medigraphic.com
ISSN 2395-8723 (Electronic)
ISSN 1405-888X (Print)
TIP Revista Especializada en Ciencias Químico-Biológicas

2017, Number 2

<< Back Next >>

TIP Rev Esp Cienc Quim Biol 2017; 20 (2)

Dehidrodiisoeugenol by dimerization of isoeugenol with cell culture of Bouvardia ternifolia

Hernández-Vázquez L, Olivera-Flores MTJ, Luna H, Navarro-Ocaña A

Language: Spanish
References: 19
Page: 15-22
PDF size: 911.83 Kb.


ABSTRACT

Cell cultures of Bouvardia ternifolia were used as catalyst for the oxidative coupling of isoeugenol, to produce dehydrodiisoeugenol, a dimer, 77% isolated yield, when using the supernatat from the cell cultures suspension having peroxidase activity. The biotransformation proceeded under very mild conditions. It was observed that an increase in the amount of hydrogen peroxide decreases the yield.


REFERENCES

  1. Anita, Y., Widiyarti, G. & Abbas, J. (2014). Synthesis and elucidation structure of O-para dehydroguaiacol prepared by crude of Brassica oleracea var. alboglabra peroxidasecatalyzed oxidation. Journal of Applied Pharmaceutical Science. 4, 062-065. DOI: 10.7324/JAPS.2014.40411

  2. Bartolomeazzi, R., Verardo, G., Liessi, A. & Callea, A. (2010). Formation of dehydrodiisoeugenol and dehydrodieugenol from the reaction of isoeugenol with DPPH radical and their Role in the radical scavenging activity. Food Chemistry. 118, 256-265. DOI: 10.1016/j.foodchem.2009.04.115

  3. Farías-Días, A. (1988). An improved high yield synthesis of dehydrodieugenol Phytochemistry 27, 3008-3009. DOI: 10.1016/0031-9422(88)80715-5

  4. Findik, E., Ceylan, M. & Elmastaş, M. (2011). Isoeugenolbased novel potent antioxidants: synthesis and reactivity. European Journal of Medicinal Chemistry. 46, 4618-4624. DOI: 10.1016/j.ejmech.2011.07.041

  5. Giri, A., Dhingra, V., Giri, C.C., Singh, A., Ward, O. P. & Narasu, M.L. (2001). Biotransformations using plant cells, organ cultures and enzyme systems: current trends and future prospects. Biotechnology Advances. 19 (3)175-199. DOI: 10.1016/S0743-9750(01)85155-9

  6. Hernández-Vázquez, L., Olivera-Flores, M.T.J., Ruiz-Terán, F., Ayala, I & Navarro-Ocaña, A. (2011). Screening of plant cell culture for their capacity to dimerize eugenol and isoeugenol: preparation of dehydrodieugenol. Journal Molecular Catalysis. B: Enzymatic. 72, 102-106. DOI: 10.1016/molcab.2011.05.005

  7. Hua, D., Ma, C., Lin, S., Song, L., Deng, Z., Maomy, Z., Zhang, Z., Yu, B. & Xu, P. (2007). Biotransformation of Isoeugenol to vainillin by a newly isolated Bacillus pumilus strain: Identification of major metabolites. Journal of Biotechnology. 130, 463-470. DOI: 10.1016/j. biotec.2007.05.003

  8. Ishihara, K.,Hamada, H., Hirata, T. & Nakajima, N. (2003). Biotransformation using plant cultured cells. Journal Molecular Catalysis. B: Enzymatic. 23 (2.6), 145–170. DOI: 10.1016/S1381-1177(03)00080-8

  9. Juhász, L., Kürti, L. & Antus, S. (2000). Simple synthesis of benzofuranoid neolignans from Myristica fragrans. Journal of Natural Products. 63, 866-870. DOI: 10.1021/ np990327h

  10. Moussouni, S., Saru, M.L., Ioannou, E., Mansour, M., Detsi, A., Roussis, V. & Kefalas, P. (2011). Crude peroxidase from onion solid waste as a tool for organic synthesis. Part II: oxidative dimerization-cyclization of methyl p-coumarate, methyl caffeate and methyl ferulate. Tetrahedron. Letters. 52, 1165-1168. DOI: 10.1016/j.tetlet.2011.01.004

  11. Murakami, Y., Shoji, M., Hirata, A., Tanaka, S., Yokoe, I. & Fujisawa, S. (2005). Dehydrodiisoeugenol, an Isoeugenol dimer, inhibits lipopolysaccharide-stimulated nuclear factor kappa B activation and cyclooxygenase-2 expression in macrophages. Archives of Biochemistry and Biophysics. 434, 326-332. DOI: 10.1016/j.abb.2004.11.013

  12. Nascimento, I. R., Lopes, L. M. X., Davin, L. B. & Lewis, N. G. (2000). Stereoselective synthesis of 8,9-llcarinediols. Tetrahedron 56 (47), 9181-9193. DOI: 10.1016/S0040- 4020(00)00873-5

  13. Pereira, A.C., Magalhães L.G., Gonçalves, U.O., Luz, P.P., Moraes, A.C.G., Rodrigues, V., Da Matta Guades, P.M., Da Silva Filho, A.A., Cunha, W.R., Bastos, J.K., Nanayakkara, N.P.D., e Silva, M.L.A. (2011). Schistosomicidal and trypanocidal structure-activity relationships for (±)-licarin A and its (-)- and (+)-enantiomers. Phytochemistry 72, 1424- 1430. DOI: 10.1016/j.phytochem.2011.04.007

  14. Ramachandra Rao, S & Ravishankar, G.A. (1999) Biotransformation of isoeugenol to vanilla flavour metabolites and capsaicin in suspended and immobilized cell cultures of Capsicum frutescens: study of the influence of β-cyclodextrin and fungal elicitor. Process Biochemistry. 35 (3-4), 341–348. DOI: 10.1016/s0032-9592(99)00077-1

  15. Sánchez de Jiménez, E. & Fernández, L. (1983). Biochemical parameters to assess cell differentiation of Bouvardia ternifolia Schlecht callus. Planta 158 (5), 377-383. DOI: 10.1007/BF00397728

  16. Shiba, T., Xiao, L., Miyakoshi, T. & Chen, C.-L. (2000). Oxidation of Isoeugenol and coniferyl alcohol catalyzed by laccases isolated from Rhus vernicifera Stokes and Pycnoporus coccineus. Journal of Molecular Catalysis. B: Enzymatic. 10 (6), 605-615. DOI: 10.1016/s1381- 1177(00)00184-3

  17. Suga, T. & Hirata, T. (1990) Biotransformation of exogenous substrates by plant cell cultures. Phytochemistry 29, 2393- 2406. DOI: 10.1016/0031-9422(90)85155-9

  18. Wang, E.-C, Wein, Y-S. & Kuo, Y-H. (2006). A concise and efficient synthesis of s alvinal from isoeugenol via a phenoxenium ion intermediate. Tetrahedron Letters. 47, 9195–9197. DOI: 10.1016/tetlet.2006.10.131

  19. Wenqiang, G., Shufen, L., Ruixiang, Y., Shaoku, T. & Can. Q. (2007). Comparison of essential oils of clove buds extracted with supercritical carbon dioxide and other tree traditional extraction methods. Food Chemistry. 101, 1558-1564. DOI: 10.1016/j.foodchem.2006.04.009




2020     |     www.medigraphic.com