Bixa - structure and biological activity
T. B. Karyagina
Abstract
Annatto is one of the oldest natural colourants, extracted from the seed pericarp of Bixa orellana L. plant. The major annatto components are the bixin and norbixin. These diapocarotenoid pigments are widely used in the food industry, cosmetics, pharmaceuticals. This review summarizes what is presently known about the structure, synthesis, biological activities of annatto pigments.
References
1. Dushenkov V., Raskin I. // Fiziologiya rastenij. 2008. T.55. S.624-628.
2. Zhou1 H., Xie X., Tang Y. // Curr.Opin.Biotech. 2008. V.19. P.590–596.
3. Cuttriss A.J., Mimica1 J.L., Howitt C.A., Pogson B.J. // The Structure and Function of Plastids, Eds. Robert R. Wise and J. Kenneth Hoober, Springer. Printed in The Netherlands. 2006. P.315–334.
4. Giuliano G., Rosati C., Bramley P.M. //Trends in Biotechnology. 2003. V.21. P.513-516.
5. Mercadante A.Z., Steck A., Pfander H., Britton G. // Phytochemistry. 1996. V.41. P.1201–1203.
6. Sticher O. // Pharmakognosie – Phytopharmazie. Hansel, R., Eds. O. Sticher; E. Steinegger, Springer-Verlag, Berlin Heidelberg. 2007. P.809-914.
7. Barber M.S., Hardisson A.// J.Chem.Soc. 1961.V.4. P.1625-1630.
8. Preston H.D., Rickard M.D.// Food Chemictry. 1980. V.5. P.47-56.
9. Cardarelli C. R., a de Toledo Benass Mart, Mercadante A. Z. // LWT - Food Science and Technology. 2008. V.41. P.1689-1693.
10. Nobre1 B.P., Mendes1 R.L., Queiroz E.M., P.Pessoa F.L., Coelho J.P., Palavra A.F. // Brazilian Journal of Chemical Engineering. 2006. V.l (23). P.251–258.
11. Lancaster F.E., Lawrence J.F. // J.Chromatogr.A. 1996. V.732. P.394-398.
12. Rosenberg E. // Anal.Bional.Chem. 2008. V.391. P.33-57.
13. Tirimanna A.S.L. // Mikrochimica Acta [Wien], II. 1981. P.11—16.
14. Mercadante A.Z., Steck A., Pfander H. // Phytochemistry. 1997. V.46. P.1379 -1383.
15. Mercadante A.Z., Steck A., Pfander H. // Phytochemistry. 1999. V.52. P.135-139.
16. Bareth A., Strohmar W.,• Kitzelmann E. // Eur.Food Res.Technol. 2002. V.215. P.359–364.
17. Schulz H., Baranska M. // Vibrational Spectroscopy. 2007. V.43. P.13–25.
18. Breithaupt D.E. // Food Chemistry. 2004. V.86. P.449–456.
19. Rehbein J., Dietrich B., Grynbaum M.D., Hentschel P., Holtin K., Kuehnle M., Schuler P., Bayer M., Albert K. // Sep.Sci. 2007. V.30. P.2382-2390.
20. Bouvier F., Rahier A., Camara B. // Progress in Lipid Research. 2005. V.44. P.357–429.
21. Bouvier F., Dogbo O., Camara B. // Science. 2003. V.300. P.2089-2091.
22. Haberli A., Pfander H. // Helvetica Chimica Acta. 1999. V.82. P.696-706.
23. de Paiva Neto V.B., da Mota T.R., OtoniW.C. // Plant Cell, Tissue and Organ Culture. 2003. V.75. P.159–167.
24. Parimalan R., Giridhar P., Ravishankar G.A. // Industrial crops and products. 2008. V.28. P.122–127.
25. Shavallikhan P.S., Prakash E., Ra K.R. // Vitro Cell.Dev.Biol.-Plant. 2002. V.38. P.186–190.
26. Parimalan R., Giridhar P., Ravishankar G.A. // Industrial crops and products. 2008. V.28. P.122–127.
27. Shilpi A.J., Taufiq-Ur-Rahman Md., Uddin S.J., Alamc Md.S., Sadhu S.K., Seidel V. // J.Ethnopharmacology. 2006. V.108. P.264–271.
28. Kuramoto Y., Yamada K., Tsuruta O., Sugano M. // Biosci.Biotechnol.Biochem. 1996. V.60. P.1713-1713.
29. Fleischer T.C., K.Ameade E.P., Mensah M.L.K., Sawer I.K. // Fitoterapia. 2003. V.74. P.136–138.
30. Yasunaka K., Abe F., Nagayama A., Okabe H., Lozada-P?erez L., L?opez-Villafranco E., Mu?niz E.E., Aguilar A., Reyes-Chilpa R. // J.Ethnopharmacology. 2005. V.97. P.293–299.
