Cryptomeria japonica (L. F.) D. Don as source of shikimic acid

Antonio Luiz Cerdeira; Sonia Claudia   Nascimento Queiroz; Marcus  Barifouse Matallo

doi:10.32712/2446-4775.2020.821

Cryptomeria japonica (L. F.) D. Don as source of shikimic acid

v. 14 n. 4 (2020)
462-468
24/07/2019
18/12/2020
https://doi.org/10.32712/2446-4775.2020.821

Antonio Luiz Cerdeira
Sonia Claudia Nascimento Queiroz
Marcus Barifouse Matallo

Palavras-chave

Resumo

Oseltamivir phosphate (OSP), marketed under the brand name of Tamiflu^Â®, is a potent inhibitor of viral neuraminidase, a glycoside hydrolase enzyme essential for viral replication. OSP is also important to control influenza virus (H1N1) and is produced mainly from shikimic acid (SA) extracted from plants. The main source of SA is from seeds of I. verum. Alternatives to meet the worldwide demand are necessary. One of this is Cryptomeria japonica. In this study, we found a content of 56.36 mg.kg^-1 of SA in dried biomass for C. japonica, while for I.verum, the traditional source, was 96.57 mg.kg^-1. Due to the fact of C. japonica is a tree, exploited for commercial production, it can be a renewable and reliable source SA for OSP production.

Referências

Lycett SJ, Duchatel F, Digard P. A brief history of bird flu. Philos Trans Royal Soc B. 2019; 374(1775). ISSN 0962-8436. [CrossRef].
Martirosyan L, Paget WJ, Jorgensen P, Brown CS, Meerhoff TJ, Pereyaslov D et al. The community impact of the 2009 influenza pandemic in the WHO European Region: a comparison with historical seasonal data from 28 countries. BMC Infect Dis [Internet]. 2012 Feb 12; 12: 36. Available from: [CrossRef] [PubMed].
Farina V, Brown JD. Tamiflu: The supply problem. Angew Chem. 2006; 45(44): 7330-4. ISSN 1433-7851. [CrossRef] [PubMed].
Abrecht S, Federspiel MC, Estermann H, Fischer R, Karpf M, Mair HJ et al. The synthetic-technical development of oseltamivir phosphate tamifluTM: A race against time. Chimia Inter J Chem. 2007; 61(3): 93-9. ISSN 0009-4293. [CrossRef].
Forleo-Neto E, Halker E, Santos VJ, Paiva TM, Toniolo-Neto J. Influenza. Rev Soc Bras Med Trop. 2003; 36(2): 267-74. ISSN 0037-8682. [CrossRef] [PubMed].
Kim CU, Lew W, Williams MA, Liu HT, Zhang LJ, Swaminathan S et al. Influenza neuraminidase inhibitors 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(4): 681-90. ISSN 0002-7863. [CrossRef] [PubMed].
Kramer M, Bongaerts J, Bovenberg R, Kremer S, Muller U, Orf S et al. Metabolic engineering for microbial production of shikimic acid. Metab Eng. 2003; 5(4): 277-83. ISSN 1096-7176. [CrossRef].
Borah JC. Shikimic acid: a highly prospective molecule in pharmaceutical industry. Curr Sci. 2015; 109(9): 1672-9. ISSN 0011-3891. [CrossRef].
Díaz Quiroz DC, Carmona SB, Bolívar F, A E. Current perspectives on applications of shikimic and aminoshikimic acids in pharmaceutical chemistry. Res Rep Med Chem. 2014; 4: 35-46. [CrossRef].
Cardoso SF, Lopes LMX, Nascimento IR. Eichhornia crassipes: an advantageous source of shikimic acid. Rev Bras Farmacogn. 2014; 24(4): 439-42. ISSN 0102-695X. [CrossRef].
Payne R, Edmonds M. Isolation of shikimic acid from star aniseed. J Chem Educ. 2005; 82(4): 599-600. ISSN 0021-9584. [CrossRef].
Sadaka M, Garcia A. Extraction of shikimic and quinic acids. Chem Eng Commun. 1999; 173(1): 91-102. ISSN 0098-6445. [CrossRef].
Raghavendra TR, Vaidyanathan P, Swathi HK, Ramesha BT, Ravikanth G, Ganeshaiah KN et al. Prospecting for alternate sources of shikimic acid, a precursor of Tamiflu, a bird-flu drug. Curr Sci. 2009; 96(6): 771-2. ISSN 0011-3891. [Link].
Bradley D. Star role for bacteria in controlling flu pandemic? Nat Rev Drug Discov. 2005; 4: 945. [CrossRef].
Kratz D, Wendling I, Brondani G.E. Concentrações de ácido indolbutírico no enraizamento de Cryptomeria japonica. J Biotec Biodivers. 2014; 2(3): 14-21. ISSN 2179-4804.
Santos CBd, Longhi SJ, Hoppe JM, Moscovich FA. Efeito do volume de tubetes e tipo de substratos na qualidade de mudas de Cryptomeria japonica (L.F.) D. Don. Cien Flore. 2000; 10(2): 1-15. [CrossRef].
Matallo MB, Almeida SDB, Cerdeira AL, Franco DA, Blanco FMG, Menezes PTC et al. Microwave-assisted solvent extraction and analysis of shikimic acid from plant tissues. Pl Dan. 2009; 27(spe): 987-94. ISSN 0100-8358. [CrossRef].
Bochkov DV, Sysolyatin SV, Kalashnikov AI, Surmacheva IA. Shikimic acid: review of its analytical, isolation, and purification techniques from plant and microbial sources. J Chem Biol. 2012; 5: 5-17. [CrossRef].
Sui R. Separation of shikimic acid from pine needles. Chem Eng Technol. 2008; 31(3): 469-73. ISSN 0930-7516. [CrossRef].
Enrich LB, Scheuermann ML, Mohadjer A, Matthias KR, Eller CF, Newman MS et al. Liquidambar styraciflua: a renewable source of shikimic acid. Tetrahedron Lett. 2008; 49(16): 2503-5. ISSN 0040-4039. [CrossRef].
Shimizu JY, Maiochi RA. Criptoméria como espécie alternativa para produção de madeira no Paraná. Pesqui Florest Bras. 2007; 5(54): 63-70. ISSN 1983-2605. [Link].

