Absolute configuration of eremophilanoids by vibrational circular dichroism

Phytochemistry

Volumn 69, Issue 11, 2008, Pages 2251-2256

  Burgueño Tapia, Eleuterio ^a   Joseph Nathan, Pedro ^b  

^a INSTITUTO POLITÉCNICO NACIONAL   (Mexico)

^b DEPARTAMENTO DE FÍSICA   (Mexico)

Author keywords

1 Angeloyloxy 8 ,10 dihydroxyeremophil 7(11) en 8 ,12 olide; 6 Acetyloxyeuryopsin; 6 Hydroxyeuryopsin; Absolute configuration; Vibrational circular dichroism

Indexed keywords

PYRROLIZIDINE ALKALOID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; CONFORMATION; EREMOPHILA (ANGIOSPERM);

CIRCULAR DICHROISM; EREMOPHILA PLANT; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PYRROLIZIDINE ALKALOIDS;

EID: 48349127385     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2008.05.011     Document Type: Article

References (44)

1. Arciniegas A., Pérez-Castorena A.L., Parada G., Villaseñor J.L., and Romo de Vivar A. 6β-Hydroxyeuryopsin, a possible precursor of eremophilanolides in Senecio toluccanus DC. var. modestus. Rev. Latinoamer. Quím. 28 (2000) 131-136
2. Bohlmann F., and Zdero C. Neue furanoeremophilane und andere sesquiterpene aus vertretern der gattung Euriops. Phytochemistry 17 (1978) 1135-1153
3. Bohlmann F., Knoll K.H., Zdero C., Mahanta P.K., Grenz M., Suwita A., Ehlers D., Le Van N., Abraham W.R., and Natu A.A. Terpen-derivate aus Senecio-arten. Phytochemistry 16 (1997) 965-985
4. 13C NMR assignments of eremophilanolides. Magn. Reson. Chem. 42 (2004) 835-905
5. Burgueño-Tapia E., Hernández-Carlos B., and Joseph-Nathan P. DFT, solution, and crystal conformation of eremophilanoids. J. Mol. Struct. 825 (2006) 115-123
6. Burgueño-Tapia E., González-Coloma A., Martín-Benito D., and Joseph-Nathan P. Antifeedant and phytotoxic activity of cacalolides and eremophilanolides. Z. Naturforsch. 62c (2007) 362-366
7. 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
8. 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
9. Cichewcz R.H., Clifford L.J., Lassen P.R., Cao X., Freedman T.B., Nafie L.A., Deschamps J.D., Kenyon V.A., Flanary J.R., Holman T.R., and Crews P. Stereochemical determination and bioactivity assessment of (S)-(+)-curcuphenol dimers isolated from the marine sponge Didiscus aceratus and synthesized through laccase biocatalysis. Bioorg. Med. Chem. 13 (2005) 5600-5612
10. Crabbé P. Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry (1965), Holden-Day, San Francisco
11. Crabbé P. Applications de la Dispersion Rotatoire Optique et du Dichroïsme Circulaire Optique en Chemie Organique (1968), Gauthier-Villars, Paris pp. 340-341
12. Djerassi C. Optical Rotatory Dispersion: Applications to Organic Chemistry (1960), McGraw-Hill, New York
13. Freedman T.B., Cao X., Dukor R.K., and Nafie L.A. Abolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism. Chirality 15 (2003) 743-758
14. Freedman T.B., Cao X., Oliveira R.V., Cass Q.B., and Nafie L.A. Determination of the absolute configuration and solution conformation of gossypol by vibrational circular dichroism. Chirality 15 (2003) 196-200
15. Furo T., Mori T., Wada T., and Inoue Y. Absolute configuration of chiral [2, 2] paracyclophanes with intramolecular charge transfer interaction. Failure of the excitation chirality method and use of the sector rule applied to the Cotton effect of the CT transition. J. Am. Chem. Soc. 127 (2005) 8242-8243
16. Gajewski J.J., Gilbert K.E., and McKelvey J. MMX an enhanced version of MM2. Adv. Mol. Mod. 2 (1990) 65-92
17. Halgren T. Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94. J. Comput. Chem. 17 (1996) 616-641
18. Halgren T.A. Merck molecular force field. II. MMFF94 van der Waals and electrostatic parameters for intermolecular interactions. J. Comput. Chem. 17 (1996) 587-615
19. Halgren T.A. Merck molecular force field. III. Molecular geometries and vibrational frequencies for MMFF94. J. Comput. Chem. 17 (1996) 553-586
20. Halgren T.A. Merck molecular force field. V. Extension of MMFF94 using experimental data, additional computational data, and empirical rules. J. Comput. Chem. 17 (1996) 490-519
21. Halgren T.A., and Nachbar R.B. Merck molecular force field. IV. Conformational energies and geometries for MMFF94. J. Comput. Chem. 17 (1996) 520-552
22. 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-hydroxysenecioyloxi-6-senecioyloxytropane. Chirality 20 (2008) 20-25
23. Krautmann M., de Riscala E.C., Burgueño-Tapia E., Mora-Pérez. Y., Catalán C.A.N., and Joseph-Nathan P. C-15 functionalized eudesmanolides from Mikania campanulata. J. Nat. Prod. 70 (2007) 1173-1179
