardt P. and Henry M., Magn. Res. Chem., 40, 618 (2002); (d) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (e) Reynolds W.F., McLean S., Burke S.J. and Jacobs H., Magn. Res. Chem., 39, 757 (2001); (f) Soliman H.S.M., Simon A., Toth G. and Duddeck H., Magn. Res. Chem., 39, 567 (2001); (g) Salazar G.C.M., Silva G.D.F., Duarte L.P., Vieira Filho S.A. and Lula I.S., Magn. Res. Chem., 38, 977 (2000); (h) Joshi B.S., Singh K.L. and Roy R., Magn. Res. Chem., 37, 295 (1999); (i) Sahu N.P., Koike K., Jia Z., Mondal N.B., Achari B. and Nikaido T., Magn. Res. Chem.,, 37, 152 (1999); (j) Elgamal M.H.A., Soliman H.S.M., Toth G., Halasz J. and Duddeck H., Magn. Res. Chem., 34, 697 (1996); (k) Ascenso J.R. and Ferreira M.J.U., Magn. Res. Chem., 35, 643 (1997); (l) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 35, 637 (1997); (m) Toth G., Simon A., Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T. and Horvath G., Magn. Res. Chem., 36, 376 (1998); (n) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 36, 151 (1998).
32. More terpene structure assignments via high-resolution NMR: (a) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (b) Belsner K., Büchele B., Werz U., Syrovets T. and Simmet T., Magn. Res. Chem., 41, 115 (2003); (c) Bouget-Bonnet S., Rochd M., Mutzenhardt P. and Henry M., Magn. Res. Chem., 40, 618 (2002); (d) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (e) Reynolds W.F., McLean S., Burke S.J. and Jacobs H., Magn. Res. Chem., 39, 757 (2001); (f) Soliman H.S.M., Simon A., Toth G. and Duddeck H., Magn. Res. Chem., 39, 567 (2001); (g) Salazar G.C.M., Silva G.D.F., Duarte L.P., Vieira Filho S.A. and Lula I.S., Magn. Res. Chem., 38, 977 (2000); (h) Joshi B.S., Singh K.L. and Roy R., Magn. Res. Chem., 37, 295 (1999); (i) Sahu N.P., Koike K., Jia Z., Mondal N.B., Achari B. and Nikaido T., Magn. Res. Chem.,, 37, 152 (1999); (j) Elgamal M.H.A., Soliman H.S.M., Toth G., Halasz J. and Duddeck H., Magn. Res. Chem., 34, 697 (1996); (k) Ascenso J.R. and Ferreira M.J.U., Magn. Res. Chem., 35, 643 (1997); (l) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 35, 637 (1997); (m) Toth G., Simon A., Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T. and Horvath G., Magn. Res. Chem., 36, 376 (1998); (n) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 36, 151 (1998).
33. More terpene structure assignments via high-resolution NMR: (a) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (b) Belsner K., Büchele B., Werz U., Syrovets T. and Simmet T., Magn. Res. Chem., 41, 115 (2003); (c) Bouget-Bonnet S., Rochd M., Mutzenhardt P. and Henry M., Magn. Res. Chem., 40, 618 (2002); (d) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (e) Reynolds W.F., McLean S., Burke S.J. and Jacobs H., Magn. Res. Chem., 39, 757 (2001); (f) Soliman H.S.M., Simon A., Toth G. and Duddeck H., Magn. Res. Chem., 39, 567 (2001); (g) Salazar G.C.M., Silva G.D.F., Duarte L.P., Vieira Filho S.A. and Lula I.S., Magn. Res. Chem., 38, 977 (2000); (h) Joshi B.S., Singh K.L. and Roy R., Magn. Res. Chem., 37, 295 (1999); (i) Sahu N.P., Koike K., Jia Z., Mondal N.B., Achari B. and Nikaido T., Magn. Res. Chem.,, 37, 152 (1999); (j) Elgamal M.H.A., Soliman H.S.M., Toth G., Halasz J. and Duddeck H., Magn. Res. Chem., 34, 697 (1996); (k) Ascenso J.R. and Ferreira M.J.U., Magn. Res. Chem., 35, 643 (1997); (l) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 35, 637 (1997); (m) Toth G., Simon A., Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T. and Horvath G., Magn. Res. Chem., 36, 376 (1998); (n) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 36, 151 (1998).
