Health-Benefiting Components in Rapeseed Oil: History
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Junjun Shen
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Yejia Liu
,
Xiaoling Wang
,
Jie Bai
,
Lizhong Lin
,
Feijun Luo
,
Haiyan Zhong

Rapeseed oil is the third most consumed culinary oil in the world. It is well-known for its high content of unsaturated fatty acids, especially polyunsaturated fatty acids, which make it of great nutritional value. Apart from unsaturated fatty acids, there are nine functional components (vitamin E, flavonoids, squalene, carotenoids, glucoraphanin, indole-3-Carbinol, sterols, phospholipids, and ferulic acid) in rapeseed oil that contribute to its anti-microbial, anti-inflammatory, anti-obesity, anti-diabetic, anti-cancer, neuroprotective, and cardioprotective, among others. 

  • rapeseed oil
  • unsaturated fatty acid
  • functional components

1. Introduction

Rapeseed oil originates from the seeds of brassica plants, which include Brassica Rapa, Brassica napus. The brassica plant is a significant cash crop because of the high oil content of its seeds [1]. During the year 1975 to 2016, more than 1.9 billion adults were overweight, which can lead to a series of diseases, such as obesity, cardiovascular diseases, hypertension, and hyperlipidemia [2]. Thus, nutritious and digestible foods are urgently needed. Rapeseed oil contains lots of USFAs and bioactive compounds, which makes it beneficial to human health. These components can be classified as antioxidants; however, most rapeseeds have low erucic acid and low glucosinolate content [3]. The nutrients of the phytochemical compound are either water soluble or lipid soluble. This makes lipids of great importance to health. The bioactive compounds in rapeseed consist of phenolic acids, phytosterols, diglycerides, flavones, vitamin E, and flavonols. Both α-linolenic acid and linoleic acid fatty acids are essential fatty acids for humans since they must be consumed from the diet. They cannot be synthesized in the human body due to the lack of specific enzymes [4]. Obviously, the advantage of rapeseed oil is rich in unsaturated fatty acids and especially famous for its high content of oleic acid and linoleic acid. However, the disadvantage of rapeseed oil is a few varieties of rapeseed contain not little erucic acid and glucosinolate which are harmful to people [5][6][7].

2. Unsaturated Fatty Acids

It is well-known that USFAs have a lot of health benefits since polyunsaturated fatty acids (PUFAs) cannot be synthesized in the human body and must be obtained from the diet [1]. Many people make their choice of culinary oils based on their nutritional value, and oils containing rich amounts of PUFA are preferred. Rapeseed oil is rich in oleic, linoleic, and γ-linolenic acids. Specifically, many kinds of rapeseed contain 75% oleic acid. All USFAs in rapeseed account for approximately 90% of the total fatty acids composition. Rapeseed oil has a higher proportion of oleic acid than mustard oil and peanut oil; meanwhile, rapeseed oil has a lower proportion of SFAs than soybean oil and sunflower oil. Perrier et al. reported that rapeseed oil is composed of monounsaturated fatty acids (MUFAs), which account for the largest proportion, SFAs, and polyunsaturated fatty acids (PUFAs) [8]. Lewinska et al. found that MUFAs in rapeseed oil account for 62.9% of the total fatty acids, which is the highest content. Among the PUFAs, oleic acid possesses the highest amount, followed by linoleic and γ-linolenic acids. It is found that people from the Mediterranean region consuming high MUFAs have a low risk of cancers of the skin, breast, and colon, as well as coronary heart diseases [4]. Oleic acid is more heat-stable and oxidation-stable than linoleic acid, and it accounts for 46–66.03% of rapeseed oil [1][9][10][11]. Oleic acid is considered as a phytochemical compound that can ameliorate cardiovascular diseases [12]. Since linoleic acid has one more olefinic bond than oleic acid, the antioxidant effect of linoleic is better than that of oleic acid. Linoleic acid is a nutritional component since it is an essential fatty acid that is important to the human body’s maintenance. Linoleic acid is useful to the human skin’s integrity, immune system, cell membrane, and eicosanoid constitution [1]. Omega-6 fatty acids are famous for their healthcare action, of which linoleic acid and its derivatives, such as γ-linolenic acid, are abundantly constituents in rapeseed oil. It has been revealed that a diet rich in γ-linolenic acid could attenuate high blood lipid, high blood pressure, and skin perspiration [13][14]. γ-linolenic acid also has certain physiological functions, including anti-cancer, anti-thrombotic cardio-cerebrovascular, and anti-diabetic functions, whereas α-linolenic possesses physiological functions, such as anti-atherosclerotic, weight loss, blood lipid-lowering, and cardiovascular and cerebrovascular disease-preventing functions [15][16][17]. The special content of fatty acids in rapeseed oil could lead to a variety of biological functions, which are beneficial for human health.

