Complete 1H and 13C NMR spectral assignment of δ-cadinene, a bicyclic sesquiterpene hydrocarbon

Magnetic Resonance in Chemistry

Volumn 34, Issue 2, 1996, Pages 156-161

  Davis, G D ^a   Essenberg, M ^a   Berlin, K D ^a   Faure, R ^b   Gaydou, E M ^c  

^a OKLAHOMA STATE UNIVERSITY   (United States)

^b CNRS   (France)

^c AIX MARSEILLE UNIVERSITY   (France)

Author keywords

13C NMR; 1H NMR; Cade oil; Cotton disease resistance; NMR; Sesquiterpene hydrocarbon; Ylang ylang essential oil; cadinene

Indexed keywords

HYDROCARBONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

13C NMR; 1H NMR; CADE OIL; CADINENE; COTTON DISEASE RESISTANCE; DISEASE RESISTANCE; SESQUITERPENE HYDROCARBONS; SPECTRAL ASSIGNMENTS; YLANG-YLANG ESSENTIAL OIL; Δ-CADINENE;

ESSENTIAL OILS;

EID: 0001252082     PISSN: 07491581     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-458X(199602)34:2<156::AID-OMR859>3.0.CO;2-2     Document Type: Article

References (49)

1. J. D. Connolly and R. A. Hill, Dictionary of Terpenoids, Vol. 1, p. 431. Chapman and Hall, London (1991).
2. M. Bordoloi, V. S. Shukla, S. C. Nath and R. P. Sharma, Phytochemistry 28, 2007 (1989).
3. J.-C. Chalchat, R.-P. Garry, A. Michet and L. Peyron, J. Essent. Oil Res. 2, 231 (1990).
4. A. A. Bell, in Cotton Physiology, edited by J. R. Mauney and J. McD. Stewart, pp. 597-621. The Cotton Foundation, Memphis, TN (1986).
5. P. A. Hedin, A. C. Thompson and R. C. Gueldner, J. Agric. Food Chem. 23, 698 (1975).
6. D. W. Connell, R. P. Hildebrand and M. D. Sutherland, Tetrahedron Lett. 519 (1968).
7. C. M. Beechan, C. Djerassi and H. Eggert, Tetrahedron 34, 2503 (1978).
8. N. H. Andersen, Y. Ohta, C.-B. Liu, C. M. Kramer, K. Allison and S. Huneck, Phytochemistry 16, 1727 (1977).
9. J. P. Minyard, J. H. Tumlinson, A. C. Thompson and P. A. Hedin, J. Agric. Food Chem. 14, 332 (1966).
10. R. G. Buttery, R. E. Lundin and L. Ling, J. Agric. Food Chem. 15, 58 (1967).
11. N. H. Andersen and D. D. Syrdal, Phytochemistry 9, 1325 (1970).
12. R. Randriamiharisoa, E. M. Gaydou, R. Faure and J. P. Bianchini, Magn. Reson. Chem. 24, 275 (1986).
13. A. F. Barrero, J. F. Sánchez, J. E. Oltra, J. Altarejos, N. Ferrol and A. Barrágan, Phytochemistry 30, 1551 (1991).
14. M. L. Oyarzún and J. A. Garbarino, Phytochemistry 27, 1121 (1988).
15. V. Formacek and K.-H. Kubeczka, Essential Oils Analysis by Capillary Gas Chromatography and Carbon-13 NMR Spectroscopy, p. 321. Wiley, Chichester (1982).
16. S. R. Milne and G. W. A. Heller (Eds), EPA/NIH Mass Spectral Data Base, Suppl. 1, p. 4441. US Government Printing Office, Washington, DC (1980).
17. Y. Ohta, K. Ohara and Y. Hirose, Tetrahedron Lett. 4181 (1968).
18. R. Vlahov, M. Holub and V. Herout, Collect. Czech. Chem. Commun. 32, 822 (1967).
19. J. D. Connolly and R. A. Hill, Dictionary of Terpenoids, Vol. 1, p. 430. Chapman and Hall, London (1991).
