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Volumn 109, Issue 9, 2015, Pages 1672-1679

Shikimic acid: A highly prospective molecule in pharmaceutical industry

Author keywords

Aromatic compounds; Pharmaceutical industry; Shikimic acid; Star anise

Indexed keywords


EID: 84952009442     PISSN: 00113891     EISSN: None     Source Type: Journal    
DOI: 10.18520/v109/i9/1672-1679     Document Type: Review
Times cited : (31)

References (45)
  • 1
    • 77957711113 scopus 로고    scopus 로고
    • Oseltamivir in seasonal, avian H5N1 and pandemic 2009 AH1N1 influenza: pharmacokinetic and pharmacodynamic characteristics
    • Widmer, N., Meylan, P., Ivanyuk, A., Aouri, M., Decosterd, L. A. and Buclin, T., Oseltamivir in seasonal, avian H5N1 and pandemic 2009 AH1N1 influenza: pharmacokinetic and pharmacodynamic characteristics. Clin. Pharmacokinet., 2010, 49, 741-765.
    • (2010) Clin. Pharmacokinet , vol.49 , pp. 741-765
    • Widmer, N.1    Meylan, P.2    Ivanyuk, A.3    Aouri, M.4    Decosterd, L.A.5    Buclin, T.6
  • 2
    • 84989999507 scopus 로고
    • Sur les principes constituants de l'Illicium religiosum (Sieb.) (Shikimi-no-ki en japonais)
    • Eykman, J. F., Sur les principes constituants de l'Illicium religiosum (Sieb.) (Shikimi-no-ki en japonais). Rec. Trav. Chim. Pays-Bas., 1885, 4, 32-54.
    • (1885) Rec. Trav. Chim. Pays-Bas , vol.4 , pp. 32-54
    • Eykman, J.F.1
  • 7
    • 85027474953 scopus 로고
    • Zur Kenntnis der Acylderivate der Chinasäure
    • Karrer, P. and Link, K. P., Zur Kenntnis der Acylderivate der Chinasäure. Helv. Chim. Acta, 1927, 10, 794-799.
    • (1927) Helv. Chim. Acta , vol.10 , pp. 794-799
    • Karrer, P.1    Link, K.P.2
  • 8
    • 0010622099 scopus 로고
    • Darstellung und Eigenschaften des Shikimialdehyds
    • Grewe, R. and Bllttner, H., Darstellung und Eigenschaften des Shikimialdehyds. Chem. Ber., 1958, 91, 2452-2458.
    • (1958) Chem. Ber , vol.91 , pp. 2452-2458
    • Grewe, R.1    Bllttner, H.2
  • 9
    • 84982059167 scopus 로고
    • Darstellung und Eigenschaften des Chinaaldehyds
    • Grewe, R. and Haendler, H., Darstellung und Eigenschaften des Chinaaldehyds. Liebigs Ann. Chem., 1962, 658, 113-119.
    • (1962) Liebigs Ann. Chem , vol.658 , pp. 113-119
    • Grewe, R.1    Haendler, H.2
  • 10
    • 84859800949 scopus 로고    scopus 로고
    • Shikimic acid: review of its analytical, isolation, and purification techniques from plant and microbial sources
    • Bochkov, D. V., Sysolyatin, S. V., Kalashnikov, A. I. and Surmacheva, I. A., Shikimic acid: review of its analytical, isolation, and purification techniques from plant and microbial sources. J. Chem. Biol., 2012, 5, 5-17.
    • (2012) J. Chem. Biol , vol.5 , pp. 5-17
    • Bochkov, D.V.1    Sysolyatin, S.V.2    Kalashnikov, A.I.3    Surmacheva, I.A.4
  • 11
    • 17244362180 scopus 로고    scopus 로고
    • Isolation of shikimic acid from star aniseed
    • Payne, R. and Edmonds, M., Isolation of shikimic acid from star aniseed. J. Chem. Educ., 2005, 82, 599-600.
    • (2005) J. Chem. Educ , vol.82 , pp. 599-600
    • Payne, R.1    Edmonds, M.2
  • 12
    • 0029959052 scopus 로고    scopus 로고
    • Pathway engineering for the production of aromatic compounds in Escherichia coli
    • Flores, N., Xiao, J., Berry, A., Bolivar, F. and Valle, F., Pathway engineering for the production of aromatic compounds in Escherichia coli. Nature Biotechnol., 1996, 14, 620-623.