3. Bioactive Compounds

3.1. Vitamin E

Vitamin E exists widely in many plants and is abundant in many kinds of plant seeds; it is a fat-soluble vitamin [15]. In plant seeds, vitamin E is found in high concentrations in the seed coat and embryo. In rapeseed oil, it is revealed that the concentration of vitamin E is up to 608.90 mg/Kg [18]. It is reported that both γ-tocotrienol and δ-tocotrienol have great antioxidant activity, which can inhibit the spoilage of rapeseed oils during storage, thus prolonging the shelf life. Furthermore, tocotrienols have been identified to possess anti-inflammatory and anti-cancer effects [19][20][21][22]. However, the concentration of γ- or δ-tocopherol that can kill half of the cancer cells, thus reaching IC50, would be a much higher concentration (25 μM or 50 μM) [23][24][25]. There are controversies over whether vitamin E can suppress Alzheimer’s disease. It is considered that supplementations with vitamins E and C can prevent cognitive decline [26]. Thus, it is proposed as a treatment for Alzheimer’s disease [27][28].

3.2. Flavonoids

Flavonoids are small phenolic molecules that possess a 2-phenyl chromogen ketone parent nucleus. They belong to a diverse class of plant phytochemical metabolites and are abundant in rapeseed [29][30][31]. They are categorized according to the position of the hydroxyl group and exist in the form of a bound flavonoid glycoside or a free flavonoid anhydride [32][33]. In general, flavonoids consist of flavonols, flavan-3-ols, flavanones, isoflavones, and anthocyanidins, among others [34]. They harbor several physiological functions, such as preventing UV, pigmentation, stimulation of nitrogen-fixing nodules, and other health-improving functions [35]. These include the isomers of flavonoids and their hydrogenation and reduced products, most of which exist in the form of glycosides or carbohydrate groups combined with sugars in plants, and a few of them exist in the free form [36]. In rapeseed oil, it has been reported that the total flavonoids are around 164.1 mg/Kg [37].
Quercetin and kaempferol are the most common flavonoids in the human diet and are present as complex glycosides in Brassica species [36][37][38]. Flavonoids act as antioxidants [39] and shielding components [40] in plants and are of special interest due to their antioxidant activity, as well as anti-inflammatory and anti-carcinogenic effects in humans [32][41][42][43][44][45]. Flavonols from copigments with anthocyanins contribute to the seed color, and the oxidation of proanthocyanidins with seed maturation forms oxidized tannins and brown color [43].

3.3. Squalene

Squalene, as a precursor of other sterols, exists in various vegetable oils. The content differs with the vegetable type, cultivar, agronomic factors, and extraction methods, among others [46][47]. In rapeseed oil, the content of squalene is reported to be approximately 47.8 mg/Kg, which is far less than that in refined olive oil (4784.28 mg/Kg).
The antioxidant activity of squalene is not strong; however, they are difficult to inhibit unless primary antioxidants are present [48][49]. Squalene, a biofunctional lipid compound, is reported to have diverse bioactivities ranging from cardioprotective, antioxidant, chemopreventive, anti-cancerous, anti-lipidemic, and membrane-stabilizing properties, among others [50]. A previous study showed that squalene could enhance serum high-density lipoprotein cholesterol levels and reduce oxidative stress [51].

3.4. Carotenoids

Carotenoids are red, yellow, and orange tetraterpenoid pigments that are universally synthesized by various plants, animals, and microorganisms, especially in rapeseed [52]. In a previous study, it was found that β-carotene not only exists in cold-press rapeseed oil, but also in rapeseed oil acquired through other processes, such as hot-press, leaching, and aqueous enzymatic extraction [53]. Carotenoids are powerful antioxidants, particularly for neutralizing superoxide anions [54]. It is recognized that carotenoids could inhibit the synthesis of tumor necrotic factor (TNF)-α in monocytes and macrophages and suppress the expression of Toll-like receptors 2 and 4 in human monocytes [55]. Carotenoids play different significant functions in the brain and have several medicinal properties, including neuroplasticity enhancement, antioxidant, anti-inflammatory, anti-diabetes, and anti-apoptotic potentials [56][57]. It also protects against UV damage [58].

