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Sesame Seed Lignans for Their Biological Scott R, Macpherson A, Yates RWS, Et Ai

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Sesame Seed Lignans for Their Biological Scott R, Macpherson A, Yates RWS, Et Ai 570/SELENlUM PDR FOR NUTRITIONAL SUPPLEMENTS Reilly C. Selenium: a new entrant into the functional food Egyptians and as the fundamental body massage oil in arena. Trends Food Sci Technol. 1998;9:114-118. Ayurvedic medicine. These days, bodybuilders use lignans Schrauzer GN. Selenomethionine: a review of its nutritional from sesame seeds for supposed performance enhancement significance, metabolism and toxicity. J Nutr. 2000; 130:1653- and weight loss. Recently, there has been a great deal of 1656. interest in studying sesame seed lignans for their biological Scott R, MacPherson A, Yates RWS, et aI. The effect of oral effects and possible health benefits. selenium supplementation on human sperm motility. J Urol. 1998;82:76-80. Sesame seed is one of the two major dietary sources of plant Selenium Intoxication-New York. Morbidity and Mortality lignans, the other major source being flaxseed. The major Weekly. 1984; Report 33, No.12:157-158. sesame seed lignan is sesamin. Sesame seed contains about Stranges S, Marshall JR, Natarajan R, et al. Effects of long- 0.4% sesamin in sesame oil or about 4 mg per gram. Sesame term selenium supplementation on the incidence of type 2 seed also contains about half as much of the lignan diabetes: a randomized trial. Ann Intern Med. 2007;147(4):217- sesamolin and smaller amounts of sesamol, sesaminol, and 223. the water-soluble lignans, sesaminol diglucoside and sesami- Suadicani P, Hein HO, Gyntelberg F. Serum selenium nol triglucoside. (The aglycosides are lipid-soluble.) In concentration and risk of ischaemic heart disease in a addition, it contains small amounts of matairesinol, lariciresi- prospective cohort study of 3,000 males. Atherosclerosis. 1992;96:33-42. nol, pinoresinol and syringaresinol. Thorpe JF, Jain S, Marczylo TH, et al. A review of phase III Sesamin, like all plant lignans, is a phenylpropanoid dimer. clinical trials of prostate cancer chemoprevention.AIIII R Coli However, in contrast with the flaxseed lignan secoisolaricire- Surg Engl. 2007;89(3):207-21 I. sinol diglucoside (see Flaxseed Lignans) and the spruce Ursini F, Heim S, Kiess M, et al. Dual function of the lignan 7-hydroxymatairesinol (see Spruce Lignans), which selenoprotein PHGPx during sperm maturation. Science. 1999;285: 1393-1396. are of the dibenzylbutyrolactone structural type, sesamin is of the tetrahydrofuran, or furofuran structural type. The two Vunta H, BeIda BJ, Arner RJ, et al. Selenium attenuates pro- inflammatorygene expression in macrophages.Mol Nutr Food major structural types of lignans in the plant kingdom are the Res. Epub: 2008 May 15. dibenzylbutyrolactone and the tetrahydrofuran, or furofuran Vunta H, Davis F, Palempalli UD, et al. The anti-inflammatory types. Sesamin and all of the sesame seed lignans are also effects of selenium are mediated through 15-deoxy-DeltaI2,14- classified as phytoestrogens. prostaglandin12 in macrophages.J Biol Chem. 2007;282(25): 17964-17973. The chemical names for sesamin are: 5,5'-(Tetrahydro- Yang G, Wang S, Zhou R, Sun S. Endemic selenium IH,3H-furo[3,4-c]furan- I,4-diyl)bis-1 ,3-benzodioxole; tetra- intoxicationof humans in China. Am J Clill Nutr. 1988;37:872- hydro-l ,4-bis[3,4-(methy lenedioxy )phenyl]-lH, 3H-furo[3,4- 881. c]furan, and 2,6-bis(3,4-methylenedioxyphenyl)-3,7-diox- Yu MW, Horng IS, Hsu KH, et al. Plasma selenium levels and abicyclo[3.3.0]octane. risk of hepatocellular carcinoma among men with chronic virus infection.Am J Epidemiol. 1999;150:367-374. The molecular formula IS C2oHlS06 and the molecular Yu SY, Zhu YJ, Li WG. Protective role of selenium against weight is 354.35. The CAS Registry Number for sesamin is hepatitis B virus and primary liver cancer in Qidong. Biol 606-80-7. The sesamin preparation obtained as a by-product Trace Elem Res. 1997;56:117-124. of the refining of edible sesame oil consists of a I: I ratio of sesamin and its epimer episesamin. Pure sesamin is available. Sesame Seed Lignans The chemical structures that follow are described within this monograph. DESCRIPTION Sesame (Sesa11lu11I indicu11I L.) has a fascinating history. It is one of the oldest cultivated plants in the world and has been around for about 6,000 years. Sesame seed and its oil have been utilized as an important foodstuff and also for medicinal purposes, including providing energy and mental tranquility and preventing aging. It has also been used as an insecticide, for the preparation of mummies by the ancient SUPPLEMENT MONOGRAPHS SESAME SEED L1GNANS /571 ty was noted in the DOCA salt hypertensive rats. It is thought that the blood pressure-lowering effect of sesamin can be partly explained by its inhibitory effect on vascular