Supercritical Fluid Extraction of Lutein Esters from Marigold Flowers and their Hydrolysis by Improved Saponification and Enzyme Biocatalysis
Lutein is a dietary oxycarotenoid which is found
to reduce the risks of Age-related Macular Degeneration
(AMD). Supercritical fluid extraction of lutein esters from
marigold petals was carried out and was found to be much
effective than conventional solvent extraction. The
saponification of pre-concentrated lutein esters to produce free
lutein was studied which showed a composition of about 88%
total carotenoids (UV-VIS spectrophotometry) and 90.7%
lutein (HPLC). The lipase catalyzed hydrolysis of lutein esters
in conventional medium was investigated. The optimal
temperature, pH, enzyme concentration and water activity
were found to be 50°C, 7, 15% and 0.33 respectively and the
activity loss of lipase was about 25% after 8 times re-use in at
50°C for 12 days. However, the lipase catalyzed hydrolysis of
lutein esters in conventional media resulted in poor
conversions (16.4%).
[1] D.E Breithaupt, A. Bamedi and U. Wirt,. Carotenol fatty acid esters:
Easy substrates for digestive enzymes? Comp Biochem Physiol B
Biochem Mol Biol. 2002, 132: pp. 721-728.
[2] Bunea Andrea.. Lutein esters from Tagetes erecta: Isolation and
enzymatic hydrolysis. Bulletin UASVM .Animal Science and
Biotechnologies. 2008, 65:pp.1-2.
[3] L. Chasan-Taber, W.C. Willet, J.M. Seddon, M.J. Stampfer, B.Rosner,
G.A. Colditz, F.E. Speizer and S.E.Hankinson. A prospective study of
carotenoid and vitamin A intakes and risk of cataract extraction in US
women. Am J Clin Nutr. 1999.70: pp.509-16.
[4] H.K. Chung, H.M. Rasmussen and E.J. Johnson. Lutein bioavailability is
higher from lutein-enriched eggs than from supplements and spinach in
men. J. Nutr. 2004.134(8):pp.1887-1893.
[5] R.E. Feeney. Chemical deterioration of proteins. Edited by J.R. Whitaker
and M. Fujimaki. American Chemical Society. Washington.
D.C.1980.pp.1-99.
[6] H. L. Goderis, B. L. Fouwe, S. M. Cauwenbergh and P. P. Tobback.
Measurement and control of water content of organic solvents. Anal.
Chem. 1986.58: pp.1561-1563.
[7] G. Gore. On the properties of liquid carbonic acid. Philosophical
Transactions of the Royal Society of London. Series A: Mathematical,
Physical and Engineering Sciences. 1861.pp.151:83.
[8] F. Granado, B. Olmedilla and I. Blanco. Serum depletion and
bioavailabilty of lutein in type I diabetic patients. Eur J Nutr.
2002.41(2):pp.47-53.
[9] J. B. Hannay and J. Hogarth. On the solubility of solids in gases.
Proceedings of the Royal Society of London Series A. 1879.pp.29:324.
[10] F.C. Huang, Y.H. Ju and C.W. Huang. Enrichment of ╬│- linolenic acid
from borage oil via lipase-catalyzed reactions. J. Am. Oil Chem. Soc.
1997. 74: pp.977-981.
[11] M. Ikeda. Public health problems of organic solvents. Toxicol Lett.
1992. 64-65: pp.191-201.
[12] P.B. Jacobs, R.D. Le Boeuf, S.A. McCommas and J.D. Tauber. The
cleavage of carotenoid esters by cholesterol esterase. ? Comp Biochem
Physiol B Biochem Mol Biol. 1982. 72B: 157-160.
[13] A.J. Jay, D.C. Steytler and M. Knights. Spectrophotometric studies of
food colors in near critical CO2. J Supercrit Fluids. 1991.4: pp.131-141.
[14] J.A. Kayanush, T.B.Hannah, M. Paula and M. Barry. Lutein is stable in
yogurt and does not affect its charecteristics. J Food Sci. 2006.71(6):
pp.467-472.
