High purity cis-cinnamic acid preparation for studying physiological role of trans-cinnamic and cis-cinnamic acids in higher plants

Environmental Control in Biology

Volumn 51, Issue 1, 2013, Pages 1-10

  Salum, María Laura ^a   Erra Balsells, Rosa ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

Caffeic Acid; Coumaric Acid; Ferulic Acid; Geometric Isomers; Sinapinic Acid

Indexed keywords

EID: 84877321717     PISSN: 1880554X     EISSN: 18830986     Source Type: Journal    
DOI: 10.2525/ecb.51.1     Document Type: Review

References (55)

1. Aberg, B. 1961. Studies on plant growth regulator XVIII some-substituted acrylic acids. Kungliga Lantbruskshogskolans Annaler 27: 99-123.
2. Armstrong, D. W., Zhang, L.-K., He, L., Gross, M. L. 2001. Ionic liquids as matrixes for matrix-assisted laser deroption/ionization mass spectrometry. Anal. Chem. 73: 3679-3686.
3. Arai, T. 1999. Photochemical cis-trans Isomerization in the Triplet State (ed. by Ramamurthy, V., Schanze, K. S.), Organic Molecular hotochemistry, Vol. 3 in the Series, Molecular and Supramolecular Photochemistry, pp 131.
4. Braun, A. M., Maurette, M. T., Oliveros, E. 1991. Photochemcial Technology, Wiley, London, chapter 12, pp. 500.
5. Buchanan, B. B., Gruissem, W., Jones, R. L. 2000. Biochemistry & Molecular Biology of Plants. American Society of Plant Physiologist, Rockville, Chapter 24, pp.1286.
6. Caccamese, S., Azzolina, R., Davino, M. 1979. Separation of cis and trans isomers of naturally occurring hydroxycinnamic acids by high-pressure liquid chromatography. Chromatograph 12: 545-547.
7. Chaloner, P. A. 1980. Geminal and vicinal 13C-13C coupling constants in carboxylic acids derivatives. J. Chem. Soc., Perkin Trans 2, 7: 1028-1032.
8. Chen, M. J., Vijaykumar, V., Lu, B. W., Xia, B., Li, N. 2005. Cis-and trans-cinnamic acids have different effects on the catalytic properties of Arabidopsis phenylalanine ammonia lyases PAL1, PAL2, and PAL4. J. Integrative Plant Biology (Formerly Acta Botanica Sinica) 47: 67-75.
9. Chen, Y. L., Huang, S. T., Sun, F. M., Chiang, Y. L., Chiang, C. J., Tsai, C. M., Weng, C. J. 2011. Transformation of cinnamic acid from trans-and cis-form raises a notable bactericidal and synergistic activity against multiple-drug resistant Mycobacterium tuberculosis. Europ. J. Pharm. Sci. 43: 188-194.
10. Cole, R. B. 2010. Electrospray and MALDI Mass Spectrometry. Fundamentals, Instrumentation, Practicalities, and Biological Applications. 2nd edition. Wiley, London.
11. Dixon, R. A. 2001. Natural products and plant disease resistance. Nature 411: 843-847.
12. Durr, H. 1990. Laurant-Bouas (Eds.), Photochromism, Molecules and Systems, Elsevier, Amsterdam, pp 122.
13. Feringa, B. L., van Delden, R. A., Koumura, N., Geertsema, E. M. 2000. Chiroptical Molecular Switches. Chem. Rev. 100: 1789-1816.
14. Graft, E. 1992. Antioxidant potential of ferulic acid. Free Radic Biol. Med. 13: 435-448.
15. Gholipour, Y., Giudicessi, S. L., Nonami, H., Erra-Balsells, R. 2010. Diamond, titamiun dioxide, strontium titanium oxide, and barium strontium titanium oxide nanoparticles for direct matrix assisted laser desorption/ionization mass spectrometry analysis of soluble carbohydrates in plant tissues. Anal. Chem. 82: 5518-5526.
16. Guo, D., Wong, W. S., Xu, W. Z., Sun, F. F., Qing, D. J., Li, N. 2011. Cis-cinnamic acid-enhanced 1 gene plays a role in regulation of Arabidopsis bolting. Plant Mol. Biol. 75: 481-495.
17. Haagen-Smit, S. A. J., Went, F. W. 1935. A physiological analysis of growth substances. Proceedings. Koninklijke Akademie van Wetenschappen te Amsterdam 38: 852-857.
