Journal of Chemical Biology

, Volume 5, Issue 1, pp 5–17 | Cite as

Shikimic acid: review of its analytical, isolation, and purification techniques from plant and microbial sources

  • Denis V. Bochkov
  • Sergey V. Sysolyatin
  • Alexander I. Kalashnikov
  • Irina A. Surmacheva
Review
First Online:
Received:
Accepted:

Abstract

Shikimic acid properties and its available analytical techniques are discussed. Plants having the highest content of shikimic acid are shown. The existing isolation methods are analyzed and the most optimal approaches to extracting this acid from natural sources (plants and microorganisms) are considered.

Keywords

Shikimic acid Shikimate pathway Hyperproducing strain Shikimate dehydrogenase Dehydroshikimate Oseltamivir 
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References

  1. 1.
    Brown SA (1964) Biochemistry of phenolic compounds. Academic, New YorkGoogle Scholar
  2. 2.
    Bradley D (2005) Nat Rev Drug Discov 4:945CrossRefGoogle Scholar
  3. 3.
    Enrich LB, Scheuermann ML, Mohadjer A, Matthias KR, Eller CF, Newman MS, Fujinaka M, Poon T (2008) Tetrahedron Lett 49:2503CrossRefGoogle Scholar
  4. 4.
    Lingens F (2003) Angew Chem Int Edit 7:350CrossRefGoogle Scholar
  5. 5.
    Mair H (2000) Patent US006130354Google Scholar
  6. 6.
    Zhang Y, Liu A, Ye ZG, Lin J, Xu LZ, Yang SL (2006) Chem Pharm Bull 54:1459CrossRefGoogle Scholar
  7. 7.
    Luhong T, Hong X, Yang S, Liying Q, Dongqun C, Chao D, Wei C (2009) Appl Biochem Biotechnol 158:408CrossRefGoogle Scholar
  8. 8.
    Huang F, Xiu Q, Sun J, Hong E (2002) J Cardiovasc Pharmacol 39:262CrossRefGoogle Scholar
  9. 9.
    Jiang S, Singh G, Boam DJ, Coggins JR (1999) Tetr Assym 10:4087CrossRefGoogle Scholar
  10. 10.
    Song C, Jiang S, Singh G (2001) Tetr Assym 42:9069Google Scholar
  11. 11.
    Gibson JM, Thomas PS, Thomas JD, Barker JL, Chandran SS, Harrup MK, Draths KM, Frost JW (2001) Angew Chem Int Ed 40:1945CrossRefGoogle Scholar
  12. 12.
    McCrindle R, Overton KH, Raphael RA (1960) J Chem Soc, p 1560Google Scholar
  13. 13.
    Wada H, Kido T, Tanaka N, Murakami T, Saiki Y, Chen CM (1992) Chem Pharm Bull 40:2099CrossRefGoogle Scholar
  14. 14.
    Snyder D, Rapoport H (1973) J Am Chem Soc 95:7821CrossRefGoogle Scholar
  15. 15.
    Shinada T, Yoshida Y, Ohfune Y (1998) Tetrahedron Lett 39:6027CrossRefGoogle Scholar
  16. 16.
    Achenbach H, Schwinn A (1995) Phytochemistry 38:1037CrossRefGoogle Scholar
  17. 17.
    Salamon II, Davis BD (1953) J Am Chem Soc 75:5567CrossRefGoogle Scholar
  18. 18.
    Weiss U, Ziffer H (1963) J Org Chem 28:1248CrossRefGoogle Scholar
  19. 19.
    Bressi JC, Verlinde CLMJ, Aronov AM, Shaw ML, Shin SS, Nguyen LN, Suresh S, Buckner FS, Van Voorhis WC, Kuntz ID, Hol WGJ, Gelb MH (2001) J Med Chem 44:2080CrossRefGoogle Scholar
  20. 20.
    Smissman EE, Suh JT, Oxman M, Daniels R (1962) J Am Chem Soc 84:1040CrossRefGoogle Scholar
  21. 21.
    Evans DA, Barnes DM (1997) Tetrahedron Lett 38:57CrossRefGoogle Scholar
  22. 22.