[15] F. Khachik. Process for isolation, purification and recrystallization of
lutein from marigold oleoresin and uses thereof. United States Patent
5382714. 1995.
[16] T.K. Kumar. Trans-lutein enriched xanthophylls ester concentrate and a
process for its preparation. 2004. United States Patent 6737535.
[17] J.T Landrum and R.A Bone. Lutein, zeaxanthin and macular pigment.
Arch Biochem Biophys. 2001.385:pp.28-40.
[18] E.W. Lusas and S. R. Gregory. New solvents and extractors. In:
Proceedings of the World Conference on Oilseed and Edible Oils
Processing.. Koseoglu, S.S., Rhee, K.C and Wilson, R.F (Eds). AOCS
Press, New York. 1996.1:204-219.
[19] Q. Ma, X. Xu, Y. Gao, Q. Wang and J. Zhao. Optimisation of
supercritical carbon dioxide extraction of lutein esters from marigold
(Tagetes erecta L.) with soybean oil as a co-solvent. Int J Food Sci
Technol. 2008. 43:pp.1763-1769.
[20] Mora-Pale, J.M. Perez-Munguia, S.Gonzalez-Mejia, J.C. Dordick and
J.S. Barzana.. The lipase catalyzed hydrolysis of lutein diesters in nonaqueous
media is favoured at extremely low water activities. Biotechnol
Bioeng. 2007. 98(3).
[21] S. Naranjo-Modad, A. Lopez-Munguia, G. Vilarem, A. Gaset and E.
Barzana.. Solubility of purified lutein diesters obtained from Tagetes
erecta in supercritical CO2 and the effect of solvent modifiers. J. Agri.
Food Chem. 2000.48: pp.5640- 5642.
[22] Rice-Evans, C.A., Sampson, J., Bramley, P.M and Holloway, D.E. 1997.
Why do we expect carotenoids to be antioxidants in vivo? Free Radical
Res. 26:381-398.
[23] A. J. Roodenburg, R. Leenen, K. H.Van het Hof, J. A. Weststrate and L.
B. Tijburg. Amount of fat in the diet affects bioavailability of lutein
esters but not of alpha-carotene, beta-carotene, and vitamin E in humans.
Am J Clin Nutr. 2000.71:pp.1187-1193.
[24] G.J. Salter and D.B. Kell. Rapid determination using dielectric
spectroscopy of the toxicity of organic solvents to intact cells. In:
Biocatalysis in non-conventional media. Tramper, J., Vermue, M.H.,
Beeftinle, H.H and Von Stockar. U (Eds). Elsevier Science Publishers
B.V. New York. 1992. 291-298.
[25] R.A. Sheldon. Chirotechnology-industrial synthesis of optically-active
compounds. Marcel Dekker Ltd. New York. 1993. pp. 448.
[26] D.M. Small. Structure and Properties of Lipids. In: Biochemical and
Physiological Aspects of Human Nutrition, Stipanuk, M.H (Ed).
Philedelphia, PA: W.B. Saunders Company. 2000. pp. 43 - 62.
[27] J. Verghese.. Focus on xanthophylls from Tagetes erecta L the giant
natural complex-I. Indian Spices. 1998. 33(4): pp.8-13.
[28] X. Xu, B. Shao, D. Zhou, S. Ye, Y. Wang and B. Chen. Process for the
isolation and purification of xanthophylls crystals from plant oleoresin.
2007. US Patent 7,271,298, B2.
[29] H. Zorn, D.E. Breithaupt, M. Takenberg, W. Schwack and R.G. Berger.
Enzymatic hydrolysis of carotenoid esters of marigold flowers (Tagetes
erecta L.) and red paprika (Capsicum annuum L.) by commercial lipases
and Pleurotus sapidus extracellular lipase. Enzyme Microb. Technol.
2003. 32. 623-628.
[1] D.E Breithaupt, A. Bamedi and U. Wirt,. Carotenol fatty acid esters:
Easy substrates for digestive enzymes? Comp Biochem Physiol B
Biochem Mol Biol. 2002, 132: pp. 721-728.
