Detailed 1H and 13C NMR structural assignment and relative stereochemistry determination for three closely related sesquiterpene lactones

Magnetic Resonance in Chemistry

Volumn 46, Issue 6, 2008, Pages 576-581

  Gomes Heleno, Vladimir Constantino ^a,b   De Oliveira, Kleber Thiago ^c   Callegari Lopes, João Luis ^c   Lopes, Norberto Peporine ^c   Ferreira, Antonio Gilberto ^a  

^a UNIVERSIDADE DE FRANCA   (Brazil)

^b FEDERAL UNIVERSITY OF SÃO CARLOS   (Brazil)

^c UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

DPFGSE NOE; Eremantholide C; Furanoheliangolides; J resolved; NMR; Sesquiterpene lactones; Stereochemistry

Indexed keywords

MOLECULAR MECHANICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOSELECTIVITY;

COMPUTATIONAL CALCULATIONS; DPFGSE-NOE; EREMANTHOLIDE C; FURANOHELIANGOLIDES; J-RESOLVED; NMR DATA; NMR SPECTRUM; NMR TECHNIQUES; SESQUITERPENE LACTONES; STRUCTURAL ASSIGNMENTS;

ESTERS;

CARBON; LACTONE; PROTON; SESQUITERPENE;

ARTICLE; CHEMISTRY; COMPARATIVE STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

CARBON ISOTOPES; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; PROTONS; SESQUITERPENES; STEREOISOMERISM;

EID: 44449125249     PISSN: 07491581     EISSN: 1097458X     Source Type: Journal    
DOI: 10.1002/mrc.2220     Document Type: Article

References (18)

1. O. Spring, H. Buschmann, A Chemotaxonomic survey of sesquiterpene lactones in Helianthinae (Compositae), in Compositae: Systematics. Proceedings of the International Compositae Conference, vol. 1 (Eds: D. J. N. Hind, H. J. Beentje), Royal Botanic Gardens: Kew, 1996.
2. R. P. Sood, K. A. Suri, O. P. Suri, K. L. Dhar, C. K. Atal, Phytochemistry 1982, 21, 2125.
3. N. H. Fischer, E. J. Olivier, H. D. Fischer, The biogenesis and chemistry of sesquiterpene lactones, in Progress in the Chemistry of Organic Natural Products, vol. 38 (Eds: W. Herz, H. Griesebach, G. W. Kirky), Springer-Verlag: Viena, 1979.
4. F. C. Seaman, Bot. Rev. 1982, 48, 123.
5. H. Yoshioka, T. J. Mabry, B. N. Timmermann, Sesquiterpene Lactones, Chemistry, N.M.R. and Plant Distribution, University of Tokyo Press: Tokyo, 1973.
6. A. K. Pieman, Biochem. Syst. Ecol. 1986, 14, 255.
7. A. B. de Oliveira, D. A. Saúde, K. S. P. Perry, D. S. Duarte, D. S. Raslan, M. A. D. Boaventura, E. Chiari, Phytother. Res. 1996, 10, 292.
8. H. T. Sakamoto, D. Flausino, E. E. Castellano, C. B. W. Stark, P. J. Gates, N. P. Lopes, J. Nat. Prod. 2003, 66, 693.
9. P. W. Le Quesne, S. B. Levery, M. D. Menachery, T. F. Brennan, R. F. Raffauf, J. Chem. Soc. Perkin Trans. 1 1978, 12, 1572.
10. F. Bohlmann, C. Zdero, R. M. King, H. Robinson, Phytochemistry 1980, 19, 2663.
11. D. A. Saúde, D. S. Raslan, J. D. Souza Filho, A. B. Oliveira, Fitoterapia 1998, 69, 90.
12. W. Vichnewski, A. M. Takahashi, A. M. T. T. Nasi, D. C. R. G. Gonçalves, D. A. Dias, J. N. C. Lopes, V. L. Goedken, A. B. Gutiérrez, W. Herz, Phytochemistry 1989, 28, 1441.
13. V. C. G. Heleno, A. E. M. Crotti, M. G. Constantino, N. P. Lopes, J. L. C. Lopes, Magn. Reson. Chem. 2004, 42, 364.
14. R. Silva, V. C. G. Heleno, S. Albuquerque, J. K. Bastos, M. L. A. Silva, P. M. Donate, G. V. J. Silva, Magn. Reson. Chem. 2004, 42, 985.
15. V. C. G. Heleno, R. Silva, S. Pedersoli, S.Albuquerque, J. K. Bastos, M. L. A. Silva, P. M. Donate, G. V. J. Silva, J. L. C. Lopes, Spectrochim. Acta A 2006, 63, 234.
16. http://artemis.ffclrp.usp.br/NMR.htm, accessed in October 29, 2007.
17. M. G. Constantino, G. V. J. Silva, V. C. G. Heleno, I.A. Borin, I. P. A. Campos, Quim. Nova 2006, 29, 160.
18. PCModel, version 7.0, Serena Software, P.O.Box 3076, Bloomington, IN 474-23076; 1999.