Skip to main content
SpringerLink
Log in

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

  • Review
  • Published:
Journal of Chemical Biology

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Brown SA (1964) Biochemistry of phenolic compounds. Academic, New York

    Google Scholar 

  2. Bradley D (2005) Nat Rev Drug Discov 4:945

    Article  CAS  Google Scholar 

  3. Enrich LB, Scheuermann ML, Mohadjer A, Matthias KR, Eller CF, Newman MS, Fujinaka M, Poon T (2008) Tetrahedron Lett 49:2503

    Article  CAS  Google Scholar 

  4. Lingens F (2003) Angew Chem Int Edit 7:350

    Article  Google Scholar 

  5. Mair H (2000) Patent US006130354

  6. Zhang Y, Liu A, Ye ZG, Lin J, Xu LZ, Yang SL (2006) Chem Pharm Bull 54:1459

    Article  CAS  Google Scholar 

  7. Luhong T, Hong X, Yang S, Liying Q, Dongqun C, Chao D, Wei C (2009) Appl Biochem Biotechnol 158:408

    Article  Google Scholar 

  8. Huang F, Xiu Q, Sun J, Hong E (2002) J Cardiovasc Pharmacol 39:262

    Article  CAS  Google Scholar 

  9. Jiang S, Singh G, Boam DJ, Coggins JR (1999) Tetr Assym 10:4087

    Article  CAS  Google Scholar 

  10. Song C, Jiang S, Singh G (2001) Tetr Assym 42:9069

    CAS  Google Scholar 

  11. Gibson JM, Thomas PS, Thomas JD, Barker JL, Chandran SS, Harrup MK, Draths KM, Frost JW (2001) Angew Chem Int Ed 40:1945

    Article  CAS  Google Scholar 

  12. McCrindle R, Overton KH, Raphael RA (1960) J Chem Soc, p 1560

  13. Wada H, Kido T, Tanaka N, Murakami T, Saiki Y, Chen CM (1992) Chem Pharm Bull 40:2099

    Article  CAS  Google Scholar 

  14. Snyder D, Rapoport H (1973) J Am Chem Soc 95:7821

    Article  CAS  Google Scholar 

  15. Shinada T, Yoshida Y, Ohfune Y (1998) Tetrahedron Lett 39:6027

    Article  CAS  Google Scholar 

  16. Achenbach H, Schwinn A (1995) Phytochemistry 38:1037

    Article  CAS  Google Scholar 

  17. Salamon II, Davis BD (1953) J Am Chem Soc 75:5567

    Article  CAS  Google Scholar 

  18. Weiss U, Ziffer H (1963) J Org Chem 28:1248

    Article  CAS  Google Scholar 

  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 44:2080

    Article  CAS  Google Scholar 

  20. Smissman EE, Suh JT, Oxman M, Daniels R (1962) J Am Chem Soc 84:1040

    Article  CAS  Google Scholar 

  21. Evans DA, Barnes DM (1997) Tetrahedron Lett 38:57

    Article  CAS  Google Scholar 

  22. Hill RK, Newkome GR (1969) J Am Chem Soc 91:5893

    Article  CAS  Google Scholar 

  23. Coblens KE, Muralidharan VB, Ganem B (1982) J Org Chem 47:5041

    Article  CAS  Google Scholar 

  24. Luthe C, Zamir LO (1983) Tetrahedron Lett 24:4409

    Article  CAS  Google Scholar 

  25. Mirza S, Harvey J (1991) Tetrahedron Lett 32:4111

    Article  CAS  Google Scholar 

  26. Brazdova B, Tan NS, Samoshina NM, Samoshin VV (2009) Carbohyd Res 344:311

    Article  CAS  Google Scholar 

  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 50:1101

    Article  CAS  Google Scholar 

  28. Reyes-Chilpa R, Estrada-Muñiz E, Apan TR, Amekraz B, Aumelas A, Jankowski CK, Vázquez-Torres M (2004) Life Sci 75:1635

    Article  CAS  Google Scholar 

  29. Shende J, McCullough KJ, Boualem M, Gurdial S, Richard HW (1997) J Chem Soc Perkin Trans 1:1805

    Google Scholar 

  30. Perkins HJ, Aronof TS (1959) Can J Biochem Physiol 37:149

    Article  CAS  Google Scholar 

  31. Zaprometov MN (1961) Biokhimiya 26:597

    CAS  Google Scholar 

  32. Yoshida S, Hasegawa M (1957) Arch Biochem Biophys 70:377

    Article  CAS  Google Scholar 

  33. Gaitonde MK, Gordon MW (1958) J Biol Chem 230:1043

    CAS  Google Scholar 

  34. Saslaw LD, Waravdekar VS (1960) Biochim Biophys Acta 37:367

    Article  CAS  Google Scholar 

  35. Millican RC (1963) Anal Biochem 6:181

    Article  CAS  Google Scholar 

  36. Payne R, Edmonds M (2005) J Chem Educ 82:599

    Article  CAS  Google Scholar 

  37. Schuster MC, Mann DA, Buchholz TJ, Johnson KM, Thomas WD, Kiessling LL (2003) Org Lett 5:140

    Article  Google Scholar 

  38. Nonaka G, Ageta M, Nishioka I (1985) Chem Pharm Bull 33:96

    Article  CAS  Google Scholar 

  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)