    Hill RK, Newkome GR (1969) J Am Chem Soc 91:5893CrossRefGoogle Scholar
  23. 23.
    Coblens KE, Muralidharan VB, Ganem B (1982) J Org Chem 47:5041CrossRefGoogle Scholar
  24. 24.
    Luthe C, Zamir LO (1983) Tetrahedron Lett 24:4409CrossRefGoogle Scholar
  25. 25.
    Mirza S, Harvey J (1991) Tetrahedron Lett 32:4111CrossRefGoogle Scholar
  26. 26.
    Brazdova B, Tan NS, Samoshina NM, Samoshin VV (2009) Carbohyd Res 344:311CrossRefGoogle Scholar
  27. 27.
    Kranich R, Busemann AS, Bock D, Schroeter-Maas S, Beyer D, Heinemann B, Meyer M, Schierhorn K, Zahlten R, Wolff G, Aydt EM (2007) J Med Chem 50:1101CrossRefGoogle Scholar
  28. 28.
    Reyes-Chilpa R, Estrada-Muñiz E, Apan TR, Amekraz B, Aumelas A, Jankowski CK, Vázquez-Torres M (2004) Life Sci 75:1635CrossRefGoogle Scholar
  29. 29.
    Shende J, McCullough KJ, Boualem M, Gurdial S, Richard HW (1997) J Chem Soc Perkin Trans 1:1805Google Scholar
  30. 30.
    Perkins HJ, Aronof TS (1959) Can J Biochem Physiol 37:149CrossRefGoogle Scholar
  31. 31.
    Zaprometov MN (1961) Biokhimiya 26:597Google Scholar
  32. 32.
    Yoshida S, Hasegawa M (1957) Arch Biochem Biophys 70:377CrossRefGoogle Scholar
  33. 33.
    Gaitonde MK, Gordon MW (1958) J Biol Chem 230:1043Google Scholar
  34. 34.
    Saslaw LD, Waravdekar VS (1960) Biochim Biophys Acta 37:367CrossRefGoogle Scholar
  35. 35.
    Millican RC (1963) Anal Biochem 6:181CrossRefGoogle Scholar
  36. 36.
    Payne R, Edmonds M (2005) J Chem Educ 82:599CrossRefGoogle Scholar
  37. 37.
    Schuster MC, Mann DA, Buchholz TJ, Johnson KM, Thomas WD, Kiessling LL (2003) Org Lett 5:140CrossRefGoogle Scholar
  38. 38.
    Nonaka G, Ageta M, Nishioka I (1985) Chem Pharm Bull 33:96CrossRefGoogle Scholar
  39. 39.
    Rukovodstvo po metodam kontrolya i bezopasnosti biologicheski aktivnykh dobavok k pishche (in Russian). Rukovodstvo. R 4.1.1672-03 (Utverzhdeno Glavnym gosudarstvennym vrachem RF 30.06.2003)Google Scholar
  40. 40.
    Bochkov DV, Sysolyatin SV, Kalashnikov AI, Surmacheva IA (2011) Issledovanie soderzhaniya shikimovoi kisloty v nekotorykh rasteniyakh Altaiskogo kraya (Study of the shikimic acid content in some plants of Altai krai). Khimiya Rastitel'nogo Syr'ya (In Russian) 1:119–122Google Scholar
  41. 41.
    Bresnahan G, Manthey F, Howatt K, Chakraborty M (2003) J Agric Food Chem 51:4004CrossRefGoogle Scholar
  42. 42.
    Silva B, Andrade P, Mendes G, Seabra R, Ferreira M (2002) J Agric Food Chem 50:2313CrossRefGoogle Scholar
  43. 43.
    Dainiak MB, Galaev IY, Mattiasson B (2002) J Chromatogr A 942:123CrossRefGoogle Scholar
  44. 44.
    García Romero E, Sánchez Muñoz G, Martín Alvarez PJ, Cabezudo Ibáñez MD (1993) J Chromatogr A 655:111CrossRefGoogle Scholar
  45. 45.
    Tusseau D, Benoit C (1987) J Chromatogr A 395:323CrossRefGoogle Scholar
  46. 46.
    Mardones C, Hitschfeld A, Contreras A, Lepe K, Gutiérrez L, Baer D (2005) J Chromatogr A 1085:285CrossRefGoogle Scholar
  47. 47.
    Nagels L, Debeuf C, Esmans E (1980) J Chromatogr A 190:411CrossRefGoogle Scholar
