Cent Eur J Public Health 2004, 12(Supplement):S16-S18

Kojic Acid and its Derivatives: History and Present State of Art

Brtko J.1, Rondahl L.1, Ficková M.1, Hudecová D.2, Eybl V.3, Uher M.4
1 Institute of Experimental Endocrinology, Slovak Academy of Sciences, Bratislava
2 Department of Biochemistry and Microbiology, Faculty of Chemical and Food Technology STU, Bratislava, Slovak Republic
3 Department of Pharmacology and Toxicology, Charles University, Faculty of Medicine in Pilsen, Plzeň, Czech Republic
4 Department of Organic Chemistry, Faculty of Chemical and Food Technology STU, Bratislava, Slovak Republic

Kojic acid (5-hydroxy-2-hydroxymethyl-4-pyranone) represents an attractive polyfunctional skeleton for development of biologically active compounds. The authors prepared a great variety of kojic acid derivatives and selected biological properties have been studied. Thus, kojic acid derivatives are promising compounds that might advantageously be used in human and/or veterinary medicine and also in preparation of new, even more biologically active preparations.

Keywords: kojic acid, 5-hydroxy-2-hydroxymethyl-4-pyranone, derivatives, chelating agent, fungicide, inhibitors of neoplastic cell growth

Published: March 1, 2004  Show citation

ACS AIP APA ASA Harvard Chicago Chicago Notes IEEE ISO690 MLA NLM Turabian Vancouver
Brtko J, Rondahl L, Ficková M, Hudecová D, Eybl V, Uher M. Kojic Acid and its Derivatives: History and Present State of Art. Cent Eur J Public Health. 2004;12(Supplement):S16-18. PubMed PMID: 15141965.
Download citation