[2] Bunea Andrea.. Lutein esters from Tagetes erecta: Isolation and
enzymatic hydrolysis. Bulletin UASVM .Animal Science and
Biotechnologies. 2008, 65:pp.1-2.
[3] L. Chasan-Taber, W.C. Willet, J.M. Seddon, M.J. Stampfer, B.Rosner,
G.A. Colditz, F.E. Speizer and S.E.Hankinson. A prospective study of
carotenoid and vitamin A intakes and risk of cataract extraction in US
women. Am J Clin Nutr. 1999.70: pp.509-16.
[4] H.K. Chung, H.M. Rasmussen and E.J. Johnson. Lutein bioavailability is
higher from lutein-enriched eggs than from supplements and spinach in
men. J. Nutr. 2004.134(8):pp.1887-1893.
[5] R.E. Feeney. Chemical deterioration of proteins. Edited by J.R. Whitaker
and M. Fujimaki. American Chemical Society. Washington.
D.C.1980.pp.1-99.
[6] H. L. Goderis, B. L. Fouwe, S. M. Cauwenbergh and P. P. Tobback.
Measurement and control of water content of organic solvents. Anal.
Chem. 1986.58: pp.1561-1563.
[7] G. Gore. On the properties of liquid carbonic acid. Philosophical
Transactions of the Royal Society of London. Series A: Mathematical,
Physical and Engineering Sciences. 1861.pp.151:83.
[8] F. Granado, B. Olmedilla and I. Blanco. Serum depletion and
bioavailabilty of lutein in type I diabetic patients. Eur J Nutr.
2002.41(2):pp.47-53.
[9] J. B. Hannay and J. Hogarth. On the solubility of solids in gases.
Proceedings of the Royal Society of London Series A. 1879.pp.29:324.
[10] F.C. Huang, Y.H. Ju and C.W. Huang. Enrichment of ╬│- linolenic acid
from borage oil via lipase-catalyzed reactions. J. Am. Oil Chem. Soc.
1997. 74: pp.977-981.
[11] M. Ikeda. Public health problems of organic solvents. Toxicol Lett.
1992. 64-65: pp.191-201.
[12] P.B. Jacobs, R.D. Le Boeuf, S.A. McCommas and J.D. Tauber. The
cleavage of carotenoid esters by cholesterol esterase. ? Comp Biochem
Physiol B Biochem Mol Biol. 1982. 72B: 157-160.
[13] A.J. Jay, D.C. Steytler and M. Knights. Spectrophotometric studies of
food colors in near critical CO2. J Supercrit Fluids. 1991.4: pp.131-141.
[14] J.A. Kayanush, T.B.Hannah, M. Paula and M. Barry. Lutein is stable in
yogurt and does not affect its charecteristics. J Food Sci. 2006.71(6):
pp.467-472.
[15] F. Khachik. Process for isolation, purification and recrystallization of
lutein from marigold oleoresin and uses thereof. United States Patent
5382714. 1995.
[16] T.K. Kumar. Trans-lutein enriched xanthophylls ester concentrate and a
process for its preparation. 2004. United States Patent 6737535.
[17] J.T Landrum and R.A Bone. Lutein, zeaxanthin and macular pigment.
Arch Biochem Biophys. 2001.385:pp.28-40.
[18] E.W. Lusas and S. R. Gregory. New solvents and extractors. In:
Proceedings of the World Conference on Oilseed and Edible Oils
Processing.. Koseoglu, S.S., Rhee, K.C and Wilson, R.F (Eds). AOCS
Press, New York. 1996.1:204-219.
[19] Q. Ma, X. Xu, Y. Gao, Q. Wang and J. Zhao. Optimisation of
supercritical carbon dioxide extraction of lutein esters from marigold
(Tagetes erecta L.) with soybean oil as a co-solvent. Int J Food Sci
Technol. 2008. 43:pp.1763-1769.
