Speculate on the Formation Mechanism of Nonanal and Decanal from LPC (18:1) and LPE (18:1) in the Steaming of Chinese Water Chestnut Based on the <i>in Vitro</i> Model Study

LUO Xiujuan; LUO Yanghe; LI Guanli; LI Xiaochun; ZHANG Yitao; NIE Hui; WU Shujie

doi:10.13386/j.issn1002-0306.2022120189

Volume 44 Issue 18

Sep. 2023

Turn off MathJax

Article Contents

Abstract

References

Science and Technology of Food Industry > 2023 > 44(18): 123-130. > DOI: 10.13386/j.issn1002-0306.2022120189

LUO Xiujuan, LUO Yanghe, LI Guanli, et al. Speculate on the Formation Mechanism of Nonanal and Decanal from LPC (18:1) and LPE (18:1) in the Steaming of Chinese Water Chestnut Based on the in Vitro Model Study[J]. Science and Technology of Food Industry, 2023, 44(18): 123−130. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2022120189.

Citation:

PDF (1811 KB)

Speculate on the Formation Mechanism of Nonanal and Decanal from LPC (18:1) and LPE (18:1) in the Steaming of Chinese Water Chestnut Based on the in Vitro Model Study

LUO Xiujuan^{1, 2,},
LUO Yanghe^{1, 2, +,},
LI Guanli²,
LI Xiaochun²,
ZHANG Yitao^{1, 2},
NIE Hui²,
WU Shujie^2, ,

1.
College of Biological and Chemical Engineering, Guangxi University of Science and Technology, Liuzhou 545006, China
2.
Guangxi Key Laboratory of Health Care Food Science and Technology, Hezhou University, Hezhou 542899, China

More Information

Received Date: December 21, 2022
Available Online: July 13, 2023

Graphical Abstract

Abstract

Abstract

The in vitro models of oleoyl lysophosphatidylcholine 18:1 (LPC(18:1)), oleoyl lysophosphatidyl ethanolamine 18:1 (LPE(18:1)) and oleic acid were constructed by simulating the pH, LPC(18:1) and LPE(18:1) contents and steaming conditions of Chinese water chestnut (CWC). The content of nonanal, decanal and oleic acid, and peroxide value (POV) produced by the in vitro models were used as indicators to investigate the formation mechanism of nonanal and decanal from LPC(18:1) and LPE(18:1) during the steaming of CWC. The results showed that the possible mechanism of the oxidation of LPC(18:1) and LPE(18:1) to form nonanal and decanal was as follows. First of all, the C8 and C11 positions close to the double bond on the unsaturated acyl chain of LPC(18:1) and LPE(18:1) lost H respectively, and then formed R·. In the second step, the R· directly reacted with O₂ and H to form 8-hydroperoxide (8-ROOH), or reacted with O₂ and H to form 9-hydroperoxide (9-ROOH) and 10-hydroperoxide (10-ROOH) after electron rearrangement. Finally, 8-ROOH split homogeneously to form decanal, 9-ROOH and 10-ROOH split homogeneously to form nonanal. The results can provide scientific reference for the formation mechanism of flavor substances and the regulation of flavor quality of fruits and vegetables.

FullText(HTML)

References (34)

