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Enrichment of linoleic acid from yellow horn seed oil through low temperature crystallization followed by urea complexation method and hypoglycemic activities

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Abstract

Yellow horn (Xanthoceras sorbifolia Bunge) contained abundant linoleic acid (LA), accounting for about 44% of its lipid. Here, LA was enriched by low temperature crystallization followed by urea complexation, and the optimal enrichment conditions were optimized with response surface methods (3:1 ratio of EtOH/FFA, crystallization at − 25 °C for 24.5 h; 2:1 ratio of urea/FFA1, 6.6:1 ratio of EtOH/urea, crystallization at − 10 °C for 22.4 h). Under these conditions, the final LA content and recovery were 97.10% and 62.09%, respectively. In vitro hypoglycemic studies suggested that the LA extract with stronger inhibition on α-glucosidase and lower one on α-amylase than acarbose exhibited a positive control for carbohydrate digestion with lower adverse effects. The enzyme kinetics and Lineweaver–Burk plots analyses revealed a reversible competitive inhibition on α-amylase and α-glucosidase. The findings of this research provided insights for the development of the LA extract as the functional component of health food.

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References

  • Burlingham BT, Widlanski TS. An intuitive look at the relationship of Ki and IC50: A more general use for the dixon plot. Journal of Chemical Education. 80: 214-218 (2003)

    Article  CAS  Google Scholar 

  • Chen QX, Song KK, Qiu L, Liu XD, Huang H, Guo HY. Inhibitory effects on mushroom tyrosinase by p-alkoxybenzoic acids. Food Chemistry. 91: 269-274 (2005)

    Article  CAS  Google Scholar 

  • Devi V, Khanam S. Study of ω-6 linoleic and ω-3 α-linolenic acids of hemp (Cannabis sativa) seed oil extracted by supercritical CO2 extraction: CCD optimization. Journal of Environmental Chemical Engineering. 7: 102818 (2019)

    Article  CAS  Google Scholar 

  • Fu J, Zhang XW, Liu K, Li QS, Zhang LR, Yang XH, Zhang ZM, Li CZ, Luo Y, He ZX, Zhu HL. Hypolipidemic activity in Sprague-Dawley rats and constituents of a novel natural vegetable oil from Cornus wilsoniana fruits. Journal of Food Science. 77: 160-169 (2012)

    Article  Google Scholar 

  • Islam MS, Christopher LP, Alam MN. Separation and purification of ω-6 linoleic acid from crude tall oil. Separations. 7: 9 (2020)

    Article  CAS  Google Scholar 

  • Ju YH, Chen TC. High-purity gamma-linoleic acid from borage oil fatty acids. Journal of the American Oil Chemists Society. 79: 29-32 (2002)

    Article  CAS  Google Scholar 

  • Kawamura-Konishi Y, Watanabe N, Saito M, Nakajima N, Sakaki T, Katayama T, Enomoto T. Isolation of a new phlorotannin, a potent inhibitor of carbohydrate-hydrolyzing enzymes, from the Brown Alga Sargassum patens. Journal of Agricultural and Food Chemistry. 60: 5565-5570 (2012)

    Article  CAS  PubMed  Google Scholar 

  • Kumari S, Meng GY, Ebrahimi M. Conjugated linoleic acid as functional food in poultry products: A review. International Journal of Food Properties. 20: 491-506 (2016)

    Article  Google Scholar 

  • Lee YW, Park HJ, Hennig B, Toborek M. Linoleic acid induces MCP-1 gene expression in human microvascular endothelial cells through an oxidative mechanism. Journal of Nutritional Biochemistry. 12: 648-654 (2001)

    Article  CAS  Google Scholar 

  • Li H, Fu X, Deng G, David A, Huang L. Extraction of oil from grape seeds (Vitis vinifera L.) using recyclable CO2-expanded ethanol. Chemical Engineering and Processing - Process Intensification. 157: 108147 (2020)

    Article  CAS  Google Scholar 

  • Lin X, Yi X, Ni S. Optimization of ultrasonic-assisted extraction and fatty acid composition of oil from Paeonia suffruticosa Andr. seed. Journal of Oleo Science. 70: 39-49 (2021)