    • (1996) Nature Biotechnol , vol.14 , pp. 620-623
    • Flores, N.1    Xiao, J.2    Berry, A.3    Bolivar, F.4    Valle, F.5
  • 13
    • 84873179221 scopus 로고    scopus 로고
    • A short overview on the medicinal chemistry of (-)-shikimic acid
    • Estévez, A. M. and Estévez, R. J., A short overview on the medicinal chemistry of (-)-shikimic acid. Mini. Rev. Med. Chem., 2012, 12, 1443-1454.
    • (2012) Mini. Rev. Med. Chem , vol.12 , pp. 1443-1454
    • Estévez, A.M.1    Estévez, R.J.2
  • 14
    • 68949208418 scopus 로고    scopus 로고
    • Rapid separation of shikimic acid from Chinese star anise (Illicium verum Hook. f.) with hot water extraction
    • Ohira, H., Torii, N., Aida, T. M., Watanabe, M. and Smith Jr, R. L., Rapid separation of shikimic acid from Chinese star anise (Illicium verum Hook. f.) with hot water extraction. Sep. Purif. Technol., 2009, 69, 102-108.
    • (2009) Sep. Purif. Technol , vol.69 , pp. 102-108
    • Ohira, H.1    Torii, N.2    Aida, T.M.3    Watanabe, M.4    Smith, R.L.5
  • 15
    • 0037471581 scopus 로고    scopus 로고
    • Shikimate accumulates in both glyphosate-sensitive and glyphosate-resistant horseweed (Conyza canadensis L. Cronq.)
    • Mueller, T. C., Massey, J. H., Hayes, R. M., Main, C. L. and Stewart Jr, C. N., Shikimate accumulates in both glyphosate-sensitive and glyphosate-resistant horseweed (Conyza canadensis L. Cronq.). Food Chem., 2003, 51, 680-684.
    • (2003) Food Chem , vol.51 , pp. 680-684
    • Mueller, T.C.1    Massey, J.H.2    Hayes, R.M.3    Main, C.L.4    Stewart, C.N.5
  • 17
    • 84899554241 scopus 로고    scopus 로고
    • Extraction technology of shikimic acid homogenate from Picea koraiensis optimized by response surface methodology
    • Yang, L., Huang, J. and Liu, T., Extraction technology of shikimic acid homogenate from Picea koraiensis optimized by response surface methodology. For. Eng., 2010, 26, 9-13.
    • (2010) For. Eng , vol.26 , pp. 9-13
    • Yang, L.1    Huang, J.2    Liu, T.3
  • 18
    • 84899581186 scopus 로고    scopus 로고
    • Extraction and chromatographic determination of shikimic acid in Chinese conifer needles with 1-benzyl-3-methylimidazolium bromide ionic liquid aqueous solutions
    • Chen, F., Hou, K., Li, S., Zu, Y. and Yang, L., Extraction and chromatographic determination of shikimic acid in Chinese conifer needles with 1-benzyl-3-methylimidazolium bromide ionic liquid aqueous solutions. J. Anal. Meth. Chem., 2014, 1-12.
    • (2014) J. Anal. Meth. Chem , pp. 1-12
    • Chen, F.1    Hou, K.2    Li, S.3    Zu, Y.4    Yang, L.5
  • 19
    • 0010586724 scopus 로고
    • Sur la recherche des acides quinique et shikimique, de la bergenine et desheterosides chez quelques hamamelidacees
    • Plouvier, V., Sur la recherche des acides quinique et shikimique, de la bergenine et desheterosides chez quelques hamamelidacees. CR Hebd. Seances Acad. Sci., 1961, 52, 599.
    • (1961) CR Hebd. Seances Acad. Sci , vol.52 , pp. 599
    • Plouvier, V.1
  • 20
    • 36949075763 scopus 로고
    • Organic acids of the rhizome of Iris pseudacorus L
    • Henshaw, G. G., Coult, D. A. and Boulter, D., Organic acids of the rhizome of Iris pseudacorus L. Nature, 1962, 194, 579.
