Review Received: 8 July 2014
Revised: 16 October 2014
Accepted article published: 4 December 2014
Published online in Wiley Online Library: 23 January 2015
(wileyonlinelibrary.com) DOI 10.1002/jsfa.7035
The relationship of antioxidant components and antioxidant activity of sesame seed oil Yin Wan,a,b Huixiao Li,a Guiming Fu,a Xueyang Chen,a Feng Chenb* and Mingyong Xiea Abstract Although sesame seed oil contains high levels of unsaturated fatty acids and even a small amount of free fatty acids in its unrefined flavored form, it shows markedly greater stability than other dietary vegetable oils. The good stability of sesame seed oil against autoxidation has been ascribed not only to its inherent lignans and tocopherols but also to browning reaction products generated when sesame seeds are roasted. Also, there is a strong synergistic effect among these components. The lignans in sesame seed oil can be categorized into two types, i.e. inherent lignans (sesamin, sesamolin) and lignans mainly formed during the oil production process (sesamol, sesamolinol, etc.). The most abundant tocopherol in sesame seed oil is 𝜸-tocopherol. This article reviews the antioxidant activities of lignans and tocopherols as well as the browning reaction and its products in sesame seed and/or its oil. It is concluded that the composition and structure of browning reaction products and their impacts on sesame ingredients need to be further studied to better explain the remaining mysteries of sesame oil. © 2014 Society of Chemical Industry Keywords: sesame seed oil; antioxidant activity; lignans; tocopherols; Maillard reaction
INTRODUCTION
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ANTIOXIDANT ACTIVITY OF SESAME SEED OIL Although SSO contains more than 800 g kg−1 unsaturated fatty acids and even a small amount of free fatty acids (7.2 g kg−1 )5 in its unrefined flavored form, it shows markedly greater stability than other dietary vegetable oils.6 Soybean oil and other oils can undergo a rapid increase in weight via autoxidation, resulting in a rancid odor after 10–20 days of storage.7 However, the unsaturated fatty acids in SSO, especially roasted SSO, did not decompose after being stored at 60 ∘ C for 50 days.8 Moreover, SSO showed better antioxidant stability than corn oil in fried bread loaf.
∗
Correspondence to: Feng Chen, Department of Food, Nutrition, and Packaging Sciences, Clemson University, Clemson, SC 29634, USA. E-mail: [email protected]
a State Key Laboratory of Food Science and Technology, Department of Food Science and Engineering, Nanchang University, Nanchang 330047, Jiangxi, China b Department of Food, Nutrition, and Packaging Sciences, Clemson University, Clemson, SC 29634, USA
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Belonging to the Pedaliaceae family, sesame (Sesamum indicum L., synonymous with Sesamum orientale L.)1 was first recorded as a crop in Babylon and Assyria over 4000 years ago and is considered one of the most ancient crops cultivated by humans.2 The major countries and areas for sesame production are located in Asia, Africa and Central and South America, such as India, Sudan, China, Burma and Ethiopia. The world’s total annual production of sesame is about 3 × 109 kg,3 with 50% from Asia and 30% from Africa. Around 65% of the annual production is consumed as an edible oil and 35% as a food ingredient. As one of the world’s major oilseeds, sesame seed has a high oil content that accounts for about 50% of its weight, which is much higher than the 20% oil content of soybean. Sesame seed oil (SSO) has of a dietary history for more than 2000 years. In Asia, especially in China, virgin SSO is also called sesame flavoring oil, which is preferably consumed without refining. Owing to the roasting of sesame seeds before oil extraction, numerous aromatic compounds and brown pigments are produced, resulting in SSOs ranging from yellow to brown in color. The multiple-step extraction technology for producing commercial SSO is similar to that for the production of other dietary oils in western countries, where SSO is generally used as a salad dressing whether refined or not. Growing in an oblong, mucronate and pubescent capsule, the sesame seed is small, oval, with different colors such as white, yellow, red, brown or black. It was reported that sesame seeds of different colors had different oil contents; the average oil contents of white, black and yellow sesame seeds were 550, 478 and 500 g kg−1 respectively.4 Two unsaturated fatty acids, oleic acid (C18:1) and linoleic acid (C18:2), account for more than 800 g kg−1 of the total fatty acids in SSO. In contrast, saturated fatty acids are present at much lower levels. Palmitic acid (C16:0) constitutes
79–120 g kg−1 of the total fatty acids in SSO, while stearic acid (C18:0) constitutes 48–61 g kg−1 . Moreover, other fatty acids such as palmitoleic acid (C16:1), linolenic acid (C18:3), arachidic acid (C20:0), etc. are present at levels below 10 g kg−1 . It is well known that SSO has remarkable storage stability. Thus it is of interest to investigate the antioxidant components and their antioxidant activities in SSO, especially during the oil production process. This article reviews the antioxidant activities of lignans and tocopherols as well as the browning reaction and its products in sesame seed and/or its oil.
www.soci.org It was reported that mixing olive oil with 900 μL of a methanolic extract of coated unroasted sesame seed could lower its peroxide value by 61% after 200 h of heat treatment at 100 ∘ C.9 Similar findings were also obtained when different sesame extracts were added to sunflower, soybean or corn oil. When SSO was heated in an oven at 50 ∘ C, it showed a peroxide value of 190.7 mmol kg−1 on day 8 and carbonyl value of 25.2 mmol kg−1 on day 6, which were similar to those of bene hull oil but lower than those of rice bran oil. SSO also had the longest time (6.92 h) of oxidative stability in the Rancimat test and the highest reducing power (258.1 mmol L−1 ) among the tested dietary oils.10 The antioxidant activities of SSO in living organisms were illustrated by some in vivo animal tests. For instance, SSO could attenuate oxidative stress in lipopolysaccharide (LPS)-treated rats. After giving SSO parenterally, lipid peroxidation, hydroxyl radical and nitrite levels in oxidative stressed model rats induced by LPS were reduced, while superoxide dismutase (SOD) and catalase concentrations increased.11 In addition, SSO-treated animal groups showed attenuated hepatic disorder, although the symptoms were different when the SSO was given orally. Superoxide anion decreased and glutathione increased in the oral SSO groups. In contrast, corn oil- or mineral oil-treated groups did not show attenuation of hepatic disorder induced by LPS.12 Dietary SSO was also shown to behave as an antioxidant, resulting in increased activity of enzymatic and non-enzymatic antioxidants in the middle cerebral artery occlusion (MCAO) + SSO group, thus protecting the model rats against MCAO-induced cerebral ischemia injury.13 Furthermore, giving SSO orally could reduce oxidative myocardial damage induced by isoproterenol,14 oxidative stress induced by chronic exposure to electromagnetic radiation (EMR)15 as well as cypermethrin-induced oxidative stress, biochemical changes, histopathological damage and genomic DNA fragmentation.16
IMPORTANT ANTIOXIDANT COMPONENTS IN SESAME SEED OIL The outstanding antioxidant activity of SSO was reported to be the result of the presence of lignans, tocopherols and brown Maillard reaction products17 as well as the synergistic action among these components.18 The structures of lignans and tocopherol are shown in Fig. 1.
