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Reviews

Recent status of sesaminol and its glucosides: Synthesis, metabolism, and biological activities

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Pages 12043-12056 | Published online: 12 Jul 2022

References

  • Afroz, M., S. Zihad, S. J. Uddin, R. Rouf, M. S. Rahman, M. T. Islam, IN. Khan, E. S. Ali, S. Aziz, J. A. Shilpi, et al. 2019. A systematic review on antioxidant and antiinflammatory activity of Sesame (Sesamum indicum L.) oil and further confirmation of antiinflammatory activity by chemical profiling and molecular docking. Phytotherapy Research: PTR 33 (10):2585–608. doi: 10.1002/ptr.6428.
  • Averous, J., B. D. Fonseca, and C. G. Proud. 2008. Regulation of cyclin D1 expression by mTORC1 signaling requires eukaryotic initiation factor 4E-binding protein 1. Oncogene 27 (8):1106–13. doi: 10.1038/sj.onc.1210715.
  • Bae, J. J., S. J. Yeon, W. J. Park, G. E. Hong, and C. H. Lee. 2016. Production of sesaminol and antioxidative activity of fermented sesame with Lactobacillus plantarum P8, Lactobacillus acidophilus ATCC 4356, Streptococcus thermophilus S10. Food Science and Biotechnology 25 (1):199–204. doi: 10.1007/s10068-016-0030-x.
  • Barath, P., K. Luciakova, Z. Hodny, R. Li, and B. D. Nelson. 1999. The growth-dependent expression of the adenine nucleotide translocase-2 (ANT2) gene is regulated at the level of transcription and is a marker of cell proliferation. Experimental Cell Research 248 (2):583–8. doi: 10.1006/excr.1999.4432.
  • Bjorkegren, J. L. M, and A. J. Lusis. 2022. Atherosclerosis: Recent developments. Cell 185 (10):1630–45. doi: 10.1016/j.cell.2022.04.004.
  • Brandt, W., E. Schulze, R. Liberman-Aloni, R. Bartelt, S. Pienkny, M. Carmeli-Weissberg, A. Frydman, and Y. Eyal. 2021. Structural modeling of two plant UDP-dependent sugar-sugar glycosyltransferases reveals a conserved glutamic acid residue that is a hallmark for sugar acceptor recognition. Journal of Structural Biology 213 (3):107777. doi: 10.1016/j.jsb.2021.107777.
  • Butterfield, D. A., A. M. Swomley, and R. Sultana. 2013. Amyloid beta-peptide (1-42)-induced oxidative stress in Alzheimer disease: Importance in disease pathogenesis and progression. Antioxidants & Redox Signaling 19 (8):823–35. doi: 10.1089/ars.2012.5027.
  • Byrne, N. J., N. S. Rajasekaran, E. D. Abel, and H. Bugger. 2021. Therapeutic potential of targeting oxidative stress in diabetic cardiomyopathy. Free Radical Biology & Medicine 169:317–42. doi: 10.1016/j.freeradbiomed.2021.03.046.
  • Cao, W., M. Dai, X. Wang, F. Yuan, F. Chen, and W. Zhang. 2013. Protective effect of sesaminol from Sesamum indicum Linn. against oxidative damage in PC12 cells. Cell Biochemistry and Function 31 (7):560–5. doi: 10.1002/cbf.2935.
  • Carreau, C., G. Flouriot, C. Bennetau-Pelissero, and M. Potier. 2008. Enterodiol and enterolactone, two major diet-derived polyphenol metabolites have different impact on ERalpha transcriptional activation in human breast cancer cells. The Journal of Steroid Biochemistry and Molecular Biology 110 (1-2):176–85. doi: 10.1016/j.jsbmb.2008.03.032.
  • Castejon, N., K. A. Thorarinsdottir, R. Einarsdottir, K. Kristbergsson, and G. Marteinsdottir. 2021. Exploring the potential of icelandic seaweeds extracts produced by aqueous pulsed electric fields-assisted extraction for cosmetic applications. Marine Drugs 19 (12):662. doi: 10.3390/md19120662.
  • Celind, J., M. Bygdell, J. Martikainen, C. Ohlsson, and J. M. Kindblom. 2022. Childhood overweight and risk of obesity-related adult cancer in men. Cancer Communications 42 (6):576–9. doi: 10.1002/cac2.12286.
  • Chang, R., X. Sun, H. Jia, Q. Xu, Z. Dong, Y. Tang, S. Luo, Q. Jiang, J. J. Loor, and C. Xu. 2022. Inhibiting nuclear factor erythroid 2 related factor 2-mediated autophagy in bovine mammary epithelial cells induces oxidative stress in response to exogenous fatty acids. Journal of Animal Science and Biotechnology 13 (1):48. doi: 10.1186/s40104-022-00695-2.
  • Chen, B., J. Zhao, R. Zhang, L. Zhang, Q. Zhang, H. Yang, and J. An. 2022. Neuroprotective effects of natural compounds on neurotoxin-induced oxidative stress and cell apoptosis. Nutritional Neuroscience 25 (5):1078–99. doi: 10.1080/1028415X.2020.1840035.
  • Chen, C. 2010. COX-2’s new role in inflammation. Nature Chemical Biology 6 (6):401–2. doi: 10.1038/nchembio.375.
  • Chen, C. C., X. Yu, C. J. Kuo, J. Min, S. Chen, L. Ma, K. Liu, and R. T. Guo. 2021. Overview of antiviral drug candidates targeting coronaviral 3C-like main proteases. The FEBS Journal 288 (17):5089–121. doi: 10.1111/febs.15696.
  • Chen, J., J. Xiao, Z. Wang, H. Cheng, Y. Zhang, B. Lin, L. Qin, and Y. Bai. 2020. Effects of reaction condition on glycosidic linkage structure, physical-chemical properties and in vitro digestibility of pyrodextrins prepared from native waxy maize starch. Food Chemistry 320:126491. doi: 10.1016/j.foodchem.2020.126491.