    • (1962) Nature , vol.194 , pp. 579
    • Henshaw, G.G.1    Coult, D.A.2    Boulter, D.3
  • 21
    • 0029951044 scopus 로고    scopus 로고
    • The shikimate pathway. Part 8. Synthesis of (-)-3(R)-amino-4(R),5(R)-dihydroxy-1-cyclohexene-1-carboxylic acid: the 3(R)-amino analogue of (-)-shikimic acid
    • Adams, H. et al., The shikimate pathway. Part 8. Synthesis of (-)-3(R)-amino-4(R),5(R)-dihydroxy-1-cyclohexene-1-carboxylic acid: the 3(R)-amino analogue of (-)-shikimic acid. Tetrahedron, 1996, 52, 8565-8580.
    • (1996) Tetrahedron , vol.52 , pp. 8565-8580
    • Adams, H.1
  • 22
    • 70349150859 scopus 로고    scopus 로고
    • Prospecting for alternate sources of shikimic acid, a precursor of Tamiflu, a bird-flu drug
    • Raghavendra, T. R. et al., Prospecting for alternate sources of shikimic acid, a precursor of Tamiflu, a bird-flu drug. Curr. Sci., 2009, 96, 771-772.
    • (2009) Curr. Sci , vol.96 , pp. 771-772
    • Raghavendra, T.R.1
  • 23
    • 0032079254 scopus 로고    scopus 로고
    • Chemical synthesis of shikimic acid and its analogues
    • Jiang, S. and Singh, G., Chemical synthesis of shikimic acid and its analogues. Tetrahedron, 1998, 54, 4697-4753.
    • (1998) Tetrahedron , vol.54 , pp. 4697-4753
    • Jiang, S.1    Singh, G.2
  • 25
    • 84951943131 scopus 로고    scopus 로고
    • Ambhaikar, 2005; https://www.scripps.edu/baran/images/grpmtgpdf/Ambhaikar_Jan_05.pdf.
    • (2005) Ambhaikar
  • 26
    • 37049055412 scopus 로고
    • A stereospecific total synthesis of D-(-)-shikimic acid
    • McCrindle, R., Overton, K. H. and Raphael, R. A., A stereospecific total synthesis of D-(-)-shikimic acid. J. Chem. Soc., 1960, 1560-1565.
    • (1960) J. Chem. Soc , pp. 1560-1565
    • McCrindle, R.1    Overton, K.H.2    Raphael, R.A.3
  • 27
  • 29
    • 84943911961 scopus 로고
    • Eine neue synthese der Skikimisäure
    • Grewe, R. and Hinrichs, I., Eine neue synthese der Skikimisäure. Chem. Ber., 1964, 97, 443-448.
    • (1964) Chem. Ber , vol.97 , pp. 443-448
    • Grewe, R.1    Hinrichs, I.2
  • 30
    • 0010552794 scopus 로고
    • Natural product synthesis via allylsilanes. 1. Synthesis and reactions of (1E, 3E)-4-acetoxy-1-(trimethylsilyl)-1,3-butadiene and its use in the total synthesis of (±)-shikimic acid
    • Koreeda, M. and Ciufolini, M. A., Natural product synthesis via allylsilanes. 1. Synthesis and reactions of (1E, 3E)-4-acetoxy-1-(trimethylsilyl)-1,3-butadiene and its use in the total synthesis of (±)-shikimic acid. J. Am. Chem. Soc., 1982, 104, 2308-2310.
    • (1982) J. Am. Chem. Soc , vol.104 , pp. 2308-2310
    • Koreeda, M.1    Ciufolini, M.A.2
  • 31
    • 0025074916 scopus 로고
    • (1E, 3E)-4-Acetoxy-1-phenyldimethylsilyl-1,3-butadiene as a surrogate for (1E,3E)-1,4-diacetoxy-1,3-butadiene: a highly efficient synthesis of (±)-shikimic acid
    • Koreeda, M., Teng, K. and Murata, T., (1E, 3E)-4-Acetoxy-1-phenyldimethylsilyl-1,3-butadiene as a surrogate for (1E,3E)-1,4-diacetoxy-1,3-butadiene: a highly efficient synthesis of (±)-shikimic acid. Tetrahedron Lett., 1990, 31, 5997-6000.
    • (1990) Tetrahedron Lett , vol.31 , pp. 5997-6000
    • Koreeda, M.1    Teng, K.2    Murata, T.3
  • 32
    • 0001471393 scopus 로고
    • Aromatic biosynthesis. XIII. Conversion of quinic acid to 5-dehydroquinic acid by quinic dehydrogenase
    • Mitsuhashi, S. and Davis, B. D., Aromatic biosynthesis. XIII. Conversion of quinic acid to 5-dehydroquinic acid by quinic dehydrogenase. Biochim. Biophys. Acta, 1954, 15, 268.