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Lignans Lignans in SSO mainly comprise sesamin, sesamolin and sesamol. Lignan glycosides present in sesame seed are not found in SSO. The content of lignans varies between 6.5 and 17.3 g kg−1 oil.19,20 Sesamin and sesamolin are the most abundant lignans in SSO, accounting for 0.7–8.85 and 0.2–4.8 g kg−1 SSO respectively.21,22 However, their concentrations vary considerably among SSOs from different places. For example, the respective contents of sesamin and sesamolin were reported to be 3.0–9.0 and 3.5–5.3 g kg−1 oil in Indian SSO20 and 0.93–2.89 and 0.3–0.74 g kg−1 oil in Thai SSO.23 Sesamol has a relatively lower content, only 50–100 mg kg−1 SSO. Sesamin is easily hydrolyzed under acidic conditions into pinoresinol during the production of SSO, which is the opposite route of the biosynthesis of sesamin from pinoresinol24 that is catalyzed by the enzyme cytochrome P450 in microsomes (CYP81Q1).25 Cytochrome P450 possesses a unique activity by catalyzing bridge formation on different aromatic rings at both ends of pinoresinol.
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Sesamolin is thermally unstable. Under different heating conditions, it can be transformed to sesamol and other products.26 The transformations of lignans during the oil production process27,28 are shown in Fig. 2. In 1986, Fukuda et al.29 found that sesamolin underwent a similar reaction to its acidic hydrolysis under heating when decolored by acidic clay in the oil refining process and was transformed into sesaminol and sesamol. In this context, sesamolin is a precursor of the natural antioxidants sesamol and sesaminol in sesame seed. In the bleaching process, sesamolin was also transformed into sesaminol. Sesamin As one of the mysterious compounds in SSO, sesamin has been investigated in many studies for its various activities such as liver fatty acid synthesis suppression and blood lipid regulation,30 – 32 liver support and liver protection,33,34 antitumor activities,35,36 antihypertension,37 oxidative stress attenuation,38 etc. Sun et al.39 reported that sesamin had good ability for inhibition of oil oxidation. The antioxidant activity of sesamin in soybean salad oil (0.4 g kg−1 ) was comparable to that of butylated hydroxytoluene (BHT) (0.2 g kg−1 ), and its antioxidant activity in soybean oil (0.4 g kg−1 ) was better than that in lard. However, it should be noted that a mixture of sesamin (685 g kg−1 ) and sesamolin (315 g kg−1 ) was used in this test. Generally, sesamin itself does not exhibit a strong antioxidant effect in vitro. The results of in vitro tests performed by Nakai et al.28 showed that sesamin had almost no scavenging or inhibitory effects on 2,2-diphenyl-1-picrylhydrazyl (DPPH• ), hydroxyl (• OH) and superoxide anion (O2•− ) radicals and lipid peroxidation. In contrast, Dai40 argued that sesamin had certain effects on scavenging free radicals in vitro, with IC50 values for scavenging DPPH• , • OH and O2•− of 7.5, 26 and 29.5 g L−1 respectively. However, Kim et al.41 suggested that the strong DPPH radical-scavenging property of sesame seed may not be much due to its inherent lignans, because the antioxidant activity of the 90% acetonitrile extract from white sesame seeds was lower than that of the same extract from black sesame seeds even though the content of sesamin and sesamolin in the former was twice that in the latter. The current widely recognized opinion is that sesamin has weak antioxidant activity in vitro but a significantly strong antioxidant effect in vivo. On giving sesamin to seven male university students (non-smokers) 2 h before bicycle ergometer exercise, their plasma lipid peroxide level was significantly suppressed, while the level in the placebo group increased significantly after exercise. Meanwhile, vitamin E was not effective in this experiment.42 The results indicated that sesamin was concentrated in the liver after entering the biosome and that its metabolites had distinctive antioxidant capacity. Therefore it has been classified as a pro-antioxidant.28 After ingestion by rats or humans, the methylenedioxyphenyl moiety of the sesamin molecule was shown to be split and converted into a monocatechol or dicatechol structure with a dihydrophenyl moiety.28,43,44 Nakai et al.28 isolated four sesamin metabolites from rat bile, three of which had dihydroxyl groups of catechol structure (Fig. 3). In vitro experiments showed that these sesamin metabolites with catechol form had stronger abilities to eliminate reactive oxygen species and inhibit lipid peroxidation generation than sesamin. Sesamolin Kamal-Eldin and Appelqvist45 noted that sesamolin basically had no antioxidant activity in vitro. In the DPPH radical-scavenging
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Antioxidant components and activity of sesame seed oil
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O O
O
H
O
OH
H
H
O
O O
O
O
O
III Episesamin
O
O H
O O
O
II Sesamin
H
H
O O
I Sesamol
O
O
O
O
O
HO H
H
O
O
O
O
O
IV Sesaminol
V Sesamolin
O OH O OCH3 H
H O
O
O O
O
H H
H3C CH3
H3CO
H3CO HO VI Sesamolinol
O
H3C CH3
HO VII Pinoresinol
CH3
CH3 CH3
CH3
VIII Tocopherol
Figure 1. Structures of lignans and tocopherol in sesame seed oil. Heating Sesamolin
Bleaching with acidic clay Metabolized in rats Acid hydrolysis
Sesamin
Decoloring Metabolized in rats
Sesamol Sesaminol + Sesamol Sesamol + Sesamolinol
Pinoresinol Episesamin Monocatechol + Dicatechol
Figure 2. Transformations of lignans during oil production process (adapted from Park et al.27 and Nakai et al.28 ). Sesamolin and sesamin are unstable. Under different processing conditions, they can be transformed into different lignans and other products.
