Solvent-free lipase-catalyzed preparation of long-chain alkyl phenylpropanoates and phenylpropyl alkanoates

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 8, 2006, Pages 2969-2976

  Vosmann, Klaus ^a   Weitkamp, Petra ^a   Weber, Nikolaus ^a  

^a FEDERAL RESEARCH INSTITUTE OF NUTRITION AND FOOD   (Germany)

Author keywords

3 (4 hydroxyphenyl) oleate; 3 phenylpropyl alkanoates; Alkyl 3 (hydroxyphenyl)propenoates; Alkyl 3 (methoxyphenyl)propenoates; Alkyl cinnamates; Immobilized Candida antarctica lipase B; Oleyl coumarates; Oleyl ferulate; Palmityl ferulate

Indexed keywords

CANDIDA ANTARCTICA; RHIZOMUCOR; RHIZOMUCOR MIEHEI;

EID: 33646501199     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf060052t     Document Type: Article

References (47)

1. Cox, B. D.; Whichelow, M. J.; Prevost, A. T. Seasonal consumption of salad vegetables and fresh fruit in relation to the development of cardiovascular disease and cancer. Public Health Nutr. 2000, 3, 19-29.
2. van't Veer, P.; Jansen, M. C. J. F.; Klerk, M.; Kok, F. J. Fruits and vegetables in the prevention of cancer and cardiovascular disease. Public Health Nutr. 2000, 3, 103-107.
3. Lee, J.; Koo, N.; Min, D. B. Reactive oxygen species, aging, and antioxidative nutraceuticals. Compr. Rev. Food Sci. Food Saf. 2004, 3, 21-33.
4. Manach, C.; Scalbert, A.; Morand, C.; Rémésy, C.; Jiménez, L. Polyphenols: food sources and bioavailability. Am. J. Clin. Nutr. 2004, 79, 727-747.
5. Ou, S.; Kwok, K.-C. Ferulic acid: pharmaceutical functions, preparation and applications in foods. J. Sci. Food Agric. 2004, 84, 1261-1269.
6. Andreasen, M. F.; Landbo, A.-K.; Christensen, L. P.; Hansen, A.; Meyer, A. S. Antioxidant effects of phenolic rye (Secale cereale L.) extracts, monomeric hydroxycinnamates, and ferulic acid dehydrodimers on human low-density lipoproteins. J. Agric. Food Chem. 2001, 49, 4090-4096.
7. Anselmi, C.; Centini, M.; Granata, P.; Sega, A.; Buonocore, A.; Bernini, A.; Facino, R. M. Antioxidant activity of ferulic acid alkyl esters in a heterophasic system: a mechanistic insight. J. Agric. Food Chem. 2004, 52, 6425-6432.
8. Chen, J.-H.; Shao, Y.; Huang, M.-T.; Chin, C.-K.; Ho, C.-T. Inhibitory effect of caffeic acid phenethyl ester on human leukemia HL-60 cells. Cancer Lett. 1996, 108, 211-214.
9. Chen, J.-H.; Ho, C.-T. Antioxidant activities of caffeic acid and its related hydroxycinnamic acid compounds. J. Agric. Food Chem. 1997, 45, 2374-2378.
10. Kikuzaki, H.; Hisamoto, M.; Hirose, K.; Akiyama, K.; Taniguchi, H. Antioxidant properties of ferulic acid and its related compounds. J. Agric. Food Chem. 2002, 50, 2161-2168.
11. Murakami, A.; Nakamura, Y.; Koshimizu, K.; Takahashi, D.; Matsumoto, K.; Hagihara, K.; Taniguchi, H.; Nomura, E.; Hosoda, A.; Tsuno, T.; Maruta, Y.; Kim, H. W.; Kawabata, K.; Ohigashi, H. FA15, a hydrophobic derivative of ferulic acid, suppresses inflammatory responses and skin tumor promotion: comparison with ferulic acid. Cancer Lett. 2002, 180, 121-129.
12. Figueroa-Espinoza, M.-C.; Villeneuve, P. Phenolic acids enzymatic lipophilization. J. Agric. Food Chem. 2005, 53, 2779-2787.
