Absolute configuration of tropane alkaloids from Schizanthus species by vibrational circular dichroism

Phytochemistry

Volumn 71, Issue 7, 2010, Pages 810-815

  Reina, Matías ^a   Burgueño Tapia, Eleuterio ^b   Bucio, María A ^c   Joseph Nathan, Pedro ^c  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

^b INSTITUTO POLITÉCNICO NACIONAL   (Mexico)

^c DEPARTAMENTO DE FÍSICA   (Mexico)

Author keywords

3 ,6 Tropanediol alkaloids; Absolute configuration; S. pinnatus; Schizanthus grahamii; Schizanthus species; Solanaceae; Vibrational circular dichroism

Indexed keywords

ALKALOID; TROPANE DERIVATIVE;

ANGIOSPERM; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ALKALOIDS; CIRCULAR DICHROISM; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SOLANACEAE; TROPANES;

MAGNOLIOPHYTA; SCHIZANTHUS; SCHIZANTHUS GRAHAMII; SCHIZANTHUS PINNATUS; SOLANACEAE;

EID: 77950367825     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2010.02.004     Document Type: Article

References (34)

1. Andzelm J., and Wimmer E. Density functional Gaussian-type-orbital approach to molecular geometries, vibrations, and reaction energies. J. Chem. Phys. 96 (1992) 1280-1303
2. Bieri S., Muñoz O., Veuthey J.L., and Christen P. Analysis of isomeric tropane alkaloids from Schizanthus grahamii by very fast gas chromatography. J. Sep. Sci. 29 (2006) 96-102
3. Bieri S., Varesio E., Muñoz O., Veuthey J.-L., and Christen P. Use of porous graphitic carbon column for the separation of natural isomeric tropane alkaloids by capillary LC and mass spectrometry. J. Pharm. Biomed. Anal. 40 (2006) 545-551
4. Burgueño-Tapia E., and Joseph-Nathan P. Absolute configuration of eremophilanoids by vibrational circular dichroism. Phytochemistry 69 (2008) 2251-2256
5. Cerda-García-Rojas C.M., García-Gutiérrez H.A., Hernández-Hernández J.D., Román-Marín L.U., and Joseph-Nathan P. Absolute configuration of verticillane diterpenoids by vibrational circular dichroism. J. Nat. Prod. 70 (2007) 1167-1172
6. Cerda-García-Rojas C.M., Catalán C.A.N., Muro A.C., and Joseph-Nathan P. Vibrational circular dichroism of africanane and lippifoliane sesquiterpenes from Lippia integrifolia. J. Nat. Prod. 71 (2008) 967-971
7. Chang G., Guida W.C., and Still W.C. An internal-coordinate Monte Carlo method for searching conformational space. J. Am. Chem. Soc. 111 (1989) 4379-4386
8. Coccuci A.A. El mecanismo floral de Schizanthus. Kurtziana 20 (1989) 113-132
9. De la Fuente G., Reina M., Muñoz O., San Martín A., and Girault P.J. Tropane alkaloids from Schizanthus pinnatus. Heterocycles 27 (1988) 1887-1897
10. Dembitsky V.M. Bioactive cyclobutane-containing alkaloids. J. Nat. Med. 62 (2008) 1-33
11. Fodor G., and Dharanipragada R. Tropane alkaloids. Nat. Prod. Rep. 12 (1994) 443-450
12. Gambaro V., Labbé C., and Castillo M. Angeloil, tigloyl and senecioyloxytropane alkaloids from Schizanthus hookerii. Phytochemistry 22 (1983) 1838-1839
13. Godbout N., Salahub D.R., Andzelm J., and Wimmer E. Optimization of Gaussian-type basis set for local spin density functional calculations. Part I. Boron through neon optimization techniques and validation. Can. J. Chem. 70 (1992) 560-571
14. Griffin W.J., and Lin G.D. Chemotaxonomy and geographical distribution of tropane alkaloids. Phytochemistry 53 (2000) 623-637
15. Gringauz A. Introduction to Medicinal Chemistry-How Drugs Act and Why (1997), VCH, New York 721p
16. Halgren T.A. Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94. J. Comp. Chem. 17 (1996) 616-641