Sesamol Sesamol has strong antioxidant activity and is regarded as a very effective antioxidant in roasted SSO. The content of sesamol (36 mg kg−1 ) in roasted SSO5 was much higher than its original level ( 𝛼-tocopherol > BHT ≥ sesamin > sesamolin The brown materials exhibited exceptional radical-scavenging effect Sesamol > sesamolin ≥ sesamin > BHT Sesamol > sesamin > sesamolin
Suja et al.46 and Shyu and Hwang83 Shyu and Hwang83 Suja et al.47 Suja et al.47
Sesamol > sesamin > sesaminol > sesamolin
Suja et al.47
Sesamin > sesamolin, sesaminol Sesaminol > pinoresinol > sesamolinol
Shimizu et al.84 Kang et al.62
Sesaminol > 𝛼-tocopherol
Kang et al.62
Sesaminol > 𝛼-tocopherol
Kang et al.62
BHT > sesaminol ≥ sesamolinol ≥ sesamol ≥ 𝛼-tocopherol > pinoresinol > sesamin > sesamolin
Kang et al.48
Sesamolinol > 𝛾-tocopherol > sesamin > sesamol 𝛼-Tocopherol > sesamol > sesamin > sesamolin
Hu and Du85 Hemalatha and Ghafoorunissa20
BHT > 𝛼-tocopherol > 𝛾-tocopherol > sesamin, sesamol, sesamolin Sesamol > sesamin, sesamolin, 𝛼-tocopherol
Hemalatha and Ghafoorunissa20 Lee and Choe86
Sesamol > sesamolin > sesamin
Budowski et al.8
Sesaminol-enriched SO extract > sesamol
Dachtler et al.49
Sesamol > sesaminol-enriched SO extract > sesamin
Dachtler et al.49
Mehta68 found that both 𝛼-tocopherol and 𝛾-tocopherol significantly inhibited arterial superoxide anion formation, lipid peroxidation and LDL oxidation and increased endogenous SOD activity, but the effects of 𝛾-tocopherol were significantly more potent than those of 𝛼-tocopherol. It was observed that nitrogen dioxide-mediated nitrosation of morpholine was inhibited effectively by 𝛾-tocopherol but not by 𝛼-tocopherol.69,70 𝛾-Tocopherol trapped peroxynitrite formed by the reaction of NO and active oxygen so that it inhibited lipid peroxidative damage more efficiently than 𝛼-tocopherol.71 Although 𝛾-tocopherol levels in blood plasma and most other tissues are only one-fifth or much less than those of 𝛼-tocopherol,72 they are equally important for their many beneficial bioactivities.
antioxidant activity too. In research by Jeong et al.,75 roasting sesame seeds at 200 ∘ C for 1 h significantly increased the content of phenolic compounds, DPPH radical-scavenging activity, reducing power and suppression of induction of lipid peroxidation compared with unroasted seeds. Furthermore, several low-molecular-weight phenolic compounds such as 2-methoxyphenol, 4-methoxy-3-methylthiophenol, 5-amino-3oxo-4-hexenoic acid, 3,4-methylenedioxyphenol (sesamol), 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, vanillic acid, filicinic acid and 3,4-dimethoxyphenol were formed during the roasting process. Jo et al.76 reported that the methanolic extract of characteristic brown color from roasted defatted sesame meal prevented lipid oxidation in turkey breast and thigh meat and significantly decreased the levels of volatile hydrocarbons (pentane, hexane, heptane and octane) and carbonyls (propanal, butanal, pentanal, hexanal and heptanal) after 5 days of storage. Konsoula and Liakopoulou-Kyriakides9 found that there was no obvious correlation between the sesamol level and peroxide value in oil samples added with SSO extract, though sesamolin decreased and sesamol increased during heat treatment. The authors suggested that other intrinsic antioxidant constituents, especially the composition of phenolic compounds of sesame extracts, would act
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Brown substances or phenolic compounds produced during roasting Lee et al.73 found that the fraction of highest browning pigment prepared with XAD-7 and silica gel column chromatography from sesame seeds showed more effective inhibition of enzymatic browning than other fractions. Yoo et al.74 reported that the methanol fraction was rich in brown substances that had J Sci Food Agric 2015; 95: 2571–2578
Reference
www.soci.org as determining factors in oil stabilization,9 which was consistent with the opinion of Jo et al.76 Fukuda77 suggested that Maillard reaction products might play an important role in the antioxidant activity of roasted sesame meal. With an increase in roasting temperature of the meal, the browning index (A420 − A550 ) of sesame methanolic extract increased significantly, while its antioxidant effects on scavenging DPPH• and inhibiting Cu2+ -induced oxidation of human LDL increased too.78 The browning index is closely related to the DPPH free radical-scavenging effect and reducing power of SSO.79 The increase in the absorbance at 420 nm was probably due to the formation of non-enzymatic browning substances during the Maillard reaction,80 which are known to have distinctive antioxidant properties.81,82 Synergistic antioxidant action among components The aforementioned components of SSO seemed to possess antioxidant activities to different degrees in different antioxidant systems (Table 1).46 – 49,51,62,83 – 86 Many studies have pointed out that the synergistic activities of these active components instead of the activity of each alone could well explain the bioactivity of SSO.87 – 89 Dachtler et al.49 reported that sesaminol showed a synergistic antioxidant activity with 𝛾-tocopherol in the increased oxidative stability of sesaminol-enriched sunflower oil. The activity of reducing the serum cholesterol level in mice was enhanced when 𝛼-tocopherol was fed together with sesamin, in spite of there being little effect of 𝛼-tocopherol alone.90 One hypothesis was that lignans increased 𝛾-tocopherol bioavailability.44,91,92 Other researchers found that sesaminol raised the levels of vitamin E in rat liver and plasma.93,94 It was suggested that the inhibition by sesamin and sesaminol of lipid peroxidation induced by a diet high in docosohexaenoic acid (DHA) was accompanied by increased 𝛼-tocopherol concentrations in the plasma, liver and brain of rats and increased antioxidant activities of themselves and their metabolites.95 Fukuda et al.96 found the highest antioxidant activity with a combination of brown product, 𝛾-tocopherol, sesamol and sesamin. It was very interesting that the combination of individual lignans and tocopherols (𝛼, 𝛾) or 𝛼-tocotrienol showed higher inhibitory activity than the sum of individual inhibitions in cumene hydroperoxide (CumOOH) and Fe2+ -ascorbate systems, suggesting the synergistic interactions.92 The results of the weight methods indicated that the browning fraction separated by column chromatography had a low antioxidant activity on oxidation of oil stored at 60 ∘ C. The activity increased dramatically when the browning fraction was mixed with 𝛾-tocopherol, 𝛾-tocopherol + sesamol, 𝛾-tocopherol + sesamin or 𝛾-tocopherol + sesamol + sesamin.18
CONCLUSIONS
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SSO has higher oxidation stability than other vegetable oils, closely related to the antioxidant activity of its inherent lignans. In addition, its inherent tocopherols and browning substances generated from the Maillard reaction also contribute their antioxidant ability. As discussed in many studies on SSO production, different processes and parameters can impact the contents of lignans and tocopherols. The brown substances generated during sesame roasting have antioxidant activity, synergistic action with other ingredients and impact on the aroma of SSO. However, there is a lack of in-depth analysis of the composition and structures of
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the brown substances or the effect of browning reactions on sesame component changes. Therefore further research is needed to explain the remaining mysteries of sesame oil.
