Grasas y Aceites, Vol 68, No 2 (2017)

Enzymatic production of sterculic acid from the novel Phoenix tree seed oil: Optimization and kinetic study


https://doi.org/10.3989/gya.0109171

X. Hou
Lipid Technology and Engineering, School of Food Science and Engineering, Henan University of Technology, China
orcid http://orcid.org/0000-0003-2976-1308

S. Sun
Lipid Technology and Engineering, School of Food Science and Engineering, Henan University of Technology, China
orcid http://orcid.org/0000-0002-3976-9250

Abstract


Phoenix tree (Firmiana simplex) seed oil is a novel oil which is rich in sterculic acid. Sterculic acid, a cyclopropene fatty acid, can be used as the inhibitor of the stearoyl-CoA desaturase system and mammary carcinomas growth. In this work, Lipozyme TLIM-catalyzed hydrolysis of the novel Phoenix tree seed oil was used to prepare sterculic acid. High temperature GC-FID and the degree of hydrolysis (DH) were used to monitor the reaction progress. Effects of reaction variables on the hydrolysis were evaluated and optimized using response surface methodology. Results showed that sterculic acid can be successfully prepared from the novel seed oil, and the effect of reaction variables on the hydrolysis decreased in the order of reaction time > enzyme load > temperature. A high yield of fatty acids (DH, 98.2±0.8%) can be obtained under optimized conditions (45 ºC, mass ratio of water to oil 10:1, enzyme load 10%, and 18 h). The Arrhenius equation for the hydrolysis was LnV0 = 9.12-4721/T. The activation energy was 39.25KJ/mol. The kinetic values for Vmax, K/m were 0.232mol/(L∙min) and 0.084 mol/L, respectively.

Keywords


Enzymatic hydrolysis; Kinetic; Lipozyme TLIM; Phoenix tree seed oil; Response surface methodology; Sterculic acid

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References


Albasi C, Bertrand N, Riba JP. 1999. Enzymatic hydrolysis of sunflower oil in a standardized agitated tank reactor. Bioprocess Eng. 20, 77–81. https://doi.org/10.1007/s004490050563

Al-Zuhair S, Hasan, Ramachandran KB. 2003. Kinetics of the enzymatic hydrolysis of palm oil by lipase. Process Biochem. 38, 1155–1163. https://doi.org/10.1016/S0032-9592(02)00279-0

AOAC, Firestone, D. (Eds.), Official Methods and Recommended Practices of the American Oil Chemistry Society, 5th Edn., AOCS Press, Champaign 1998, IL. Methods Cd 3d-63.

Aued-Pimentel S, Lago JHG, Chaves MH, Kumagai EE. 2004. Evaluation of a methylation procedure to determine cyclopropenoids fatty acids from Sterculia striata St. Hil. Et Nauds seed oil. J. Chromatogr. A 1054, 235–239. https://doi.org/10.1016/j.chroma.2004.07.090 PMid:15553149

Bai H, Li S, Yin F, Hu L. 2005. Isoprenylated Naphthoquinone Dimers Firmianones A, B, and C from Firmiana platanifolia. J. Nat. Prod. 68, 1159–1163. https://doi.org/10.1021/np050019l PMid:16124753

Chen W, Sun S, Liang S, Peng L, Wang Y, Shen M. 2014. Lipase-catalyzed Hydrolysis of Linseed Oil : Optimization Using Response Surface Methodology. J. Oleo Sci. 63, 619–628. https://doi.org/10.5650/jos.ess13189 PMid:24829129

Goswami D, Basu JK, De S. 2011. Lipase applications in oil hydrolysis with a case study on castor oil: a review. Crit. Rev. Biotechnol. 33, 81–96. https://doi.org/10.3109/07388551.2012.672319 PMid:22676042

Hasan F, Shah AA, Hameed A. 2006. Industrial applications of microbial lipases. Enzyme Microb. Technol. 39, 235–251. https://doi.org/10.1016/j.enzmictec.2005.10.016

James AT, Harris P, Bezard J. 1968. The inhibition of unsaturated fatty acid biosynthesis in plants by sterculic acid. Eur. J. Biochem. 3, 318–325. https://doi.org/10.1111/j.1432-1033.1968.tb19532.x PMid:5645527

Jeffcoat R, Pollard MR. 1968. Studies on the inhibition of the desaturases by cyclopropenoid fatty acids. Lipids 12, 480–485. https://doi.org/10.1007/BF02535446

Kim JW, Yang H, Cho N, Kim B, Kim YC, Sung SH. 2015. Hepatoprotective constituents of Firmiana simplex stem bark against ethanol insult to primary rat hepatocytes. Pharmacogn. Mag. 11, 55–60. https://doi.org/10.4103/0973-1296.149704 PMid:25709211 PMCid:PMC4329633