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Autor(es)

Antonio Luiz Cerdeira
Embrapa Environment, Highway SP 340 - Km 127.5, Jaguariúna, CEP 13820-000, SP, Brazil.
http://orcid.org/0000-0003-3636-8416
Sonia Claudia Nascimento Queiroz
Embrapa Meio Ambiente, Rodovia SP 340 - Km 127,5, Jaguariúna, CEP 13820-000, SP, Brasil.
http://orcid.org/0000-0002-1725-183X
Marcus Barifouse Matallo
Embrapa Meio Ambiente, Rodovia SP 340 - Km 127,5, Jaguariúna, CEP 13820-000, SP, Brasil.
http://orcid.org/0000-0003-0789-437X

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Como Citar

Cryptomeria japonica (L. F.) D. Don as source of shikimic acid . Rev Fitos [Internet]. 18º de dezembro de 2020 [citado 26º de dezembro de 2024];14(4):462-8. Disponível em: https://revistafitos.far.fiocruz.br/index.php/revista-fitos/article/view/821

Este trabalho está licenciado sob uma licença Creative Commons Attribution 4.0 International License.

[1] Lycett SJ, Duchatel F, Digard P. A brief history of bird flu. Philos Trans Royal Soc B. 2019; 374(1775). ISSN 0962-8436. [CrossRef].

[2] Martirosyan L, Paget WJ, Jorgensen P, Brown CS, Meerhoff TJ, Pereyaslov D et al. The community impact of the 2009 influenza pandemic in the WHO European Region: a comparison with historical seasonal data from 28 countries. BMC Infect Dis [Internet]. 2012 Feb 12; 12: 36. Available from: [CrossRef] [PubMed].

[3] Farina V, Brown JD. Tamiflu: The supply problem. Angew Chem. 2006; 45(44): 7330-4. ISSN 1433-7851. [CrossRef] [PubMed].

[4] Abrecht S, Federspiel MC, Estermann H, Fischer R, Karpf M, Mair HJ et al. The synthetic-technical development of oseltamivir phosphate tamifluTM: A race against time. Chimia Inter J Chem. 2007; 61(3): 93-9. ISSN 0009-4293. [CrossRef].