3.5. Glucoraphanin (GRN)

GRN, a member of the glucosinolate family, is a well-known nutritional compound and the precursor of sulforaphane (SFN). Both the content of GRN and SFN in rapeseed oil have anti-cancer effects [59][60]. GRN is found in trace amounts in rapeseed oil, specifically within the range of 0–1.53 μmol/g [61]. SFN, the isothiocyanate derivative of GRN, has attracted much attention in recent years because of its significant health-improving effects [62]. It has been shown that SFN could modulate phase I and phase II detoxifying enzymes, blocking cancer and autoimmune diseases [63].

3.6. Indole-3-Carbinol

Indole-3-carbinol (I3C) is an important anti-cancer and chemopreventive phytochemical that acts via further hydrolysis of indol-3-methyl isothiocyanate found in rapeseed [64]. The I3C compound has been revealed to inhibit the proliferation of cancer cells by regulating genes involved in growth, signal transduction, and carcinogenesis. It suppresses the expression of drug resistance-related genes and induces apoptosis [65][66][67][68]. Preliminary clinical trials revealed that I3C could be used to protect against hormone-mediated human cancers [69]. 3′3-diindolylmethane is derived from acid-catalyzed condensation of I3C, which has a biological function [70].

3.7. Sterols

Phytosterols occur in many plants and therefore exist in various edible oils. Among all the identified phytosterols, β-sitosterol is the most commonly reported. Other significant phytosterols existing in edible plants include campesterol, brassicasterol, cycloartenol, and stigmasterol [71]. Phytosterols have been reported to exhibit anti-inflammatory, anti-microbial, and anti-cancer activities [72][73]. These compounds are structurally similar to cholesterol, which exist in animal cells, whereas sterols exist in plants. It is indicated that phytosterols reduce intestinal cholesterol absorption by regulating several transporters [74][75].

3.8. Phospholipids

In rapeseed, phospholipids are very abundant, and they include glycerolphosphatidic acid and phosphatidylinositol, among others [76]. There are differences in the form of phospholipids in rapeseed in terms of different storage conditions, even in the form of hemolysis compounds. In general, phospholipids in rapeseed oil are extracted by physical or chemical extraction. The simple method is to select various organic solvents for multiple extractions [77].

3.9. Ferulic Acid (FA)

FA is a health-benefit trace compound found in rapeseed oil, which is a hydroxycinnamic acid. A previous study showed that dietary FA attenuated metabolism syndrome-associated hyperuricemia in rats [78]. It was also reported that FA could ameliorate aflatoxin B1-induced duodenal barrier damage in rats [79]. FA effectively prevents high-fat diet-induced fatty liver disease by activating the PPARα signaling pathway to decrease the accumulation of triacylglycerol in the liver and increase the consumption of energy [80]. FA acid has a cardioprotective effect induced by severe endoplasmic reticulum stress [81].

4. Conclusions

Rapeseed is globally known as a huge source of valuable nutrients. A significant advantage of rapeseed oil is that it is rich in unsaturated fatty acids. Thus, rapeseed oil has health-promoting effects on diabetes, metabolic syndrome, and type 2 diabetes. Furthermore, it can promote lipid metabolism in healthy people and patients. Each content of rapeseed has its unique biological functions; thus, it can be inferred that rapeseed oil has a series of biological functions. The rapeseed processing technology should be improved to ensure the good retention of its nutrients. To sum up, in order to preserve the functional components as much as possible the cold-pressed process is proposed. Some of the nutrients are lost during the deodorization process, while some are lost during color removal. In addition, the refining processes may cause the loss of vitamin E, flavonoids, carotenoids, and major phospholipids. Therefore, to maintain the nutrients, high temperature and chemical refining should be replaced by physical refining. The rapeseed oil not only supplies vitamin E directly, but it also includes vitamin E derived from carotenoids. Flavonoids are well-known phytochemicals that can be made for drug and healthcare products, which exert antioxidant, anti-inflammatory, and anti-carcinogenic effects in humans. Phospholipids are often used to improve brain supplements, which are very popularly used for adolescents and children. Thus, the optimization of rapeseed processing for maximum retention of nutrients is very crucial, considering its potential benefits to food processing industries and consumers.

