Carbon-13 Assignments and Revision of the Stereostructures of the Cadinanes 2-Hydroxy-8α-angeloyloxycalamenene and 2-Hydroxy-8α-hydroxycalamenene

Spectroscopy Letters

Volumn 29, Issue 5, 1996, Pages 799-818

  Rugutt, Joseph K ^a   Fischer, Nikolaus H ^a   Nauman, Marcus A ^a   Schmidt, Thomas J ^a   Berner, Dana K ^a,b  

^a LOUISIANA STATE UNIVERSITY   (United States)

^b INTERNATIONAL INSTITUTE OF TROPICAL AGRICULTURE   (Nigeria)

Author keywords

2 hydroxy 8 angeloyloxycalamenene; 2 hydroxy 8 hydroxycalamenene; 13C nuclear magnetic resonance spectroscopy; 1H nuclear magnetic resonance spectroscopy; Cadinanes; COLOC; COSY; DEPT; HETCOR; Heterotheca subaxillaris; NOESY

Indexed keywords

EID: 0013337090     PISSN: 00387010     EISSN: None     Source Type: Journal    
DOI: 10.1080/00387019608001611     Document Type: Article

References (17)

1. Lincoln, D. E. and Lawrence, B. M. The volatile constituents of camphorweed, Heterotheca subaxillaris. Phytochemistry, 1984, 23, 933-934.
2. Kalsi, P. S. and Talwar, K. K. A dramatic effect of stereochemistry on the plant growth activity of the cadinane group of terpenoids. Phytochemistry, 1981, 20, 511-513.
3. Borg-Karlson, A-K. and Norin, T. Configurations and conformations of torreyol (δ-cadinol), α-cadinol, T-muurolol and T-cadinol. Tetrahedron, 1981, 37, 425-430.
4. Bordoloi, M., Shukla, V. S., Nath, S. C. and Sharma, R. P. Naturally occurring cadinenes. Review article number 45. Phytochemistry, 1989, 28, 2007-2037.
5. Vlahov, R., Holub, M. and Herout, V. The structure of two hydrocarbons of cadalene type isolated from Mentha piperita oil of Bulgarian origin. Collect. Czech. Chem. Commun., 1967, 32, 823-829.
6. Bax, A., Aszalos, A., Dinya, Z. and Sudo, K. Structure elucidation of the antibiotic desertomycin through the use of new two-dimensional NMR techniques. J. Am. Chem. Soc., 1986, 108, 8056-8063.
7. Doddrell, D. M. Pegg, D. T. and Bendall, M. R. Distortional enhancement of NMR signals by polarization transfer. J. Magn. Resort., 1982, 48, 323-327.
8. Derome, A. E. The use of N.M.R. spectroscopy in the structure determination of natural products: Two-dimensional methods, Nat. Prod. Rep., 1989, 6, 111-141.
9. 13C- and proton-NMR. J. Nat. Prod., 1984, 47, 226-259.
10. Bax, A. and Morris, G. A. An improved method for heteronuclear chemical shift correlation by two-dimensional NMR. J. Magn. Reson., 1981, 42, 501-505.
11. Davila-Huerta, G., Hamada, H., Davis, G. D., Stipanovic, R. D., Adams, C. M. and Essenberg, M. Cadinane-type sesquiterpenes induced in Gossypium cotyledons by bacterial inoculation. Phytochemistry, 1995, 39, 531-536.
12. Kessler, H., Griesinger, C., Zarbrock, J. and Loosli, H. R. Assignment of carbonyl carbons and sequence analysis in peptides by heteronuclear shift correlation via small couplings constants with broad band decoupling in ti (COLOC). J. Magn. Reson., 1984, 57, 331-336.
13. Bohlmann, F. and Zdero, C. Neue cadinan-derivate aus Heterotheca subaxillaris. Phytochemistry, 1979, 18, 1185-1187.
14. Aue, W. P., Bartholdi, E. and Ernst, R. R. Two-dimensional spectroscopy. Application to nuclear magnetic resonance. J. Chem. Phys., 1976, 64, 2229-2246.
15. Silverstein, R. M.; Basler, G. C. and Morrill, T. C. Spectrometric Identification of Organic Compounds, 5th Edn, John Wiley & Sons Inc., New York, 1991, pp. 227-248.
16. Fischer, N. H. Sesquiterpenoid Lactones. "Methods in Plant Biochemistry". Ed. by B. V. Charlwood and D. V. Banthorpe, Academic Press, London, 1991, vol. 7, Chapter 5, pp. 187-211.
17. Pelletier, S. W., Chokshi, H. P. and Desai, H. K. Separation of diterpenoid alkaloid mixtures using vacuum liquid chromatography. J. Nat. Prod., 1986, 49, 892-900.