ACKNOWLEDGEMENT The authors gratefully acknowledge the National Natural Science Foundation of China for financial support (Grant No. 3136039).
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25 Jiao Y, Davin LB and Lewis NG, Furanofuran lignan metabolism as a function of seed maturation in Sesamum indicum: methylenedioxy bridge formation. Phytochemistry 49:387–394 (1998). 26 Wu J, The introduction of natural antioxidants in sesame. Food Ind 4:11–15 (2001). 27 Park SH, Ryu SN, Bu Y, Kim H, Simon JE and Kim KS, Antioxidant components as potential neuroprotective agents in sesame (Sesamum indicum L.). Food Rev Int 26:103–121 (2010). 28 Nakai M, Harada M, Nakahara K, Akimoto K, Shibata H, Miki W, et al., Novel antioxidative metabolites in rat liver with ingested sesamin. J Agric Food Chem 51:1666–1670 (2003). 29 Fukuda Y, Nagata M, Osawa T and Namiki M, Contribution of lignan analogues to antioxidative activity of refined unroasted sesame seed oil. J Am Oil Chem Soc 63:1027–1031 (1986). 30 Umeda-Sawada R, Ogawa M, Nakamura M and Igarashi O, Effect of sesamin on mitochondrial and peroxisomal 𝛽-oxidation of arachidonic and eicosapentaenoic acids in rat liver. Lipids 36:483–489 (2001). 31 Ide T, Ashakumary L, Takahashi K, Kushiro M, Fukuda N and Sugano M, Sesamin, a sesame lignan, decreases fatty acid synthesis in rat liver accompanying the down-regulation of sterol regulatory element binding protein-1. Biochim Biophys Acta Mol Cell Biol Lipids 1534:1–13 (2001). 32 Guo L, Yang J and Kong X, Effects of sesamin on lipidemia and non-alcoholic steatohepatitis in hyperlipidemia rats. Chin J Exp Tradit Med Formulae 15:55–58 (2009). 33 Wang W and Song J, Effects of artesunate on proliferation of HSCs. Pharmacol Clin Chin Mater Med 22:27–31 (2006). 34 Qiao Y, Wei Y and Jiang X, Protective effect of sesamin on carbon tetrachloride-induced chronic liver injury in rats. Hebei J TCM 32:1711–1713 (2010). 35 Miyahara Y, Komiya T, Katsuzaki H, Imai K, Nakagawa M, Ishi Y, et al., Sesamin and episesamin induce apoptosis in human lymphoid leukemia Molt 4B cells. Int J Mol Med 6:43–46 (2000). 36 Hibasami H, Fujikawa T, Takeda H, Nishibe S, Satoh T, Fujisawa T, et al., Induction of apoptosis by Acanthopanax senticosus HARMS and its component, sesamin in human stomach cancer KATO III cells. Oncol Rep 7:1213–1219 (2000). 37 Miyawaki T, Aono H, Toyoda-Ono Y, Maeda H, Kiso Y and Moriyama K, Antihypertensive effects of sesamin in humans. J Nutr Sci Vitaminol 55:87–91 (2009). 38 Lei H, Han J, Wang Q, Guo S, Sun H and Zhang X, Effects of sesamin on streptozotocin (STZ)-induced NIT-1 pancreatic 𝛽-cell damage. Int J Mol Sci 13:16961–16970 (2012). 39 Sun M, Zhou J, Wang H, Li X and Shi X, Studies on antioxidative activity of sesamin. Food Ferment Ind 31:41–42 (2005). 40 Dai H, Study on extraction, purification and antioxidant activity of sesamin from sesame oil residue. Dissertation, Jiangnan University, Wuxi (2004). 41 Kim JH, Seo WD, Lee SK, Lee YB, Park CH, Ryu HW, et al., Comparative assessment of compositional components, antioxidant effects, and lignan extractions from Korean white and black sesame (Sesamum indicum L.) seeds for different crop years. J Funct Foods 7:495–505 (2014). 42 Kiso Y and Moritani T, Antioxidative effects of sesamin during high intensity exercise. Med Sci Sports Exerc 35:S269 (2003). 43 Yasuda K, Ikushiro S, Kamakura M, Ohta M and Sakaki T, Metabolism of sesamin by cytochrome P450 in human liver microsomes. Drug Metabol Dispos 38:2117–2123 (2010). 44 Peñalvo JL, Heinonen SM, Aura AM and Adlercreutz H, Dietary sesamin is converted to enterolactone in humans. J Nutr 135:1056–1062 (2005). 45 Kamal-Eldin A and Appelqvist LÅ, Variations in the composition of sterols, tocopherols and lignans in seed oils from four Sesamum species. J Am Oil Chem Soc 71:149–156 (1994). 46 Suja KP, Jayalekshmy A and Arumughan C, Free radical scavenging behavior of antioxidant compounds of sesame (Sesamum indicum L.) in DPPH system. J Agric Food Chem 52:912–915 (2004). 47 Suja KP, Jayalekshmy A and Arumughan C, In vitro studies on antioxidant activity of lignans isolated from sesame cake extract. J Sci Food Agric 85:1779–1783 (2005). 48 Kang MH, Naito M, Tsujihara N and Osawa T, Sesamolin inhibits lipid peroxidation in rat liver and kidney. J Nutr 128:1018–1022 (1988). 49 Dachtler M, van de Put FHM, Stijn F, Beindorff CM and Fritsche J, On-line LC-NMR-MS characterization of sesame oil extracts and assessment
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www.soci.org 74 Yoo MA, Kim HW, Kang MH and Kim KH, Antioxidant effect of brown substances separated from defatted roasted sesame dregs. Food Sci Biotechnol 13:274–278 (2004). 75 Jeong SM, Kim SY, Kim DR, Nam KC, Ahn DU and Lee SC, Effect of seed roasting conditions on the antioxidant activity of defatted sesame meal extracts. J Food Sci 69:377–381 (2004). 76 Jo SC, Nam KC, Min BR, Ahn DU and Lee SC, Antioxidant activities of defatted sesame meal extracts in cooked turkey breast and thigh meats. J Sci Food Agric 87:2141–2146 (2007). 77 Fukuda Y, Food chemical studies on the antioxidants in sesame seed. J Jpn Soc Food Sci 37:484–492 (1990). 78 Shyu YS, Hwang JY and Hwang LS, Effect of roasting condition on the antioxidative activity of the methanolic extract from defatted sesame meal. J Food Drug Anal 17:300–317 (2009). 79 Wu Y, The effect of different heating pretreatments to the antioxidant of sesame oil. Dissertation, National Ilan University (2007). 