13. Sultana, R.; Ravagna, A.; Mohmmad-Abdul, H.; Calabrese, V.; Butterfield, D. A. Ferulic acid ethyl ester protects neurons against amyloid b-peptide(1-42)-induced oxidative stress and neurotoxicity: relationship to antioxidant activity. J. Neurochem. 2005, 92, 749-758.
14. Adams, T. B.; Cohen, S. M.; Doull, J.; Feron, V. J.; Goodman, J. I.; Marnett, L. J.; Munro, I. C.; Portoghese, P. S.; Smith, R. L.; Waddell, W. J.; Wagner, B. M. The FEMA GRAS assessment of cinnamyl derivatives used as flavor ingredients. Food Chem. Toxicol. 2004, 42, 157-185.
15. Compton, D. L.; Laszlo, J. A.; Isbell, T. A. Cinnamoyl esters of lesquerella and castor oil: novel sunscreen active ingredients. J. Am. Oil Chem. Soc. 2004, 81, 945-951.
16. Compton, D. L.; Isbell, T. A.; Harry-O'kuru, R. E. Novel sunscreen reagents from hydroxy-substituted acylglycerides. U.S. Patent Appl. 20040258743 A1, Dec 23, 2004.
17. Schneider, S.; Deckhardt, K.; Hellwig, J.; Küttler, K.; Mellert, W.; Schulte, S.; van Ravenzwaay, B. Octyl methoxycinnamate: Two generation reproduction toxicity in Wistar rats by dietary administration. Food Chem. Toxicol. 2005, 43, 1083-1092.
18. Taniguchi, H.; Nomura, E.; Tsuno, T.; Minami, S. Ferulic acid ester antioxidant/UV absorbent. Eur. Patent Appl. 0681825 A2, Nov 15, 1991.
19. Krygier, K.; Sosulski, F.; Hogge, L. 2. Composition of phenolic acids in rapeseed flour and hulls. J. Agric. Food Chem. 1982, 30, 334-336.
20. Krygier, K.; Sosulski, F.; Hogge, L. 3. Composition of phenolic acids in cereal and potato flours. J. Agric. Food Chem. 1982, 30, 337-340.
21. Ralph, J.; Grabber, J. H.; Hatfield, R. D. Lignin-ferulate cross-links in grasses: active incorporation of ferulate polysaccharide esters into ryegrass lignins. Carbohydr. Res. 1995, 275, 167-178.
22. Faulds, C. B.; Williamson, G. The role of hydroxycinnamates in the plant cell wall. J. Sci. Food Agric. 1999, 79, 393-395.
23. Sun, R. C.; Sun, X.-F.; Zhang, S.-H. Quantitative determination of hydroxycinnamic acids in wheat, rice, rye, and barley straws, maize stems, oil palm frond fiber, and fast-growing poplar wood. J. Agric. Food Chem. 2001, 49, 5122-5129.
24. Zhou, Z.; Robards, K.; Helliwell, S.; Blanchard, C. The distribution of phenolic acids in rice. Food Chem. 2004, 87, 401-406.
25. Mendez, J. Dihydrocinnamic acids in Pteridium aquilinum. Food Chem. 2005, 93, 251-252.
26. Adamovics, J. A.; Johnson, G.; Stermitz, F. R. Ferulates from cork layers of Solanum tuberosum and Pseudotsuga menziesii. Phytochemistry 1977, 16, 1089-1090.
27. Baldé, A. M.; Claeys, M.; Pieters, L. A.; Wray, V.; Vlietinck, A. J. Ferulic acid esters from stem bark of Pavetta owariensis. Phytochemistry 1991, 30, 1024-1026.
28. Laver, M. L.; Fang, H. H.-L. Ferulic acid esters from bark of Pseudotsuga menziesii. J. Agric. Food Chem. 1989, 37, 114-116.
29. Chatterjee, A.; Dhara, K. P.; Rej, R. N.; Ghosh, P. C. Hexaco-sylferulate, a phenolic constituent of Pinus roxburghii. Phytochemistry 1977, 16, 397-398.
30. Kawanishi, K.; Yasufuku, J.; Ishikawa, A.; Hashimoto, Y. Long-chain alkyl ferulates in three varieties of Ipomoea batatas (L.) Lam. J. Agric. Food Chem. 1990, 38, 105-108.
31. Sarker, S. D.; Shaheen, E. M.; Eynon, E.; Nahar, L. Caffeic acid decyl ester: an antioxidant principle from Phleum pratense. Chem. Nat. Compd. 2005, 41, 293-296.