    Article  CAS  PubMed  Google Scholar 

  • Lv H, Chen S, Xu X, Zhu M, Zhao W, Liu K, Liu K. Isolation of linoleic acid from Sambucus williamsii seed oil extracted by high pressure fluid and its antioxidant, antiglycemic, hypolipidemic activities. International Journal of Food Engineering. 11: 383-391 (2015)

    Article  CAS  Google Scholar 

  • Magallanes LM, Tarditto LV, Grosso NR, Pramparo MC, Gayol MF. Highly concentrated omega-3 fatty acid ethyl esters by urea complexation and molecular distillation. Journal of the Science of Food and Agriculture. 99: 877-884 (2019)

    Article  CAS  PubMed  Google Scholar 

  • Meng Y, Su A, Yuan S, Zhao H, Tan S, Hu C, Deng H, Guo Y. Evaluation of total flavonoids, myricetin, and quercetin from Hovenia dulcis Thunb. as inhibitors of α-amylase and α-glucosidase. Plant Foods for Human Nutrition. 71: 444-449 (2016)

    Article  CAS  PubMed  Google Scholar 

  • NIST (2023) NIST Standard Reference Database Number 69. NIST Chemistry WebBook. https://doi.org/10.18434/T4D303

  • Nunes DO, Marques VB, Almenara CCP, Marcarini WD, Ribeiro RF, Padilha AS. Linoleic acid reduces vascular reactivity and improves the vascular dysfunction of the small mesentery in hypertension. Journal of Nutritional Biochemistry. 62: 18-27 (2018)

    Article  CAS  PubMed  Google Scholar 

  • Patil D, Nag A. Production of PUFA concentrates from poultry and fish processing waste. Journal of the American Oil Chemists Society. 88: 589-593 (2011)

    Article  CAS  Google Scholar 

  • Phan MAT, Wang J, Tang J, Lee YZ, Ng K. Evaluation of α-glucosidase inhibition potential of some flavonoids from Epimedium brevicornum. LWT - Food Science and Technology. 53: 492-498 (2013)

    Article  CAS  Google Scholar 

  • Qin G, Xu W, Liu J, Zhao L, Chen G. Purification, characterization and hypoglycemic activity of glycoproteins obtained from pea (Pisum sativum L.). Food Science and Human Wellness. 10: 297-307 (2021)

    Article  CAS  Google Scholar 

  • Salimon J, Abdullah B M, Salih N. Selectively increasing of polyunsaturated (18:2) and monounsaturated (18:1) fatty acids in jatropha curcas seed oil by crystallization using d-optimal design. Chemistry Central Journal. 6: 65 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Santoso M, Ong LL, Aijijiyah NP, Wati FA, Azminah A, Annuur RM, Fadlan A, Judeh ZMA. Synthesis, α-glucosidase inhibition, α-amylase inhibition, and molecular docking studies of 3,3-di(indolyl)indolin-2-ones. Heliyon. 8: e09045 (2022)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Su CH, Hsu CH, Ng LT. Inhibitory potential of fatty acids on key enzymes related to type 2 diabetes. Biofactors. 39: 415-421 (2013a)

    Article  CAS  PubMed  Google Scholar 

  • Su CH, Lu TM, Lai MN, Ng LT. Inhibitory potential of Grifola frondosa bioactive fractions on α-amylase and α-glucosidase for management of hyperglycemia. Biotechnology and Applied Biochemistry. 60: 446-452 (2013b)

    Article  CAS  PubMed  Google Scholar 

  • Su J, Wang H, Ma C, Lou Z, Liu C, Rahman MT, Gao C, Nie R. Anti-diabetic activity of peony seed oil, a new resource food in STZ-induced diabetic mice. Food and Function. 6: 2930-2938 (2015)

    Article  CAS  PubMed  Google Scholar 

  • Tu TH, Kim H, Yang S, Kim JK, Kim JG. Linoleic acid rescues microglia inflammation triggered by saturated fatty acid. Biochemical and Biophysical Research Communications. 513: 201-206 (2019)

    Article  CAS  PubMed  Google Scholar 

  • Vázquez L, Akoh CC. Enrichment of stearidonic acid in modified soybean oil by low temperature crystallisation. Food Chemistry. 130: 147-155 (2011)

    Article  Google Scholar 

  • Wang J, Zhang JL, Wu FA. Enrichment process for α-linolenic acid from silkworm pupae oil. European Journal of Lipid science and Technology. 115: 791-799 (2013)