    • (1954) Biochim. Biophys. Acta , vol.15 , pp. 268
    • Mitsuhashi, S.1    Davis, B.D.2
  • 33
    • 4243905968 scopus 로고
    • A thiobarbituric acid assay for shikimic acid
    • Millican, R. C., A thiobarbituric acid assay for shikimic acid. Biochim. Biophys. Acta, 1962, 57, 407-409.
    • (1962) Biochim. Biophys. Acta , vol.57 , pp. 407-409
    • Millican, R.C.1
  • 34
    • 84929577032 scopus 로고    scopus 로고
    • Current perspectives on applications of shikimic and aminoshikimic acids in pharmaceutical chemistry
    • Quiroz, D. C. D., Carmona, S. B., Bolívar, F. and Adelfo Escalante, A., Current perspectives on applications of shikimic and aminoshikimic acids in pharmaceutical chemistry. Res. Rep. Med. Chem., 2014, 4, 35-46.
    • (2014) Res. Rep. Med. Chem , vol.4 , pp. 35-46
    • Quiroz, D.C.D.1    Carmona, S.B.2    Bolívar, F.3    Adelfo Escalante, A.4
  • 35
    • 84871833125 scopus 로고    scopus 로고
    • Influenza neuraminidase inhibitors: antiviral action and mechanisms of resistance
    • McKimm-Breschkin, J. L., Influenza neuraminidase inhibitors: antiviral action and mechanisms of resistance. Influenza Respir. Viruses, 2013, 7, 25-36.
    • (2013) Influenza Respir. Viruses , vol.7 , pp. 25-36
    • McKimm-Breschkin, J.L.1
  • 36
    • 0031048319 scopus 로고    scopus 로고
    • Influenza neuraminidase inhibitor possessing a novel hydrophobic interaction in the enzyme active site: design, synthesis, and structural analysis of carbocyclic sialic acid analogues with potent anti-influenza activity
    • Kim, C. U. et al., Influenza neuraminidase inhibitor possessing a novel hydrophobic interaction in the enzyme active site: design, synthesis, and structural analysis of carbocyclic sialic acid analogues with potent anti-influenza activity. J. Am. Chem. Soc., 1997, 119, 681-690.
    • (1997) J. Am. Chem. Soc , vol.119 , pp. 681-690
    • Kim, C.U.1
  • 37
    • 0032568893 scopus 로고    scopus 로고
    • Practical total synthesis of the anti-influenza drug GS-4104
    • Rohloff, J. C. et al., Practical total synthesis of the anti-influenza drug GS-4104. J. Org. Chem., 1998, 63, 4545-4550.
    • (1998) J. Org. Chem , vol.63 , pp. 4545-4550
    • Rohloff, J.C.1
  • 38
    • 0035937274 scopus 로고    scopus 로고
    • New, azide-free transformation of epoxides into 1,2-diamino compounds:?? synthesis of the antiinfluenza neuraminidase inhibitor oseltamivir phosphate (Tamiflu)
    • Karpf, M. and Trussardi, R., New, azide-free transformation of epoxides into 1,2-diamino compounds:?? synthesis of the antiinfluenza neuraminidase inhibitor oseltamivir phosphate (Tamiflu). J. Org. Chem., 2001, 66, 2044-2051.
    • (2001) J. Org. Chem , vol.66 , pp. 2044-2051
    • Karpf, M.1    Trussardi, R.2
  • 39
    • 0033435755 scopus 로고    scopus 로고
    • Industrial synthesis of the key precursor in the synthesis of the anti-influenza drug oseltamivir phosphate (Ro 64-0796/002, GS-4104-02): ethyl (3R,4S,5S)-4,5-epoxy-3-(1-ethyl-propoxy)-cyclohex-1-ene-1-carboxylate
    • Federspiel, M. et al., Industrial synthesis of the key precursor in the synthesis of the anti-influenza drug oseltamivir phosphate (Ro 64-0796/002, GS-4104-02): ethyl (3R,4S,5S)-4,5-epoxy-3-(1-ethyl-propoxy)-cyclohex-1-ene-1-carboxylate. Org. Proc. Res. Dev., 1999, 3, 266-274.