References

[1]	李官丽, 伍淑婕, 罗秀娟, 等. 基于SPME-GC-MS萃取荸荠挥发性风味物质研究[J]. 食品研究与开发,2022,43(14):70−78. [LI G L, WU S J, LUO X J, et al. Extraction of volatile flavor substances from Chinese water chestnut based on SPME-GC-MS[J]. Food Reserch and Development,2022,43(14):70−78. LI G L, WU S J, LUO X J, et al. Extraction of volatile flavor substances from Chinese water chestnut based on SPME-GC-MS[J]. Food Reserch and Development. 2022, 43(14): 70-78.
[2]	ANTEQUERA T, LÓPEZ-BOTE C J, CÓRDOBA J J, et al. Lipid oxidative changes in the processing of Iberian pig hams[J]. Food Chemistry,1992,45(2):105−110. doi: 10.1016/0308-8146(92)90018-W
[3]	BRUNA J M , ORDONEZ J A , FERNANDEZ M, et al. Microbial and physico-chemical changes during the ripening of dry fermented sausages superficially inoculated with or having added an intracellular cell-free extract of Penicillium aurantiogriseum[J]. Meat Science,2001,59(1):87−96. doi: 10.1016/S0309-1740(01)00057-2
[4]	ANDRES A I, CAVA R, VENTANAS J, et al. Lipid oxidative changes throughout the ripening of dry-cured Iberian hams with different salt contents and processing conditions[J]. Food Chemistry,2004,84(3):375−381. doi: 10.1016/S0308-8146(03)00243-7
[5]	USDA. National Nutrient Database for Standard [EB/OL]. https://ndb.nal.usda.gov/ndb/foods/show/302149 (most recent access April 12, 2021)
[6]	PIKUL J, LESZCZYNSKI D E, KUMMEROW F A. Relative role of phospholipids, triacylglycerols, and cholesterol esters on malonaldehyde formation in fat extracted from chicken meat[J]. Journal of Food Science,1984,49(3):704−708. doi: 10.1111/j.1365-2621.1984.tb13192.x
[7]	SASAKI K, MITSUMOTO M, KAWABATA K. Relationship between lipid peroxidation and fat content in Japanese Black beef longissimus muscle during storage[J]. Meat Science,2001,59(4):407−410. doi: 10.1016/S0309-1740(01)00093-6
[8]	HUAN Y J, ZHOU G H, ZHAO G M, et al. Changes in flavor compounds of dry-cured Chinese Jinhua ham during processing[J]. Meat Science,2005,71(2):291−299. doi: 10.1016/j.meatsci.2005.03.025
[9]	PENG C Y, LAN C H, LIN P C, et al. Effects of cooking method, cooking oil, and food type on aldehyde emissions in cooking oil fumes[J]. Journal of Hazardous Materials,2017,324:160−167. doi: 10.1016/j.jhazmat.2016.10.045
[10]	ZHANG J H, CAO J, PEI Z S, et al. Volatile flavour components and the mechanisms underlying their production in golden pompano (Trachinotus blochii) fillets subjected to different drying methods: A comparative study using an electronic nose, an electronic tongue and SDE-GC-MS[J]. Food Research International,2019,123:217−225. doi: 10.1016/j.foodres.2019.04.069
[11]	PORTER N A. Mechanisms for the autoxidation of polyunsaturated lipids[J]. Accounts of Chemical Research,1986,19(9):262−268. doi: 10.1021/ar00129a001
[12]	PAQUETTE G, KUPRANYCZ D B, VAN DE VOORT F R. The mechanisms of lipid autoxidation I. Primary oxidation products[J]. Canadian Institute of Food Science and Technology Journal,1985,18(2):112−118. doi: 10.1016/S0315-5463(85)71767-1
[13]	AHMED M, PICKOVA J, AHMAD T, et al. Oxidation of lipids in foods[J]. Sarhad Journal of Agriculture,2016,32(3):230−238. doi: 10.17582/journal.sja/2016.32.3.230.238
[14]	SILVAGNI A, FRANCO L, BAGNO A, et al. Thermo-induced lipid oxidation of a culinary oil: The effect of materials used in common food processing on the evolution of oxidised species[J]. Food Chemistry,2012,133(3):754−759. doi: 10.1016/j.foodchem.2012.01.088
[15]	FRANKEL E N. Recent advances in lipid oxidation[J]. Journal of the Science of Food and Agriculture,1991,54(4):495−511. doi: 10.1002/jsfa.2740540402
[16]	SCHAICH K M. Lipid oxidation: Theoretical aspects[J]. Bailey's Industrial Oil and Fat Products,2005,6(6):269−355.
[17]	IGENE J O, PEARSON A M, DUGAN L R, et al. Role of triglycerides and phospholipids on development of rancidity in model meat systems during frozen storage[J]. Food Chemistry,1980,5(4):263−276. doi: 10.1016/0308-8146(80)90048-5
[18]	ZAMORA R, HIDALGO F J. Contribution of lipid oxidation products to acrylamide formation in model systems[J]. Journal of Agricultural and Food Chemistry,2008,56(15):6075−6080. doi: 10.1021/jf073047d