  • Chevrollier, A., D. Loiseau, B. Chabi, G. Renier, O. Douay, Y. Malthiery, and G. Stepien. 2005. ANT2 isoform required for cancer cell glycolysis. Journal of Bioenergetics and Biomembranes 37 (5):307–16. doi: 10.1007/s10863-005-8642-5.
  • Cypess, A. M., L. S. Weiner, C. Roberts-Toler, E. Franquet Elia, S. H. Kessler, P. A. Kahn, J. English, K. Chatman, S. A. Trauger, A. Doria, et al. 2015. Activation of human brown adipose tissue by a beta3-adrenergic receptor agonist. Cell Metabolism 21 (1):33–8. doi: 10.1016/j.cmet.2014.12.009.
  • Dachtler, M., F. H. M. van de Put, F. v. Stijn, C. M. Beindorff, and J. Fritsche. 2003. On‐line LC‐NMR‐MS characterization of sesame oil extracts and assessment of their antioxidant activity. European Journal of Lipid Science and Technology 105 (9):488–96. doi: 10.1002/ejlt.200300835.
  • Dar, A. A., and N. Arumugam. 2013. Lignans of sesame: Purification methods, biological activities and biosynthesis–a review. Bioorganic Chemistry 50:1–10. doi: 10.1016/j.bioorg.2013.06.009.
  • Das, R., C. Bhattacharjee, and S. Ghosh. 2011. Novel approach to recover natural antioxidants from oil seed meal in ultrafiltration-nanofiltration-based technique. Industrial & Engineering Chemistry Research 50 (21):12124–33. doi: 10.1021/ie200485a.
  • Davin, L. B., H. B. Wang, A. L. Crowell, D. L. Bedgar, D. M. Martin, S. Sarkanen, and N. G. Lewis. 1997. Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center. Science (New York, N.Y.) 275 (5298):362–6. doi: 10.1126/science.275.5298.362.
  • Divakaran, S. J., S. Srivastava, A. Jahagirdar, R. Rajendran, S. V. Sukhdeo, and S. Rajakumari. 2020. Sesaminol induces brown and beige adipocyte formation through suppression of myogenic program. FASEB Journal: Official Publication of the Federation of American Societies for Experimental Biology 34 (5):6854–70. doi: 10.1096/fj.201902124R.
  • Dong, P., X. Fu, X. Wang, W. M. Wang, W. M. Cao, and W. Y. Zhang. 2015. Protective effects of sesaminol on BEAS-2B cells impaired by cigarette smoke extract. Cell Biochemistry and Biophysics 71 (2):1207–13. doi: 10.1007/s12013-014-0330-9.
  • Eom, S. J., H. D. Zu, J. Lee, M. C. Kang, J. Park, K. M. Song, and N. H. Lee. 2021. Development of an ultrasonic system for industrial extraction of unheated sesame oil cake. Food Chemistry 354:129582. doi: 10.1016/j.foodchem.2021.129582.
  • Fitwi, M, and G. Tadesse. 2013. Effect of sesame cake supplementation on feed intake, body weight gain, feed conversion efficiency and carcass parameters in the ration of sheep fed on wheat bran and teff (Eragrostis teff) straw. Momona Ethiopian Journal of Science 5 (1):89–106. doi: 10.4314/mejs.v5i1.85333.
  • Fu, Y, and F. L. Chung. 2018. Oxidative stress and hepatocarcinogenesis. Hepatoma Research 4 (8):39. doi: 10.20517/2394-5079.2018.29.
  • Fukuda, Y., M. Nagata, T. Osawa, and M. Namiki. 1986. Contribution of lignan analogues to antioxidative activity of refined unroasted sesame seed oil. Journal of the American Oil Chemists’ Society 63 (8):1027–31. doi: 10.1007/BF02673792.
  • Fukuda, Y., T. Osawa, M. Namiki, and T. Ozaki. 1985. Studies on antioxidative substances in sesame seed. Agricultural and Biological Chemistry 49 (2):301–6. doi: 10.1080/00021369.1985.10866739.
  • Gao, J., R. Wang, X. Lu, C. Jia, Q. Sun, J. Huang, S. Wei, and L. Ma. 2021. Enzymatic preparation and structure-activity relationship of sesaminol. Journal of Oleo Science 70 (9):1261–74. doi: 10.5650/jos.ess21112.
  • Gerstenmeyer, E., S. Reimer, E. Berghofer, H. Schwartz, and G. Sontag. 2013. Effect of thermal heating on some lignans in flax seeds, sesame seeds and rye. Food Chemistry 138 (2–3):1847–55. doi: 10.1016/j.foodchem.2012.11.117.
  • Han, S., Y. Yang, Y. Lu, J. Guo, X. Han, Y. Gao, W. Huang, Y. You, and J. Zhan. 2021. Cyanidin-3-O-glucoside regulates the expression of Ucp1 in brown adipose tissue by activating Prdm16 gene. Antioxidants 10 (12):1986. doi: 10.3390/antiox10121986.
  • Harada, E., J. Murata, E. Ono, H. Toyonaga, A. Shiraishi, K. Hideshima, M. P. Yamamoto, and M. Horikawa. 2020. (+)-Sesamin-oxidising CYP92B14 shapes specialised lignan metabolism in sesame. The Plant Journal: For Cell and Molecular Biology 104 (4):1117–28. doi: 10.1111/tpj.14989.
  • Huang, J., G. Song, L. Zhang, Q. Sun, and X. Lu. 2012. A novel conversion of sesamolin to sesaminol by acidic cation exchange resin. European Journal of Lipid Science and Technology 114 (7):842–8. doi: 10.1002/ejlt.201100247.
  • Hung, W.-L., C.-D. Liao, W.-C. Lu, C.-T. Ho, and L. S. Hwang. 2016. Lignan glycosides from sesame meal exhibit higher oral bioavailability and antioxidant activity in rat after nano/submicrosizing. Journal of Functional Foods 23:511–22. doi: 10.1016/j.jff.2016.03.008.
  • Ikeda, S., T. Tohyama, and K. Yamashita. 2002. Dietary sesame seed and its lignans inhibit 2,7,8-trimethyl- 2(2’-carboxyethyl)-6-hydroxychroman excretion into urine of rats fed gamma-tocopherol. The Journal of Nutrition 132 (5):961–6. doi: 10.1093/jn/132.5.961.