80 Kawakishi S, Satake A, Komiya T and Nagoya MN, Oxidative degradation of 𝛽-cyclodextrin induced by lipid peroxidation. Starch/Stärke 35:54–57 (1983). 81 Borrelli RC, Mennella C, Barba F, Russo M, Russo GL, Krome K, et al., Characterization of coloured compounds obtained by enzymatic extraction of bakery products. Food Chem Toxicol 41:1367–1374 (2003). 82 Wagner KH, Derkits S, Herr M, Schuh W and Elmadfa I, Antioxidative potential of melanoidins isolated from a roasted glucose–glycine model. Food Chem 78:375–382 (2002). 83 Shyu YS and Hwang LS, Antioxidative activity of the crude extract of lignan glycosides from unroasted Burma black sesame meal. Food Res Int 35:357–365 (2002). 84 Shimizu S, Akimoto K, Shinmen Y, Kawashima H, Sugano M and Yamada H, Sesamin is a potent and specific inhibitor of Δ5 desaturase in polyunsaturated fatty acid biosynthesis. Lipids 26:512–516 (1991). 85 Hu C and Du W, The antioxidants in sesame. Guangzhou Chem Ind 24:14–18 (1996).
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86 Lee J and Choe E, Extraction of lignan compounds from roasted sesame oil and their effects on the autoxidation of methyl linoleate. J Food Sci 71:430–436 (2006). 87 Yoshida H, Shigezaki J, Takagi S and Kajimoto G, Variation in the composition of various acyl lipid, tocopherols and lignans in sesame seed oil roasted in a microwave oven. J Sci Food Agric 68:407–415 (1995). 88 Namiki M, Fukuda Y, Takei Y, Namiki K and Koizumi Y, Changes in functional factors of sesame seed and oil during various types of processing. ACS Symp Ser 816:85–104 (2002). 89 Yoshida H and Takagi S, Antioxidative effects of sesamol and tocopherols at various concentrations in oils during microwave heating. J Sci Food Agric 79:220–226 (1999). 90 Hirose N, Inoue T, Nishihara K, Sugano M, Akimoto K, Shimizu S, et al., Inhibition of cholesterol absorption and synthesis in rats by sesamin. J Lipid Res 32:629–638 (1991). 91 Sontag TJ and Parker RS, Cytochrome P450 𝜔-hydroxylase pathway of tocopherol catabolism: novel mechanism of regulation of vitamin E status. J Biol Chem 277:25290–25296 (2002). 92 Ghafoorunissa, Hemalatha S and Rao MVV, Sesame lignans enhance antioxidant activity of vitamin E in lipid peroxidation systems. Mol Cell Biochem 262:195–202 (2004). 93 Yamashita K, Iizuka Y, Imai T and Namiki M, Sesame seed and its lignans produce marked enhancement of vitamin E activity in rats fed a low 𝛼-tocopherol diet. Lipids 30:1019–1028 (1995). 94 Kamal-Eldin A, Pettersson D and Appelqvist LÅ, Sesamin (a compound from sesame oil) increases tocopherol levels in rats fed ad libitum. Lipids 30:499–505 (1995). 95 Ikeda S, Kagaya M, Kobayashi K, Tohyama T, Kiso Y, Higuchi N, et al., Dietary sesame lignans decrease lipid peroxidation in rats fed docosahexaenoic acid. J Nutr Sci Vitaminol 49:270–276 (2003). 96 Fukuda Y, Koizumi Y, Ito R and Namiki M, Marked antioxidative activity of seed oils developed by roasting of oil seeds. II. Synergistic action of the antioxidative components in roasted sesame seed oil. J Jpn Soc Food Sci 43:1272–1277 (1996).
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Revised: 16 October 2014
Accepted article published: 4 December 2014
Published online in Wiley Online Library: 23 January 2015
(wileyonlinelibrary.com) DOI 10.1002/jsfa.7035
The relationship of antioxidant components and antioxidant activity of sesame seed oil Yin Wan,a,b Huixiao Li,a Guiming Fu,a Xueyang Chen,a Feng Chenb* and Mingyong Xiea Abstract Although sesame seed oil contains high levels of unsaturated fatty acids and even a small amount of free fatty acids in its unrefined flavored form, it shows markedly greater stability than other dietary vegetable oils. The good stability of sesame seed oil against autoxidation has been ascribed not only to its inherent lignans and tocopherols but also to browning reaction products generated when sesame seeds are roasted. Also, there is a strong synergistic effect among these components. The lignans in sesame seed oil can be categorized into two types, i.e. inherent lignans (sesamin, sesamolin) and lignans mainly formed during the oil production process (sesamol, sesamolinol, etc.). The most abundant tocopherol in sesame seed oil is 𝜸-tocopherol. This article reviews the antioxidant activities of lignans and tocopherols as well as the browning reaction and its products in sesame seed and/or its oil. It is concluded that the composition and structure of browning reaction products and their impacts on sesame ingredients need to be further studied to better explain the remaining mysteries of sesame oil. © 2014 Society of Chemical Industry Keywords: sesame seed oil; antioxidant activity; lignans; tocopherols; Maillard reaction
INTRODUCTION
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ANTIOXIDANT ACTIVITY OF SESAME SEED OIL Although SSO contains more than 800 g kg−1 unsaturated fatty acids and even a small amount of free fatty acids (7.2 g kg−1 )5 in its unrefined flavored form, it shows markedly greater stability than other dietary vegetable oils.6 Soybean oil and other oils can undergo a rapid increase in weight via autoxidation, resulting in a rancid odor after 10–20 days of storage.7 However, the unsaturated fatty acids in SSO, especially roasted SSO, did not decompose after being stored at 60 ∘ C for 50 days.8 Moreover, SSO showed better antioxidant stability than corn oil in fried bread loaf.