18. Hanai, K., Kuwae, A., Takai, T., Senda, H., Kunimoto, K. 2001. A comparative vibrational and RMN study of cis-cinnamic acid polymorph and trans-cinnamic acid. Spectrochim. Acta Part A, 57: 513-519.
19. Herrero, M., Simo, C., Garc-a-Canas, V., Ibanez, E., Cifuentes, A. 2012. Foodomics: MS-based strategies in modern food science and nutrition. Mass Spectrom. Rev. 31: 49-69.
20. Hiradate, S., Morita, S., Furubayashi, A., Fujii, Y., Harada, J. 2005. Plant growth inhibition by cis-cinnamoyl glucosides and cis-cinnamic acid. J. Chem. Ecol. 31: 591-601.
21. Jung, M. Y., Joen, B. S., Bock, J. Y. 2002. Free, esterified, and insoluble-bond phenolic acids in white and red Korean ginsengs (Panax ginseng C. A. Meyer). J. Agric. Food Chem. 79: 105-111.
22. Kirk-Othmer. 1996. Encyclopedia of Chemical Technology, 4th Ed., Wiley, London, Vol. 18, pp. 799.
23. Klessinger, M., Michl, J. 1995. Excited States and Photochemistry of Organic Molecules, VCH Publishers, Inc. New York, pp. 362.
24. Krygier, K., Sosulski, F., Hogge, L. 1982. Free, esterified, and insoluble-bond phenolic acids. 2. Composition of phenolic acids in rapeseed flour and hulls. J. Agric. Food Chem. 30: 334-338.
25. Landoni, M., Duschak, V. G., Erra-Balsells, R., Couto, A. S. 2008. UV-MALDI mass spectrometry analysis of NBDglycosphingolipids without an external matrix. J. Am. Soc. Mass Spectrom. 19: 923-926.
26. Lee, H., Senda, H., Kuwae, A., Hanai, K. 1994. Crystal and molecular structures of a low-melting polymorph of allocinnamic acid. Bull. Chem. Soc. Jpn. 67: 1475-1468.
27. Letham, D. S. 1978. Natural-occuring plant growth regulations other than the principal hormones of higher plants. In "Phytohormones and Related Compounds:a Comprehensive Tratise" (ed. by Letham, D. S., Goodwin, P. B., Higgins, T. J. V.), Elsevier, Amsterdam, pp 349.
28. Mesaros, M., Tarzi, O. I., Erra-Balsells, R., Bilmes, G. M. 2006. The photophysics of some UV-MALDI matrices studied by using spectroscopic, photoacoustic and luminescence techniques. Chem. Phys. Lett. 426: 334-340.
29. Mori, T., Inoue, Y. 2005. C=C Photoinduced Isomerization Reactions (ed. by Griesbeck, A. G., Mattay, J.) Synthetic Organic Photochemistry, Marcel Dekker, New York, pp 417-452.
30. Nieuwendaal, R. C., Bertmer, M., Hayes, S. E. 2008. An unexpected phase transition during the [22] photocycloaddition reaction of cinnamic acid to truxillic acid: Changes in polymorphism monitored by solid-state NMR J. Phys. Chem. B 112: 12920-12926.
31. Nonami, H., Fukui, S., Erra-Balsells, R. 1997.-Carboline alkaloids as matrices for matrix-assisted ultraviolet laser desorption time-of flight mass spectrometry of proteins and sulfated oligosaccharides: A comparative study using phenylcarbonyl compounds, carbazoles and classical matrices. J. Mass Spectrom. 32: 287-296.
32. Nonami, H., Tanaka, K., Fukuyama, Y., Erra-Balsells, R. 1998.-carboline alkaloids as matrices for UV-matrix-assisted laser desorption/ionization time-of-flight mass spectrometry in positive and negative ion modes. Analysis of proteins of high molecular mass, and of cyclic and acyclic oligosaccharides. Rapid Commun. Mass Spectrom. 12: 285-296.
33. Petroselli, G., Gara, P. D., Bilmes, G. M., Erra-Balsells, R. 2012. Photoacoustic and luminescence characterization of nitrogen heterocyclic aromatic UV-MALDI matrices in solution. Photochem. Photobiol. Sci. 11: 1062-1068.
34. Raes, J., Rohde, A., Christensen, J. H., Van de Peer, Y., Boerjan, W. 2003. Genome-wide characterization of the lignification toolbox in Arabidopsis. Plant Physiol. 133: 1051-1071.
35. Rao, Y., Filler, R. 1976. Trans-to cis-isomerization of cinnamic acids and related carbonyl compounds. J. Chem. Soc., Chem. Commun. 12: 471-472.