Khoo DE, Fermor B, Miller J, Wood CB, Apostolov K, Barker W, Williamson RC, Habib NA. 1991. Manipulation of body fat composition with sterculic acid can inhibit mammary carcinomas in vivo. Br. J. Cancer 63, 97–101. https://doi.org/10.1038/bjc.1991.20 PMid:1989672 PMCid:PMC1971644

Leng CCS, Baharin BS, Man YC, Tan CP. 2008. Optimisation of enzymatic hydrolysis for concentration of squalene in palm fatty acid distillate. J. Sci. Food Agric. 88, 1512–1517. https://doi.org/10.1002/jsfa.3237

Mendes AA, Oliveira PC, de Castro HF. 2012. Properties and biotechnological applications of porcine pancreatic lipase. J. Mol. Catal. B: Enzym. 78, 119–134. https://doi.org/10.1016/j.molcatb.2012.03.004

Murty VR, Bhat J, Muniswaran PKA. 2002. Hydrolysis of oils by using immobilized lipase enzyme: a review. Biotechnol. Bioprocess Eng. 7, 57–66. https://doi.org/10.1007/BF02935881

Phuah ET, Lai OM, Choong TS, Tan CP, Lo SK. 2012. Kinetic study on partial hydrolysis of palm oil catalyzed by Rhizomucor miehei lipase. J. Mol. Catal. B: Enzym. 78, 91–97. https://doi.org/10.1016/j.molcatb.2012.03.009

Prado GHC, Salda-a MDA. 2013. Optimization of enzymatic hydrolysis of sacha inchi oil using conventional and supercritical carbon dioxide processes. J. Am. Oil Chem. Soc. 90, 731–742. https://doi.org/10.1007/s11746-013-2205-4

Reiser R, Raju PK. 1964. The inhibition of saturated fatty acid dehydrogenation by dietary fat containing sterculic and malvalic acids. Biochem. Biophys. Res. Commun. 17, 8-11. https://doi.org/10.1016/0006-291X(64)90291-8

Satyarthi JK, Srinivas D, Ratnasamy P. 2011. Hydrolysis of vegetable oils and fats to fatty acids over solid acid catalysts. Appl. Catal. A. 391, 427–435. https://doi.org/10.1016/j.apcata.2010.03.047

Santos KC, Cassimiro DMJ, Avelar MHM, Hirata DB, de Castro HF, Fernández-Lafuente R, Mendes AA. 2013. Characterization of the catalytic properties of lipases from plant seeds for the production of concentrated fatty acids from different vegetable oils. Ind. Crops Prod. 49, 462–470. https://doi.org/10.1016/j.indcrop.2013.05.035

Son YK, Lee MH, Han YN. 2005. A new antipsychotic effective neolignan from Firmiana simplex. Arch. Pharm. Res. 28, 34–38. https://doi.org/10.1007/BF02975132 PMid:15742805

Sun S, Chen X. 2015. Kinetics of enzymatic synthesis of monoferuloyl glycerol and diferuloyl glycerol by transesterification in [BMIM]PF6. Biochem. Eng. J. 97, 25–31. https://doi.org/10.1016/j.bej.2015.02.002

Sun S, Li X. 2016. Physicochemical properties and fatty acid profile of Phoenix tree seed and its oil. J. Am. Oil Chem. Soc. 93, 1111–1114. https://doi.org/10.1007/s11746-016-2861-2

Syam AM, Rashid U, Yunus R, Hamid HA, Al-Resayesc SI, Nehdic IA, Al-Muhtaseb AH. 2016. Conversion of Oleum papaveris seminis oil into methyl esters via esterification process: Optimization and kinetic study. Grasas Aceites 67, 1–9.

Tang Q, Tang X, Hu M, Li Z, Chen Y, Lou P. 2010. Removal of Cd(II) from aqueous solution with activated Firmiana Simplex leaf: Behaviors and affecting factors. J. Hazard. Mater. 179, 95–103. https://doi.org/10.1016/j.jhazmat.2010.02.062 PMid:20303655

Upson TM, Cullen J. 2012. Firmiana simplex. Curtis's Bot. Mag. 29, 170–181. https://doi.org/10.1111/j.1467-8748.2012.01783.x

Wältermann M, Steinbüchel A. 2000. In vitro effects of sterculic acid on lipid biosynthesis in Rhodococcus opacus strain PD630 and isolation of mutants defective in fatty acid desaturation. FEMS Microbiol. Lett. 190, 45–50. https://doi.org/10.1111/j.1574-6968.2000.tb09260.x PMid:10981688

Woo KW, Choi SU, Kim KH, Lee KR. 2015. Ursane saponins from the stems of Firmiana simplex and their cytotoxic activity. J. Braz. Chem. Soc. 26, 1450–1456.

Woo KW, Suh WS, Subedi L, Kim SY, Kim A, Lee KR. 2016. Bioactive lignan derivatives from the stems of Firmiana simplex. Bioorg. Med. Chem. Lett. 26, 730–733. https://doi.org/10.1016/j.bmcl.2016.01.008 PMid:26774654




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