[5] Forleo-Neto E, Halker E, Santos VJ, Paiva TM, Toniolo-Neto J. Influenza. Rev Soc Bras Med Trop. 2003; 36(2): 267-74. ISSN 0037-8682. [CrossRef] [PubMed].

[6] Kim CU, Lew W, Williams MA, Liu HT, Zhang LJ, Swaminathan S et al. Influenza neuraminidase inhibitors 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(4): 681-90. ISSN 0002-7863. [CrossRef] [PubMed].

[7] Kramer M, Bongaerts J, Bovenberg R, Kremer S, Muller U, Orf S et al. Metabolic engineering for microbial production of shikimic acid. Metab Eng. 2003; 5(4): 277-83. ISSN 1096-7176. [CrossRef].

[8] Borah JC. Shikimic acid: a highly prospective molecule in pharmaceutical industry. Curr Sci. 2015; 109(9): 1672-9. ISSN 0011-3891. [CrossRef].

[9] Díaz Quiroz DC, Carmona SB, Bolívar F, A E. Current perspectives on applications of shikimic and aminoshikimic acids in pharmaceutical chemistry. Res Rep Med Chem. 2014; 4: 35-46. [CrossRef].

[10] Cardoso SF, Lopes LMX, Nascimento IR. Eichhornia crassipes: an advantageous source of shikimic acid. Rev Bras Farmacogn. 2014; 24(4): 439-42. ISSN 0102-695X. [CrossRef].

[11] Payne R, Edmonds M. Isolation of shikimic acid from star aniseed. J Chem Educ. 2005; 82(4): 599-600. ISSN 0021-9584. [CrossRef].

[12] Sadaka M, Garcia A. Extraction of shikimic and quinic acids. Chem Eng Commun. 1999; 173(1): 91-102. ISSN 0098-6445. [CrossRef].

[13] Raghavendra TR, Vaidyanathan P, Swathi HK, Ramesha BT, Ravikanth G, Ganeshaiah KN et al. Prospecting for alternate sources of shikimic acid, a precursor of Tamiflu, a bird-flu drug. Curr Sci. 2009; 96(6): 771-2. ISSN 0011-3891. [Link].

[14] Bradley D. Star role for bacteria in controlling flu pandemic? Nat Rev Drug Discov. 2005; 4: 945. [CrossRef].

[15] Kratz D, Wendling I, Brondani G.E. Concentrações de ácido indolbutírico no enraizamento de Cryptomeria japonica. J Biotec Biodivers. 2014; 2(3): 14-21. ISSN 2179-4804.

[16] Santos CBd, Longhi SJ, Hoppe JM, Moscovich FA. Efeito do volume de tubetes e tipo de substratos na qualidade de mudas de Cryptomeria japonica (L.F.) D. Don. Cien Flore. 2000; 10(2): 1-15. [CrossRef].

[17] Matallo MB, Almeida SDB, Cerdeira AL, Franco DA, Blanco FMG, Menezes PTC et al. Microwave-assisted solvent extraction and analysis of shikimic acid from plant tissues. Pl Dan. 2009; 27(spe): 987-94. ISSN 0100-8358. [CrossRef].

[18] Bochkov DV, Sysolyatin SV, Kalashnikov AI, Surmacheva IA. Shikimic acid: review of its analytical, isolation, and purification techniques from plant and microbial sources. J Chem Biol. 2012; 5: 5-17. [CrossRef].

[19] Sui R. Separation of shikimic acid from pine needles. Chem Eng Technol. 2008; 31(3): 469-73. ISSN 0930-7516. [CrossRef].

[20] Enrich LB, Scheuermann ML, Mohadjer A, Matthias KR, Eller CF, Newman MS et al. Liquidambar styraciflua: a renewable source of shikimic acid. Tetrahedron Lett. 2008; 49(16): 2503-5. ISSN 0040-4039. [CrossRef].

[21] Shimizu JY, Maiochi RA. Criptoméria como espécie alternativa para produção de madeira no Paraná. Pesqui Florest Bras. 2007; 5(54): 63-70. ISSN 1983-2605. [Link].