  • Ishikawa, R., N. Yoshida, Y. Akao, Y. Kawabe, M. Inai, T. Asakawa, Y. Hamashima, and T. Kan. 2014. Total syntheses of (+)-sesamin and (+)-sesaminol. Chemistry Letters 43 (10):1572–4. doi: 10.1246/cl.140613.
  • Jahagirdar, A., D. Usharani, M. Srinivasan, and R. Rajasekharan. 2018. Sesaminol diglucoside, a water-soluble lignan from sesame seeds induces brown fat thermogenesis in mice. Biochemical and Biophysical Research Communications 507 (1–4):155–60. doi: 10.1016/j.bbrc.2018.10.195.
  • Jan, K. C, and C. T. Ho. 2014. Inhibitory activity of sesaminol and sesaminol triglycoside on cytochrome P450 enzymes and theirpharmacokinetics in rats. Journal of Functional Foods 7:142–9. doi: 10.1016/j.jff.2013.08.014.
  • Jan, K. C., K. L. Ku, Y. H. Chu, L. S. Hwang, and C. T. Ho. 2010. Tissue distribution and elimination of estrogenic and anti-inflammatory catechol metabolites from sesaminol triglucoside in rats. Journal of Agricultural and Food Chemistry 58 (13):7693–700. doi: 10.1021/jf1009632.
  • Jan, K. C., K. L. Ku, Y. H. Chu, L. S. Hwang, and C. T. Ho. 2011. Intestinal distribution and excretion of sesaminol and its tetrahydrofuranoid metabolites in rats. Journal of Agricultural and Food Chemistry 59 (7):3078–86. doi: 10.1021/jf105012v.
  • Jan, K. C., L. S. Hwang, and C. T. Ho. 2009a. Biotransformation of sesaminol triglucoside to mammalian lignans by intestinal microbiota. Journal of Agricultural and Food Chemistry 57 (14):6101–6. doi: 10.1021/jf901215j.
  • Jan, K. C., L. S. Hwang, and C. T. Ho. 2009b. Tissue distribution and elimination of sesaminol triglucoside and its metabolites in rat. Molecular Nutrition & Food Research 53 (7):815–25. doi: 10.1002/mnfr.200800380.
  • Jan, K. C., Y. W. Chang, L. S. Hwang, and C. T. Ho. 2012. Tissue distribution and cytochrome P450 inhibition of sesaminol and its tetrahydrofuranoid metabolites. Journal of Agricultural and Food Chemistry 60 (35):8616–23. doi: 10.1021/jf302699f.
  • Ji, Y. R., C. C. Cheng, A. L. Lee, J. C. Shieh, H. J. Wu, A. P. Huang, Y. H. Hsu, and T. H. Young. 2021. Poly(allylguanidine)-coated surfaces regulate TGF-beta in glioblastoma cells to induce apoptosis via NF-kappaB pathway activation. ACS Applied Materials & Interfaces 13 (49):59400–10. doi: 10.1021/acsami.1c21027.
  • Jiang, Q. 2022. Metabolism of natural forms of vitamin E and biological actions of vitamin E metabolites. Free Radical Biology & Medicine 179:375–87. doi: 10.1016/j.freeradbiomed.2021.11.012.
  • Jin, J. S, and M. Hattori. 2009. Further studies on a human intestinal bacterium Ruminococcus sp. END-1 for transformation of plant lignans to mammalian lignans. Journal of Agricultural and Food Chemistry 57 (16):7537–42. doi: 10.1021/jf900902p.
  • Jung, S. J., E. S. Jung, K. C. Ha, H. I. Baek, Y. K. Park, S. K. Han, S. W. Chae, S. O. Lee, and Y. C. Chung. 2021. Efficacy and safety of sesame oil cake extract on memory function improvement: A 12-week, randomized, double-blind, placebo-controlled pilot study. Nutrients 13 (8):2606. doi: 10.3390/nu13082606.
  • Kaji, H., I. Matsui-Yuasa, K. Matsumoto, A. Omura, K. Kiyomoto, and A. Kojima-Yuasa. 2020. Sesaminol prevents Parkinson’s disease by activating the Nrf2-ARE signaling pathway. Heliyon 6 (11):e05342. doi: 10.1016/j.heliyon.2020.e05342.
  • Kammeyer, A., and R. M. Luiten. 2015. Oxidation events and skin aging. Ageing Research Reviews 21:16–29. doi: 10.1016/j.arr.2015.01.001.
  • Kan, T., Y. Hamashima, M. Inai, R. Ishikawa, N. Yoshida, N. Shirakawa, Y. Akao, Y. Kawabe, T. Asakawa, and M. Egi. 2015. Stereocontrolled total syntheses of optically active furofuran lignans. Synthesis 47 (22):3513–21. doi: 10.1055/s-0034-1378812.
  • Kang, M. H., H. Katsuzaki, and T. Osawa. 1998. Inhibition of 2,2’-azobis(2,4-dimethylvaleronitrile)-induced lipid peroxidation by sesaminols. Lipids 33 (10):1031–6. doi: 10.1007/s11745-998-0302-y.
  • Kang, M. H., M. Naito, K. Sakai, K. Uchida, and T. Osawa. 2000. Mode of action of sesame lignans in protecting low-density lipoprotein against oxidative damage in vitro. Life Sciences 66 (2):161–71. doi: 10.1016/S0024-3205(99)00574-3.
  • Kang, M. H., Y. Kawai, M. Naito, and T. Osawa. 1999. Dietary defatted sesame flour decreases susceptibility to oxidative stress in hypercholesterolemic rabbits. The Journal of Nutrition 129 (10):1885–90. doi: 10.1093/jn/129.10.1885.
  • Katayama, S., H. Sugiyama, S. Kushimoto, Y. Uchiyama, M. Hirano, and S. Nakamura. 2016. Effects of sesaminol feeding on brain Abeta accumulation in a senescence-accelerated mouse-prone 8. Journal of Agricultural and Food Chemistry 64 (24):4908–13. doi: 10.1021/acs.jafc.6b01237.