31. Navarro Garc??a V.M., Gonzalez A., Fuentes M., Aviles M., Rios M.Y., Zepeda G., Rojas M.G. // J.Ethnopharmacology. 2003. V.87. P.85–88.
32. Kumar V.P., Chauhan N.S., Padh H., Rajani M. // J.Ethnopharmacology. 2006. V.107. P.182–188.
33. Braga F.G., L?ucia M., Bouzada M., Fabri R.L., Matos M.de O., Moreira F.O., Scio E., Coimbra E.S. // J.Ethnopharmacology. 2007. V.111. P.396–402.
34. Kiokias S., Oreopoulou V. // Innovative Food Science and Emerging Technologies. 2006. V.7. P.132–139.
35. Kiokias S., Gordon M.H. // Food Chemistry. 2003. V.83. P.523–529.
36. Lyng S.M.O., Passos M., Fontana J.D. // Process Biochemistry. 2005. V.40. P.865–872.
37. Cardarelli C.R., Toledo Benassi M.de, Mercadante A.Z. // LWT - Food Science and Technology. 2008. V.41. P.1689-1693.
38. Rios A.de O., Antunes L.M.G., Bianchi M.de L.P. // Food Chemistry. 2009. V.113. P.1113–1118.
39. Thresiamma K.C., George J.and Kuttan R. // J.Experimental and Clinical Cancer Research. 1998. V.17. P.431-434.
40. Antonio Jr.C.T.S., Asad L.M.B.O., De Oliveira E.B., Kovary K., Asad N.R., Felzenszwald I. // Genetics and Molecular Research. 2005. V.4. P.94-99.
41. Paumgarttena F.J.R., De-Carvalhoa R.R., Araujob I.B., Pintoa F.M., Borgesa O.O., Souzaa C.A.M., Kuriyamaa S.N. // Food and Chemical Toxicology. 2002. V.40. P.1595–1601.
42. Alves de Lima R.O., Azevedo L., Ribeiro L.R., Salvadori D.M.F. // Food and Chemical Toxicology. 2003. V.41. P.189–192.
43. Hagiwara A., Imai N., Ichihara T., Sano M., Tamano S., Aoki H., Yasuhara K., Koda T., Nakamura M., Shirai T. // Food and Chemical Toxicology. 2003. V.41. P.1157–1164.
44. Bautista A.R.P.L., Moreira E.L.T., Batista M.S., Miranda M.S., Gome I.C.S. // Food and Chemical Toxicology. 2004. V.42. P.625–629.
45. Agner A.R., Barbisan L.F., Scolastici C., Salvadori D.M.F. // Food and Chemical Toxicology. 2004. V.42. P.1687–1693.
References
1. Dushenkov V., Raskin I. // Fiziologiya rastenij. 2008. T.55. S.624-628.
2. Zhou1 H., Xie X., Tang Y. // Curr.Opin.Biotech. 2008. V.19. P.590–596.
3. Cuttriss A.J., Mimica1 J.L., Howitt C.A., Pogson B.J. // The Structure and Function of Plastids, Eds. Robert R. Wise and J. Kenneth Hoober, Springer. Printed in The Netherlands. 2006. P.315–334.
4. Giuliano G., Rosati C., Bramley P.M. //Trends in Biotechnology. 2003. V.21. P.513-516.
5. Mercadante A.Z., Steck A., Pfander H., Britton G. // Phytochemistry. 1996. V.41. P.1201–1203.
6. Sticher O. // Pharmakognosie – Phytopharmazie. Hansel, R., Eds. O. Sticher; E. Steinegger, Springer-Verlag, Berlin Heidelberg. 2007. P.809-914.
7. Barber M.S., Hardisson A.// J.Chem.Soc. 1961.V.4. P.1625-1630.
8. Preston H.D., Rickard M.D.// Food Chemictry. 1980. V.5. P.47-56.
9. Cardarelli C. R., a de Toledo Benass Mart, Mercadante A. Z. // LWT - Food Science and Technology. 2008. V.41. P.1689-1693.
10. Nobre1 B.P., Mendes1 R.L., Queiroz E.M., P.Pessoa F.L., Coelho J.P., Palavra A.F. // Brazilian Journal of Chemical Engineering. 2006. V.l (23). P.251–258.
11. Lancaster F.E., Lawrence J.F. // J.Chromatogr.A. 1996. V.732. P.394-398.
12. Rosenberg E. // Anal.Bional.Chem. 2008. V.391. P.33-57.
13. Tirimanna A.S.L. // Mikrochimica Acta [Wien], II. 1981. P.11—16.
14. Mercadante A.Z., Steck A., Pfander H. // Phytochemistry. 1997. V.46. P.1379 -1383.
15. Mercadante A.Z., Steck A., Pfander H. // Phytochemistry. 1999. V.52. P.135-139.
16. Bareth A., Strohmar W.,• Kitzelmann E. // Eur.Food Res.Technol. 2002. V.215. P.359–364.
17. Schulz H., Baranska M. // Vibrational Spectroscopy. 2007. V.43. P.13–25.
18. Breithaupt D.E. // Food Chemistry. 2004. V.86. P.449–456.
19. Rehbein J., Dietrich B., Grynbaum M.D., Hentschel P., Holtin K., Kuehnle M., Schuler P., Bayer M., Albert K. // Sep.Sci. 2007. V.30. P.2382-2390.