20. E. M. Gaydou, R. Randriamiharisoa and J.-P. Bianchini, J. Agric. Food Chem. 34, 481 (1986).
21. G. Davis and M. Essenberg, unpublished results.
22. M. Essenberg, P. B. Grover, Jr and E. C. Cover, Phytochemistry, 29, 3107 (1990).
23. H. C. Krebs, J. V. Rakotoarimanga and G. G. Habermehl, Magn. Reson. Chem. 28, 124 (1990).
24. G. W. Elzen, H. J. Williams and S. B. Vinson, J. Chem. Ecol. 10, 1251 (1984).
25. B. A. Nagasampagi, L. Yankov and S. Dev, Tetrahedron Lett. 1913 (1968).
26. R. Croteau and D. E. Cane, in Methods Enzymol. 110, 383 (1985).
27. D. E. Cane, Chem. Rev. 90, 1089 (1990)
28. P. Claeson, R. Andersson and G. Samuelsson, Planta Med. 57, 352 (1991).
29. J. A. Wenninger, R. L. Yates and M. Dolinsky, J. Assoc. Off. Anal. Chem. 50, 1313 (1967).
30. S. Hosozawa, I. Miura, M. Kido, O. Munoz and M. Castillo, Phytochemistry 24, 2317 (1985).
31. F. Bohlmann, C. Zdero, H. Robinson and R. M. King, Phytochemistry 18, 1675 (1979).
32. F. Bohlmann and C. Zdero, Phytochemistry 18, 1185 (1979).
33. W. F. Reynolds, R. G. Enriquez, L. I. Escobar and X. Lozoya, Can. J. Chem. 62, 2421 (1984).
34. C. Kruk, H. C. Cox and J. W. de Leeuw, Magn. Reson. Chem. 26, 228 (1988).
35. R. Faure, E. J. Vincent, E. M. Gaydou and O. Rakotonirainy, Magn. Reson. Chem. 24, 883 (1986).
36. E. M. Gaydou, R. Faure, J.-P. Bianchini, G. Lamaty, O. Rakotonirainy and R. Randriamiharisoa, J. Agric. Food Chem. 37, 1032 (1989).
37. H. Hamada and M. Essenberg, unpublished results.
38. N. Platzer, N. Goasdoue and D. Davoust, Magn. Reson. Chem. 25, 311 (1987).
39. N. H. Fischer, D. Vargas and M. Memelaou, in Recent Advances in Photochemistry, edited by N. H. Fischer, M. B. Isman and H. A. Stafford, Vol. 25, p. 271. Plenum Press, New York (1991).
40. J. F. Sanz, V. García-Lliso, J. A. Marco and J. Vallés-Xirau, Phytochemistry 30, 4167 (1991).
41. J. F. Sanz and J. A. Marco, Phytochemistry 30, 2788 (1991).
42. J. Jakupovic, C. Zdero, M. Grenz, F. Tsichritzis, L. Lehmann, S. M. Hashemi-Nejad and F. Bohlmann, Phytochemistry 28, 1119 (1989).
43. L. R. Rodriguez-Avial Franke, H. Wolf and V. Wray, Tetrahedron 40, 3491 (1984).
44. D. E. Cane, B. J. Rawlings and C-C. Yang, J. Antibiot. 40, 1331 (1987).
45. F. Fringuelli, F. Pizzo, A. Taticchi, V. F. Ferreira, E. L. Michelotti, B. Porter and E. Wenkert, J. Org. Chem. 50, 890 (1985).
46. Personal communication from Destilerias Muñoz Gálvez SA (Murcia, Spain), distiller and exporter of cade oil (message conveyed by John D. Walsh Co., Glen Rock, NJ, USA, importer of cade oil).
47. M. Jacobson, E. C. Uebel, W. R. Lusby and R. M. Waters, J. Agric. Food Chem. 35, 798 (1987)
48. J. Beyer, H. Becker and R. Martin, J. Liq. Chromatgr. 9, 2433 (1986).
49. B. C. Clark, Jr, T. S Chamblee and G. A. Iacobucci, J Agric. Food Chem. 35, 514 (1987).