[19]	刘欢. 北京烤鸭关键挥发性风味物质鉴别及其形成机制研究[D]. 北京: 中国农业科学院, 2020 LIU H. Identification of key volatile flavor substances of Peking duck and their formation mechanism[D]. Beijing: Chinese Academy of Agricultural Sciences, 2022.
[20]	黄淑霞. 反-2-壬烯醛对啤酒新鲜度的影响与调控机制研究[D]. 无锡: 江南大学, 2017 HUANG S X. Effect of trans-2-nonenal on beer freshness and its regulation mechanism [D]. Wuxi: Jiangnan University, 2017.
[21]	HUANG L S, KANG J S, KIN M R, et al. Oxygenation of arachidonoyl lysophospholipids by lipoxygenases from soybean, porcine leukocyte, or rabbit reticulocyte[J]. Journal of Agricultural and Food Chemistry,2008,56(4):1224−1232. doi: 10.1021/jf073016i
[22]	HUANG L S, KIM M R, SOK D E. Regulation of lipoxygenase activity by polyunsaturated lysophosphatidylcholines or their oxygenation derivatives[J]. Journal of Agricultural and Food Chemistry,2008,56(17):7808−7814. doi: 10.1021/jf801082x
[23]	HUANG L S, KIM M R, SOK D E. Linoleoyl lysophosphatidylcholine is an efficient substrate for soybean lipoxygenase-1[J]. Archives of Biochemistry and Biophysics,2006,455(2):119−126. doi: 10.1016/j.abb.2006.09.015
[24]	CAO J, JIANG X, CHEN Q Y, et al. Oxidative stabilities of olive and camellia oils: Possible mechanism of aldehydes formation in oleic acid triglyceride at high temperature[J]. LWT,2020,118(C):108858.
[25]	程华峰, 林琳, 葛孟甜, 等. 3种生态环境中华绒螯蟹肉挥发性风味特征的比较[J]. 食品与发酵工业,2019,45(23):247−256. [CHENG H F, LIN L, GE M T, et al. Comparison of volatile flavor characteristics of Chinese mitten crab meat in three ecological environments[J]. Food and Fermentation Industries,2019,45(23):247−256. CHENG H F, LIN L, GE M T, et al. Comparison of volatile flavor characteristics of Chinese mitten crab meat in three ecological environments[J]. Food and Fermentation Industries, 2019, 45(23): 247-256.
[26]	张唯, 高斌富, 常新, 等. 紫外法与碘量法测定食用植物油中过氧化值的比较[J]. 中国油脂,1993(5):37−39. [ZHANG W, GAO B F, CHANG X, et al. Comparison of ultraviolet and iodometric methods for the determination of peroxide in edible vegetable oils[J]. China Oils Fats,1993(5):37−39. ZHANG W, GAO B F, CHANG X, et al. Comparison of ultraviolet and iodometric methods for the determination of peroxide in edible vegetable oils[J]. China Oils Fats. 1993(5): 37-39.
[27]	青岛啤酒股份有限公司. 瓶内甲酯化-顶空固相微萃取-气相色谱质谱联用测定啤酒中游离脂肪酸的检测方法: 中国, 102539609B[P]. 2014-07-16 Tsingtao Brewery Company Limited. Determination of free fatty acids in beer by in-bottle methylation with headspace solid-phase microextraction coupled with gas chromatography-mass spectrometry: China, 102539609B[P]. 2014-07-16.
[28]	李官丽, 聂辉, 苏可珍, 等. 基于感官评价和电子鼻分析不同蒸煮时间荸荠挥发性风味物质[J]. 食品工业科技,2020,41(15):1−7,14. [LI G L, NIE H, SU K Z, et al. Analysis of volatile flavor compounds in Water chestnut with different steaming and cooking time based on sensory evaluation and electronic nose[J]. Science and Technology of Food Industry,2020,41(15):1−7,14. LI G L, NIE H, SU K Z, et al. Analysis of volatile flavor compounds in Water chestnut with different steaming and cooking time based on sensory evaluation and electronic nose. Science and Technology of Food Industry, 2020, 41(15): 1-7.
[29]	LEA C H. Recent developments in the study of oxidative deterioration of lipids[J]. Chem. Ind. (London),1953,49:1303−1309.
[30]	ESTÉVEZ M, MORCUENDE D, VENTANAS S, et al. Analysis of volatiles in meat from Iberian pigs and lean pigs after refrigeration and cooking by using SPME-GC-MS[J]. Journal of Agricultural and Food Chemistry,2003,51(11):3429−3435. doi: 10.1021/jf026218h
[31]	REIS A, SPICKETT C M. Chemistry of phospholipid oxidation[J]. Biochimica et Biophysica Acta (BBA)-Biomembranes,2012,1818(10):2374−2387. doi: 10.1016/j.bbamem.2012.02.002
[32]	PORTER N A, CALDWELL S E, MILLS K A. Mechanisms of free radical oxidation of unsaturated lipids[J]. Lipids,1995,30(4):277−290. doi: 10.1007/BF02536034
[33]	BALAKRISHNA M, MA J, LIU T, et al. Hydrolysis of oxidized phosphatidylcholines by crude enzymes from chicken, pork and beef muscles[J]. Food Chemistry,2020,313:125956. doi: 10.1016/j.foodchem.2019.125956
[34]	LU F S H, NIELSEN N S, BARON C P, et al. Marine phospholipids: The current understanding of their oxidation mechanisms and potential uses for food fortification[J]. Critical Reviews in Food Science and Nutrition,2017,57(10):2057−2070. doi: 10.1080/10408398.2014.925422