34. More terpene structure assignments via high-resolution NMR: (a) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (b) Belsner K., Büchele B., Werz U., Syrovets T. and Simmet T., Magn. Res. Chem., 41, 115 (2003); (c) Bouget-Bonnet S., Rochd M., Mutzenhardt P. and Henry M., Magn. Res. Chem., 40, 618 (2002); (d) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (e) Reynolds W.F., McLean S., Burke S.J. and Jacobs H., Magn. Res. Chem., 39, 757 (2001); (f) Soliman H.S.M., Simon A., Toth G. and Duddeck H., Magn. Res. Chem., 39, 567 (2001); (g) Salazar G.C.M., Silva G.D.F., Duarte L.P., Vieira Filho S.A. and Lula I.S., Magn. Res. Chem., 38, 977 (2000); (h) Joshi B.S., Singh K.L. and Roy R., Magn. Res. Chem., 37, 295 (1999); (i) Sahu N.P., Koike K., Jia Z., Mondal N.B., Achari B. and Nikaido T., Magn. Res. Chem.,, 37, 152 (1999); (j) Elgamal M.H.A., Soliman H.S.M., Toth G., Halasz J. and Duddeck H., Magn. Res. Chem., 34, 697 (1996); (k) Ascenso J.R. and Ferreira M.J.U., Magn. Res. Chem., 35, 643 (1997); (l) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 35, 637 (1997); (m) Toth G., Simon A., Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T. and Horvath G., Magn. Res. Chem., 36, 376 (1998); (n) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 36, 151 (1998).
35. More terpene structure assignments via high-resolution NMR: (a) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (b) Belsner K., Büchele B., Werz U., Syrovets T. and Simmet T., Magn. Res. Chem., 41, 115 (2003); (c) Bouget-Bonnet S., Rochd M., Mutzenhardt P. and Henry M., Magn. Res. Chem., 40, 618 (2002); (d) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (e) Reynolds W.F., McLean S., Burke S.J. and Jacobs H., Magn. Res. Chem., 39, 757 (2001); (f) Soliman H.S.M., Simon A., Toth G. and Duddeck H., Magn. Res. Chem., 39, 567 (2001); (g) Salazar G.C.M., Silva G.D.F., Duarte L.P., Vieira Filho S.A. and Lula I.S., Magn. Res. Chem., 38, 977 (2000); (h) Joshi B.S., Singh K.L. and Roy R., Magn. Res. Chem., 37, 295 (1999); (i) Sahu N.P., Koike K., Jia Z., Mondal N.B., Achari B. and Nikaido T., Magn. Res. Chem.,, 37, 152 (1999); (j) Elgamal M.H.A., Soliman H.S.M., Toth G., Halasz J. and Duddeck H., Magn. Res. Chem., 34, 697 (1996); (k) Ascenso J.R. and Ferreira M.J.U., Magn. Res. Chem., 35, 643 (1997); (l) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 35, 637 (1997); (m) Toth G., Simon A., Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T. and Horvath G., Magn. Res. Chem., 36, 376 (1998); (n) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 36, 151 (1998).
