One-pot synthesis of linoleic acid hydroperoxide (LA-HPOD) catalyzed by soymeal was developed coupled with ultrasonic treatment. The influence of pH, temperature, dosage of reactants and solvents were investigated. The results showed that ultrasonic treatment could shorten the reaction time and obviously improved the yield of LA-HPOD. Under the ultrasonic irradiation of 40 kHz and 100 W, 1.5 g of soymeal and 1.5 g of linoleic acid in 7.5 mL borate buffer (pH 9.0) with ethanol volume of 0.5 mL at 15 ℃ for 40 min, the yield of LA-HPOD reached to 89%. Ultrasonic irradiation was successfully applied to lipoxygenase catalyzed reaction with soybean meal. The aim of low-cost, green and efficient synthesis of LA-HPOD with high substrate concentration was achieved.
CAI Yan
,
YAN Xin
,
ZHU Zhendong
,
CHEN Tingting
,
CHEN Jiao
. Ultrasonic assisted one-pot synthesis of linoleic acid hydroperoxide catalyzed by soymeal[J]. Food and Fermentation Industries, 2021
, 47(17)
: 156
-160
.
DOI: 10.13995/j.cnki.11-1802/ts.025844
[1] KESSLER A.Silencing the jasmonate cascade:Induced plant defenses and insect populations[J].Science,2004,305(5 684):665-668.
[2] MASHIMA R,OKUYAMA T.The role of lipoxygenases in pathophysiology;new insights and future perspectives[J].Redox Biology,2015,6:297-310.
[3] NEWCOMER M E,BRASH A R.The structural basis for specificity in lipoxygenase catalysis[J].Protein Science,2015,24(3):298-309.
[4] MARTINI D,IACAZIO G,FERRAND D,et al.Optimization of large-scale preparation of 13-(S)-hydroperoxy-9Z,11E-octadecadienoic acid using soybean lipoxygenase.Application to the chemoenzymatic synthesis of (+)-coriolic acid[J].Biocatalysis,1994,11(1):47-63.
[5] GAFFNEY B J.Connecting lipoxygenase function to structure by electron paramagnetic resonance[J].Accounts of Chemical Research,2014,47(12):3 588-3 595.
[6] HU S S,OFFENBACHER A R,LU E D,et al.Comparative kinetic isotope effects on first-and second-order rate constants of soybean lipoxygenase variants uncover a substrate-binding network[J].Journal of Biological Chemistry,2019,294(48):18 069-18 076.
[7] SOLER J,SAURA P,GARCÍA-LÓPEZ D,et al.How can linoleic acid be the preferential substrate of the enzyme 15-lipoxygenase-1? A QM/MM approach[J].The Journal of Physical Chemistry B,2016,120(8):1 950-1 960.
[8] ZHAO J H,WU J N,CHEN Y.Gel properties of soy protein isolate modified by lipoxygenase-catalyzed linoleic acid oxidation and their influence on pepsin diffusion and in vitro gastric digestion[J].Journal of Agricultural and Food Chemistry,2020,68(20):5 691-5 698.
[9] ZHAO J,SU G W,ZHAO M M,et al.Physicochemical changes and in vitro gastric digestion of modified soybean protein induced by lipoxygenase catalyzed linoleic acid oxidation[J].Journal of Agricultural and Food Chemistry,2019,67(50):13 978-13 985.
[10] PERRY S C,KALYANARAMAN C,TOURDOT B E,et al.15-Lipoxygenase-1 biosynthesis of 7S,14S-diHDHA implicates 15-lipoxygenase-2 in biosynthesis of resolvin D5[J].Journal of Lipid Research,2020,61(7):1 087-1 103.
[11] PAVLENKO I M,KUPTSOVA O S,KLYACHKO N L,et al.The lipase/lipoxygenase bienzyme system in AOT reversed micelles in octane[J].Russian Journal of Bioorganic Chemistry,2002,28(1):44-49.
[12] OFFENBACHER A R,SHARMA A,DOAN P E,et al.The soybean lipoxygenase-substrate complex:Correlation between the properties of tunneling-ready states and ENDOR-detected structures of ground states[J].Biochemistry,2020,59(7):901-910.
[13] CHAVAN P,BANGALE S,PANSARE D,et al.Synthesis of substituted pyrimidine using ZnFe2O4nanocatalyst via one pot multi-component reaction ultrasonic irradiation[J].Journal of Heterocyclic Chemistry,2020,57(9):3 326-3 333.
[14] PASCOAL C V P,OLIVEIRA A L L,FIGUEIREDO D D,et al.Optimization and kinetic study of ultrasonic-mediated in situ transesterification for biodiesel production from the almonds of Syagrus cearensis[J].Renewable Energy,2020,147:1 815-1 824.
[15] BHANGU S K,GUPTA S,ASHOKKUMAR M.Ultrasonic enhancement of lipase-catalysed transesterification for biodiesel synthesis[J].Ultrasonics Sonochemistry,2017,34:305-309.
[16] ZHANG F,HE Z,TU R,et al.Influence of ultrasonic/torrefaction assisted deep eutectic solvents on the upgrading of bio-oil from corn stalk[J].ACS Sustainable Chemistry & Engineering,2020,8(23):8 562-8 576.
[17] FALLAH KELARIJANI A,GHOLIPOUR ZANJANI N,KAMRAN PIRZAMAN A.Ultrasonic assisted transesterification of rapeseed oil to biodiesel using nano magnetic catalysts[J].Waste and Biomass Valorization,2020,11(6):2 613-2 621.
[18] CAI Y,LIU Y J,XU H,et al.Soymeal-catalyzed facile and economic bioproduction of soybean oil hydroperoxide[J].Biocatalysis and Biotransformation,2011,29(1):31-36.
[19] SURREY K.Spectrophotometric method for determination of lipoxidase activity[J].Plant Physiology,1964,39(1):65-70.
[20] GAY C,COLLINS J,GEBICKI J M.Hydroperoxide assay with the ferric-xylenol orange complex[J].Analytical Biochemistry,1999,273(2):149-155.