This entry is adapted from the peer-reviewed paper 10.3390/nu15040999

References

  1. Chew, S.C. Cold-pressed rapeseed (Brassica napus) oil: Chemistry and functionality. Food Res. Int. 2020, 131, 108997.
  2. Mathews, R.; Shete, V.; Chu, Y. The effect of cereal β-glucan on body weight and adiposity: A review of efficacy and mechanism of action. Crit. Rev. Food Sci. Nutr. 2021.
  3. Zeb, A. A comprehensive review on different classes of polyphenolic compounds present in edible oils. Food Res. Int. 2021, 143, 110312.
  4. Konuskan, D.B.; Arslan, M.; Oksuz, A. Physicochemical properties of cold pressed sunflower, peanut, rapeseed, mustard and olive oils grown in the Eastern Mediterranean region. Saudi J. Biol. Sci. 2019, 26, 340–344.
  5. Liu, N.; Tang, T.; Fan, Q.; Meng, D.; Li, Z.; Chen, J. Effects of site, sowing date and nitrogen application amount on economical characters, quality traits of high erucic acid rapeseed. J. Gansu Agric. Univ. 2015, 3, 68–72.
  6. Wang, P.; Xiong, X.; Zhang, X.; Wu, G.; Liu, F. A Review of Erucic Acid Production in Brassicaceae Oilseeds: Progress and Prospects for the Genetic Engineering of High and Low-Erucic Acid Rapeseeds (Brassica napus). Front. Plant Sci. 2022, 13, 899076.
  7. Kumar, S.; Chauhan, J.S.; Kumar, A. Screening for erucic acid and glucosinolate content in rapeseed-mustard seeds using near infrared reflectance spectroscopy. J. Food Sci. Technol. 2010, 47, 690–692.
  8. Perrier, A.; Delsart, C.; Boussetta, N.; Grimi, N.; Citeau, M.; Vorobiev, E. Effect of ultrasound and green solvents addition on the oil extraction efficiency from rapeseed flakes. Ultrason.—Sonochem. 2017, 39, 58–65.
  9. Coughlan, R.; Moane, S.; Larkin, T. Variability of Essential and Nonessential Fatty Acids of Irish Rapeseed Oils as an Indicator of Nutritional Quality. Int. J. Food Sci. 2022, 2022, 7934565.
  10. Lewinska, A.; Zebrowski, J.; Duda, M.; Gorka, A.; Wnuk, M. Fatty Acid Profile and Biological Activities of Linseed and Rapeseed Oils. Molecules 2015, 20, 22872–22880.
  11. Kampa, J.; Frazier, R.; Rodriguez-Garcia, J. Physical and Chemical Characterisation of Conventional and Nano/Emulsions: Influence of Vegetable Oils from Different Origins. Foods 2022, 11, 681.
  12. Liu, H.; Hong, Y.; Lu, Q.; Li, H.; Gu, J.; Ren, L.; Deng, L.; Zhou, B.; Chen, X.; Liang, X. Integrated Analysis of Comparative Lipidomics and Proteomics Reveals the Dynamic Changes of Lipid Molecular Species in High-Oleic Acid Peanut Seed. J. Agric. Food Chem. 2020, 68, 426–438.
  13. Tasset-Cuevas, I.; Fernández-Bedmar, Z.; Lozano-Baena, M.D.; Campos-Sánchez, J.; de Haro-Bailón, A.; Munoz-Serrano, A.; Alonso-Moraga, Á. Protective effect of borage seed oil and gamma linolenic acid on DNA: In vivo and in vitro studies. PLoS ONE 2013, 8, e56986.
  14. Tso, P.; Caldwell, J.; Lee, D.; Boivin, G.P.; DeMichele, S.J. Comparison of growth, serum biochemistries and n-6 fatty acid metabolism in rats fed diets supplemented with high-gamma-linolenic acid safflower oil or borage oil for 90 days. Food Chem. Toxicol. 2012, 50, 1911–1919.
  15. Xue, L. Research on the Composition and Distribution of Characteristic Nutritional Components in Edible Vegetable Oils; Chinese Academy Chinese Academy of Agricultural Sciences: Beijing, China, 2018.
  16. Wu, Q.G.; Du, B.; Cai, Y.L.; Liang, Z.H.; Lin, Z.G.; Qiu, G.L.; Dong, L.J. Research development of alpha-linolenic acid. Sci. Technol. Food Ind. 2016, 37, 386.