  • Kato, M. J., A. Chu, L. B. Davin, and N. G. Lewis. 1998. Biosynthesis of antioxidant lignans in Sesamum indicum seeds. Phytochemistry 47 (4):583–91. doi: 10.1016/S0031-9422(97)00727-9.
  • Katsuzaki, H., S. Kawakishi, and T. Osawa. 1994. Sesaminol glucosides in sesame seeds. Phytochemistry 35 (3):773–6. doi: 10.1016/S0031-9422(00)90603-4.
  • Khanal, P., T. Duyu, B. M. Patil, Y. N. Dey, I. Pasha, R. S. Kavalapure, S. Chand, and S. Gurav. 2021. Screening of JAK-STAT modulators from the antiviral plants of Indian traditional system of medicine with the potential to inhibit 2019 novel coronavirus using network pharmacology. 3 Biotech 11 (3):119. doi: 10.1007/s13205-021-02664-4.
  • Kobayashi, S., J. Watanabe, J. Kawabata, E. Fukushi, and H. Shinmoto. 2004. A novel method for producing a foodstuff from defatted black sesame seed that inhibits allergen absorption. Bioscience, Biotechnology, and Biochemistry 68 (2):300–5. doi: 10.1271/bbb.68.300.
  • Koizumi, Y., K. Namiki, M. Kawai, S. Nishibori, and M. Namiki. 2007. Antithrombosis effect of sesame seeds and flour cultured with microorganisms. Nippon Shokuhin Kagaku Kogaku Kaishi 54 (1):9–17. doi: 10.3136/nskkk.54.9.
  • Kolapalli, S. P., R. Sahu, N. R. Chauhan, K. K. Jena, S. Mehto, S. K. Das, A. Jain, M. Rout, R. Dash, R. K. Swain, et al. 2021. RNA-binding RING E3-ligase DZIP3/hRUL138 stabilizes cyclin D1 to drive cell-cycle and cancer progression. Cancer Research 81 (2):315–31. doi: 10.1158/0008-5472.CAN-20-1871.
  • Kumar, A., D. C. Mishra, U. B. Angadi, R. Yadav, A. Rai, and D. Kumar. 2021. Inhibition potencies of phytochemicals derived from sesame against SARS-CoV-2 main protease: A molecular docking and simulation study. Frontiers in Chemistry 9:744376. doi: 10.3389/fchem.2021.744376.
  • Kumazawa, S., M. Koike, Y. Usui, T. Nakayama, and Y. Fukuda. 2003. Isolation of sesaminols as antioxidative components from roasted sesame seed oil. Journal of Oleo Science 52 (6):303–7. doi: 10.5650/jos.52.303.
  • Lee, C. H., M. J. Kim, H. H. Lee, J. C. Paeng, Y. J. Park, S. W. Oh, Y. J. Chai, Y. A. Kim, G. J. Cheon, K. W. Kang, et al. 2019. Adenine nucleotide translocase 2 as an enzyme related to [(18)F] FDG accumulation in various cancers. Molecular Imaging and Biology 21 (4):722–30. doi: 10.1007/s11307-018-1268-x.
  • Lee, J., J. W. Lim, and H. Kim. 2022. Lycopene inhibits IL-6 expression by upregulating NQO1 and HO-1 via activation of Nrf2 in ethanol/lipopolysaccharide-stimulated pancreatic acinar cells. Antioxidants 11 (3):519. doi: 10.3390/antiox11030519.
  • Lee, S. Y., D. J. Son, Y. K. Lee, J. W. Lee, H. J. Lee, Y. W. Yun, T. Y. Ha, and J. T. Hong. 2006. Inhibitory effect of sesaminol glucosides on lipopolysaccharide-induced NF-kappaB activation and target gene expression in cultured rat astrocytes. Neuroscience Research 56 (2):204–12. doi: 10.1016/j.neures.2006.06.005.
  • Lee, S. Y., T. Y. Ha, D. J. Son, S. R. Kim, and J. T. Hong. 2005. Effect of sesaminol glucosides on beta-amyloid-induced PC12 cell death through antioxidant mechanisms. Neuroscience Research 52 (4):330–41. doi: 10.1016/j.neures.2005.04.003.
  • Li, M., Q. Cai, Y. T. Gao, A. A. Franke, X. Zhang, Y. Zhao, W. Wen, Q. Lan, N. Rothman, Y. Shyr, et al. 2022. Phytoestrogens and lung cancer risk: A nested case-control study in never-smoking Chinese women. The American Journal of Clinical Nutrition 115 (3):643–51. doi: 10.1093/ajcn/nqab358.
  • Li, Q., Z. Wang, Q. Zheng, and S. Liu. 2020. Potential clinical drugs as covalent inhibitors of the priming proteases of the spike protein of SARS-CoV-2. Computational and Structural Biotechnology Journal 18:2200–8. doi: 10.1016/j.csbj.2020.08.016.
  • Liao, C. D., W. L. Hung, W. C. Lu, K. C. Jan, D. Y. Shih, A. I. Yeh, C. T. Ho, and L. S. Hwang. 2010b. Differential tissue distribution of sesaminol triglucoside and its metabolites in rats fed with lignan glycosides from sesame meal with or without nano/submicrosizing. Journal of Agricultural and Food Chemistry 58 (1):563–9. doi: 10.1021/jf9028046.
  • Liao, C.-D., W.-L. Hung, K.-C. Jan, A.-I. Yeh, C.-T. Ho, and L. S. Hwang. 2010a. Nano/sub-microsized lignan glycosides from sesame meal exhibit higher transport and absorption efficiency in Caco-2 cell monolayer. Food Chemistry 119 (3):896–902. doi: 10.1016/j.foodchem.2009.07.056.
  • Lim, E. W., D. Aarsland, D. Ffytche, R. N. Taddei, D. J. van Wamelen, Y. M. Wan, E. K. Tan, K. R. Chaudhuri, and M. Kings Parcog group, Kings Parcog Group MDS Nonmotor Study Group. 2019. Amyloid-beta and Parkinson’s disease. Journal of Neurology 266 (11):2605–19. doi: 10.1007/s00415-018-9100-8.