    Article  CAS  Google Scholar 

  • Wang L, Zhang B, Xiao J, Huang Q, Li C, Fu X. Physicochemical, functional, and biological properties of water-soluble polysaccharides from Rosa roxburghii Tratt fruit. Food Chemistry. 249: 127-135 (2018)

    Article  CAS  PubMed  Google Scholar 

  • Wang Y, Yang Z, Wei X. Sugar compositions, α-glucosidase inhibitory and amylase inhibitory activities of polysaccharides from leaves and flowers of Camellia sinensis obtained by different extraction methods. International Journal of Biological Macromolecules. 47: 534-539 (2010)

    Article  CAS  PubMed  Google Scholar 

  • Warren FJ, Zhang B, Waltzer G, Gidley MJ, Dhital S. The interplay of α-amylase and amyloglucosidase activities on the digestion of starch in in vitro enzymic systems. Carbohydrate Polymers. 117: 192-200 (2015)

    Article  CAS  PubMed  Google Scholar 

  • Xiao H, Chen C, Li C, Huang Q, Fu X. Physicochemical characterization, antioxidant and hypoglycemic activities of selenized polysaccharides from Sargassum pallidum. International Journal of Biological Macromolecules. 132: 308-315 (2019)

    Article  CAS  PubMed  Google Scholar 

  • Yan J, Zhang G, Pan J, Wang Y. α-Glucosidase inhibition by luteolin: kinetics, interaction and molecular docking. International Journal of Biological Macromolecules. 64: 213-23 (2014)

    Article  CAS  PubMed  Google Scholar 

  • Zhang S, Zu YG, Fu YJ, Luo M, Liu W, Li J, Efferth T. Supercritical carbon dioxide extraction of seed oil from yellow horn (Xanthoceras sorbifolia Bunge.) and its anti-oxidant activity. Bioresource Technology. 101: 2537-2544 (2010)

    Article  CAS  PubMed  Google Scholar 

  • Zheng Z, Dai Z, Shen Q. Enrichment of polyunsaturated fatty acids from seal oil through urea adduction and the fatty acids change rules during the process. Journal of Food Processing and Preservation. 42: e13593 (2018)

    Article  Google Scholar 

  • Zhou Y, Wang T, Zhai S, Li W, Meng Q. Linoleic acid and breast cancer risk: a meta-analysis. Public Health Nutrition. 19: 1457-1463 (2016)

    Article  PubMed  Google Scholar 

Download references

Acknowledgements

This work was supported by Shiny-Leaf Yellowhorn Industry Research Institute, and PAPD. We are grateful to the teachers of the Advanced Analysis and Testing Center of Nanjing Forestry University for their great help.

Funding

This study was supported by Shandong Woqi Rural Revitalization Industry Development Co., Ltd, and Priority Academic Program Development of Jiangsu Higher Education Institutions.

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Authors and Affiliations

  1. College of Science, Nanjing Forestry University, Nanjing, 210037, People’s Republic of China

    Kang Yang, Huayu Xue & Li Xu

  2. Advanced Analysis and Testing Center, Nanjing Forestry University, Nanjing, 210037, People’s Republic of China

    Ying Tang & Xiaoyue Ji

  3. School of Environmental Engineering, Nanjing Polytechnic Institute, Nanjing, 210048, People’s Republic of China

    Huayu Xue

  4. College of Forestry, Nanjing Forestry University, Nanjing, 210037, People’s Republic of China

    Fuliang Cao

  5. Co-Innovation Center for Sustainable Forestry in Southern China, Nanjing Forestry University, Nanjing, 210037, People’s Republic of China

    Fuliang Cao & Li Xu

  6. Shandong Woqi Rural Revitalization Industry Development Co., Ltd, Weifang, 261101, People’s Republic of China

    Shouke Li

  7. Institute of Material Physics & Chemistry, Nanjing Forestry University, Nanjing, 210037, People’s Republic of China

    Li Xu

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  1. Kang Yang
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Correspondence to Li Xu.

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Yang, K., Tang, Y., Xue, H. et al. Enrichment of linoleic acid from yellow horn seed oil through low temperature crystallization followed by urea complexation method and hypoglycemic activities. Food Sci Biotechnol 33, 145–157 (2024). https://doi.org/10.1007/s10068-023-01327-9

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