32. Yunoki, K.; Musa, R.; Kinoshita, M.; Tazaki, H.; Oda, Y.; Ohnishi, M. Presence of higher alcohols as ferulates in potato pulp and its radical-scavenging activity. Biosci., Biotechnol., Biochem. 2004, 68, 2619-2622.
33. Whitaker, B. D.; Schmidt, W. F.; Kirk, M. C.; Barnes, S. Novel fatty acid esters of p-coumaryl alcohol in epicuticular wax of apple fruit. J. Agric. Food Chem. 2001, 49, 3787-3792.
34. Cefarelli, G.; Abrosca, B. D.; Fiorentino, A.; Izzo, A.; Monaco, P. Isolation, characterization, and antioxidant activity of E- and Z-p-coumaryl fatty acid esters from cv. annurca apple fruits. J. Agric. Food Chem. 2005, 53, 3525-3529.
35. Bernards, M. A.; Lewis, N. G. Alkyl ferulates in wound healing potato tubers. Phytochemistry 1992, 31, 3409-3412.
36. Condo, A. M., Jr.; Baker, D. C.; Moreau, R. A.; Hicks, K. B. Improved method for the synthesis of trans-feruloyl-β-sitostanol. J. Agric. Food Chem. 2001, 49, 4961-4964.
37. Compton, D. L.; Laszlo, J. A.; Berhow, M. A. Lipase-catalyzed synthesis of ferulate esters. J. Am. Oil Chem. Soc. 2000, 77, 513-519.
38. Giuliani, S.; Piana, C.; Setti, L.; Hochkoeppler, A.; Pifferi, P. G.; Williamson, G.; Faulds, C. B. Synthesis of pentylferulate by a feruloyl esterase from Aspergillus niger using water-in-oil microemulsions. Biotechnol. Lett. 2001, 23, 325-330.
39. Guyot, B.; Bosquette, B.; Pina, M.; Graille, J. Esterification of phenolic acids from green coffee with an immobilized lipase from Candida antarctica in solvent-free medium. Biotechnol. Lett. 1997, 19, 529-532.
40. Stamatis, H.; Sereti, V.; Kolisis, F. N. Studies on the enzymatic synthesis of lipophilic derivatives of natural antioxidants. J. Am. Oil Chem. Soc. 1999, 12, 1505-1510.
41. Stamatis, H.; Sereti, V.; Kolisis, F. N. Enzymatic synthesis of hydrophilic and hydrophobic derivates of natural phenolic acids in organic media. J. Mol. Catal. B: Enzym. 2001, 11, 323-328.
42. Topakas, E.; Stamatis, H.; Biely, P.; Kekos, D.; Macris, B. J.; Christakopoulos, P. Purification and characterization of a feruloyl esterase from Fusarium oxysporum catalyzing esterification of phenolic acids in ternary water-organic solvent mixtures. J. Biotechnol. 2003, 102, 33-44.
43. Twu, Y.-K.; Shih, I.-L.; Yen, Y.-H.; Ling, Y.-F.; Shieh, C.-J. Optimization of lipase-catalyzed synthesis of octyl hydroxyphenylpropionate by response surface methodology. J. Agric. Food Chem. 2005, 53, 1012-1016.
44. Jung, M. Y.; Jeon, B. S.; Bock, J. Y. Free, esterified, and insoluble-bound phenolic acids in white and red Korean ginsengs (Panax ginseng C.A. Meyer). Food Chem. 2002, 79, 105-111.
45. Lutz, A.; Knörr, W.; Spiteller, G. Produkte des reduktiven Abbaus von α-(Acyloxy)plasmalogenen aus Rindergewebe-Lipiden mit LiAlH4. Liebigs Ann. Chem. 1991, 1151-1155.
46. Weber, N.; Weitkamp, P.; Mukherjee, K. D. Fatty acid steryl, stanyl and steroid esters by esterification and transesterification in vacuo using Candida rugosa lipase as catalyst. J. Agric. Food Chem. 2001, 49, 67-71.
47. Weber, N.; Weitkamp, P.; Mukherjee, K. D. Steryl and stanyl esters of fatty acids by solvent-free esterification and transesterification in vacuo using lipases from Rhizomucor miehei, Candida antarctica, and Carica papaya. J. Agric. Food Chem. 2001, 49, 5210-5216.