  • Ling, S., L. Nheu, and P. A. Komesaroff. 2012. Cell adhesion molecules as pharmaceutical target in atherosclerosis. Mini Reviews in Medicinal Chemistry 12 (2):175–83. doi: 10.2174/138955712798995057.
  • Liu, H., J. Liu, S. Wang, Z. Zeng, T. Li, Y. Liu, E. Mastriani, Q. H. Li, H. X. Bao, Y. J. Zhou, et al. 2017. Enterolactone has stronger effects than enterodiol on ovarian cancer. Journal of Ovarian Research 10 (1):49. doi: 10.1186/s13048-017-0346-z.
  • Liu, L., Z. Shi, X. Ji, W. Zhang, J. Luan, T. Zahr, and L. Qiang. 2022. Adipokines, adiposity, and atherosclerosis. Cellular and Molecular Life Sciences: CMLS 79 (5):272. doi: 10.1007/s00018-022-04286-2.
  • Long, J. M, and D. M. Holtzman. 2019. Alzheimer disease: An update on pathobiology and treatment strategies. Cell 179 (2):312–39. doi: 10.1016/j.cell.2019.09.001.
  • Lu, T, and G. R. Stark. 2015. NF-kappaB: Regulation by methylation. Cancer Research 75 (18):3692–5. doi: 10.1158/0008-5472.CAN-15-1022.
  • Mali, A. V., A. A. Joshi, M. V. Hegde, and S. S. Kadam. 2018. Enterolactone modulates the ERK/NF-kappaB/Snail signaling pathway in triple-negative breast cancer cell line MDA-MB-231 to revert the TGF-beta-induced epithelial-mesenchymal transition. Cancer Biology & Medicine 15 (2):137–56. doi: 10.20892/j.issn.2095-3941.2018.0012.
  • Mei, L., Y. M. Zheng, T. Song, V. R. Yadav, L. C. Joseph, L. Truong, S. Kandhi, M. M. Barroso, H. Takeshima, M. A. Judson, et al. 2020. Rieske iron-sulfur protein induces FKBP12.6/RyR2 complex remodeling and subsequent pulmonary hypertension through NF-kappaB/cyclin D1 pathway. Nature Communications 11 (1):3527. doi: 10.1038/s41467-020-17314-1.
  • Michailidis, D., A. Angelis, N. Aligiannis, S. Mitakou, and L. Skaltsounis. 2019. Recovery of sesamin, sesamolin, and minor lignans from sesame oil using solid support-free liquid-liquid extraction and chromatography techniques and evaluation of their enzymatic inhibition properties. Frontiers in Pharmacology 10:723. doi: 10.3389/fphar.2019.00723.
  • Miyahara, Y., H. Hibasami, H. Katsuzaki, K. Imai, T. Osawa, K. Ina, and T. Komiya. 2001. Sesaminol from sesame seed induces apoptosis in human lymphoid leukemia Molt 4B cells. International Journal of Molecular Medicine 7 (5):485–8. doi: 10.3892/ijmm.7.4.369.
  • Miyake, Y., S. Fukumoto, M. Okada, K. Sakaida, Y. Nakamura, and T. Osawa. 2005. Antioxidative catechol lignans converted from sesamin and sesaminol triglucoside by culturing with Aspergillus. Journal of Agricultural and Food Chemistry 53 (1):22–7. doi: 10.1021/jf048743h.
  • Moazzami, A. A., R. E. Andersson, and A. Kamal-Eldin. 2006. HPLC analysis of sesaminol glucosides in sesame seeds. Journal of Agricultural and Food Chemistry 54 (3):633–8. doi: 10.1021/jf051541g.
  • Mochizuki, M., Y. Tsuchie, N. Yamada, Y. Miyake, and T. Osawa. 2010. Effect of sesame lignans on TNF-alpha-induced expression of adhesion molecules in endothelial cells. Bioscience, Biotechnology, and Biochemistry 74 (8):1539–44. doi: 10.1271/bbb.100095.
  • Mochizuki, M., Y. Tsuchie, Y. Nakamura, and T. Osawa. 2009. Identification and characterization of sesaminol metabolites in the liver. Journal of Agricultural and Food Chemistry 57 (21):10429–34. doi: 10.1021/jf901939m.
  • Moon, S. M., S. A. Lee, S. H. Han, B. R. Park, M. S. Choi, J. S. Kim, S. G. Kim, H. J. Kim, H. S. Chun, D. K. Kim, et al. 2018. Aqueous extract of Codium fragile alleviates osteoarthritis through the MAPK/NF-kappaB pathways in IL-1beta-induced rat primary chondrocytes and a rat osteoarthritis model. Biomedicine & Pharmacotherapy  97:264–70. doi: 10.1016/j.biopha.2017.10.130.
  • Murata, J., E. Ono, S. Yoroizuka, H. Toyonaga, A. Shiraishi, S. Mori, M. Tera, T. Azuma, A. J. Nagano, M. Nakayasu, et al. 2017. Oxidative rearrangement of (+)-sesamin by CYP92B14 co-generates twin dietary lignans in sesame. Nature Communications 8 (1):2155. doi: 10.1038/s41467-017-02053-7.
  • Nagata, M., T. Osawa, M. Namiki, Y. Fukuda, and T. Ozaki. 1987. Stereochemical structures of antioxidative bisepoxylignans, sesaminol and its isomers, transformed from sesamolin. Agricultural and Biological Chemistry 51 (5):1285–9. doi: 10.1080/00021369.1987.10868187.
  • Nair, A., A. Kuwahara, A. Nagase, H. Yamaguchi, T. Yamazaki, M. Hosoya, A. Omura, K. Kiyomoto, M. A. Yamaguchi, T. Shimoyama, et al. 2013. Purification, gene cloning, and biochemical characterization of a beta-glucosidase capable of hydrolyzing sesaminol triglucoside from Paenibacillus sp. KB0549. PloS One 8 (4):e60538. doi: 10.1371/journal.pone.0060538.
  • Nakamura, M. T, and T. Y. Nara. 2004. Structure, function, and dietary regulation of delta6, delta5, and delta9 desaturases. Annual Review of Nutrition 24:345–76. doi: 10.1146/annurev.nutr.24.121803.063211.
