Lipase-catalyzed esterification of betulinic acid using phthalic anhydride in organic solvent media: Study of reaction parameters

Journal of Applied Sciences

Volumn 10, Issue 4, 2010, Pages 337-342

  Ahmad, F B H ^a   Basri, M ^a   Ghaffari Moghaddam, M ^a   Abdul Rahman, M B ^a,b  

^a UNIVERSITY PUTRA MALAYSIA   (Malaysia)

^b UNIVERSITI KEBANGSAAN MALAYSIA   (Malaysia)

Author keywords

Betulinic acid; Betulinic acid ester; Novozym 435; Phthalic anhydride

Indexed keywords

BETULINIC ACID; CANDIDA ANTARCTICA; CATALYTIC REACTIONS; NOVOZYM435; OPTIMUM CONDITIONS; ORGANIC SOLVENT MEDIA; PHTHALIC ANHYDRIDES; REACTION PARAMETERS;

CATALYSIS; ENZYMES; ESTERIFICATION; ESTERS;

ORGANIC SOLVENTS;

EID: 76449083504     PISSN: 18125654     EISSN: 18125662     Source Type: Journal    
DOI: 10.3923/jas.2010.337.342     Document Type: Article

References (24)

1. Ahmad, F.B., H.J. Omar and A.M. Ali, 1999. Chemical examination of local plant: Triterpene from leaf of Malaysian Callistemon speciosus D.E. Ultra Sci., 11: 357-359.
2. Basri, M., A. Ngah, M.B. Abdul-Rahman, R.N.Z. Abdul-Rahman, C.A.N. Razak and A.B. Salleh, 2001. Synthesis of medium chain glycerides from caprylic acid and glycerol using lipase from Candida rugosa. Asia Pacific J. Mol. Biol. Microb., 9: 67-70.
3. Berger, B., C.G. Rabiller, K. Konigsberger, K. Faber and H. Griengl, 1990. Enzymatic acylation using acid anhydrides: Crucial removal of acid. Tetrahedron: Asymmetry, 1: 541-546.
4. Castillo, E., V. Dossatl, A. Marty, J.S. Condoret and D. Combes, 1997. The role of silica gel in lipase-catalyzed esterification reactions of high-polar substrates. J. Am. Oil Chem. Soc., 74: 77-85.
5. Facioli, N.L. and A.D. Barrera, 2001. Optimisation of enzymatic esterification of soybean oil deoderiser distillate. J. Sci. Food Agric., 12: 1193-1198.
6. Fulda, S. and K.M. Debatin, 2000. Betulinic acid induces apoptosis through a direct effect on mitochondria in neuroectodermal tumors. Med. Pediatr. Oncol., 35: 616-618.
7. Fulda, S., I. Jeremias, H.H. Steiner, T. Pietsch and K.M. Debatin, 1999. Betulinic acid: A new cytotoxic agent against malignant brain-tumor cells. Int. J. Cancer, 82: 435-441.
8. Garros, B.S., N. Razafindramboa and A.A. Pavia, 1998. Optimisation of lipase-catalyzed synthesis of (z)-3-hexen-1-yl acetate by direct esterification in hexane and solvent-free medium. Enzyme Microb. Technol., 22: 240-245.
9. Gauthier, C., J. Legault, S. Lavoie, S. Rondeau, S. Tremblay and A. Pichette, 2008. Synthesis of two natural betulinic acid saponins containing a-1-Rhamnopyranosyl, a-1-Arabinopyranose and their anologues. Tetrahedron, 64: 7386-7399.
10. Krishna, S.H., B. Manohar, S. Divakar, S.G. Prapulla and N.G. Karanth, 2000. Optimization of isoamyl acetate production by using immobilized lipase from mucor miehei by Response Surface Methodology. Enzyme Microb. Technol., 26: 131-136.
11. Krishna, S.H., S. Divakar, S.G. Prapulla and N.G. Karanth, 2001. Enzymatic synthesis of isoamyl acetate using immobilized lipase from Rhizomucor miehei. J. Biotechnol., 87: 193-201.
12. Kvasnica, M., J. Sarek, E. Klinotova, P. Dzubak and M. Hajduch, 2005. Synthesis of phthalates of betulinic acid and betulin with cytotoxic activity. Bioorg. Med. Chem., 13: 3447-3454.
13. Lozano, P., D.T. Diego, D. Carrie, M. Vaultier and J. Iborra, 2003. Enzymatic ester synthesis in ionic liquids. J. Mol. Catal. B-Enzym., 21: 9-13.
14. Pisha, E., H. Chai, I.S. Lee, T.E. Chagwedera and N.R. Farnsworth et al., 1995. Discovery of betulinic acid as a selective inhibitor of human melanoma that functions by induction of apoptosis. Nature Med., 1: 1046-1050.
15. Radzi, S.M., M. Basri, A.B. Salleh, A. Ariff, R. Mohamad, M.B. Abdul Rahman and R.N.Z. Abdul Rahman, 2005. Large scale production of liquid wax ester by immobilized lipase. J. Oleo Sci., 54: 203-209.
16. Radzi, S.M., M. Basri, A.B. Salleh, A.M. Ariff and R. Rosfarizan et al., 2005. High performance enzymatic synthesis of oleyl oleate using immobilized lipase from Candida antartica. Electron. J. Biotechn., 8: 291-298.
17. Thibeault, D., C. Gauthier, J. Legault, J. Bouchard, P. Dufour and A. Pichette, 2007. Synthesis and structure-activity relationship study of cytotoxic germanicane and lupane-type 3ß-O-monodesmosidic saponins starting from betulin. Bioorg. Med. Chem., 15: 6144-6157.
18. Villeneuve, P., J.M. Muderhwa, J. Graille and M.J. Haas, 2000. Customizing lipases for biocatalysis: A survey of chemical, physical and molecular biological approaches. J. Mol. Catalysis B-Enzymatic, 9: 113-148.
19. Xu, J., J. Zhu, T. Kawamato, T. Atso and Y. Hu, 1997. Comparison of acid anhydrides with carboxylic acids in enantioselectivity enzymatic esterification of racemic menthol. Chinese J. Biotecnol., 13: 263-269.
20. Xu, J.H., J.M. Liu, X.S. Xu and Q.S. Yuan, 1998. Enantioselective esterification of racemic acid catalyzed by lipase in a mixed solvent system. Ann. N. Y. Acad. Sci., 864: 405-408.
21. Yasin, Y., M. Basri, F.B.H. Ahmad and A.B. Salleh, 2008. Response surface methodology as a tool to study the lipase-catalyzed synthesis of betulinic acid ester. J. Chem. Technol. Biotech., 83: 694-698.
22. Yoggeswari, P. and D. Sriram, 2005. Betulinic acid and its derivatives: A review on their biological activities. Curr. Med. Chem., 12: 657-660.
23. Zhuang, Y.P., J.H. Xu and S.L. Zhang, 1998. Effects of organic solvent and acylating agent on lipase-catalyzed esterification of a chiral chlorohydrin in nonaqueous media. Ann. N. Y. Acad. Sci., 864: 656-659.
24. Zuco, V., R. Supino, S.C. Righetti, L. Cleris, E. Marchesi, C. Gambacorti-Passerini and F. Formelli, 2002. Selective cytotoxicity of betulinic acid on tumor cell lines, but not on normal cells. Cancer Lett., 175: 17-25.