36. More terpene structure assignments via high-resolution NMR: (a) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (b) Belsner K., Büchele B., Werz U., Syrovets T. and Simmet T., Magn. Res. Chem., 41, 115 (2003); (c) Bouget-Bonnet S., Rochd M., Mutzenhardt P. and Henry M., Magn. Res. Chem., 40, 618 (2002); (d) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (e) Reynolds W.F., McLean S., Burke S.J. and Jacobs H., Magn. Res. Chem., 39, 757 (2001); (f) Soliman H.S.M., Simon A., Toth G. and Duddeck H., Magn. Res. Chem., 39, 567 (2001); (g) Salazar G.C.M., Silva G.D.F., Duarte L.P., Vieira Filho S.A. and Lula I.S., Magn. Res. Chem., 38, 977 (2000); (h) Joshi B.S., Singh K.L. and Roy R., Magn. Res. Chem., 37, 295 (1999); (i) Sahu N.P., Koike K., Jia Z., Mondal N.B., Achari B. and Nikaido T., Magn. Res. Chem.,, 37, 152 (1999); (j) Elgamal M.H.A., Soliman H.S.M., Toth G., Halasz J. and Duddeck H., Magn. Res. Chem., 34, 697 (1996); (k) Ascenso J.R. and Ferreira M.J.U., Magn. Res. Chem., 35, 643 (1997); (l) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 35, 637 (1997); (m) Toth G., Simon A., Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T. and Horvath G., Magn. Res. Chem., 36, 376 (1998); (n) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 36, 151 (1998).
37. More terpene structure assignments via high-resolution NMR: (a) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (b) Belsner K., Büchele B., Werz U., Syrovets T. and Simmet T., Magn. Res. Chem., 41, 115 (2003); (c) Bouget-Bonnet S., Rochd M., Mutzenhardt P. and Henry M., Magn. Res. Chem., 40, 618 (2002); (d) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (e) Reynolds W.F., McLean S., Burke S.J. and Jacobs H., Magn. Res. Chem., 39, 757 (2001); (f) Soliman H.S.M., Simon A., Toth G. and Duddeck H., Magn. Res. Chem., 39, 567 (2001); (g) Salazar G.C.M., Silva G.D.F., Duarte L.P., Vieira Filho S.A. and Lula I.S., Magn. Res. Chem., 38, 977 (2000); (h) Joshi B.S., Singh K.L. and Roy R., Magn. Res. Chem., 37, 295 (1999); (i) Sahu N.P., Koike K., Jia Z., Mondal N.B., Achari B. and Nikaido T., Magn. Res. Chem.,, 37, 152 (1999); (j) Elgamal M.H.A., Soliman H.S.M., Toth G., Halasz J. and Duddeck H., Magn. Res. Chem., 34, 697 (1996); (k) Ascenso J.R. and Ferreira M.J.U., Magn. Res. Chem., 35, 643 (1997); (l) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 35, 637 (1997); (m) Toth G., Simon A., Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T. and Horvath G., Magn. Res. Chem., 36, 376 (1998); (n) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 36, 151 (1998).
38. More terpene structure assignments via high-resolution NMR: (a) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (b) Belsner K., Büchele B., Werz U., Syrovets T. and Simmet T., Magn. Res. Chem., 41, 115 (2003); (c) Bouget-Bonnet S., Rochd M., Mutzenhardt P. and Henry M., Magn. Res. Chem., 40, 618 (2002); (d) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (e) Reynolds W.F., McLean S., Burke S.J. and Jacobs H., Magn. Res. Chem., 39, 757 (2001); (f) Soliman H.S.M., Simon A., Toth G. and Duddeck H., Magn. Res. Chem., 39, 567 (2001); (g) Salazar G.C.M., Silva G.D.F., Duarte L.P., Vieira Filho S.A. and Lula I.S., Magn. Res. Chem., 38, 977 (2000); (h) Joshi B.S., Singh K.L. and Roy R., Magn. Res. Chem., 37, 295 (1999); (i) Sahu N.P., Koike K., Jia Z., Mondal N.B., Achari B. and Nikaido T., Magn. Res. Chem.,, 37, 152 (1999); (j) Elgamal M.H.A., Soliman H.S.M., Toth G., Halasz J. and Duddeck H., Magn. Res. Chem., 34, 697 (1996); (k) Ascenso J.R. and Ferreira M.J.U., Magn. Res. Chem., 35, 643 (1997); (l) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 35, 637 (1997); (m) Toth G., Simon A., Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T. and Horvath G., Magn. Res. Chem., 36, 376 (1998); (n) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 36, 151 (1998).