20. Bouvier F., Rahier A., Camara B. // Progress in Lipid Research. 2005. V.44. P.357–429.
21. Bouvier F., Dogbo O., Camara B. // Science. 2003. V.300. P.2089-2091.
22. Haberli A., Pfander H. // Helvetica Chimica Acta. 1999. V.82. P.696-706.
23. de Paiva Neto V.B., da Mota T.R., OtoniW.C. // Plant Cell, Tissue and Organ Culture. 2003. V.75. P.159–167.
24. Parimalan R., Giridhar P., Ravishankar G.A. // Industrial crops and products. 2008. V.28. P.122–127.
25. Shavallikhan P.S., Prakash E., Ra K.R. // Vitro Cell.Dev.Biol.-Plant. 2002. V.38. P.186–190.
26. Parimalan R., Giridhar P., Ravishankar G.A. // Industrial crops and products. 2008. V.28. P.122–127.
27. Shilpi A.J., Taufiq-Ur-Rahman Md., Uddin S.J., Alamc Md.S., Sadhu S.K., Seidel V. // J.Ethnopharmacology. 2006. V.108. P.264–271.
28. Kuramoto Y., Yamada K., Tsuruta O., Sugano M. // Biosci.Biotechnol.Biochem. 1996. V.60. P.1713-1713.
29. Fleischer T.C., K.Ameade E.P., Mensah M.L.K., Sawer I.K. // Fitoterapia. 2003. V.74. P.136–138.
30. Yasunaka K., Abe F., Nagayama A., Okabe H., Lozada-P?erez L., L?opez-Villafranco E., Mu?niz E.E., Aguilar A., Reyes-Chilpa R. // J.Ethnopharmacology. 2005. V.97. P.293–299.
31. Navarro Garc??a V.M., Gonzalez A., Fuentes M., Aviles M., Rios M.Y., Zepeda G., Rojas M.G. // J.Ethnopharmacology. 2003. V.87. P.85–88.
32. Kumar V.P., Chauhan N.S., Padh H., Rajani M. // J.Ethnopharmacology. 2006. V.107. P.182–188.
33. Braga F.G., L?ucia M., Bouzada M., Fabri R.L., Matos M.de O., Moreira F.O., Scio E., Coimbra E.S. // J.Ethnopharmacology. 2007. V.111. P.396–402.
34. Kiokias S., Oreopoulou V. // Innovative Food Science and Emerging Technologies. 2006. V.7. P.132–139.
35. Kiokias S., Gordon M.H. // Food Chemistry. 2003. V.83. P.523–529.
36. Lyng S.M.O., Passos M., Fontana J.D. // Process Biochemistry. 2005. V.40. P.865–872.
37. Cardarelli C.R., Toledo Benassi M.de, Mercadante A.Z. // LWT - Food Science and Technology. 2008. V.41. P.1689-1693.
38. Rios A.de O., Antunes L.M.G., Bianchi M.de L.P. // Food Chemistry. 2009. V.113. P.1113–1118.
39. Thresiamma K.C., George J.and Kuttan R. // J.Experimental and Clinical Cancer Research. 1998. V.17. P.431-434.
40. Antonio Jr.C.T.S., Asad L.M.B.O., De Oliveira E.B., Kovary K., Asad N.R., Felzenszwald I. // Genetics and Molecular Research. 2005. V.4. P.94-99.
41. Paumgarttena F.J.R., De-Carvalhoa R.R., Araujob I.B., Pintoa F.M., Borgesa O.O., Souzaa C.A.M., Kuriyamaa S.N. // Food and Chemical Toxicology. 2002. V.40. P.1595–1601.
42. Alves de Lima R.O., Azevedo L., Ribeiro L.R., Salvadori D.M.F. // Food and Chemical Toxicology. 2003. V.41. P.189–192.
43. Hagiwara A., Imai N., Ichihara T., Sano M., Tamano S., Aoki H., Yasuhara K., Koda T., Nakamura M., Shirai T. // Food and Chemical Toxicology. 2003. V.41. P.1157–1164.
44. Bautista A.R.P.L., Moreira E.L.T., Batista M.S., Miranda M.S., Gome I.C.S. // Food and Chemical Toxicology. 2004. V.42. P.625–629.
45. Agner A.R., Barbisan L.F., Scolastici C., Salvadori D.M.F. // Food and Chemical Toxicology. 2004. V.42. P.1687–1693.
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