Comparison of the phytoestrogen trans-resveratrol (3,4′,5- trihydroxystilbene) structures from x-ray diffraction and solution NMR

Magnetic Resonance in Chemistry

Volumn 43, Issue 7, 2005, Pages 567-572

  Commodari, Fernando ^a   Khiat, Abdesslem ^b   Ibrahimi, Sanae ^c   Brizius, Alison R ^a   Kalkstein, Noah ^a  

^a ALBERT EINSTEIN COLLEGE OF MEDICINE   (United States)

^b UNIVERSITY OF MONTREAL   (Canada)

^c INRS INSTITUT ARMAND FRAPPIER   (Canada)

Author keywords

3,4 ,5 trihydroxystilbene; 13C NMR; 1H NMR; NMR; Trans resveratrol; X ray

Indexed keywords

CRYSTAL STRUCTURE; DIHEDRAL ANGLE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY DIFFRACTION;

13C NMR; 1H NMR; 3,4′,5-TRIHYDROXYSTILBENE; CRYSTAL X-RAY STRUCTURE; NMR SPECTRUM; PHENOLIC RINGS; PHYTO-OESTROGENS; SOLUTION NMR; SOLUTION STRUCTURES; TRANS-RESVERATROL;

RESVERATROL;

DIMETHYL SULFOXIDE; PHYTOESTROGEN; RESVERATROL;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CRYSTALLIZATION; MEDICAL LITERATURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY DIFFRACTION;

EID: 20544434206     PISSN: 07491581     EISSN: None     Source Type: Journal    
DOI: 10.1002/mrc.1583     Document Type: Article

References (43)

1. Hing H, Tong W, Fang H, Shi L, Xie Q, Wu J, Perkins R, Walker JD, Branham W, Sheehan DM. Environ. Health. Perspect. 2002; 110: 29.
2. Snedeker SM. Environ. Health Perspect. 2001; 109(Suppl. 1): 35.
3. Langcake P, Pryce RJ. Specialia 1977; 15: 151.
4. Jang M, Cai L, Udeani GO, Slowing KV, Thomas CF, Beecher CWW, Fong HHS, Farnsworth NR, Kinghorn AD, Menta RG, Moon RC, Pezzuto JM. Science 1997; 275: 218.
5. Calabrese G. Drugs Exp. Clin. Res. 1999; 25: 111.
6. Pace-Asciak CR, Rounova O, Hahn S, Diamandis EP, Soleas G, Goldberg DM. Clin. Chim. Acta 1995; 235: 207.
7. Pace-Asciak CR, Rounova O, Hahn S, Diamandis EP, Goldberg DM. Clin. Chim. Acta 1996; 246: 163.
8. Fauconneau B, Waffo-Teguo P, Huguet F, Barrier L, Decendit A, Merillon JM. Life Sci. 1997; 61: 2103.
9. Mgbonyebi OP, Russo J, Russo IH. Int. J. Oncol. 1998; 12: 865.
10. Hsieh CT, Burfeind P, Laud K, Bacher JM, Traganos F, Darzynkiewicz Z, Wu JM. Int. J. Oncol. 1999; 15: 865.
11. Kimura Y, Okuda H, Arichi S. Biochim. Biophys. Acta 1985; 834: 275.
12. Rotondo S, Rajtar G, Manarini S, Celardo A, Rotilio D, de Gaetano G, Evangelista V, Cerletti C. Br. J. Pharmacol. 1998; 123: 1691.
13. Jang DS, Kang BS, Ryu SY, Chang IM, Min KR, Kim Y. Biochem. Pharmacol. 1999; 57: 705.
14. Frankel EN, Waterhouse AL, Kinsella JE. Lancet 1993; 341: 1103.
15. Kerry NL, Abbey M. Atherosclerosis 1997; 135: 93.
16. Macarone M, Lorenzon T, Guerrieri P, Finazzi Agro A. Eur. J. Biochem. 1999; 265: 27.
17. Gehm BD, McAndrews JM, Chien PY, Jameson JL. Proc. Natl. Acad. Sci. USA 1997; 94: 14138.
18. Lu R, Serrero G. J. Cell Physiol. 1999; 179: 297.
19. Arichi H, Kimura Y, Okuda H, Baba K, Kozawa M, Arichi S. Chem. Pharm. Bull. 1982; 30: 1766.
20. Goldberg DM, Hahn SE, Parkes JG. Clin. Chim. Acta 1995; 237: 155.
21. Hung L, Chen J, Huang S, Lee R, Su M. Cardiovasc. Res. 2000; 47: 549.
22. Lin J, Tsai S. Proc. Natl. Sci. Counc. ROC (B) 1999; 23: 99.
23. Stivala LA, Savio M, Carafoli F, Perucca P, Bianchi L, Maga G, Forti L, Pagnoni UM, Albini A, Prosperi E, Vannini V. J. Biol. Chem. 2001; 276: 22 586.
24. Klabunde T, Petrassi HM, Oza VB, Raman P, Kelly JW, Sacchettini JC. Nat. Struct. Biol. 2000; 7: 312.
25. Ferrer JL, Jez JM, Bowman ME, Dixon RA, Noel JP. Nat. Struct. Biol. 1999; 6: 775.
26. Casabuono AC, Pomilio AB. Phytochemistry 1994; 35: 479.
27. Lee JP, Min BY, An RB, Na MK, Lee SM, Lee HK, Kim JG, Bae KH, Kang SS. Phytochemistry 2003; 64: 759.
28. Koh D, Park KH, Jung J, Yang H, Mok KH, Lim Y. Magn. Reson. Chem. 2001; 39: 768.
29. Brzozowski AM, Pike ACW, Dauter Z, Hubbard RE, Bonn T, Engstrom O, Ohman L, Greene GL, Gustafsson JA, Carlquist M. Nature 1997; 389: 753.
30. Sorenson OW, Eich GW, Levitt MH, Bodenhausen G, Ernst RR. Prog. Nucl. Magn. Reson. Spectrosc. 1983; 16: 163.
31. Bothner-By AA, Stephens RL, Lee J, Warren CD, Jeanloz RW. J. Am. Chem. Soc. 1984; 106: 811.
32. Bax A, Davis DG. J. Magn. Reson. 1985; 63: 207.
33. States DJ, Haberkorn RA, Ruben DJ. J. Magn. Reson. 1982; 48: 286.
34. Sanders JKM, Mersh JD. Prog. Nucl. Magn. Reson. Spectrosc. 1982; 13: 353, and references cited therein.
35. Bax A, Subramanian S. J. Magn. Reson. 1986; 67: 565.
36. Bax A, Summers MF. J. Am. Chem. Soc. 1986; 108: 2093.
37. Pegg DT, Doddrell DM, Brooks WM, Bendall MR. J. Magn. Reson. 1981; 44: 32.
38. Bax A, Freeman R, Frenkiel TA. J. Am. Chem. Soc. 1981; 103: 2102.
39. Palmer III AG, Cavanagh J, Wright PE, Rance M. J. Magn. Reson. 1991; 93: 151.
40. Powell MJD. Math. Program. 1977; 12: 241.
41. Dinur U, Hagler AT. In Review of Computational Chemistry, Lipkowitz KB, Boyd DB (eds). VCH: New York, 1991; Chapt. 4.
42. Crippen GM, Havel TF. Distance Geometry and Molecular Conformation. Research Studies Press: New York, 1988.
43. Stewart JJP. QCPE Bull. 1990; 455.