  • Nantarat, N., K. Nakagawa, R. Miyamoto, S. Chansakaow, J. Sirithunyalug, and P. Leelapornpisid. 2019. Free radical scavenging capability of various defatted sesame seed cakes and hulls using EPR compared with in vitro testing and HPLC analysis. Journal of Oleo Science 68 (12):1279–85. doi: 10.5650/jos.ess19203.
  • Nantarat, N., M. Mueller, W.-C. Lin, S.-C. Lue, H. Viernstein, S. Chansakaow, J. Sirithunyalug, and P. Leelapornpisid. 2020. Sesaminol diglucoside isolated from black sesame seed cake and its antioxidant, anti-collagenase and anti-hyaluronidase activities. Food Bioscience 36:100628. doi: 10.1016/j.fbio.2020.100628.
  • Natesh, J., P. Mondal, D. Penta, A. A. Abdul Salam, and S. M. Meeran. 2021. Culinary spice bioactives as potential therapeutics against SARS-CoV-2: Computational investigation. Computers in Biology and Medicine 128:104102. doi: 10.1016/j.compbiomed.2020.104102.
  • Nedergaard, J., V. Golozoubova, A. Matthias, A. Asadi, A. Jacobsson, and B. Cannon. 2001. UCP1: The only protein able to mediate adaptive non-shivering thermogenesis and metabolic inefficiency. Biochimica et Biophysica Acta 1504 (1):82–106. doi: 10.1016/S0005-2728(00)00247-4.
  • Nguyen, M, and C. Osipo. 2022. Targeting breast cancer stem cells using naturally occurring phytoestrogens. International Journal of Molecular Sciences 23 (12):6813. doi: 10.3390/ijms23126813.
  • Noguchi, A., Y. Fukui, A. Iuchi-Okada, S. Kakutani, H. Satake, T. Iwashita, M. Nakao, T. Umezawa, and E. Ono. 2008. Sequential glucosylation of a furofuran lignan, (+)-sesaminol, by Sesamum indicum UGT71A9 and UGT94D1 glucosyltransferases. The Plant Journal: For Cell and Molecular Biology 54 (3):415–27. doi: 10.1111/j.1365-313X.2008.03428.x.
  • Ohtsuki, T., J. Akiyama, T. Shimoyama, S. Yazaki, S. Ui, Y. Hirose, and A. Mimura. 2003. Increased production of antioxidative sesaminol glucosides from sesame oil cake through fermentation by Bacillus circulans strain YUS-2. Bioscience, Biotechnology, and Biochemistry 67 (10):2304–6. doi: 10.1271/bbb.67.2304.
  • Ono, E., M. Nakai, Y. Fukui, N. Tomimori, M. Fukuchi-Mizutani, M. Saito, H. Satake, T. Tanaka, M. Katsuta, T. Umezawa, et al. 2006. Formation of two methylenedioxy bridges by a Sesamum CYP81Q protein yielding a furofuran lignan, (+)-sesamin. Proceedings of the National Academy of Sciences of the United States of America 103 (26):10116–21. doi: 10.1073/pnas.0603865103.
  • Ono, E., T. Waki, D. Oikawa, J. Murata, A. Shiraishi, H. Toyonaga, M. Kato, N. Ogata, S. Takahashi, M. A. Yamaguchi, et al. 2020. Glycoside-specific glycosyltransferases catalyze regio-selective sequential glucosylations for a sesame lignan, sesaminol triglucoside. The Plant Journal: For Cell and Molecular Biology 101 (5):1221–33. doi: 10.1111/tpj.14586.
  • Othman, S. B., N. Katsuno, Y. Kanamaru, and T. Yabe. 2015. Water-soluble extracts from defatted sesame seed flour show antioxidant activity in vitro. Food Chemistry 175:306–14. doi: 10.1016/j.foodchem.2014.11.155.
  • Pang, L., H. Shah, Y. Xu, and S. Qian. 2021. Delta-5-desaturase: A novel therapeutic target for cancer management. Translational Oncology 14 (11):101207. doi: 10.1016/j.tranon.2021.101207.
  • Papadopoulos, A. G., N. Nenadis, and M. P. Sigalas. 2016. DFT study of radical scavenging activity of sesame oil lignans and selected in vivo metabolites of sesamin. Computational and Theoretical Chemistry 1077:125–32. doi: 10.1016/j.comptc.2015.11.016.
  • Paré, P. W., H.-B. Wang, L. B. Davin, and N. G. Lewis. 1994. (+)-Pinoresinol synthase: A stereoselective oxidase catalysing 8,8′-lignan formation in Forsythia intermedia. Tetrahedron Letters 35 (27):4731–4. doi: 10.1016/S0040-4039(00)76953-X.
  • Peng, Z., Y. Xu, Q. Meng, H. Raza, X. Zhao, B. Liu, and C. Dong. 2016. Preparation of sesaminol from sesaminol triglucoside by β-glucosidase and cellulase hydrolysis. Journal of the American Oil Chemists’ Society 93 (6):765–72. doi: 10.1007/s11746-016-2819-4.
  • Rao, D. M., D. T. Phan, M. J. Choo, M. R. Weaver, R. E. Oberley-Deegan, R. P. Bowler, and F. Gally. 2019. Impact of fatty acid binding protein 5-deficiency on COPD exacerbations and cigarette smoke-induced inflammatory response to bacterial infection. Clinical and Translational Medicine 8 (1):7. doi: 10.1186/s40169-019-0227-8.
  • Roshani, M., A. Jafari, A. Loghman, A. H. Sheida, T. Taghavi, S. S. Tamehri Zadeh, M. R. Hamblin, M. Homayounfal, and H. Mirzaei. 2022. Applications of resveratrol in the treatment of gastrointestinal cancer. Biomedicine & Pharmacotherapy 153:113274. doi: 10.1016/j.biopha.2022.113274.
  • Ryu, S. N., C. T. Ho, and T. Osawa. 1998. High performance liquid chromatographic determination of antioxidant lignan glycosides in some varieties of sesame. Journal of Food Lipids 5 (1):17–28. doi: 10.1111/j.1745-4522.1998.tb00104.x.
