1,3-Diferuloyl-sn-glycerol from the biocatalytic transesterification of ethyl 4-hydroxy-3-methoxy cinnamic acid (ethyl ferulate) and soybean oil

Biotechnology Letters

Volumn 31, Issue 6, 2009, Pages 889-896

  Compton, David L ^a   Laszlo, Joseph A ^a  

^a NATIONAL CENTER FOR AGRICULTURAL UTILIZATION RESEARCH   (United States)

Author keywords

Diferuloyl glycerol; Ethyl ferulate; Novozym 435; Soybean oil; Sunscreen; Transesterification

Indexed keywords

DIFERULOYL GLYCEROL; ETHYL FERULATE; NOVOZYM 435; SOYBEAN OIL; SUNSCREEN;

ACIDS; BIOLOGICAL WATER TREATMENT; ESTERIFICATION; PILOT PLANTS; SUN HOODS; TRANSESTERIFICATION;

GLYCEROL;

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 2,2-DIPHENYL-1-PICRYLHYDRAZYL; ANTIOXIDANT; BIPHENYL DERIVATIVE; CAFFEIC ACID DERIVATIVE; COUMARIC ACID; DRUG DERIVATIVE; ETHYL FERULATE; FERULIC ACID; GLYCEROL; PICRIC ACID; SOYBEAN OIL; SUNSCREEN;

ARTICLE; BIOREACTOR; CHEMISTRY; ISOLATION AND PURIFICATION; METABOLISM; SOYBEAN; SPECTROSCOPY; ULTRAVIOLET RADIATION;

ANTIOXIDANTS; BIOREACTORS; BIPHENYL COMPOUNDS; CAFFEIC ACIDS; COUMARIC ACIDS; GLYCEROL; PICRATES; SOYBEAN OIL; SOYBEANS; SPECTRUM ANALYSIS; SUNSCREENING AGENTS; ULTRAVIOLET RAYS;

GLYCINE MAX;

EID: 67349231801     PISSN: 01415492     EISSN: 15736776     Source Type: Journal    
DOI: 10.1007/s10529-009-9952-1     Document Type: Article

References (30)