  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) 1:119–122

    Google Scholar 

  41. Bresnahan G, Manthey F, Howatt K, Chakraborty M (2003) J Agric Food Chem 51:4004

    Article  CAS  Google Scholar 

  42. Silva B, Andrade P, Mendes G, Seabra R, Ferreira M (2002) J Agric Food Chem 50:2313

    Article  CAS  Google Scholar 

  43. Dainiak MB, Galaev IY, Mattiasson B (2002) J Chromatogr A 942:123

    Article  CAS  Google Scholar 

  44. García Romero E, Sánchez Muñoz G, Martín Alvarez PJ, Cabezudo Ibáñez MD (1993) J Chromatogr A 655:111

    Article  Google Scholar 

  45. Tusseau D, Benoit C (1987) J Chromatogr A 395:323

    Article  CAS  Google Scholar 

  46. Mardones C, Hitschfeld A, Contreras A, Lepe K, Gutiérrez L, Baer D (2005) J Chromatogr A 1085:285

    Article  CAS  Google Scholar 

  47. Nagels L, Debeuf C, Esmans E (1980) J Chromatogr A 190:411

    Article  CAS  Google Scholar 

  48. Heimler D, Pieroni A (1994) Chromatographia 38:475

    Article  CAS  Google Scholar 

  49. Molnár-Perl I, Vasanits A, Horváth K (1998) Chromatographia 48:111

    Article  Google Scholar 

  50. Horváth K, Molnár-Perl I (1998) Chromatographia 48:120

    Article  Google Scholar 

  51. Jaroszynska J (2003) Anal Bioanal Chem 377:702

    Article  CAS  Google Scholar 

  52. Liu HC, Li QW, Tang LB (2007) J Zhejiang Univ Sci B 8:272

    Article  CAS  Google Scholar 

  53. Ibarz MJ, Ferreira V, Hernandez-Orte P, Loscos N, Cacho J (2006) J Chromatogr A 1116:217

    Article  Google Scholar 

  54. Eykman JF (1885) Rec Trav Chim 4:32

    Article  Google Scholar 

  55. Wallace KK, Reynolds KA, Koch K, McArthur HAI, Brown MS, Wax RG, Moore BS (1994) J Am Chem Soc 116:11600

    Article  CAS  Google Scholar 

  56. Flores N, Xiao J, Berry A, Bolivar F, Valle F (1996) Nature Biotechnol 14:620

    Article  CAS  Google Scholar 

  57. Herlt AJ, Rickards RW, Wu JP (1985) J Antibiot 38:516

    CAS  Google Scholar 

  58. Jones AL, Keller U (1997) In: Strohl WR (ed) Biochemistry and genetics of actinomycin production. Marcel Dekker, New York