  • Sakurai, A., S. Hongo, A. Nair, T. Waki, D. Oikawa, T. Nishio, T. Shimoyama, S. Takahashi, S. Yamashita, and T. Nakayama. 2018. Identification and characterization of a novel bacterial beta-glucosidase that is highly specific for the beta-1,2-glucosidic linkage of sesaminol triglucoside. Bioscience, Biotechnology, and Biochemistry 82 (9):1518–21. doi: 10.1080/09168451.2018.1476123.
  • Sheng, H., Y. Hirose, K. Hata, Q. Zheng, T. Kuno, N. Asano, Y. Yamada, A. Hara, T. Osawa, and H. Mori. 2007. Modifying effect of dietary sesaminol glucosides on the formation of azoxymethane-induced premalignant lesions of rat colon. Cancer Letters 246 (1–2):63–8. doi: 10.1016/j.canlet.2006.01.030.
  • Shi, M., J. Wang, F. Bi, and Z. Bai. 2022. Diosmetin alleviates cerebral ischemia-reperfusion injury through Keap1-mediated Nrf2/ARE signaling pathway activation and NLRP3 inflammasome inhibition. Environmental Toxicology 37 (6):1529–42. doi: 10.1002/tox.23504.
  • Shimizu, S., K. Akimoto, Y. Shinmen, H. Kawashima, M. Sugano, and H. Yamada. 1991. Sesamin is a potent and specific inhibitor of delta 5 desaturase in polyunsaturated fatty acid biosynthesis. Lipids 26 (7):512–6. doi: 10.1007/BF02536595.
  • Shimoyama, T., N. B. Johari, A. Tsuruya, A. Nair, and T. Nakayama. 2014. Paenibacillus relictisesami sp. nov., isolated from sesame oil cake. International Journal of Systematic and Evolutionary Microbiology 64 (Pt 5):1534–9. doi: 10.1099/ijs.0.057133-0.
  • Shin, M. K., Y. D. Jeon, and J. S. Jin. 2019. Apoptotic effect of enterodiol, the final metabolite of edible lignans, in colorectal cancer cells. Journal of the Science of Food and Agriculture 99 (5):2411–9. doi: 10.1002/jsfa.9448.
  • Shokri, Y., A. Variji, M. Nosrati, A. Khonakdar-Tarsi, A. Kianmehr, Z. Kashi, A. Bahar, A. Bagheri, and A. Mahrooz. 2020. Importance of paraoxonase 1 (PON1) as an antioxidant and antiatherogenic enzyme in the cardiovascular complications of type 2 diabetes: Genotypic and phenotypic evaluation. Diabetes Research and Clinical Practice 161:108067. doi: 10.1016/j.diabres.2020.108067.
  • Shyu, Y.-S, and L. S. Hwang. 2002. Antioxidative activity of the crude extract of lignan glycosides from unroasted Burma black sesame meal. Food Research International 35 (4):357–65. doi: 10.1016/S0963-9969(01)00130-2.
  • Snyder, A. G, and A. Oberst. 2021. The antisocial network: Cross talk between cell death programs in host defense. Annual Review of Immunology 39:77–101. doi: 10.1146/annurev-immunol-112019-072301.
  • Soomro, S. 2019. Oxidative stress and inflammation. Open Journal of Immunology 9 (1):1–20. doi: 10.4236/oji.2019.91001.
  • Suja, K. P., A. Jayalekshmy, and C. Arumughan. 2004. Free radical scavenging behavior of antioxidant compounds of sesame (Sesamum indicum L.) in DPPH(*) system. Journal of Agricultural and Food Chemistry 52 (4):912–5. doi: 10.1021/jf0303621.
  • Sun, J., S. S. H. Ho, X. Niu, H. Xu, L. Qu, Z. Shen, J. Cao, H.-C. Chuang, and K.-F. Ho. 2022. Explorations of tire and road wear microplastics in road dust PM2.5 at eight megacities in China. The Science of the Total Environment 823:153717. doi: 10.1016/j.scitotenv.2022.153717.
  • Sun, S. C. 2017. The non-canonical NF-kappaB pathway in immunity and inflammation. Nature Reviews. Immunology 17 (9):545–58. doi: 10.1038/nri.2017.52.
  • Um, M. Y., J. Y. Ahn, M. K. Kim, and T. Y. Ha. 2012. Sesaminol glucosides protect beta-amyloid induced apoptotic cell death by regulating redox system in SK-N-SH cells. Neurochemical Research 37 (4):689–99. doi: 10.1007/s11064-011-0658-0.
  • Um, M. Y., J. Y. Ahn, S. Kim, M. K. Kim, and T. Y. Ha. 2009. Sesaminol glucosides protect beta-amyloid peptide-induced cognitive deficits in mice. Biological & Pharmaceutical Bulletin 32 (9):1516–20. doi: 10.1248/bpb.32.1516.
  • Waddell, I. S., and C. Orfila. 2022. Dietary fiber in the prevention of obesity and obesity-related chronic diseases: From epidemiological evidence to potential molecular mechanisms. Critical Reviews in Food Science and Nutrition:1–16. doi: 10.1080/10408398.2022.2061909.
  • Wang, B., E. E. Tsakiridis, S. Zhang, A. Llanos, E. M. Desjardins, J. M. Yabut, A. E. Green, E. A. Day, B. K. Smith, J. S. V. Lally, et al. 2021. The pesticide chlorpyrifos promotes obesity by inhibiting diet-induced thermogenesis in brown adipose tissue. Nature Communications 12 (1):5163. doi: 10.1038/s41467-021-25384-y.
  • Watanabe, M., Y. Iizumi, M. Sukeno, M. Iizuka-Ohashi, Y. Sowa, and T. Sakai. 2017. The pleiotropic regulation of cyclin D1 by newly identified sesaminol-binding protein ANT2. Oncogenesis 6 (4):e311. doi: 10.1038/oncsis.2017.10.