  48. 48.
    Heimler D, Pieroni A (1994) Chromatographia 38:475CrossRefGoogle Scholar
  49. 49.
    Molnár-Perl I, Vasanits A, Horváth K (1998) Chromatographia 48:111CrossRefGoogle Scholar
  50. 50.
    Horváth K, Molnár-Perl I (1998) Chromatographia 48:120CrossRefGoogle Scholar
  51. 51.
    Jaroszynska J (2003) Anal Bioanal Chem 377:702CrossRefGoogle Scholar
  52. 52.
    Liu HC, Li QW, Tang LB (2007) J Zhejiang Univ Sci B 8:272CrossRefGoogle Scholar
  53. 53.
    Ibarz MJ, Ferreira V, Hernandez-Orte P, Loscos N, Cacho J (2006) J Chromatogr A 1116:217CrossRefGoogle Scholar
  54. 54.
    Eykman JF (1885) Rec Trav Chim 4:32CrossRefGoogle Scholar
  55. 55.
    Wallace KK, Reynolds KA, Koch K, McArthur HAI, Brown MS, Wax RG, Moore BS (1994) J Am Chem Soc 116:11600CrossRefGoogle Scholar
  56. 56.
    Flores N, Xiao J, Berry A, Bolivar F, Valle F (1996) Nature Biotechnol 14:620CrossRefGoogle Scholar
  57. 57.
    Herlt AJ, Rickards RW, Wu JP (1985) J Antibiot 38:516Google Scholar
  58. 58.
    Jones AL, Keller U (1997) In: Strohl WR (ed) Biochemistry and genetics of actinomycin production. Marcel Dekker, New YorkGoogle Scholar
  59. 59.
    Wilson DJ, Patton S, Florova G, Hale V, Reynold KA (1998) J Ind Microbiol Biot 20:299CrossRefGoogle Scholar
  60. 60.
    Bentley R (1990) Biochem Mol Biol 25:307CrossRefGoogle Scholar
  61. 61.
    Hasegawa M, Nakagawa T, Yoshida S (1957) J Jap For Soc 39:159Google Scholar
  62. 62.
    Henshaw GG, Coult DA, Boulter D (1962) Nature 194:579CrossRefGoogle Scholar
  63. 63.
    Neish AC (1958) Can J Botany 36:649CrossRefGoogle Scholar
  64. 64.
    Hulme AC (1956) Nature Lond 178:991CrossRefGoogle Scholar
  65. 65.
    Whiting GC (1957) Nature 179:531CrossRefGoogle Scholar
  66. 66.
    Hillis WE, Carle A (1958) Holzforschung 12:136CrossRefGoogle Scholar
  67. 67.
    Hasegawa M, Tateoka T (1960) J Jap For Soc 42:224Google Scholar
  68. 68.
    Awang DVC, Blumenthal M (2006) HerbalGram 70:58Google Scholar
  69. 69.
    Anet EF, Birch AJ, Massy-Westropp RA (1957) Aust J Chem 10:93CrossRefGoogle Scholar
  70. 70.
    Bharathi A, Wang YH, Smillie TG, Khan IA (2009) Chromatographia 69:307CrossRefGoogle Scholar
  71. 71.
    Adams H, Bailey N, Brettle R, Cross R, Frederickson M, Haslam E, MacBeath F, Davies G (1996) Tetrahedron 52:8565CrossRefGoogle Scholar
  72. 72.
    Wang XQ, Guo YD, Yang CB (2001) Zhongguo Zhongyao Zazh (Chinese) 26:447Google Scholar
  73. 73.
    Weinstein LH, Porter CA, Laurencot HJ (1962) Contrib Boyce Thompson Inst 21:439Google Scholar
  74. 74.
    Underhill EW, Watkin JE, Neish AC (1957) Can J Biochem Physiol 35:219CrossRefGoogle Scholar
  75. 75.
    Li S, Yuan W, Wang P, Zhang Z, Zhang W, Ownby S (2007) Processes for the extraction and purification of shikimic acid and the products of such processes. Patent US2007/0161818Google Scholar
  76. 76.
    Sui R (2008) Chem Eng Technol 31:469CrossRefGoogle Scholar
  77. 77.
    Mitsuhashi S, Davis BD (1954) Biochim Biophys Acta 15:268CrossRefGoogle Scholar