  17. Zhao, X.; Xiang, X.; Huang, J.; Ma, Y.; Zhu, D. Studying the Evaluation Model of the Nutritional Quality of Edible Vegetable Oil Based on Dietary Nutrient Reference Intake. ACS Omega 2021, 6, 6691–6698.
  18. Zhang, Y.; Qi, X.; Wang, X.; Wang, X.; Ma, F.; Yu, L.; Mao, J.; Jiang, J.; Zhang, L.; Li, P. Contribution of Tocopherols in Commonly Consumed Foods to Estimated Tocopherol Intake in the Chinese Diet. Front. Nutr. 2022, 9, 829091.
  19. Shen, J.; Yang, T.; Xu, Y.; Luo, Y.; Zhong, X.; Shi, L.; Hu, T.; Guo, T.; Luo, F.; Lin, Q. δ-Tocotrienol, Isolated from Rice Bran, Exerts an Anti-Inflammatory Effect via MAPKs and PPARs Signaling Pathways in Lipopolysaccharide-Stimulated Macrophages. Int. J. Mol. Sci. 2018, 19, 3022.
  20. Shen, J.; Yang, T.; Tang, Y.; Guo, T.; Guo, T.; Hu, T.; Luo, F.; Lin, Q. δ-Tocotrienol induces apoptosis and inhibits proliferation of nasopharyngeal carcinoma cells. Food Funtion 2021, 12, 6374.
  21. Ng, L.T.; Ko, H.J. Comparative effects of tocotrienol-rich fraction, α-tocopherol and α-tocopheryl acetate on inflammatory mediators and nuclear factor kappa B expression in mouse peritoneal macrophages. Food Chem. 2012, 134, 920–925.
  22. Wallert, M.; Schmölz, L.; Koeberle, A.; Krauth, V.; Glei, M.; Galli, F.; Werz, O.; Birringer, M.; Lorkowski, S. α-Tocopherol long-chain metabolite α-13′-COOH affects the inflammatory response of lipopolysaccharide-activated murine RAW264.7 macrophages. Mol. Nutr. Food. Res. 2015, 59, 1524–1534.
  23. Jiang, Q.; Rao, X.; Kim, C.Y.; Freiser, H.; Zhang, Q.; Jiang, Z.; Li, G. Gamma-tocotrienol induces apoptosis and autophagy in prostate cancer cells by increasing intracellular dihydrosphingosine and dihydroceramide. Int. J. Cancer 2012, 130, 685–693.
  24. Shah, S.; Syivester, P.W. Tocotrienol-induced caspase-8 activation is unrelated to death receptor apoptotic signaling in neoplastic mammary epithelial cells. Exp. Biol. Med. 2004, 229, 745–755.
  25. Wali, V.B.; Bachawal, S.V.; Sylvester, P.W. Endoplasmic reticulum stress mediciates gamma-tocotrienol-induced apoptosis in mammary tumor cells. Apoptosis 2009, 14, 1366–1377.
  26. Basambombo, L.L.; Carmichael, P.H.; Côté, S.; Laurin, D. Use of vitamin E and C supplements for the prevention of cognitive decline. Ann. Pharmacother. 2017, 51, 118–124.
  27. de Wilde, M.C.; Vellas, B.; Girault, E.; Yavuz, A.C.; Sijben, J.W. Lower brain and blood nutrient status in Alzheimer’s disease: Results from meta-analyses. Alzheimers Dement. 2017, 3, 416–431.
  28. Dong, Y.; Chen, X.; Liu, Y.; Shu, Y.; Chen, T.; Xu, L.; Li, M.; Guan, X. Do low-serum vitamin E levels increase the risk of Alzheimer disease in older people? Evidence from a meta-analysis of case-control studies. Int. J. Geriatr. Psych. 2018, 33, e257–e263.
  29. Koes, R.E.; Quattrocchio, F.; Mol, J.N.M. The flavonoid biosynthetic pathway in plants: Function and evolution. BioEssays 1994, 16, 123–132.
  30. Williams, C.A.; Grayer, R.J. Anthocyanins and other flavonoids. Nat. Prod. Rep. 2004, 21, 539–573.
  31. Grotewold, E. The Science of Flavonoids; Springer: Columbus, GA, USA, 2006.
  32. Chen, A.Y.; Chen, Y.C. A review of the dietary flavonoid, kaempferol on human health and cancer chemoprevention. Food Chem. 2013, 138, 2099–2107.
  33. Dias, M.C.; Pinto, D.C.G.A.; Freitas, H.; Santos, C.; Silva, A.M.S. The antioxidant system in Olea europaea to enhanced UV-B radiation also depends on flavonoids and secoiridoids. Phytochemistry 2020, 170, 112199.