∗
Correspondence to: Feng Chen, Department of Food, Nutrition, and Packaging Sciences, Clemson University, Clemson, SC 29634, USA. E-mail: [email protected]
a State Key Laboratory of Food Science and Technology, Department of Food Science and Engineering, Nanchang University, Nanchang 330047, Jiangxi, China b Department of Food, Nutrition, and Packaging Sciences, Clemson University, Clemson, SC 29634, USA
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Belonging to the Pedaliaceae family, sesame (Sesamum indicum L., synonymous with Sesamum orientale L.)1 was first recorded as a crop in Babylon and Assyria over 4000 years ago and is considered one of the most ancient crops cultivated by humans.2 The major countries and areas for sesame production are located in Asia, Africa and Central and South America, such as India, Sudan, China, Burma and Ethiopia. The world’s total annual production of sesame is about 3 × 109 kg,3 with 50% from Asia and 30% from Africa. Around 65% of the annual production is consumed as an edible oil and 35% as a food ingredient. As one of the world’s major oilseeds, sesame seed has a high oil content that accounts for about 50% of its weight, which is much higher than the 20% oil content of soybean. Sesame seed oil (SSO) has of a dietary history for more than 2000 years. In Asia, especially in China, virgin SSO is also called sesame flavoring oil, which is preferably consumed without refining. Owing to the roasting of sesame seeds before oil extraction, numerous aromatic compounds and brown pigments are produced, resulting in SSOs ranging from yellow to brown in color. The multiple-step extraction technology for producing commercial SSO is similar to that for the production of other dietary oils in western countries, where SSO is generally used as a salad dressing whether refined or not. Growing in an oblong, mucronate and pubescent capsule, the sesame seed is small, oval, with different colors such as white, yellow, red, brown or black. It was reported that sesame seeds of different colors had different oil contents; the average oil contents of white, black and yellow sesame seeds were 550, 478 and 500 g kg−1 respectively.4 Two unsaturated fatty acids, oleic acid (C18:1) and linoleic acid (C18:2), account for more than 800 g kg−1 of the total fatty acids in SSO. In contrast, saturated fatty acids are present at much lower levels. Palmitic acid (C16:0) constitutes
79–120 g kg−1 of the total fatty acids in SSO, while stearic acid (C18:0) constitutes 48–61 g kg−1 . Moreover, other fatty acids such as palmitoleic acid (C16:1), linolenic acid (C18:3), arachidic acid (C20:0), etc. are present at levels below 10 g kg−1 . It is well known that SSO has remarkable storage stability. Thus it is of interest to investigate the antioxidant components and their antioxidant activities in SSO, especially during the oil production process. This article reviews the antioxidant activities of lignans and tocopherols as well as the browning reaction and its products in sesame seed and/or its oil.
www.soci.org It was reported that mixing olive oil with 900 μL of a methanolic extract of coated unroasted sesame seed could lower its peroxide value by 61% after 200 h of heat treatment at 100 ∘ C.9 Similar findings were also obtained when different sesame extracts were added to sunflower, soybean or corn oil. When SSO was heated in an oven at 50 ∘ C, it showed a peroxide value of 190.7 mmol kg−1 on day 8 and carbonyl value of 25.2 mmol kg−1 on day 6, which were similar to those of bene hull oil but lower than those of rice bran oil. SSO also had the longest time (6.92 h) of oxidative stability in the Rancimat test and the highest reducing power (258.1 mmol L−1 ) among the tested dietary oils.10 The antioxidant activities of SSO in living organisms were illustrated by some in vivo animal tests. For instance, SSO could attenuate oxidative stress in lipopolysaccharide (LPS)-treated rats. After giving SSO parenterally, lipid peroxidation, hydroxyl radical and nitrite levels in oxidative stressed model rats induced by LPS were reduced, while superoxide dismutase (SOD) and catalase concentrations increased.11 In addition, SSO-treated animal groups showed attenuated hepatic disorder, although the symptoms were different when the SSO was given orally. Superoxide anion decreased and glutathione increased in the oral SSO groups. In contrast, corn oil- or mineral oil-treated groups did not show attenuation of hepatic disorder induced by LPS.12 Dietary SSO was also shown to behave as an antioxidant, resulting in increased activity of enzymatic and non-enzymatic antioxidants in the middle cerebral artery occlusion (MCAO) + SSO group, thus protecting the model rats against MCAO-induced cerebral ischemia injury.13 Furthermore, giving SSO orally could reduce oxidative myocardial damage induced by isoproterenol,14 oxidative stress induced by chronic exposure to electromagnetic radiation (EMR)15 as well as cypermethrin-induced oxidative stress, biochemical changes, histopathological damage and genomic DNA fragmentation.16
IMPORTANT ANTIOXIDANT COMPONENTS IN SESAME SEED OIL The outstanding antioxidant activity of SSO was reported to be the result of the presence of lignans, tocopherols and brown Maillard reaction products17 as well as the synergistic action among these components.18 The structures of lignans and tocopherol are shown in Fig. 1.