24. Kuppens T., Vandyck K., Van der Eycken J., Herrebout W., van der Veken B.J., and Bultinck P. Determination of the absolute configuration of three as-hydrindacene compounds by vibrational circular dichroism. J. Org. Chem. 70 (2005) 9103-9114
25. Lassen P.R., Skytte D.M., Hemmingsen L., Nielsen S.F., Freedman T.B., Nafie L.A., and Christensen S.B. Structure and absolute configuration of nyasol and hinokiresinol via synthesis and vibrational circular dichroism spectroscopy. J. Nat. Prod. 68 (2005) 1603-1609
26. Mace L., Shanmugham M.S., White J.D., and Drew G.B. A new route to furanoeremophilane sesquiterpenoids. Synthesis of Senecio metabolites (±)-1,10-epoxy-6-hydroxyeuryopsin, (±)-toluccanolide A and (±)-toluccanolide C. Org. Biomol. Chem. 4 (2006) 1020-1031
27. Mennucci B., Claps M., Evidente A., and Rosini C. Absolute configuration of natural cyclohexene oxides by time dependent density functional theory calculation of the optical rotation: the absolute configuration of (-)-sphaeropsidone and (-)-episphaeropsidone revised. J. Org. Chem. 72 (2007) 6680-6691
28. Min H.M., Aye M., Taniguchi T., Miura N., Monde K., Ohzawa K., Nikai T., Niwa M., and Tayaka Y. A structure and an absolute configuration of (+)-alternamine, a new coumarin from Murraya alternans having antidote activity against snake venom. Tetrahedron Lett. 48 (2007) 6155-6158
29. Monde K., Taniguchi T., Muira N., Kutschi P., Curillová Z., Pilátová M., and Mojzis J. Chiral cruciferous phytoalexins: preparation, absolute configuration, and biological activity. Bioorg. Med. Chem. 13 (2005) 5206-5212
30. Monde K., Taniguchi T., Muira N., Vairappan C.S., and Suzuki M. Absolute configuration of endoperoxides determined by vibrational circular dichroism (VCD). Tetrahedron Lett. 47 (2006) 4389-4392
31. Muñoz M.A., Muñoz O., and Joseph-Nathan P. Absolute configuration of natural diastereoisomers of 6β-hydroxyhyoscynamine by vibrational circular dichroism. J. Nat. Prod. 69 (2006) 1335-1340
32. Nafie L.A. Vibrational circular dichroism: a new tool for the solution-state determination of the structure and absolute configuration of chiral natural product molecules. Nat. Prod. Commun. 3 (2008) 451-466
33. Perdew J.P. Density-functional approximation for the correlation energy of the inhomogeneous electron gas. Phys. Rev. B 33 (1986) 8822-8824
34. Pérez A.L., Vidales P., Cárdenas J., and Romo de Vivar A. Eremophilanolides from Senecio toluccanus DC. var. modestus. Phytochemistry 30 (1991) 905-908
35. Romo J., Joseph-Nathan P., and Díaz F. Aromatin and aromaticin, new sesquiterpene lactones isolated from Helenium aromaticum. Chem. Ind. (1963) 1839
36. Romo J., Joseph-Nathan P., and Díaz F. The constituents of Helenium aromaticum (Hook) Bailey. The structures of aromatin and aromaticin. Tetrahedron 20 (1964) 79-85
37. Stephens P.J., Devlin F.J., Gasparrini F., Ciogli A., Spinelli D., and Cosimelli B. Determination of the absolute configuration of a chiral oxadiazol-3-one calcium channel blocker, resolved using chiral chromatography, via concerted density functional theory calculations of its vibrational circular dichroism, electronic circular dichroism, and optical rotation. J. Org. Chem. 72 (2007) 4707-4715
38. Stephens P.J., Pan J.J., Devlin F.J., Krohn K., and Kurtán T. Determination of the absolute configurations of natural products via density functional theory calculations of vibrational circular dichroism, electronic circular dichroism, and optical rotation: the iridoids plumericin and isoplumericin. J. Org. Chem. 72 (2007) 3521-3536
39. Stephens P.J., Pan J.J., Devlin F.J., Urbanová M., and Hájícek J. Determination of the absolute configurations of natural products via density functional theory calculations of vibrational circular dichroism, electronic circular dichroism, and optical rotation: the Schizozygane alkaloid schizozygine. J. Org. Chem. 72 (2007) 2508-2524
40. Stephens P.J., Pan J.J., and Krohn K. Determination of the absolute configurations of pharmacological natural products via density functional theory calculations of vibrational circular dichroism: the new cytotoxic iridoid prismatomerin. J. Org. Chem. 72 (2007) 7641-7649
41. Terabe M., Tada M., and Takahashi T. Absolute stereochemistry of cacalol. Bull. Chem. Soc. Jpn. 51 (1978) 661-662
42. Walls F., Padilla J., Joseph-Nathan P., Giral F., and Romo J. The structures of α- and β-pipitzols. Tetrahedron Lett. (1965) 1577-1582
43. Walls F., Padilla J., Joseph-Nathan P., Giral F., Escobar M., and Romo J. Studies in perezone derivatives. Structure of the pipitzols and perezinone. Tetrahedron 22 (1966) 2387-2399
44. Wang Q., Mu Q., Shibano M., Morris-Natschke S.L., Lee K.-H., and Chen D.-F. Eremophilane sesquiterpenes from Ligularia macrophylla. J. Nat. Prod. 70 (2007) 1259-1262