References

  1. Beelik A: Kojic acid. Adv Carbohyd Chem 1956; 11: 145-183. Go to original source...
  2. Bajpai P, Agrawal PK, Vishwanathan L: Kojic acid: Synthesis and properties. J Sci Indust Res 1982; 41: 185-194.
  3. Dobias J, Brtko J, Bálint Š, Sadloň J: Aspergillus tamarii CCM F-781. CS Patent No. 251532, 1988.
  4. Dobias J, Brtko J, Bálint Š, Sadloň J: Aspergillus tamarii CCM F-780. CS Patent No. 251533, 1988.
  5. Bálint Š, Forsthoffer J, Brtko J, Dobias J: Kojic acid production. CS Patent No. 252880, 1988.
  6. Bálint Š, Forsthoffer J, Brtko J, Dobias J: Enlargement of yield of kojic acid production. CS Patent No. 252881, 1988.
  7. Uher M, Bransová J, Brtko J, Hudecová D, Dobias J, Filipčík P: 2-Thiocyanato-methyl-5-benzyloxy-4H-pyran-4-one. SK Patent No. 278075, 1995.
  8. Hudecová D, Jantová S, Melník M, Uher M: New azidometalkojates and their biological activity. Folia Microbiol 1996; 41: 473-476. Go to original source... Go to PubMed...
  9. Baláž Š, Šturdík E, Ujhelyová R, Valigura D, Uher M, Veverka M, Konečný V, Adamcová J, Michalík P, Brtko J: Biologically important physicochemical propereties of kojic acid derivatives. Collect Czech Chem Commun 1993; 58: 693-701. Go to original source...
  10. Baláž Š, Uher M, Brtko J, Veverka M, Bransová J, Dobias J, Pódová M, Buchvald J: Relationship between antifungal activity and hydrophobicity of kojic acid derivatives. Folia Microbiol 1993; 38: 387-391. Go to original source... Go to PubMed...
  11. Piršelová K, Baláž Š, Ujhelyiová R, Šturdík E, Veverka M, Uher M, Brtko J: Quantitative structure-time-activity relationships (QSTAR): Growth inhibition of Escherichia coli by nonionizable kojic acid derivatives. Quant Struct-Act Relat 1996; 15: 87-93. Go to original source...
  12. Uher M, Hudecová D, Brtko J, Dobias J, Kováč J, Šturdík E, Konečný V, Varkonda Š, Ujhelzová L, Pódová M, Buchvlad J: Fungicide preparation for agriculture, human and veterinary medicine. CS Patent No. 259592, 1989.
  13. Hudecová D, Uher M, Brtko J: Halogenderivatives of kojic acid with antifungal effects. Biologia 1992; 47: 483-488.
  14. Brtko J, Uher M, Pódová M, Dobias J, Melník M: Fungicide preparation. CS Patent No. 277376, 1992.
  15. Melník M, Uher M, Brtko J, Mrozińska D, Mroziński J: Cooper (II) kojates and their antifungal effects. Polish J Chem 1993; 67: 12191225.
  16. Uher M, Kyselicová L, Rajniaková O, Hudecová D, Bransová J, Brtko J: Derivatives of 4H-pyran-4-one with the atom of sulfur in the side chain. Chem Papers 1997; 51: 421-426. S18
  17. Sansho Seiyaku Co.: Kojic acid as an anti-inflammatory and analgesic agent. Japan Kokai Tokkyo Koho JP 80154916, 1980.
  18. Kotulová D, UherM, Brtko J:Anti-inflammatory preparation. SK Patent No. 277821, 1994.
  19. Bransová, J, Brtko J, Uher M, Novotný L: Antileukemic activity of 4-pyranone derivatives. Int J Biochem Cell Biol 1995; 27: 701-706. Go to original source...
  20. Bransová J, Uher M, Brtko J: Regulation of selected biological processes in neoplastic cell lines by halogen derivatives of 5-hydroxy2-hydroxymethyl-4-pyranone. Anticancer Res 1998; 18: 4423-4428.
  21. Bransová J, Uher M, Novotný L, Brtko J: 5-Benzyloxy-2-thiocyanatoethyl-4-pyranone, a novel heterocyclic compound: Synthesis, structure determination and effects on neoplastic cell growth.Anticancer Res 1997; 17: 1175-1178.
  22. VachálkováA, Bransová J, Brtko J, UherM, Novotný L: Polarographic behaviour of kojic acid and its derivatives, determination of potential carcinogenity and correlation of these properties with their other attributes. Neoplasma 1996; 43: 265-269. Go to PubMed...
  23. Rondahl L, Uher M, Brtko J: Syntheses and structure determinations of some selenocyanato- and thiocyanato-kojic acid derivatives. Heterocycl Commun 2003; 9: 257-258. Go to original source...
  24. Mishima Y, Hatta S, Ohyama Y, Inazu M: Induction of melanogenesis supression: Cellular pharmacology and mode of differential action. Pigment Cell Res 1988; 1: 367-374. Go to original source...
  25. Niwa Y, Akamatsu H: Kojic acid scavenges free radicals while potentiating leukocyte functions including free radical generation. Inflammation 1991; 15: 303-315. Go to original source... Go to PubMed...
  26. Dobiás J, Nemec P, Brtko J: The inhibitory effect of kojic acid and its two derivatives on the development of Drosophila melanogaster. Biologia 1977; 32: 417-421.
  27. Brtko J, Dobiás J, Nemec P: Insecticidal 5-Acetoxy-2-acetoxymethylpyron-4, seine Herstellung und Verwendung als Insectizid. Ger. Patent No. 3014618, 1980.
  28. Shibua T, Murota T, Sakamoto K, Iwahara S, Ikeno M: Mutagenicity and dominant lethal test of kojic acid. J Toxicol Sci 1982; 7: 255-262. Go to original source...
  29. Wei, C.I., Huang, T.S., Fernando, S.Y., Chung, K.T.: Mutagenity studies of kojic acid. Toxicol Lett 59, 1991, 213-220. Go to original source...
  30. Fujimoto N, Onodera H, Mitsumori K, Tamura T, Maruzama S, Ito A: Changes in thyroid function during development of thyroid hyperplasia induced by kojic acid in F344 rats. Carcinogenesis 1999; 20: 1567-1571. Go to original source...
  31. Fujimoto N, Watanabe H, Nakatani T, Roy G, Ito A: Induction of thyroid tumours in (C57BL/6N x C3H/N)F1 mice by oral administration of kojic acid. Food Chem Toxicol 1998; 36: 697-703. Cent Eur J Publ Health 2004; 12, Suppl, p. S18-S20 Go to original source... Go to PubMed...