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Lignans Lignans in SSO mainly comprise sesamin, sesamolin and sesamol. Lignan glycosides present in sesame seed are not found in SSO. The content of lignans varies between 6.5 and 17.3 g kg−1 oil.19,20 Sesamin and sesamolin are the most abundant lignans in SSO, accounting for 0.7–8.85 and 0.2–4.8 g kg−1 SSO respectively.21,22 However, their concentrations vary considerably among SSOs from different places. For example, the respective contents of sesamin and sesamolin were reported to be 3.0–9.0 and 3.5–5.3 g kg−1 oil in Indian SSO20 and 0.93–2.89 and 0.3–0.74 g kg−1 oil in Thai SSO.23 Sesamol has a relatively lower content, only 50–100 mg kg−1 SSO. Sesamin is easily hydrolyzed under acidic conditions into pinoresinol during the production of SSO, which is the opposite route of the biosynthesis of sesamin from pinoresinol24 that is catalyzed by the enzyme cytochrome P450 in microsomes (CYP81Q1).25 Cytochrome P450 possesses a unique activity by catalyzing bridge formation on different aromatic rings at both ends of pinoresinol.
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Sesamolin is thermally unstable. Under different heating conditions, it can be transformed to sesamol and other products.26 The transformations of lignans during the oil production process27,28 are shown in Fig. 2. In 1986, Fukuda et al.29 found that sesamolin underwent a similar reaction to its acidic hydrolysis under heating when decolored by acidic clay in the oil refining process and was transformed into sesaminol and sesamol. In this context, sesamolin is a precursor of the natural antioxidants sesamol and sesaminol in sesame seed. In the bleaching process, sesamolin was also transformed into sesaminol. Sesamin As one of the mysterious compounds in SSO, sesamin has been investigated in many studies for its various activities such as liver fatty acid synthesis suppression and blood lipid regulation,30 – 32 liver support and liver protection,33,34 antitumor activities,35,36 antihypertension,37 oxidative stress attenuation,38 etc. Sun et al.39 reported that sesamin had good ability for inhibition of oil oxidation. The antioxidant activity of sesamin in soybean salad oil (0.4 g kg−1 ) was comparable to that of butylated hydroxytoluene (BHT) (0.2 g kg−1 ), and its antioxidant activity in soybean oil (0.4 g kg−1 ) was better than that in lard. However, it should be noted that a mixture of sesamin (685 g kg−1 ) and sesamolin (315 g kg−1 ) was used in this test. Generally, sesamin itself does not exhibit a strong antioxidant effect in vitro. The results of in vitro tests performed by Nakai et al.28 showed that sesamin had almost no scavenging or inhibitory effects on 2,2-diphenyl-1-picrylhydrazyl (DPPH• ), hydroxyl (• OH) and superoxide anion (O2•− ) radicals and lipid peroxidation. In contrast, Dai40 argued that sesamin had certain effects on scavenging free radicals in vitro, with IC50 values for scavenging DPPH• , • OH and O2•− of 7.5, 26 and 29.5 g L−1 respectively. However, Kim et al.41 suggested that the strong DPPH radical-scavenging property of sesame seed may not be much due to its inherent lignans, because the antioxidant activity of the 90% acetonitrile extract from white sesame seeds was lower than that of the same extract from black sesame seeds even though the content of sesamin and sesamolin in the former was twice that in the latter. The current widely recognized opinion is that sesamin has weak antioxidant activity in vitro but a significantly strong antioxidant effect in vivo. On giving sesamin to seven male university students (non-smokers) 2 h before bicycle ergometer exercise, their plasma lipid peroxide level was significantly suppressed, while the level in the placebo group increased significantly after exercise. Meanwhile, vitamin E was not effective in this experiment.42 The results indicated that sesamin was concentrated in the liver after entering the biosome and that its metabolites had distinctive antioxidant capacity. Therefore it has been classified as a pro-antioxidant.28 After ingestion by rats or humans, the methylenedioxyphenyl moiety of the sesamin molecule was shown to be split and converted into a monocatechol or dicatechol structure with a dihydrophenyl moiety.28,43,44 Nakai et al.28 isolated four sesamin metabolites from rat bile, three of which had dihydroxyl groups of catechol structure (Fig. 3). In vitro experiments showed that these sesamin metabolites with catechol form had stronger abilities to eliminate reactive oxygen species and inhibit lipid peroxidation generation than sesamin. Sesamolin Kamal-Eldin and Appelqvist45 noted that sesamolin basically had no antioxidant activity in vitro. In the DPPH radical-scavenging
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Antioxidant components and activity of sesame seed oil
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O O
O
H
O
OH
H
H
O
O O
O
O
O
III Episesamin
O
O H
O O
O
II Sesamin
H
H
O O
I Sesamol
O
O
O
O
O
HO H
H
O
O
O
O
O
IV Sesaminol
V Sesamolin
O OH O OCH3 H
H O
O
O O
O
H H
H3C CH3
H3CO
H3CO HO VI Sesamolinol
O
H3C CH3
HO VII Pinoresinol
CH3
CH3 CH3
CH3
VIII Tocopherol
Figure 1. Structures of lignans and tocopherol in sesame seed oil. Heating Sesamolin
Bleaching with acidic clay Metabolized in rats Acid hydrolysis
Sesamin
Decoloring Metabolized in rats
Sesamol Sesaminol + Sesamol Sesamol + Sesamolinol
Pinoresinol Episesamin Monocatechol + Dicatechol
Figure 2. Transformations of lignans during oil production process (adapted from Park et al.27 and Nakai et al.28 ). Sesamolin and sesamin are unstable. Under different processing conditions, they can be transformed into different lignans and other products.