  78. 78.
    Millican RC (1962) Biochim Biophys Acta 57:407CrossRefGoogle Scholar
  79. 79.
    Iomantas YAV, Abalkina EG, Polanuer BM, Yampolskaya TA, Bachina TA, Kozlov YI (1999) Sposob polucheniya shikimovoi kisloty. Patent RU2206612C2 (in Russian)Google Scholar
  80. 80.
    Iomantas YAV, Abalkina EG, Polanuer BM, Yampolskaya TA, Bachina TA, Kozlov YI (2002) Method for producing shikimic acid. Patent US6,436,664Google Scholar
  81. 81.
    Frost JW (2007) Methods and materials for the production of shikimic acid. Patent US2007/087424Google Scholar
  82. 82.
    Draths KM, Knop DR, Frost JW (1999) J Am Chem Soc 121:1603CrossRefGoogle Scholar
  83. 83.
    Johansson L, Lindskog A, Silfversparre G, Cimander C, Nielsen K, Lide G (2005) Biotechnol Bioeng 92:541CrossRefGoogle Scholar
  84. 84.
    Van der Does T, Booij J, Kers EE, Leenderts EJAM, Sibeijn M, Agayn V (2002) Process for the recovery of shikimic acid. Patent WO02/06203Google Scholar
  85. 85.
    Adachi O, Ano Y, Toyama H, Matsushita K (2006) Biosci Biotechnol Biochem 70:2579CrossRefGoogle Scholar
  86. 86.
    Adachi O, Tanaspawat S, Yoshihara N, Toyama H, Matsushita K (2003) Biosci Biotechnol Biochem 67:2124CrossRefGoogle Scholar
  87. 87.
    Adachi O, Tanaspawat S, Yoshihara N, Toyama H, Matsushita K (2003) Biosci Biotechnol Biochem 67:2112Google Scholar
  88. 88.
    Adachi O, Moonmangmee D, Toyama H, Yamada M, Shinagawa E, Matsushita K (2003) Appl Microbiol Biotechnol 60:643Google Scholar
  89. 89.
    Adachi O, Moonmangmee D, Shinagawa E, Toyama H, Yamada M, Matsushita K (2003) Biosci Biotechnol Biochem 67:10Google Scholar
  90. 90.
    Metzenberg RL, Mitchell HK (1958) Biochem J 68:168Google Scholar
  91. 91.
    Hathway DE (1956) Biochem J 63:380Google Scholar
  92. 92.
    Hennig K, Burkhardt R (1958) Weinberg Keller 5:542Google Scholar
  93. 93.
    Gordon HT, Thornburg W, Werun LN (1956) Anal Chem 28:849CrossRefGoogle Scholar
  94. 94.
    Simonart P, Wiaux A (1960) Nature 186:78CrossRefGoogle Scholar
  95. 95.
    Hillis WE, Carle A (1960) Biochem J 74:607Google Scholar
  96. 96.
    Davis BD, Mingioli ES (1953) J Bacteriol 66:129Google Scholar
  97. 97.
    Coulson CB, Evans WC (1958) J Chromatog 1:374CrossRefGoogle Scholar
  98. 98.
    Carr JG, Pollard A, Whiting GC, Williams AH (1957) Biochem J 66:283Google Scholar
  99. 99.
    Holmes GW, Kurth EF (1961) Tappi 44:893Google Scholar
  100. 100.
    Tachi I, Sato A (1960) Bull Agr Chem Soc Japan 24:633CrossRefGoogle Scholar
  101. 101.
    Hattori S, Yoshida S, Hasegawa M (1958) Arch Biochem Biophys 74:480CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2011

Authors and Affiliations

  • Denis V. Bochkov
    • 1
  • Sergey V. Sysolyatin
    • 1
  • Alexander I. Kalashnikov
    • 1
  • Irina A. Surmacheva
    • 1
  1. 1.Institute for Problems of Chemical and Energetic TechnologiesSiberian Branch of the Russian Academy of Sciences (IPCET SB RAS)BiyskRussia

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