Tertiary alkaloid fraction of Strychnos atlantica: Confirmation of the identity and structures of indole alkaloids by high field nuclear magnetic resonance spectroscopy

Phytochemical Analysis

Volumn 8, Issue 3, 1997, Pages 115-119

  Mukherjee, Rabindranath ^a   Da Silva, Tania M S ^a   Guimarães, João B L ^a   Oliveira, Eduardo De J ^a   Keifer, Paul A ^b   Shoolery, James N ^b  

^a FEDERAL UNIVERSITY OF PARAÍBA   (Brazil)

^b Varian NMR Applications Laboratory   (United States)

Author keywords

Bisnordihydrotoxiferine; Loganiaceae; Longicaudatine; Normacusine B; Nuclear magnetic resonance spectroscopy; Strychnos atlantica

Indexed keywords

ALKALOIDS; METABOLITES; NUCLEAR MAGNETIC RESONANCE; POLYCYCLIC AROMATIC HYDROCARBONS;

BISNORDIHYDROTOXIFERINE; HIGH-FIELD; INDOLE ALKALOIDS; LOGANIACEA; LONGICAUDATINE; NORMACUSINE B; SPECTRAL ASSIGNMENTS; STRYCHNO ATLANTICUM;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ALKALOID; BISUORDIHYDROTOXIFERINE; INDOLE ALKALOID; LONGICAUDATINE; NORMACUSINE; PLANT EXTRACT; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG STRUCTURE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYTOCHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE;

STRYCHNOS ATLANTICA;

EID: 0030958999     PISSN: 09580344     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1565(199705)8:3<115::AID-PCA340>3.0.CO;2-5     Document Type: Article

References (19)

1. Bax, A. and Marion, D. (1988). Improved resolution and sensitivity in proton-detected heteronuclear multiple-bond correlation spectroscopy. J. Magn. Reson. 78, 186-191.
2. Bax, A. and Subramanian, S. (1986). Sensitivity-enhanced two-dimensional heteronuclear shift correlation NMR spectroscopy. J. Magn. Reson. 67, 565-569.
3. Bax, A. and Summers, M. F. (1986). Proton and carbon-13 assignments from sensitivity-enhanced detection of heteronuclear multiple-bond connectivity by 2D multiple quantum NMR. J. Am. Chem. Soc. 108, 2093-2094.
4. Bax, A., Freeman, R. and Morris, G. (1981). Correlation of proton chemical shifts by two-dimensional Fourier transform NMR. J. Magn. Reson. 42, 164-168.
5. Clivio, P., Richard, B., Deverre, J. R., Sevenet, T., Zeches, M. and Le Men-Olivier, L. (1991). Alkaloids from leaves and root bark of Ervatamia hirta. Phytochemistry, 30, 3785-3792.
6. Doddrell, D. M., Pegg, D. T. and Bendall, M. R. (1982). Distortionless enhancement of NMR signals by polarization transfer. J. Magn. Reson. 48, 323-327.
7. Griesinger, C., Otting, G., Wüethrich, K. and Ernst, R. R. (1988). Clean TOCSY four proton spin system identification in macromolecules. J. Am. Chem. Soc. 110, 7870-7872.
8. Keeler, J. (1993). Knowing the unknown. Chem. Brit. 29, 593-595.
9. Krukoff, B. A. (1972). American species of Strychnos. Lloydia 35, 193-271.
10. Ley, S. V., Lovell, H. and Williams, D. J. (1992). Chemistry of insect antifeedants from Azadirachta indica, Part 14. Absolute configuration of azadiractine. J. Chem. Soc. Chem. Commun. 1304-1306.
11. Massiot, G., Zeches, M., Mirand, C., Le Men-Olivier, L., Delaude, C., Baser, K. H. C., Bavovada, R., Bisset, N. G., Hylands, P. J., Strombom, J. and Verpoorte, R. (1983). Occurrence of longicaudatine, A new type of bis-indole base and bisnor-C-alkaloid H in Strychnos Species. J. Org. Chem. 48, 1869-1872.
12. Melo, M. F. F., Santos, C. A. M., Chiappeta, A. A., Mello, J. F. and Mukherjee, R. (1987). Chemistry and pharmacology of a tertiary alkaloid from Strychnos trinervis root bark. J. Ethnopharmacol. 19, 319-325.
13. Mukherjee, R. (1993). Indole alkaloids of Strychnos from the northeast of Brazil. In Traditional Medicine (Mukherjee, B., ed.), pp. 229-234. Oxford and IBH Publishing, New Delhi.
14. Mukherjee, R., Melo, M. F. F., Santos, C. A. M., Guittet, E. and Das, B. C. (1990). Trinervine, a new indole alkaloid from Strychnos trinervis. Heterocycles 31, 1819-1822.
15. Mukherjee, R., Silva, B. A., Das, B. C., Keifer, P. A. and Shoolery, J. N. (1991). Structure and stereochemistry of divaricine, a new bisindole alkaloid from Strychnos divaricans Ducke. Heterocycles 32, 985-990.
16. Mukherjee, R., Das, B. C., Keifer, P. A. and Shoolery, J. N. (1994). Structure and stereochemistry of divarine: Another new bisindole alkaloid from Strychnos divaricans Ducke. Heterocycles 38, 1965-1970.
17. States, D. J., Haberkorn, R. A. and Ruben, D. J. (1982). A two-dimensional nuclear Overhauser experiment with pure absorption phase in four quadrants. J. Magn. Reson. 48, 286-292.
18. 12 through the use of new two-dimensional NMR experiments. J. Am. Chem. Soc. 108, 4285-4294.
19. Verpoorte, R., Hylands, P. J. and Bisset, N. G. (1977). Carbon-13 NMR spectroscopy of some Strychnos alkaloids. Org. Magn. Reson. 9, 567-571.