    • (1999) Org. Proc. Res. Dev , vol.3 , pp. 266-274
    • Federspiel, M.1
  • 40
    • 33749381842 scopus 로고    scopus 로고
    • New approach to the total synthesis of (-)-zeylenone from shikimic acid
    • Zhang, Y., Liu, A., Ye, Z. G., Lin, J., Xu, L. Z. and Yang, S. L., New approach to the total synthesis of (-)-zeylenone from shikimic acid. Chem. Pharm. Bull. (Tokyo), 2006, 54, 1459-1461.
    • (2006) Chem. Pharm. Bull. (Tokyo) , vol.54 , pp. 1459-1461
    • Zhang, Y.1    Liu, A.2    Ye, Z.G.3    Lin, J.4    Xu, L.Z.5    Yang, S.L.6
  • 41
    • 0025728850 scopus 로고
    • Shikimic acid complexes of platinum, Preparation, reactivity, and antitumor activity of (R,R-1,2-diaminocyclohexane) bis(shikimate) platinum (II). Evidence for a novel rearrangement involving platinum-carbon bond formation
    • Farrell, N., Roberts, J. D. and Hacker, M. P., Shikimic acid complexes of platinum. Preparation, reactivity, and antitumor activity of (R,R-1,2-diaminocyclohexane) bis(shikimate) platinum (II). Evidence for a novel rearrangement involving platinum-carbon bond formation. J. Inorg. Biochem., 1991, 42, 237-246.
    • (1991) J. Inorg. Biochem , vol.42 , pp. 237-246
    • Farrell, N.1    Roberts, J.D.2    Hacker, M.P.3
  • 42
    • 0036150511 scopus 로고    scopus 로고
    • Anti-platelet and antithrombotic effects of triacetylshikimic acid in rats
    • Huang, F., Xiu, Q., Sun, J. and Hong, E., Anti-platelet and antithrombotic effects of triacetylshikimic acid in rats. J. Cardiovasc. Pharmacol., 2002, 39, 262-270.
    • (2002) J. Cardiovasc. Pharmacol , vol.39 , pp. 262-270
    • Huang, F.1    Xiu, Q.2    Sun, J.3    Hong, E.4
  • 43
    • 33745714341 scopus 로고    scopus 로고
    • Novel and efficient syntheses of (-)-methyl 4-epishikimate and 4,5-epoxyquinic and-shikimic acid derivatives as key precursors to prepare new analogues
    • Sanchez-Abella, L., Fernández, S., Armesto, N., Ferrero, M. and Gotor, V., Novel and efficient syntheses of (-)-methyl 4-epishikimate and 4,5-epoxyquinic and-shikimic acid derivatives as key precursors to prepare new analogues. J. Org. Chem., 2006, 71, 5396-5399.
    • (2006) J. Org. Chem , vol.71 , pp. 5396-5399
    • Sanchez-Abella, L.1    Fernández, S.2    Armesto, N.3    Ferrero, M.4    Gotor, V.5
  • 44
    • 84884904392 scopus 로고    scopus 로고
    • Total syntheses of (+)-valiolamine and (-)-1-epi-valiolamine from naturally abundant (-)-shikimic acid
    • Quan, N., Nie, L. D., Zhu, R. H., Shi, X. X., Ding, W. and Lu, X., Total syntheses of (+)-valiolamine and (-)-1-epi-valiolamine from naturally abundant (-)-shikimic acid. Eur. J. Org. Chem., 2013, 78, 6389-6396.
    • (2013) Eur. J. Org. Chem , vol.78 , pp. 6389-6396
    • Quan, N.1    Nie, L.D.2    Zhu, R.H.3    Shi, X.X.4    Ding, W.5    Lu, X.6
  • 45
    • 84877742688 scopus 로고    scopus 로고
    • Expanding horizons of shikimic acid. Recent progresses in production and its endless frontiers in application and market trends
    • Rawat, G., Tripathi, P. and Saxena, R. K., Expanding horizons of shikimic acid. Recent progresses in production and its endless frontiers in application and market trends. Appl. Microbiol. Biotechnol., 2013, 97, 4277-4287.
    • (2013) Appl. Microbiol. Biotechnol , vol.97 , pp. 4277-4287
    • Rawat, G.1    Tripathi, P.2    Saxena, R.K.3


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