39. More terpene structure assignments via high-resolution NMR: (a) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (b) Belsner K., Büchele B., Werz U., Syrovets T. and Simmet T., Magn. Res. Chem., 41, 115 (2003); (c) Bouget-Bonnet S., Rochd M., Mutzenhardt P. and Henry M., Magn. Res. Chem., 40, 618 (2002); (d) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (e) Reynolds W.F., McLean S., Burke S.J. and Jacobs H., Magn. Res. Chem., 39, 757 (2001); (f) Soliman H.S.M., Simon A., Toth G. and Duddeck H., Magn. Res. Chem., 39, 567 (2001); (g) Salazar G.C.M., Silva G.D.F., Duarte L.P., Vieira Filho S.A. and Lula I.S., Magn. Res. Chem., 38, 977 (2000); (h) Joshi B.S., Singh K.L. and Roy R., Magn. Res. Chem., 37, 295 (1999); (i) Sahu N.P., Koike K., Jia Z., Mondal N.B., Achari B. and Nikaido T., Magn. Res. Chem.,, 37, 152 (1999); (j) Elgamal M.H.A., Soliman H.S.M., Toth G., Halasz J. and Duddeck H., Magn. Res. Chem., 34, 697 (1996); (k) Ascenso J.R. and Ferreira M.J.U., Magn. Res. Chem., 35, 643 (1997); (l) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 35, 637 (1997); (m) Toth G., Simon A., Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T. and Horvath G., Magn. Res. Chem., 36, 376 (1998); (n) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 36, 151 (1998).
40. More terpene structure assignments via high-resolution NMR: (a) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (b) Belsner K., Büchele B., Werz U., Syrovets T. and Simmet T., Magn. Res. Chem., 41, 115 (2003); (c) Bouget-Bonnet S., Rochd M., Mutzenhardt P. and Henry M., Magn. Res. Chem., 40, 618 (2002); (d) Weis R. and Seebache W., Magn. Res. Chem., 40, 455 (2002); (e) Reynolds W.F., McLean S., Burke S.J. and Jacobs H., Magn. Res. Chem., 39, 757 (2001); (f) Soliman H.S.M., Simon A., Toth G. and Duddeck H., Magn. Res. Chem., 39, 567 (2001); (g) Salazar G.C.M., Silva G.D.F., Duarte L.P., Vieira Filho S.A. and Lula I.S., Magn. Res. Chem., 38, 977 (2000); (h) Joshi B.S., Singh K.L. and Roy R., Magn. Res. Chem., 37, 295 (1999); (i) Sahu N.P., Koike K., Jia Z., Mondal N.B., Achari B. and Nikaido T., Magn. Res. Chem.,, 37, 152 (1999); (j) Elgamal M.H.A., Soliman H.S.M., Toth G., Halasz J. and Duddeck H., Magn. Res. Chem., 34, 697 (1996); (k) Ascenso J.R. and Ferreira M.J.U., Magn. Res. Chem., 35, 643 (1997); (l) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 35, 637 (1997); (m) Toth G., Simon A., Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T. and Horvath G., Magn. Res. Chem., 36, 376 (1998); (n) Elgamal M.H.A., Soliman H.S.M., Elmunajjed D.T., Toth G., Simon A. and Duddeck H., Magn. Res. Chem., 36, 151 (1998).
41. Lenti Kit R.T. (Cavadi, Tech., Uppsala, Sweden) compared to nevirapine, a non-nucleoside HIV reverse transcriptase inhibitor.
42. Kappa-CCD software, Nonius BV, Delft, The Netherlands, 1998.
43. Otwinowski Z. and Minor W., Methods Enzymol., 276, 307 (1997).
44. Sheldrick G.M., SHELXS-97 and SHELXL-97, University of Göttingen, Germany, 1997.
45. Sheldrick G.M., SHELXTL, Version 5.1, Bruker AXS Inc., Madison, WI, USA, 1999.