17. Halgren T.A. Merck molecular force field. II. MMFF94 van der Waals and electrostatic parameters for intermolecular interactions. J. Comp. Chem. 17 (1996) 587-615
18. Halgren T.A. Merck molecular force field. III. Molecular geometries and vibrational frequencies for MMFF94. J. Comp. Chem. 17 (1996) 553-586
19. Halgren T.A. Merck molecular force field. V. Extension of MMFF94 using experimental data, additional computational data, and empirical rules. J. Comp. Chem. 17 (1996) 490-519
20. Halgren T.A., and Nachbar R.B. Merck molecular force field. IV. Conformational energies and geometries for MMFF94. J. Comp. Chem. 17 (1996) 520-552
21. Hartmann R., San-Martin A., Muñoz O., and Breitmaier E. Grahamine, an unusual tropane alkaloid from Schizanthus grahamii. Angew. Chem. Int. Ed. Engl. 29 (1990) 385-386
22. Humam M., Bieri S., Geiser L., Muñoz O., Veuthey J.-L., and Christen P. Separation of four isomeric tropane alkaloids from Schizanthus grahamii by non-aqueous capillary electrophoresis. Phytochem. Anal. 16 (2005) 349-356
23. Humam M., Christen P., Muñoz O., Hostettmann K., and Jeannerat D. Absolute configuration of tropane alkaloids bearing two α,β-unsaturated ester functions using electronic CD spectroscopy: application to (R,R)-trans-3-hydroxysenecioyloxy-6-senecioloxytropane. Chirality 20 (2008) 20-25
24. Lounasmaa M., and Tamminen T. The tropane alkaloids. In: Cordell G.A. (Ed). The Alkaloids vol. 44 (1993), Academic Press, San Diego 1-114
25. Moore J.M., Casale J.F., and Cooper D.A. Comparative determination of total isomeric truxillines in illicit, refined, South American cocaine hydrochloride using capillary gas chromatography-electron capture detection. J. Chromatogr. A 756 (1996) 193-201
26. Muñoz O., Hartmann R., and Breitmaier E. Schizanthine X, a new alkaloid from Schizanthus grahamii. J. Nat. Prod. 54 (1991) 1094-1096
27. Muñoz M.A., Muñoz O., and Joseph-Nathan P. Absolute configuration of natural diastereoisomers of 6β-hydroxyhyoscyamine by vibrational circular dichroism. J. Nat. Prod. 69 (2006) 1335-1340
28. Muñoz M.A., Areche C., San-Martín A., Robirosa J., and Joseph-Nathan P. VCD determination of the absolute configuration of stypotriol. Nat. Prod. Comm. 4 (2009) 1037-1040
29. Muñoz M.A., Muñoz O., and Joseph-Nathan P. Absolute configuration determination and conformational analysis of (-)-(3S, 6S)-3α,6β-diacetoxytropane using vibrational circular dichroism and DFT techniques. Chirality 22 (2010) 234-241
30. Perdew J.P. Density-functional approximation for the correlation energy of the inhomogeneous electron gas. Phys. Rev. B 33 (1986) 8822-8824
31. San Martín A., Rovirosa J., Gambaro V., and Castillo M. Tropane alkaloids from Schizanthus hookeri. Phytochemistry 19 (1980) 2007-2008
32. San Martín A., Labbé C., Muñoz O., Castillo M., Reina M., De la Fuente G., and González A. Tropane alkaloids from Schizanthus grahamii. Phytochemistry 26 (1987) 819-822
33. Silva G.L., Cui B., Chávez D., You M., Chai H.-B., Rasoanaivo P., Lynn S.M., ÓNeill M.J., Lewis J.A., Besterman J.-M., Monks A., Farnsworth N.R., Cordell G.A., Pezzuto J.M., and Kinghorn A.D. Modulation of the multidrug-resistance phenotype by new tropane alkaloid aromatic esters from Erytroxylum pervillei. J. Nat. Prod. 64 (2001) 1514-1520
34. Zanolari B., Wolfender J.-L., Guilet D., Marston A., Queiroz E.F., Paulo M.Q., and Hostettmann K. On-line identification of tropane alkaloids from Erythroxylum vacciniifolium by liquid chromatography-UV detection-multiple mass spectrometry and liquid chromatography-nuclear magnetic resonance spectrometry. J. Chromatogr. A 1020 (2003) 75-89