  34. Saito, K.; Yonekura-Sakakibara, K.; Nakabayashi, R.; Higashi, Y.; Yamazaki, M.; Tohge, T.; Fernie, A.R. The flavonoid biosynthetic pathway in Arabidopsis: Structural and genetic diversity. Plant Physiol. Bioch. 2013, 72, 21–34.
  35. Harbaum, B.; Hubbermann, E.M.; Wolff, C.; Herges, R.; Zhu, Z.; Schwarz, K. Identification of flavonoids and hydroxycinnamic acids in pak choi varieties (Brassica campestris L. ssp. chinensis var. communis) by HPLC-ESI-MSN and NMR and their quantification by HPLC-DAD. J. Agri. Food Chem. 2007, 55, 8251–8260.
  36. Cartea, M.E.; Francisco, M.; Soengas, P.; Velasco, P. Phenolic compounds in Brassica vegetables. Molecules 2011, 16, 251–280.
  37. Teh, S.S.; Birch, J. Physicochemical and quality characteristics of cold-pressed hemp, flax and canola seed oils. J. Food Compos. Anal. 2013, 30, 26–41.
  38. Mageney, V.; Neugart, S.; Albach, D.C. A guide to the variability of flavonoids in Brassica oleracea. Molecules 2017, 22, 252.
  39. Zietz, M.; Weckmuller, A.; Schmidt, S.; Rohn, S.; Schreiner, M.; Krumbein, A.; Kroh, L.W. Genotypic and climatic influence on the antioxidant activity of flavonoids in kale (Brassica oleracea var. sabellica). J. Agri. Food Chem. 2010, 58, 2123–2130.
  40. Agati, G.; Brunetti, C.; Ferdinando, D.; Ferrini, M.; Pollastri, F.S.; Tattini, M. Functional roles of flavonoids in photoprotection-new evidence, lessons from the past. Plant Physiol. Bioch. 2013, 72, 35–45.
  41. Bumke-Vogt, C.; Osterhoff, M.A.; Borchert, A.; Guzman-Perez, V.; Sarem, Z.; Birkenfeld, A.L.; Bähr, V.; Pfeiffer, A.F. The Flavones Apigenin and Luteolin Induce FOXO1 Translocation but Inhibit Gluconeogenic and Lipogenic Gene Expression in Human Cells. PLoS ONE 2014, 9, e104321.
  42. Pan, M.H.; Lai, C.S.; Ho, C.T. Anti-inflammatory activity of natural dietary flavonoids. Food Funct. 2010, 1, 15–31.
  43. Lepiniec, L.; Debeaujon, I.; Routaboul, J.M.; Baudry, A.; Pourcel, L.; Nesi, N.; Caboche, M. Genetics and biochemistry of seed flavonoids. Annu. Rev. Plant Biol. 2006, 57, 405–430.
  44. Shahidi, F.; Ambigaipalan, P. Phenolics and polyphenolics in foods, beverages and spices: Antioxidant activity and health effects—A review. J. Funct. Foods. 2015, 18, 820–897.
  45. Zardo, I.; Rodrigues, N.P.; Sarkis, J.R.; Marczak, L.D. Extraction and identification by mass spectrometry of phenolic compounds from canola seed cake. J. Sci. Food Agric. 2020, 100, 578–586.
  46. Paramasivan, K.; Mutturi, S. Recent advances in the microbial production of squalene. World J. Microbiol. Biotechnol. 2022, 38, 91.
  47. Naziri, E.; Consonni, R.; Tsimidou, M.Z. Squalene oxidation products: Monitoring the formation, characterisation and pro-oxidant activity. Eur. J. Lipid Sci. Technol. 2014, 116, 1400–1411.
  48. Kumar, L.R.G.; Kumar, H.S.; Tejpal, C.S.; Anas, K.K.; Ravishankar, C.N. Exploring the physical and quality attributes of muffins incorporated with microencapsulated squalene as a functional food additive. J. Food Sci. Technol. 2021, 58, 4674–4684.
  49. Kim, S.K.; Karadeniz, F. Biological importance and applications of squalene and squalane. Adv. Food Nutr. Res. 2012, 65, 223–233.
  50. Gabas-Rivera, C.; Barranquero, C.; Martinez-Beamonte, R.; Navarro, M.A.; Surra, J.C.; Osada, J. Dietary squalene increases high density lipoprotein-cholesterol and paraoxonase 1 and decreases oxidative stress in mice. PLoS ONE 2014, 9, e104224.