superoxide production. Blood pressure is regulated by arteriolar vascular tone. The endothelial bioavailability of endothelial nitric oxide (NO), produced by eNOS (endothelial nitric oxide synthase), is the major factor in the regulation of vascular tone. Superoxide anions react with NO-producing peroxynitrite, resulting in decreased endothelial bioavailability of vascular NO, arterio- lar constriction and elevation of blood pressure. NADPH oxidase, a member of the NOX family of enzymes, produces superoxide anions, which is a major factor in the dysregula- Sesamin tion of arteriolar tone. Inhibition of NADPH oxidase could a play a major role in the maintenance of normal blood pressure. A recent paper (Nakano, et aI., 2008) demonstrated suppression of aortic NADPH oxidase by administration of sesamin to DOCA hypertensive rats. More research and human studies are certainly warranted to determine if sesamin could have a role in the treatment of hypertension in humans. Antioxidant/Pro-antioxidant: Sesamin itself does not appear Enterolactone to have antioxidant activity in vitro. Sesamin does not demonstrate radical scavenging effects on superoxide anions ACTIONS AND PHARMACOLOGY (02-) or DPPH (2,2-diphenyl-2-picrylhydrazyl hydrate) radi- ACTIONS Sesamin has possible anticancer, antihypertensive, antioxi- cals. Neither does it show inhibitory effects against lipid dantJpro-antioxidant/hepatoprotecti ve, estrogenic/antiestro- peroxidation. On the other hand, the minor sesame seed genic, neuroprotective, lipid metabolism and hypo- lignans that carry a phenolic hydroxyl group (sesamin does cholesterolemic activities. not)-sesaminol, episesaminol and sesamolinol--do exhibit antioxidant activity in vitro. It turns out that when sesamin MECHANISM OF ACTION was orally administered to rats, at least three compounds Anticancer: Sesamin was shown to downregulate cyclin D I were formed via metabolism in the rats' livers, compounds protein expression in the human tumor cell line, MCF-7. that possessed phenolic hydroxyl groups and which did have Cyclin DI belongs to a family of cyclin proteins that strong superoxide anion (02-) and hydroxyl radical (OH) function as subunits of cyclinlcyclin-dependent kinase ho- scavenging activities. The methylenedioxyphenyl moiety in loenzymes that regulate entry into and progression through the structure of sesamin was shown to be converted into a the cell cycle. Overexpression of cyclin D I may be involved methylenedihydrophenyl or catechol moiety. Sesamin has in several cancers, including prostate, breast and colon been shown to possess hepatoprotective activity against liver cancer. damage caused by ethanol or carbon tetrachloride. The Sesamin was found to suppress the carcinogenic effect of 7, mechanism of action of this hepatoprotective effect is most 12-dimethylbenz[a]anthracene (DMBA)-induced mammary likely due to the antioxidant metabolites formed in the liver carcinogenesis in female Sprague-Dawley rats. The mecha- from sesamin. nism of action of this effect is unclear. Possibilities include In addition, sesamin is converted in the large intestine to the immunopotentiation and increased antioxidant activity. mammalian lignan, enterolactone (ENL), which is known to Antihypertensive: The antihypertensive effect of sesamin has have antioxidant properties. been demonstrated in three animal models of hypertension- the two kidney, one clip (2k,lc) renal hypertension rat Prodrugs are drugs that are inactive but become active when model, the stroke-prone spontaneous hypertensive rat (SHR) they get metabolized. In this sense, sesamin can be consid- model and the deoxycorticosterone acetate (DOCA) salt ered a pro-antioxidant in that it does not have antioxidant hypertensive rat model. The greatest antihypertensive activi- activity until it is metabolized to active antioxidants. 572/SESAME SEED LIGNANS PDR FOR NUTRITIONAL SUPPLEMENTS Estrogen/Antiestrogen: In a study of postmenopausal wom- and neurodegenerative processes. Bacterial lipopolysaccha- en, it was found that ingestion of sesame seed caused an ride (LPS), cytokines and amyloid all rapidly cause the increase in sex hormone binding protein (SHBP) and also an transcription and expression of inducible nitric oxide syn- increase in urinary 2-hydroxyestrone. This has also been thase (iNOS) in microglia. Activated microglia facilitate seen in studies with flaxseed lignans and is possibly due to tumor necrosis factor (TNF)-alpha or NO-mediated neuronal an estrogen/anti estrogen effect of an important metabolite of cell death. Sesamin has been shown to suppress LPS-induced both sesame seed lignans and flaxseed lignans, the mamma- NO production in microglia via inhibition of signal transduc- lian lignan, enterolactone. The amount of sesamin in the tion pathways or via inhibition of nuclear transcription sesame seeds was approximately 250 mg and the total
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