Monatshefte für Chemie - Chemical Monthly

, Volume 144, Issue 12, pp 1767–1773 | Cite as

Properties of dihydroasparagusic acid and its use as an antidote against mercury(II) poisoning

  • Armandodoriano Bianco
  • Emilio Bottari
  • Maria Rosa FestaEmail author
  • Lorella Gentile
  • Anna Maria Serrilli
  • Alessandro Venditti
Original Paper


Dihydroasparagusic acid is the first naturally occurring dimercaptanic compound that was isolated in 1948 from Asparagus concentrate. Although several synthetic procedures were proposed in the past decades for this natural substance, most of its chemical properties remain unstudied. In this work the capacity of the acid to act as an antidote against mercury(II) toxicity was evaluated in a simple biological model system, Saccharomyces cerevisiae, and is explained by the formation of a precipitate between mercury(II) and dihydroasparagusic acid. The precipitate was analyzed and studied. The solubility was determined by measuring in equilibrated solutions either the concentration of the total mercury(II) present in solution or the free concentration of hydrogen ions. The protonation constants were determined at 25 °C and in 1.00 M NaCl, as constant ionic medium, by means of potential difference measurements of a galvanic cell with a glass electrode. The experimental data are explained by proposing the chemical composition of the precipitate and the value of its solubility product. As the solubility of the precipitate increases by increasing the concentration of dihydroasparagusic acid, the further formation of a complex between mercury(II) and dihydroasparagusic acid is assumed.

Graphical abstract


Dihydroasparagusic acid Antidote towards mercury(II) Solubility product Coordination chemistry Protonation complexes Stability constant 

Supplementary material

706_2013_1095_MOESM1_ESM.doc (28 kb)
Supplementary material 1 (DOC 28 kb)


  1. 1.
    Jansen EF (1948) J Biol Chem 176:657Google Scholar
  2. 2.
    Casas JS, Jones MM (1980) J Inorg Nucl Chem 42:99CrossRefGoogle Scholar
  3. 3.
    Coates RL, Jones M (1978) J Inorg Nucl Chem 39:677CrossRefGoogle Scholar
  4. 4.
    Lenz GR, Martell AE (1964) Biochemistry 3:745CrossRefGoogle Scholar
  5. 5.
    Van der Linden WE, Beers C (1974) Anal Chim Acta 68:143CrossRefGoogle Scholar
  6. 6.
    Kuchinskas EJ, Rosen Y (1962) Arch Biochem Biophys 97:370CrossRefGoogle Scholar
  7. 7.
    Sugiura Y, Yokoyama A, Tanaka H (1970) Chem Pharm Bull 18:693CrossRefGoogle Scholar
  8. 8.
    Bottari E, Festa MR (1997) Talanta 44:1705CrossRefGoogle Scholar
  9. 9.
    Apruzzese F, Bottari E, Festa MR (2002) Talanta 56:459CrossRefGoogle Scholar
  10. 10.
    Apruzzese F, Bottari E, Festa MR (2003) J Sol Chem 32:65CrossRefGoogle Scholar
  11. 11.
    Apruzzese F, Bottari E, Festa MR (2004) Ann Chim (Rome) 94:45CrossRefGoogle Scholar
  12. 12.
    Basinger MM, Casas JS, Jones MM, Weaver AD, Weinstein NH (1981) J Inorg Nucl Chem 43:1419CrossRefGoogle Scholar
  13. 13.
    Peters RA, Stocken LA, Thompson RHS (1945) Nature 156:616CrossRefGoogle Scholar
  14. 14.
    Venditti A, Mandrone M, Serrilli AM, Bianco A, Iannello C, Antognoni F, Poli F (2013) J Agric Food Chem 61:6848CrossRefGoogle Scholar
  15. 15.
    Biedermann G, Sillèn LG (1953) Ark Kemi 5:425Google Scholar
  16. 16.
    Sillèn LG (1956) Acta Chem Scand 10:186CrossRefGoogle Scholar
  17. 17.
    Bottari E, Coccitto T, Curzio G, Festa MR, Jasionowska R (1988) Ann Chim (Rome) 78:635Google Scholar
  18. 18.
    Di Stefano C, Mineo P, Rigano C, Sammartano S (1993) Ann Chim (Rome) 83:343Google Scholar
  19. 19.
    Ciavatta L, Grimaldi M (1968) J Inorg Nucl Chem 30:197CrossRefGoogle Scholar
  20. 20.
    Rossotti F, Whewell R (1977) J Chem Soc Dalton Trans Inorg Chem (12):1223 Google Scholar
  21. 21.
    Ciavatta L, Grimaldi M (1968) J Inorg Nucl Chem 30:563CrossRefGoogle Scholar
  22. 22.
    Yanagawa H, Kato T, Sagami H, Kitahara Y (1973) Synthesis 10:607CrossRefGoogle Scholar
  23. 23.
    Schotte L, Ström H (1956) Acta Chem Scand 10:687CrossRefGoogle Scholar
  24. 24.
    Singh R, Whitesides GM (1990) J Am Chem Soc 112:1190CrossRefGoogle Scholar
  25. 25.
    Zervas L, Photarki I, Ghelis N (1963) J Am Chem Soc 85:1337CrossRefGoogle Scholar
  26. 26.
    Venditti A, Serrilli AM, Campanella L, Bianco A (2010) In: Proceedings of the 24th international symposium on organic chemistry of sulfur (ISOCS-24), Firenze, 25–30 July 2010Google Scholar
  27. 27.
    Schwarzenbach G, Flaschka H (1965) Die Komplexometrische titration. Ferdinand Enke Verlag, StuttgartGoogle Scholar
  28. 28.
    Brown AS (1934) J Am Chem Soc 56:646CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Wien 2013

Authors and Affiliations

  • Armandodoriano Bianco
    • 1
  • Emilio Bottari
    • 1
  • Maria Rosa Festa
    • 1
    Email author
  • Lorella Gentile
    • 1
  • Anna Maria Serrilli
    • 1
  • Alessandro Venditti
    • 1
  1. 1.Dipartimento di ChimicaUniversità di Roma “La Sapienza”RomeItaly

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