Sesamol Sesamol has strong antioxidant activity and is regarded as a very effective antioxidant in roasted SSO. The content of sesamol (36 mg kg−1 ) in roasted SSO5 was much higher than its original level ( 𝛼-tocopherol > BHT ≥ sesamin > sesamolin The brown materials exhibited exceptional radical-scavenging effect Sesamol > sesamolin ≥ sesamin > BHT Sesamol > sesamin > sesamolin
Suja et al.46 and Shyu and Hwang83 Shyu and Hwang83 Suja et al.47 Suja et al.47
Sesamol > sesamin > sesaminol > sesamolin
Suja et al.47
Sesamin > sesamolin, sesaminol Sesaminol > pinoresinol > sesamolinol
Shimizu et al.84 Kang et al.62
Sesaminol > 𝛼-tocopherol
Kang et al.62
Sesaminol > 𝛼-tocopherol
Kang et al.62
BHT > sesaminol ≥ sesamolinol ≥ sesamol ≥ 𝛼-tocopherol > pinoresinol > sesamin > sesamolin
Kang et al.48
Sesamolinol > 𝛾-tocopherol > sesamin > sesamol 𝛼-Tocopherol > sesamol > sesamin > sesamolin
Hu and Du85 Hemalatha and Ghafoorunissa20
BHT > 𝛼-tocopherol > 𝛾-tocopherol > sesamin, sesamol, sesamolin Sesamol > sesamin, sesamolin, 𝛼-tocopherol
Hemalatha and Ghafoorunissa20 Lee and Choe86
Sesamol > sesamolin > sesamin
Budowski et al.8
Sesaminol-enriched SO extract > sesamol
Dachtler et al.49
Sesamol > sesaminol-enriched SO extract > sesamin
Dachtler et al.49
Mehta68 found that both 𝛼-tocopherol and 𝛾-tocopherol significantly inhibited arterial superoxide anion formation, lipid peroxidation and LDL oxidation and increased endogenous SOD activity, but the effects of 𝛾-tocopherol were significantly more potent than those of 𝛼-tocopherol. It was observed that nitrogen dioxide-mediated nitrosation of morpholine was inhibited effectively by 𝛾-tocopherol but not by 𝛼-tocopherol.69,70 𝛾-Tocopherol trapped peroxynitrite formed by the reaction of NO and active oxygen so that it inhibited lipid peroxidative damage more efficiently than 𝛼-tocopherol.71 Although 𝛾-tocopherol levels in blood plasma and most other tissues are only one-fifth or much less than those of 𝛼-tocopherol,72 they are equally important for their many beneficial bioactivities.
antioxidant activity too. In research by Jeong et al.,75 roasting sesame seeds at 200 ∘ C for 1 h significantly increased the content of phenolic compounds, DPPH radical-scavenging activity, reducing power and suppression of induction of lipid peroxidation compared with unroasted seeds. Furthermore, several low-molecular-weight phenolic compounds such as 2-methoxyphenol, 4-methoxy-3-methylthiophenol, 5-amino-3oxo-4-hexenoic acid, 3,4-methylenedioxyphenol (sesamol), 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, vanillic acid, filicinic acid and 3,4-dimethoxyphenol were formed during the roasting process. Jo et al.76 reported that the methanolic extract of characteristic brown color from roasted defatted sesame meal prevented lipid oxidation in turkey breast and thigh meat and significantly decreased the levels of volatile hydrocarbons (pentane, hexane, heptane and octane) and carbonyls (propanal, butanal, pentanal, hexanal and heptanal) after 5 days of storage. Konsoula and Liakopoulou-Kyriakides9 found that there was no obvious correlation between the sesamol level and peroxide value in oil samples added with SSO extract, though sesamolin decreased and sesamol increased during heat treatment. The authors suggested that other intrinsic antioxidant constituents, especially the composition of phenolic compounds of sesame extracts, would act
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Brown substances or phenolic compounds produced during roasting Lee et al.73 found that the fraction of highest browning pigment prepared with XAD-7 and silica gel column chromatography from sesame seeds showed more effective inhibition of enzymatic browning than other fractions. Yoo et al.74 reported that the methanol fraction was rich in brown substances that had J Sci Food Agric 2015; 95: 2571–2578
Reference
www.soci.org as determining factors in oil stabilization,9 which was consistent with the opinion of Jo et al.76 Fukuda77 suggested that Maillard reaction products might play an important role in the antioxidant activity of roasted sesame meal. With an increase in roasting temperature of the meal, the browning index (A420 − A550 ) of sesame methanolic extract increased significantly, while its antioxidant effects on scavenging DPPH• and inhibiting Cu2+ -induced oxidation of human LDL increased too.78 The browning index is closely related to the DPPH free radical-scavenging effect and reducing power of SSO.79 The increase in the absorbance at 420 nm was probably due to the formation of non-enzymatic browning substances during the Maillard reaction,80 which are known to have distinctive antioxidant properties.81,82 Synergistic antioxidant action among components The aforementioned components of SSO seemed to possess antioxidant activities to different degrees in different antioxidant systems (Table 1).46 – 49,51,62,83 – 86 Many studies have pointed out that the synergistic activities of these active components instead of the activity of each alone could well explain the bioactivity of SSO.87 – 89 Dachtler et al.49 reported that sesaminol showed a synergistic antioxidant activity with 𝛾-tocopherol in the increased oxidative stability of sesaminol-enriched sunflower oil. The activity of reducing the serum cholesterol level in mice was enhanced when 𝛼-tocopherol was fed together with sesamin, in spite of there being little effect of 𝛼-tocopherol alone.90 One hypothesis was that lignans increased 𝛾-tocopherol bioavailability.44,91,92 Other researchers found that sesaminol raised the levels of vitamin E in rat liver and plasma.93,94 It was suggested that the inhibition by sesamin and sesaminol of lipid peroxidation induced by a diet high in docosohexaenoic acid (DHA) was accompanied by increased 𝛼-tocopherol concentrations in the plasma, liver and brain of rats and increased antioxidant activities of themselves and their metabolites.95 Fukuda et al.96 found the highest antioxidant activity with a combination of brown product, 𝛾-tocopherol, sesamol and sesamin. It was very interesting that the combination of individual lignans and tocopherols (𝛼, 𝛾) or 𝛼-tocotrienol showed higher inhibitory activity than the sum of individual inhibitions in cumene hydroperoxide (CumOOH) and Fe2+ -ascorbate systems, suggesting the synergistic interactions.92 The results of the weight methods indicated that the browning fraction separated by column chromatography had a low antioxidant activity on oxidation of oil stored at 60 ∘ C. The activity increased dramatically when the browning fraction was mixed with 𝛾-tocopherol, 𝛾-tocopherol + sesamol, 𝛾-tocopherol + sesamin or 𝛾-tocopherol + sesamol + sesamin.18
CONCLUSIONS
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SSO has higher oxidation stability than other vegetable oils, closely related to the antioxidant activity of its inherent lignans. In addition, its inherent tocopherols and browning substances generated from the Maillard reaction also contribute their antioxidant ability. As discussed in many studies on SSO production, different processes and parameters can impact the contents of lignans and tocopherols. The brown substances generated during sesame roasting have antioxidant activity, synergistic action with other ingredients and impact on the aroma of SSO. However, there is a lack of in-depth analysis of the composition and structures of
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the brown substances or the effect of browning reactions on sesame component changes. Therefore further research is needed to explain the remaining mysteries of sesame oil.
ACKNOWLEDGEMENT The authors gratefully acknowledge the National Natural Science Foundation of China for financial support (Grant No. 3136039).
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