  • Wrobel, A. G., D. J. Benton, C. Roustan, A. Borg, S. Hussain, S. R. Martin, P. B. Rosenthal, J. J. Skehel, and S. J. Gamblin. 2022. Evolution of the SARS-CoV-2 spike protein in the human host. Nature Communications 13 (1):1178. doi: 10.1038/s41467-022-28768-w.
  • Wu, M. S., L. B. B. Aquino, M. Y. U. Barbaza, C. L. Hsieh, K. A. Castro-Cruz, L. L. Yang, and P. W. Tsai. 2019. Anti-inflammatory and anticancer properties of bioactive compounds from Sesamum indicum L.-A review. Molecules 24 (24):4426. doi: 10.3390/molecules24244426.
  • Xin, S., C. Mueller, S. Pfeiffer, V. A. N. Kraft, J. Merl-Pham, X. Bao, R. Feederle, X. Jin, S. M. Hauck, P. Schmitt-Kopplin, et al. 2022. MS4A15 drives ferroptosis resistance through calcium-restricted lipid remodeling. Cell Death and Differentiation 29 (3):670–86. doi: 10.1038/s41418-021-00883-z.
  • Xu, X. Y., D. Y. Wang, Y. P. Li, S. T. Deyrup, and H. J. Zhang. 2022. Plant-derived lignans as potential antiviral agents: A systematic review. Phytochemistry Reviews: Proceedings of the Phytochemical Society of Europe 21 (1):239–89. doi: 10.1007/s11101-021-09758-0.
  • Xu, X., A. Liu, S. Hu, I. Ares, M. R. Martinez-Larranaga, X. Wang, M. Martinez, A. Anadon, and M. A. Martinez. 2021. Synthetic phenolic antioxidants: Metabolism, hazards and mechanism of action. Food Chemistry 353:129488. doi: 10.1016/j.foodchem.2021.129488.
  • Yamashita, K., S. Ikeda, Y. Iizuka, and I. Ikeda. 2002. Effect of sesaminol on plasma and tissue alpha-tocopherol and alpha-tocotrienol concentrations in rats fed a vitamin E concentrate rich in tocotrienols. Lipids 37 (4):351–8. doi: 10.1007/s11745-002-0902-6.
  • Yamashita, K., Y. Iizuka, T. Imai, and M. Namiki. 1995. Sesame seed and its lignans produce marked enhancement of vitamin E activity in rats fed a low alpha-tocopherol diet. Lipids 30 (11):1019–28. doi: 10.1007/BF02536287.
  • Yamashita, K., Y. Yamada, S. Kitou, S. Ikeda, C. Abe, N. M. Saarinen, and R. Santti. 2007. Hydroxymatairesinol and sesaminol act differently on tocopherol concentrations in rats. Journal of Nutritional Science and Vitaminology 53 (5):393–9. doi: 10.3177/jnsv.53.393.
  • Yamauchi, S., T. Ina, T. Kirikihira, and T. Masuda. 2004. Synthesis and antioxidant activity of oxygenated furofuran lignans. Bioscience, Biotechnology, and Biochemistry 68 (1):183–92. doi: 10.1271/bbb.68.183.
  • Ye, Z. J., X. A. He, J. P. Wu, J. Li, X. W. Chang, J. Tan, W. Y. Lv, H. Zhu, H. H. Sun, W. X. Wang, et al. 2020. New prenylflavonol glycosides with xanthine oxidase inhibitory activity from the leaves of Cyclocarya paliurus. Bioorganic Chemistry 101:104018. doi: 10.1016/j.bioorg.2020.104018.
  • Yu, H., L. Lin, Z. Zhang, H. Zhang, and H. Hu. 2020. Targeting NF-kappaB pathway for the therapy of diseases: Mechanism and clinical study. Signal Transduction and Targeted Therapy 5 (1):209. doi: 10.1038/s41392-020-00312-6.
  • Zhang, H., N. Chen, Z. Deng, Y. Mai, L. Deng, G. Chen, Y. Li, B. Pan, and W. Zhong. 2021. Suppression of ANT2 by miR-137 inhibits prostate tumorigenesis. Frontiers in Genetics 12:687236. doi: 10.3389/fgene.2021.687236.
  • Zhao, X., X. Shi, Q. Liu, and X. Li. 2022. Tea polyphenols alleviates acetochlor-induced apoptosis and necroptosis via ROS/MAPK/NF-kappaB signaling in Ctenopharyngodon idellus kidney cells. Aquatic Toxicology (Amsterdam, Netherlands) 246:106153. doi: 10.1016/j.aquatox.2022.106153.
  • Zhao, Y., Y. Yang, M. Liu, X. Qin, X. Yu, H. Zhao, X. Li, and W. Li. 2022. COX-2 is required to mediate crosstalk of ROS-dependent activation of MAPK/NF-kappaB signaling with pro-inflammatory response and defense-related NO enhancement during challenge of macrophage-like cell line with Giardia duodenalis. PLoS Neglected Tropical Diseases 16 (4):e0010402. doi: 10.1371/journal.pntd.0010402.
  • Zheng, H., N. Xu, Z. Zhang, F. Wang, J. Xiao, and X. Ji. 2022. Setanaxib (GKT137831) ameliorates doxorubicin-induced cardiotoxicity by inhibiting the NOX1/NOX4/reactive oxygen species/MAPK pathway. Frontiers in Pharmacology 13:823975. doi: 10.3389/fphar.2022.823975.
  • Zhou, L., R. Liu, X. Liang, S. Zhang, W. Bi, M. Yang, Y. He, J. Jin, S. Li, X. Yang, et al. 2020. lncRNA RP11-624L4.1 is associated with unfavorable prognosis and promotes proliferation via the CDK4/6-Cyclin D1-Rb-E2F1 pathway in NPC. Molecular Therapy. Nucleic Acids 22:1025–39. doi: 10.1016/j.omtn.2020.10.017.
  • Zhu, X., X. Zhang, Y. Sun, D. Su, Y. Sun, B. Hu, and X. Zeng. 2013. Purification and fermentation in vitro of sesaminol triglucoside from sesame cake by human intestinal microbiota. Journal of Agricultural and Food Chemistry 61 (8):1868–77. doi: 10.1021/jf304643k.

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