36. Rao, V. J. 1999. Photochemical cis-trans Isomerization from the Singlet State (ed. by Ramamurthy, V., Schanze, K. S.) Organic Molecular Photochemistry, Vol. 3 in the Series, Molecular and Supramolecular Photochemistry, New York, pp 169.
37. Reed, G. A., Dimmel, D. R., Malcolm, E. W. 1993. Influence of nucleophilles on the higth temperature aqueous isomerization of cis-to trans-cinnamic acid. J. Org. Chem. 58: 6364-6371.
38. Robinson, H. V. W., Cambell, J. T. 1933. The relationship between the three forms of cis-cinnamic acid. J. Chem. Soc.: 1453-1454.
39. Salum, M. L., Erra-Balsells, R. 2009. Ionic liquid transcinamics and cis-cinamics, synthesis and applications. Photosynthesis of cis-cinamic acids from ionic liquid transcinamics. Argentine Patent. CONICET 20090105020; 21/12/ 2009.
40. Salum, M. L., Robles, C. J., Erra-Balsells, R. 2010. Photoisomerization of ionic liquids ammonium cinnamates: One-pot synthesis-isolation of z-cinnamic acids. Org. Lett. 12: 4808-4811.
41. Shahadi, F., Naczk, M. 2004. Phenolics in food and nutraceuticals. CRC Press LLC, Florida, pp. 4.
42. Sun, F. M., Smith, J. L., Vittimberga, B. M., Traxler, R. W. 2002. Effect of food processing on bioactive compounds in foods: A new method for separation and identification of cis-cinnamic acid from its racemic mixture. In Bioactive Coumpounds in Foods, Charpter 17, ACS Symposium Series 816, pp 228.
43. Sun, F. M. 2003. The study of the possible metabolic pathway of cis-cinnamic acids in rat liver. Food Sci. Agr. Chem. 5: 47-52.
44. Taiz, L., Zeiger, E. 2006. Plant Physiology, 4th ed. Sinauer Associated Inc. Pub., Sunderland, MA. Chapter 13, pp 322.
45. Tarzi, O. I., Nonami, H., Erra-Balsells, R. 2009. Temperature effect on the stability of compounds used as UV-MALDI-MS matrix: 2,5-Dihydroxybenzoic acid, 2,4,6-Trihydroxyacetophenone, trans-Cyano-4-hydroxycinnamic acid, 3,5-Dimethoxy-4-hydroxycinnamic acid, nor-Harmane and Harmane. J. Mass Spectrom. 44: 260-277.
46. Tholey, A., Heinzle, E. 2006. Ionic (liquid) matrices for matrixassisted laser desorption/ionization mass spectrometryapplications and perspectives. Anal. Bioanal. Chem. 386: 24-37.
47. Turro, N. J., Ramamurthy, V., Scaiano, J. C. 2009. Principles of Molecular Photochemistry: An Introduction, University Science Books, Sausalito, CA, pp 319.
48. Ullmann's Encyclopedia of Industrial Chemistry. 1991. Ed. 5, VCH, Weinheim, Vol. A 19, pp 573.
49. Veldstra, H. 1944. Researches on plant growth substances IV & V: Relation between chemical structures and physiological activity I & II. Enzymologia 11: 97-163.
50. Wasserscheid, P., Cramer, P., Welton, T. 2002. Ionic Liquids in Synthesis, Wiley VCH, Weinheim, pp 10.
51. Wong, W. S., Guo, D., Wang, X. L., Yin, Z. Q., Xia, B., Li, N. 2005. Study of cis-cinnamic acids in Arabidopsis thaliana. Plant Physiol. Biochem. 43: 929-937 (and references therein).
52. Yang, X. X., Choi, H. W., Yang, S. F., Li, N. 1999. A UV-light activated cinnamic acid isomer regulates plant growth and gravitropism via an ethylene receptor-independent pathway. Aust. J. Plant Physiol. 26: 325-335.
53. Yen, G. C., Chen, Y. L., Sun, F. M., Chiang, Y. L., Lu, S. H., Weng, C. J. 2011. A comparative study on the effectiveness of cis-and trans-form of cinnamic acid treatment for inhibiting invasive activity of human lung adenocarcinoma cells. Europ. J. Phar. Sci. 44: 281-287.
54. Yin, Z., Wong, W., Ye, W., Li, N. 2003. Biologically active ciscinnamic acid occurs naturally in Brassica parachinensis. Chinese Sci. Bull. 48: 555-558.
55. Young M. R., Neish, A. C. 1966. Properties of the ammonialyases deaminating phenylalanine and related compounds in Triticum sestivum and Pteridium aquilinum. Phytochemistry 5-1121-1132.