    Google Scholar 

  59. Wilson DJ, Patton S, Florova G, Hale V, Reynold KA (1998) J Ind Microbiol Biot 20:299

    Article  Google Scholar 

  60. Bentley R (1990) Biochem Mol Biol 25:307

    Article  CAS  Google Scholar 

  61. Hasegawa M, Nakagawa T, Yoshida S (1957) J Jap For Soc 39:159

    CAS  Google Scholar 

  62. Henshaw GG, Coult DA, Boulter D (1962) Nature 194:579

    Article  CAS  Google Scholar 

  63. Neish AC (1958) Can J Botany 36:649

    Article  Google Scholar 

  64. Hulme AC (1956) Nature Lond 178:991

    Article  CAS  Google Scholar 

  65. Whiting GC (1957) Nature 179:531

    Article  CAS  Google Scholar 

  66. Hillis WE, Carle A (1958) Holzforschung 12:136

    Article  CAS  Google Scholar 

  67. Hasegawa M, Tateoka T (1960) J Jap For Soc 42:224

    CAS  Google Scholar 

  68. Awang DVC, Blumenthal M (2006) HerbalGram 70:58

    Google Scholar 

  69. Anet EF, Birch AJ, Massy-Westropp RA (1957) Aust J Chem 10:93

    Article  CAS  Google Scholar 

  70. Bharathi A, Wang YH, Smillie TG, Khan IA (2009) Chromatographia 69:307

    Article  Google Scholar 

  71. Adams H, Bailey N, Brettle R, Cross R, Frederickson M, Haslam E, MacBeath F, Davies G (1996) Tetrahedron 52:8565

    Article  CAS  Google Scholar 

  72. Wang XQ, Guo YD, Yang CB (2001) Zhongguo Zhongyao Zazh (Chinese) 26:447

    CAS  Google Scholar 

  73. Weinstein LH, Porter CA, Laurencot HJ (1962) Contrib Boyce Thompson Inst 21:439

    CAS  Google Scholar 

  74. Underhill EW, Watkin JE, Neish AC (1957) Can J Biochem Physiol 35:219

    Article  CAS  Google Scholar 

  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 US2007/0161818

  76. Sui R (2008) Chem Eng Technol 31:469

    Article  CAS  Google Scholar 

  77. Mitsuhashi S, Davis BD (1954) Biochim Biophys Acta 15:268

    Article  CAS  Google Scholar 

  78. Millican RC (1962) Biochim Biophys Acta 57:407

    Article  CAS  Google Scholar 

  79. Iomantas YAV, Abalkina EG, Polanuer BM, Yampolskaya TA, Bachina TA, Kozlov YI (1999) Sposob polucheniya shikimovoi kisloty. Patent RU2206612C2 (in Russian)

  80. Iomantas YAV, Abalkina EG, Polanuer BM, Yampolskaya TA, Bachina TA, Kozlov YI (2002) Method for producing shikimic acid. Patent US6,436,664

  81. Frost JW (2007) Methods and materials for the production of shikimic acid. Patent US2007/087424

  82. Draths KM, Knop DR, Frost JW (1999) J Am Chem Soc 121:1603

    Article  CAS  Google Scholar 

  83. Johansson L, Lindskog A, Silfversparre G, Cimander C, Nielsen K, Lide G (2005) Biotechnol Bioeng 92:541

    Article  CAS  Google Scholar 

  84. Van der Does T, Booij J, Kers EE, Leenderts EJAM, Sibeijn M, Agayn V (2002) Process for the recovery of shikimic acid. Patent WO02/06203

  85. Adachi O, Ano Y, Toyama H, Matsushita K (2006) Biosci Biotechnol Biochem 70:2579

    Article  CAS  Google Scholar 

  86. Adachi O, Tanaspawat S, Yoshihara N, Toyama H, Matsushita K (2003) Biosci Biotechnol Biochem 67:2124

    Article  CAS  Google Scholar 

  87. Adachi O, Tanaspawat S, Yoshihara N, Toyama H, Matsushita K (2003) Biosci Biotechnol Biochem 67:2112

    Google Scholar 

  88. Adachi O, Moonmangmee D, Toyama H, Yamada M, Shinagawa E, Matsushita K (2003) Appl Microbiol Biotechnol 60:643

    CAS  Google Scholar 

  89. Adachi O, Moonmangmee D, Shinagawa E, Toyama H, Yamada M, Matsushita K (2003) Biosci Biotechnol Biochem 67:10

    Google Scholar 

  90. Metzenberg RL, Mitchell HK (1958) Biochem J 68:168

    CAS  Google Scholar 

  91. Hathway DE (1956) Biochem J 63:380

    CAS  Google Scholar 

  92. Hennig K, Burkhardt R (1958) Weinberg Keller 5:542

    Google Scholar 

  93. Gordon HT, Thornburg W, Werun LN (1956) Anal Chem 28:849

    Article  CAS  Google Scholar 

  94. Simonart P, Wiaux A (1960) Nature 186:78

    Article  CAS  Google Scholar 

  95. Hillis WE, Carle A (1960) Biochem J 74:607

    CAS  Google Scholar 

  96. Davis BD, Mingioli ES (1953) J Bacteriol 66:129

    CAS  Google Scholar 

  97. Coulson CB, Evans WC (1958) J Chromatog 1:374

    Article  CAS  Google Scholar 

  98. Carr JG, Pollard A, Whiting GC, Williams AH (1957) Biochem J 66:283

    CAS  Google Scholar 

  99. Holmes GW, Kurth EF (1961) Tappi 44:893

    CAS  Google Scholar 

  100. Tachi I, Sato A (1960) Bull Agr Chem Soc Japan 24:633

    Article  CAS  Google Scholar 

  101. Hattori S, Yoshida S, Hasegawa M (1958) Arch Biochem Biophys 74:480

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences (IPCET SB RAS), ul. Socialisticheskaya, 1, Biysk, 659322, Russia

    Denis V. Bochkov, Sergey V. Sysolyatin, Alexander I. Kalashnikov & Irina A. Surmacheva

Authors
  1. Denis V. Bochkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sergey V. Sysolyatin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Alexander I. Kalashnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Irina A. Surmacheva
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Denis V. Bochkov.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bochkov, D.V., Sysolyatin, S.V., Kalashnikov, A.I. et al. Shikimic acid: review of its analytical, isolation, and purification techniques from plant and microbial sources. J Chem Biol 5, 5–17 (2012). https://doi.org/10.1007/s12154-011-0064-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12154-011-0064-8

Keywords

Search

Navigation