  51. Abuobeid, R.; Sánchez-Marco, J.; Felices, M.J.; Arnal, C.; Burillo, J.C.; Lasheras, R.; Busto, R.; Lasunción, M.A.; Rodríguez-Yoldi, M.J.; Martínez-Beamonte, R.; et al. Squalene through Its Post-Squalene Metabolites Is a Modulator of Hepatic Transcriptome in Rabbits. Int. J. Mol. Sci. 2022, 23, 4172.
  52. Li, Y.; Zhang, L.; Xu, Y.; Li, I.; Cao, P.; Liu, Y. Evaluation of the functional quality of rapeseed oil obtained by different extraction processes in a Sprague-Dawley rat model. Food Funct. 2019, 10, 6503–6516.
  53. Galano, A.R.; Vargas, A.; Martínez, A. Carotenoids can act as antioxidants by oxidizing the superoxide radical anion. Phys. Chem. Chem. Phys. 2010, 12, 193–200.
  54. Lin, P.; Ren, Q.; Wang, Q.; Wu, J. Carotenoids Inhibit Fructose-Induced Inflammatory Response in Human Endothelial Cells and Monocytes. Mediat. Inflamm. 2020, 2020, 5373562.
  55. Roohbakhsh, A.; Karimi, G.; Iranshahi, M. Carotenoids in the treatment of diabetes mellitus and its complications: A mechanistic review. Biomed. Pharmacother. 2017, 91, 31–42.
  56. Stahl, W.; Sies, H. β-Carotene and other carotenoids in protection from sunlight. Am. J. Clin. Nutr. 2012, 96, 1179S–1184S.
  57. Bhosale, P.; Serban, B.; Zhao, D.Y.; Bernstein, P.S. Identification and metabolic transformations of carotenoids in ocular tissues of the Japanese quail Coturnix japonica. Biochemistry 2007, 46, 9050–9057.
  58. Della Penna, D.; Pogson, B.J. Vitamin synthesis in plants: Tocopherols and carotenoids. Annu. Rev. Plant Biol. 2006, 57, 711–738.
  59. Soundararajan, P.; Park, S.G.; Won, S.Y.; Moon, M.S.; Park, H.W.; Ku, K.M.; Kim, S.J. Influence of Genotype on High Glucosinolate Synthesis Lines of Brassica rapa. Int. J. Mol. Sci. 2021, 22, 7301.
  60. Houghton, C.A. Sulforaphane: Its “Coming of Age” as a Clinically Relevant Nutraceutical in the Prevention and Treatment of Chronic Disease. Oxid. Med. Cell. Longev. 2019, 2019, 2716870.
  61. Mahn, A.; Castillo, A. Potential of Sulforaphane as a Natural Immune System Enhancer: A Review. Molecules 2021, 26, 752.
  62. Pereyra, K.V.; Andrade, D.C.; Toledo, C.; Schwarz, K.; Uribe-Ojeda, A.; Ríos-Gallardo, A.P.; Mahn, A.; Del Rio, R. Dietary supplementation of a sulforaphane-enriched broccoli extract protects the heart from acute cardiac stress. J. Funct. Foods 2020, 75, 104267.
  63. Martins, T.; Colaço, B.; Venâncio, C.; Pires, M.J.; Oliveira, P.A.; Rosa, E.; Antunes, L.M. Potential effects of sulforaphane to fight obesity. J. Sci. Food Agric. 2018, 98, 2837–2844.
  64. Lee, Y.R.; Chen, M.; Lee, J.D.; Zhang, J.; Lin, S.Y.; Fu, T.M.; Chen, H.; Ishikawa, T.; Chiang, S.Y.; Katon, J.; et al. Reactivation of PTEN tumor suppressor for cancer treatment through inhibition of a MYC-WWP1 inhibitory pathway. Science 2019, 364, eaau0159.
  65. Marconett, C.N.; Singhal, A.K.; Sundar, S.N.; Firestone, G.L. Indole-3-carbinol disrupts estrogen receptor-alpha dependent expression of insulin-like growth factor-1 receptor and insulin receptor substrate-1 and proliferation of human breast cancer cells. Mol. Cell. Endocrinol. 2021, 363, 74–84.
  66. Arora, A.; Kalra, N.; Shukla, Y. Modulation of P-glycoprotein-mediated multidrug resistance in K562 leukemic cells by indole-3-carbinol. Toxicol. Appl. Pharm. 2005, 202, 237–243.
  67. Megna, B.W.; Carney, P.R.; Nukaya, M.; Geiger, P.; Kennedy, G.D. Indole-3-carbinol induces tumor cell death: Function follows form. J. Surg. Res. 2016, 204, 47–54.