[20] Mora-Pale, J.M. Perez-Munguia, S.Gonzalez-Mejia, J.C. Dordick and
J.S. Barzana.. The lipase catalyzed hydrolysis of lutein diesters in nonaqueous
media is favoured at extremely low water activities. Biotechnol
Bioeng. 2007. 98(3).
[21] S. Naranjo-Modad, A. Lopez-Munguia, G. Vilarem, A. Gaset and E.
Barzana.. Solubility of purified lutein diesters obtained from Tagetes
erecta in supercritical CO2 and the effect of solvent modifiers. J. Agri.
Food Chem. 2000.48: pp.5640- 5642.
[22] Rice-Evans, C.A., Sampson, J., Bramley, P.M and Holloway, D.E. 1997.
Why do we expect carotenoids to be antioxidants in vivo? Free Radical
Res. 26:381-398.
[23] A. J. Roodenburg, R. Leenen, K. H.Van het Hof, J. A. Weststrate and L.
B. Tijburg. Amount of fat in the diet affects bioavailability of lutein
esters but not of alpha-carotene, beta-carotene, and vitamin E in humans.
Am J Clin Nutr. 2000.71:pp.1187-1193.
[24] G.J. Salter and D.B. Kell. Rapid determination using dielectric
spectroscopy of the toxicity of organic solvents to intact cells. In:
Biocatalysis in non-conventional media. Tramper, J., Vermue, M.H.,
Beeftinle, H.H and Von Stockar. U (Eds). Elsevier Science Publishers
B.V. New York. 1992. 291-298.
[25] R.A. Sheldon. Chirotechnology-industrial synthesis of optically-active
compounds. Marcel Dekker Ltd. New York. 1993. pp. 448.
[26] D.M. Small. Structure and Properties of Lipids. In: Biochemical and
Physiological Aspects of Human Nutrition, Stipanuk, M.H (Ed).
Philedelphia, PA: W.B. Saunders Company. 2000. pp. 43 - 62.
[27] J. Verghese.. Focus on xanthophylls from Tagetes erecta L the giant
natural complex-I. Indian Spices. 1998. 33(4): pp.8-13.
[28] X. Xu, B. Shao, D. Zhou, S. Ye, Y. Wang and B. Chen. Process for the
isolation and purification of xanthophylls crystals from plant oleoresin.
2007. US Patent 7,271,298, B2.
[29] H. Zorn, D.E. Breithaupt, M. Takenberg, W. Schwack and R.G. Berger.
Enzymatic hydrolysis of carotenoid esters of marigold flowers (Tagetes
erecta L.) and red paprika (Capsicum annuum L.) by commercial lipases
and Pleurotus sapidus extracellular lipase. Enzyme Microb. Technol.
2003. 32. 623-628.
@article{"International Journal of Biological, Life and Agricultural Sciences:53180", author = "A. Peter Amala Sujith and T.V. Hymavathi and P. Yasoda Devi", title = "Supercritical Fluid Extraction of Lutein Esters from Marigold Flowers and their Hydrolysis by Improved Saponification and Enzyme Biocatalysis", abstract = "Lutein is a dietary oxycarotenoid which is found
to reduce the risks of Age-related Macular Degeneration
(AMD). Supercritical fluid extraction of lutein esters from
marigold petals was carried out and was found to be much
effective than conventional solvent extraction. The
saponification of pre-concentrated lutein esters to produce free
lutein was studied which showed a composition of about 88%
total carotenoids (UV-VIS spectrophotometry) and 90.7%
lutein (HPLC). The lipase catalyzed hydrolysis of lutein esters
in conventional medium was investigated. The optimal
temperature, pH, enzyme concentration and water activity
were found to be 50°C, 7, 15% and 0.33 respectively and the
activity loss of lipase was about 25% after 8 times re-use in at
50°C for 12 days. However, the lipase catalyzed hydrolysis of
lutein esters in conventional media resulted in poor
conversions (16.4%).", keywords = "lutein, preconcentration, saponification, lipase", volume = "4", number = "1", pages = "43-10", }
