trans-Resveratrol-d4, a Molecular Tracer of
the Wild-Type Phytoalexin; Synthesis and Spectroscopic
Properties

Bartolo Gabriele; Hicham Benabdelkamel; Pierluigi Plastina; Alessia Fazio; Giovanni Sindona; Leonardo Di 
Donna

doi:10.1055/s-2008-1067239

PAPER

trans-Resveratrol-d ₄, a Molecular Tracer of the Wild-Type Phytoalexin; Synthesis and Spectroscopic Properties

Bartolo Gabriele*^a, Hicham Benabdelkamel^b, Pierluigi Plastina^b, Alessia Fazio^a, Giovanni Sindona^b, Leonardo Di Donna^b
^a Dipartimento di Scienze Farmaceutiche, Università della Calabria, 87036 Arcavacata di Rende (Cosenza), Italy
Fax: +39(984)492044; e-Mail: b.gabriele@unical.it;
^b Dipartimento di Chimica, Università della Calabria, 87036 Arcavacata di Rende (Cosenza), Italy

Abstract

Alle Artikel dieser Rubrik

Abstract

A convenient, six-step synthesis of the so far unknown trans-resveratrol-d ₄, (E)-3′,4,5′-trihydroxy-2,3,5,6-tetradeuterostilbene, starting from commercially available phenol-d ₆, with an overall yield of 25%, is described. The final labeled resveratrol was fully characterized by MS, IR, and ^¹H and ^¹³C NMR spectroscopy. The isotopic distribution of the final product, determined by high resolution mass spectrometry, was as follows: d ₄, 96%; d ₃, 4%.

Key words

deuterated resveratrol - olefination - resveratrol - stable isotope dilution assay

Volltext

Referenzen

References

1a Burns J. Yokota T. Ashihara H. Lean ME. Crozier A. J. Agric. Food Chem. 2002, 50: 3337

1b Siemann EH. Creasy LL. Am. J. Enol. Vitic. 1992, 43: 49

2 For a recent review see: Labisnkyy N. Csiszar A. Veress G. Stef G. Pacher P. Oroszi G. Wu J. Ungvari ZC. Curr. Med. Chem. 2006, 13: 989

See, for example:

3a Bureau G. Longpre F. Martinoli MG. J. Neurosci. Res. 2008, 86: 403

3b Kirimlioglu H. Ecevit A. Yilmaz S. Kirimlioglu V. Karabulut AB. Transpl. Proc. 2008, 40: 285

3c Kumar A. Kaundal RK. Iyer S. Sharma SS. Life Sci. 2007, 80: 1236

3d Ou HC. Chou FP. Sheen HM. Lin TM. Yang CH. Sheu WHH. Clin. Chim. Acta 2006, 364: 196

3e Jang JH. Surh YJ. Free Radical Biol. Med. 2003, 34: 1100

3f Kalra N. Roy P. Prasad S. Shukla Y. Life Sci. 2008, 82: 348

3g Fremont L. Belguendouz L. Delpal S. Life Sci. 1999, 64: 2511

See, for example:

4a Nicotra G. Peracchio C. Castino R. Isidoro C. Carcinogenesis 2008, 29: 381

4b Trincheri NF. Nicotra G. Follo C. Castino R. Isidoro C. Carcinogenesis 2007, 28: 922

4c Tinchieri NF. Follo C. Zhang W. Fei Z. Zhen HN. Zhang JN. Zhang X. J. Neurooncol. 2007, 8: 231

4d Li Y. Liu JY. Liu XP. Xing KF. Wang Y. Li FY. Yao LB. Appl. Biochem. Biotechnol. 2006, 135: 181

4e Le Corre L. Chalabi N. Delort L. Bignon YJ. Bernard-Gallon DJ. Mol. Nutr. Food Res. 2005, 49: 462

4f Bhat KPL. Pezzuto JM. Cancer Res. 2001, 61: 6137

4g Nakagawa H. Kiyozuka Y. Uemura Y. Senzaki H. Shibata N. Hioki K. Tsubura A. J. Cancer Res. Clin. Oncol. 2001, 127: 258

4h Bowers JL. Tyulmenkov VV. Jernigan SC. Klinge CM. Endocrinology 2000, 141: 3657

4i Hsieh TC. Burfeind P. Laud K. Backer JM. Traganos F. Darzynkiewicz Z. Wu JM. Int. J. Oncol. 1999, 15: 245

4j Mgbonyebi OP. Russo J. Russo IH. Int. J. Oncol. 1998, 12: 865

4k Gehm BD. McAndrews JM. Chien PY. Jameson JL. Proc. Natl. Acad. Sci. U.S.A. 1997, 94: 14138

4l Jang MS. Cai EN. Udeani GO. Slowing KV. Thomas CF. Beecher CWW. Fong HHS. Farnsworth NR. Kinghorn AD. Mehta RG. Moon RC. Pezzuto JM. Science 1997, 275: 218

See, for example:

5a Rychlik M. Asam S. Anal. Bioanal. Chem. 2008, 390: 617

5b Mosandl A. J. Chromatogr. 1992, 624: 267

5c Mazzotti F. Di Donna L. Maiuolo L. Napoli A. Salerno R. Sajjad A. J. Agric. Food Chem. 2008, 56: 63

5d De Nino A. Di Donna L. Mazzotti F. Muzzalupo E. Perri E. Sindona G. Tagarelli A. Anal. Chem. 2005, 77: 5961

6 Kendall JT. J. Labelled Compd. Radiopharm. 2000, 43: 917

7 Vougioukalakis GC. Chronakis N. Orfanopoulos M. Org. Lett. 2003, 5: 4603

8 Branytska O. Neumann R. Synlett 2004, 1575

9 Gao M. Wang M. Miller KD. Sledge GW. Hutchins GD. Zheng QH. Bioorg. Med. Chem. Lett. 2006, 16: 5767

10 Ali MA. Kondo K. Tsuda Y. Chem. Pharm. Bull. 1992, 40: 1130

trans-Resveratrol-d 4, a Molecular Tracer of the Wild-Type Phytoalexin; Synthesis and Spectroscopic Properties

trans-Resveratrol-d ₄, a Molecular Tracer of the Wild-Type Phytoalexin; Synthesis and Spectroscopic Properties