  68. Licznerska, B.; Baer-Dubowska, W. Indole-3-Carbinol and Its Role in Chronic Diseases. Adv. Exp. Med. Biol. 2016, 928, 131–154.
  69. Munakarmi, S.; Shrestha, J.; Shin, H.B.; Lee, G.H.; Jeong, Y.J. 3,3-Diindolylmethane Suppresses the Growth of Hepatocellular Carcinoma by Regulating Its Invasion, Migration, and ER Stress-Mediated Mitochondrial Apoptosis. Cells 2021, 10, 1178.
  70. Li, W.X.; Chen, L.P.; Sun, M.Y.; Li, J.T.; Liu, H.Z.; Zhu, W. 3′3-Diindolylmethane inhibits migration, invasion and metastasis of hepatocellular carcinoma by suppressing FAK signaling. Oncotarget 2015, 6, 23776–23792.
  71. Othman, R.A.; Moghadasian, M.H. Beyond cholesterol-lowering effects of plant sterols: Clinical and experimental evidence of anti-inflammatory properties. Nutr. Rev. 2011, 69, 371–382.
  72. Amiot, M.J.; Knol, D.; Cardinault, N.; Nowicki, M.; Bott, R.; Antona, C.; Borel, P.; Bernard, J.P.; Duchateau, G.; Lairon, D. Phytosterol ester processing in the small intestine: Impact on cholesterol availability for absorption and chylomicron cholesterol incorporation in healthy humans. J. Lipid Res. 2011, 52, 1256–1264.
  73. De Smet, E.; Mensink, R.P.; Plat, J. Effects of plant sterols and stanols on intestinal cholesterol metabolism: Suggested mechanisms from past to present. Mol. Nutr. Food Res. 2012, 56, 1058–1072.
  74. Sanclemente, T.; Marques-Lopes, I.; Fajó-Pascual, M.; Cofán, M.; Jarauta, E.; Ros, E.; Puzo, J.; García-Otín, A.L. Naturally occurring phytosterols in the usual diet influence cholesterol metabolism in healthy subjects. Nutr. Metab. Cardiovas. 2011, 22, 849–855.
  75. Polagruto, J.A.; Wang-Polagruto, J.F.; Braun, M.M.; Lee, L.; Kwik-Uribe, C.; Keen, C.L. Cocoa flavanol-enriched snack bars containing phytosterols effectively lower total and low-density lipoprotein cholesterol levels. J. Am. Diet. Assoc. 2006, 106, 1804–1813.
  76. Na, S.; Jin, C.; Di, W.; Lin, S. Advance in food-derived: Sources, molecular species and structure as well as their biological activities. Trends Food Sci. Technol. 2018, 80, 199–211.
  77. Meng, X.; Ye, Q.; Pan, Q.; Ding, Y.; Wei, M.; Liu, Y.; Van De Voort, F.R. Total phospholipids in edible oils by in-vial solvent extraction coupled with FTIR analysis. J. Agric. Food Chem. 2014, 62, 3101–3107.
  78. Zhang, N.; Zhou, J.; Zhao, L.; Wang, O.; Zhang, L.; Zhou, F. Dietary Ferulic Acid Ameliorates Metabolism Syndrome-Associated Hyperuricemia in Rats via Regulating Uric Acid Synthesis, Glycolipid Metabolism, and Hepatic Injury. Front. Nutr. 2022, 9, 946556.
  79. Wang, X.; Yang, F.; Na, L.; Jia, M.; Ishfaq, M.; Zhang, Y.; Liu, M.; Wu, C. Ferulic acid alleviates AFB1-induced duodenal barrier damage in rats via up-regulating tight junction proteins, down-regulating ROCK, competing CYP450 enzyme and activating GST. Ecotoxicol. Environ. 2022, 241, 113805.
  80. Luo, Z.; Li, M.; Yang, Q.; Zhang, Y.; Liu, F.; Gong, L.; Han, L.; Wang, M. Ferulic Acid Prevents Nonalcoholic Fatty Liver Disease by Promoting Fatty Acid Oxidation and Energy Expenditure in C57BL/6 Mice Fed a High-Fat Diet. Nutrients 2022, 14, 2530.
  81. Monceaux, K.; Gressette, M.; Karoui, A.; Pires Da Silva, J.; Piquereau, J.; Ventura-Clapier, R.; Garnier, A.; Mericskay, M.; Lemaire, C. Ferulic Acid, Pterostilbene, and Tyrosol Protect the Heart from ER-Stress-Induced Injury by Activating SIRT1-Dependent Deacetylation of eIF2α. Int. J. Mol. Sci. 2022, 3, 6628.
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