Crystal structure of tricolorin A: Molecular rationale for the biological properties of resin glycosides found in some Mexican herbal remedies

Angewandte Chemie - International Edition

Volumn 43, Issue 44, 2004, Pages 5918-5922

  Rencurosi, Anna ^b   Mitchell, Edward P ^c   Cioci, Gianluca ^b   Pérez, Serge ^b   Pereda Miranda, Rogelio ^a   Imberty, Anne ^b  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b CENTRE DE RECHERCHES SUR LES MACROMOLÉCULES VÉGÉTALES CERMAV CNRS   (France)

^c EUROPEAN SYNCHROTRON RADIATION FACILITY   (France)

Author keywords

Conformation analysis; Glycolipids; Glycosides; Natural products; Structure elucidation

Indexed keywords

CRYSTAL STRUCTURE; MOLECULAR STRUCTURE; POROSITY; PROTEINS; TOXICITY;

AMPHIPATHIC FEATURES; GLYCOSIDE; TRICOLORIN A;

RESINS;

CALONYCTIN A; GLYCOSIDE; HERBACEOUS AGENT; NATURAL PRODUCT; RESIN; TRICOLORIN A; UNCLASSIFIED DRUG;

ARTICLE; CORRELATION ANALYSIS; CRYSTAL STRUCTURE; CRYSTALLIZATION; CYTOTOXICITY; DRUG CONFORMATION; DRUG DESIGN; DRUG STRUCTURE; ENZYME INHIBITION; HUMAN; NONHUMAN; PHYTOTOXICITY; STRUCTURE ANALYSIS;

CARBOHYDRATE SEQUENCE; CRYSTALLOGRAPHY, X-RAY; GLYCOSIDES; MEDICINE, HERBAL; MEXICO; MODELS, BIOLOGICAL; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; RESINS, PLANT;

EID: 9244259622     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460327     Document Type: Article

References (29)

1. R. Pereda-Miranda, M. Bah, Curr. Top. Med. Chem. 2003, 3, 111.
2. R. Pereda-Miranda, R. Mata, A. L. Anaya, D. B. Wickramaratne, J. M. Pezzuto, A. D. Kinghorn, J. Nat. Prod. 1993, 56, 571.
3. M. Bah, R. Pereda-Miranda, Tetrahedron 1996, 52, 13063.
4. M. Bah, R. Pereda-Miranda, Tetrahedron 1997, 53, 9007.
5. D. P. Larson, C. H. Heathcock, J. Org. Chem. 1997, 62, 8406.
6. S. F. Lu, Q. O'Yang, Z. W. Guo, B. Yu, Y. Z. Hui, J. Org. Chem. 1997, 62, 8400.
7. A. Fürstner, T. Müller, J. Org. Chem. 1998, 63, 424.
8. A. Fürstner, T. Müller, J. Am. Chem. Soc. 1999, 121, 7814.
9. A. Fürstner, F. Jeanjean, P. Razon, C. Wirtz, R. Mynott, Chem. Eur. J. 2003, 9, 307.
10. M. V. Castelli, J. C. Cortes, A. M. Escalante, M. Bah, R. Pereda-Miranda, J. C. Ribas, S. A. Zacchino, Planta Med. 2002, 68, 739.
11. L. Achnine, R. Pereda-Miranda, R. Iglesias-Prieto, R. Moreno-Sanchez, B. Lotina-Hennsen, Physiol. Plant. 1999, 106, 246.
12. -1) and complete separation of tricolorin A to homogeneity (20 mg) was achieved after twelve consecutive cycles on the same aminopropyl column.
13. S. Pérez, C. Gautier, A. Imberty in Oligosaccharides in Chemistry and Biology: A Comprehensive Handbook (Eds.: B. Ernst, G. Hart, P. Sinay), Wiley-VCH, Weinheim, 2000, pp. 969.
14. -1 in EtOH) mixed with PEG 200 (2 μL) and mineral oil (2 μL). The drop was seeded with the microcrystals obtained previously. The reservoir solution was composed of 75% water, 10% PEG 200, and 15% EtOH.
15. -3. CCDC 228071 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk).
16. Energy maps were calculated for each constituent disaccharide moiety as a function of two glycosidic linkage torsion angles defined as Φ = Θ (O5-C1-O1-Cx) and Ψ = Θ (C1-O1-Cx-C(x + 1)). Each disaccharide was built with the POLYS software[23] and energies were calculated by using the MM3 program[24,25] and employing a previously described procedure[26] involving full optimization of the structure at each point of the (Φ,Ψ) map except for the two driven angles. To allow consideration of the three possible orientations of the hydroxymethylene group of the glucose unit and the clockwise or anticlockwise possibilities for the hydrogen bonding network around each ring, several starting structures, a step of 20°, and a dielectric constant ε = 80 were used for these calculations. The single relaxed maps were combined to provide unique adiabatic maps by a procedure designed by our group.[26] The corresponding plots were generated with the X-Farbe program.[27]
17. C. W. Lehman, A. Fürstner, T. Müller, Z. Kristallogr. 2000, 215, 114.
18. Z. H. Jiang, A. Geyer, R. R. Schmidt, Angew. Chem. 1995, 107, 2730; Angew. Chem. Int. Ed. Engl. 1995, 34, 2520.
19. Z. H. Jiang, A. Geyer, R. R. Schmidt, Angew. Chem. 1995, 107, 2730; Angew. Chem. Int. Ed. Engl. 1995, 34, 2520.
20. M. C. Wiener, S. H. White, Biophys. J. 1992, 61, 437.
21. A. G. W. Leslie, Joint CCP4 + ESF-EAMCB Newslett. Protein Cryst. 1992, 26.
22. M. C. Burla, M. Camalli, B. Carrozzini, G. L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna, J. Appl. Crystallogr. 2003, 36, 1103.
23. G. M. Sheldrick, University of Gottingen, 1997.
24. S. Perez, M. Kouwijzer, K. Mazeau, S. B. Engelsen, J. Mol. Graphics 1996, 14, 307.
25. N. L. Allinger, Y. H. Yuh, J.-H. Lii, J. Am. Chem. Soc. 1989, 111, 8551.
26. N. L. Allinger, M. Rahman, J.-H. Lii, J. Am. Chem. Soc. 1990, 112, 8293.
27. A. Imberty, S. Pérez, Chem. Rev. 2000, 100, 4567.
28. A. Preusser, ACM Trans. Math. Software 1989, 15, 79.
29. A. L. Spek, J. Appl. Crystallogr. 1988, 21, 578.