1. American Oil Chemists Society (AOCS) (1994) Acid value. Official methods and recommended practices of the American Oil Chemists' Society, 4th edn. AOCS, Champaign, pp Cd 3d-63
2. C Anselmi M Centini P Granata A Sega A Buonocore A Bernini RM Facino 2004 Antioxidant activity of ferulic acid alkyl esters in a heterophasic system: a mechanistic insight J Agric Food Chem 52 6425 6432
3. DI Batovska T Kishimoto VS Bankova ZG Kamenarska M Ubukata 2005 Synthesis of some phenylpropanoid monoglycerides via the mitsunobu protocol Molecules 10 552 558 (Pubitemid 40727445)
4. Chigorimbo-Murefu NTL, Riva S, Burton SG (2008) Lipase-catalysed synthesis of esters of ferulic acid with natural compounds and evaluation of their antioxidant properties. J Mol Catal B Enzym. doi: 10.1016/j.molcatb.2008. 05.017
5. Choo W-S, Birch EJ (2009) Radical scavenging activity of lipophilized products from lipase-catalyzed transesterification of triolein with cinnamic and ferulic acid. Lipids 44(2):145-152. doi: 10.1007/s11745-008-3242-x
6. Compton DL, Laszlo JA (2002) Novel sunscreens from vegetable oil and plant phenols. U.S. Patent 6,346,236
7. DL Compton JA Laszlo MA Berhow 2000 Lipase-catalyzed synthesis of ferulate esters J Am Oil Chem Soc 77 513 519
8. DL Compton JA Laszlo MA Berhow 2006 Identification and quantification of feruloylated mono- and diacylglycerols from vegetable oils J Am Oil Chem Soc 83 753 758 (Pubitemid 44562596)
9. DL Compton JA Kenar JA Laszlo 2007 Starch-encapsulated, soy-based ultraviolet-absorbing composites with feruloylated monoacyl- and diacylglycerol lipids Indiana Crop Prod 25 17 23
10. R Copper HG Gottlieb D Lavie 1978 New phenolic diglycerides from Aegilops ovata Phytochemistry 17 1673 1675
11. J Graça H Pereira 2000 Suberin structure in potato periderm: glycerol, long-chain monomers, and glyceryl and feruloyl dimmers J Agric Food Chem 48 5476 5483
12. RA Holser 2008 Kinetics of cinnamoyl glycerol formation J Am Oil Chem Soc 85 221 225
13. RA Holser TR Mitchell RE Harry-O'kuru SF Vaughn E Walter D Himmelsbach 2008 Preparation and characterization of 4-methoxy cinnamoyl glycerol J Am Oil Chem Soc 85 347 351
14. D Huang B Ou RL Prior 2005 The chemistry behind antioxidant capacity assays J Agric Food Chem 53 1841 1856
15. H Kikuzaki M Hisamoto K Hirose K Akiyama H Taniguchi 2002 Antioxidant properties of ferulic acid and its related compounds J Agric Food Chem 50 2161 2168 (Pubitemid 34260027)
16. King HGC (1964) Caffeoyl glycerides. U.S. Patent 3,153,659
17. JA Laszlo DL Compton 2006 Enzymatic glycerolysis and transesterification of soybean oil for enhanced production of feruloylated mono- and diacylglycerols J Am Oil Chem Soc 83 765 770 (Pubitemid 44562598)
18. JA Laszlo DL Compton FJ Eller SL Taylor TA Isbell 2003 Packed-bed bioreactor synthesis of feruloylated monoacyl- and diacylglycerols: clean production of a "green" sunscreen Green Chem 5 382 386 (Pubitemid 37027226)
19. N Nenadis H-Y Zhang MZ Tsimidou 2003 Structure-antioxidant activity relationship of ferulic acid derivatives: effect of carbon side chain characteristic groups J Agric Food Chem 51 1874 1879
20. J Rozema AJ Noordijk RA Broekman AM van Beem B Meijkamp NVJ de Bakker JWM van de Staaij M Stroetenga SJP Bohncke M Konert S Kars H Peat RIL Smith P Convey 2001 (Poly)phenolic compounds in pollen and spores of antarctic plants as indicators of solar UV-B Plant Ecol 154 9 26
21. CT Ruhland TA Day 2000 Effects of ultraviolet-B radiation on leaf elongation, production and phenylpropanoid concentrations of Deschampsia antarctica and Colobanthus quitensis in Antarctica Physiol Plant 109 244 251 (Pubitemid 30448389)
22. K Sabally S Karboune FK Yeboah S Kermasha 2005 Lipase-catalyzed esterification of selected phenolic acids with linolenyl alcohols in organic solvent media Appl Biochem Biotechnol 127 17 27 (Pubitemid 41367757)
23. K Sabally S Karboune R St-Louis S Kermasha 2006 Lipase-catalyzed transesterification of dihydrocaffeic acid with flaxseed oil for the synthesis of phenolic lipids J Biotechnol 127 167 176 (Pubitemid 46107127)
24. A Saija A Tomaino R Lo Cascio D Trombetta A Proteggente A De Pasquale N Uccella F Bonina 1999 Ferulic and caffeic acids as potential protective agents against photooxidative skin damage J Sci Food Agric 79 476 480 (Pubitemid 29150603)
25. S Sun L Shan Y Liu Q Jin X Wang Z Wang 2007 A novel, two consecutive enzyme synthesis of feruloylated monoacyl- and diacyl-glycerols in a solvent-free system Biotechnol Lett 29 1947 1950 (Pubitemid 350043618)
26. S Sun L Shan Q Jin Y Liu X Wang 2007 Solvent-free synthesis of glyceryl ferulate using a commercial microbial lipase Biotechnol Lett 29 945 949 (Pubitemid 46643646)
27. Sun S, Shan L, Liu Y, Jin Q, Song Y, Wang X (2008) Solvent-free enzymatic synthesis of feruloylated diacylglycerols and kinetic Study. J Mol Catal B Enzym. doi: 10.1016/j.molcatb.2008.07.010
28. M Tsuchiyama T Sakamoto T Fujita S Murata H Kawasaki 2006 Esterification of ferulic acid with polyols using a ferulic acid esterase from Aspergillus niger Biochim Biophys Acta 1760 1071 1079 (Pubitemid 43867930)
29. Yadav GD, Dhoot SB (2008) Immobilized lipase-catalysed synthesis of cinnamoyl laurate in non-aqueous media. J Mol Catal B Enzym. doi: 10.1016/j.molcatb.2008.06.01
30. K Yagi N Ohishi 1979 Action of ferulic acid and its derivatives as antioxidants J Nutr Sci Vitaminol 25 127 130 (Pubitemid 9218051)