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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/02/16 10:07:02」(JST)
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Sesamin
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| Names |
| IUPAC name
5,5'-(1S,3aR,4S,6aR)-tetrahydro-1H,3H- furo[3,4-c]furan-1,4-diylbis(1,3-benzodioxole)
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Other names
Fagarol
Sezamin
pseudocubebin
Episesamin
Asarinin
D-(+)-Sesamin
d-Sesamin
(+)-Sesamin
l-sesamin |
| Identifiers |
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CAS Number
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607-80-7 Y |
| ChEBI |
CHEBI:66470 N |
| ChEMBL |
ChEMBL252915 N |
| ChemSpider |
65258 N |
| Jmol interactive 3D |
Image |
| KEGG |
C10882 N |
| PubChem |
5204 |
InChI
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InChI=1S/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19+,20+/m0/s1 N
Key: PEYUIKBAABKQKQ-AFHBHXEDSA-N N
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InChI=1/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19+,20+/m0/s1
Key: PEYUIKBAABKQKQ-AFHBHXEDBX
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SMILES
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c1cc2c(cc1[C@@H]3[C@H]4CO[C@@H]([C@H]4CO3)c5ccc6c(c5)OCO6)OCO2
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| Properties |
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Chemical formula
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C20H18O6 |
| Molar mass |
354.35 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| N verify (what is YN ?) |
| Infobox references |
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Sesamin is a lignan isolated from the bark of Fagara plants and from sesame oil. It has been used as a dietary fat-reduction supplement, although no controlled studies on this application have been performed.[1] Its major metabolite is enterolactone, which has an elimination half life of less than 6 hours.[2] Sesamin and sesamolin are minor components of sesame oil,[3] on average comprising only 0.14% of the oil by mass.[4]
See also
- Sesamol, another phenolic component of sesame oil
References
- ^ Kamal-Eldin A, Moazzami A, Washi S (January 2011). "Sesame seed lignans: potent physiological modulators and possible ingredients in functional foods & nutraceuticals". Recent Pat Food Nutr Agric 3 (1): 17–29. doi:10.2174/2212798411103010017. PMID 21114470.
- ^ Peñalvo JL, Heinonen SM, Aura AM, Adlercreutz H (May 2005). "Dietary sesamin is converted to enterolactone in humans". J. Nutr. 135 (5): 1056–1062. PMID 15867281.
- ^ Lim JS, Adachi Y, Takahashi Y and Ide T (Jan 2007). "Comparative analysis of sesame lignans (sesamin and sesamolin) in affecting hepatic fatty acid metabolism in rats.". Br J Nutr 97 (1): 85–95. doi:10.1017/S0007114507252699. PMID 17217563.
- ^ Ikan, Raphael (1991). Natural Products: A Laboratory Guide 2nd Ed. San Diego: Academic Press, Inc. p. 50. ISBN 0123705517.
External links
- Effect of sesamin on serum cholesterol and triglycerides levels in LDL receptor-deficient mice
- A short and stereoselective total synthesis of (±)-sesamin by radical cyclisation of an epoxide using a transition-metal radical source
- Sesamin and episesamin induce apoptosis in human lymphoid leukemia Molt 4B cells.
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Types of lignans
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| Lignans |
- Arboreol
- Arctigenin
- Chamaecypanone A and B
- Eudesmin
- Globoidnan A
- Gmelanone
- Gmelinol
- Gummadiol
- Isootobanone
- Lyoniresinol
- Macelignan
- Matairesinol
- Obtulignolide
- Pinoresinol
- Pluviatilol
- Podophyllotoxin
- Secoisolariciresinol
- Sesamin
- Sesamolin
- Steganacin
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| Lignan glycosides |
- Arctiin
- Aviculin (isolariciresinol-9'-rhamnopyranoside)
- Secoisolariciresinol diglucoside
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| Mammalian lignans (enterolignans) |
- Enterodiol
- Enterolactone
- Lariciresinol
- Hydroxymatairesinol
- Syringaresinol
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| Neolignans |
- Balanophonin
- Eusiderin
- Honokiol
- Linderin A
- Magnolol
- Megaphone
- 4-O-Methylhonokiol
- Rhaphidecursinol A
- Rhaphidecursinol B
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| Flavonolignans |
- Cinchonain-Ib
- Dehydrosilybin
- Deoxysilycistin
- Deoxysilydianin
- Hydnocarpin
- Hydnowightin
- Neosilyhermin
- Palstatin
- Rhodiolin
- Salcolin A
- Salcolin B
- Scutellaprostin A, B, C, D, E and F
- Silandrin
- Silyamandin
- Silibinin
- Silybinome
- Silicristin
- Silydianin
- Silyhermin
- Tricin 4'-O-(erythro-beta-guaiacylglyceryl) ether
- Tricin 4'-O-(threo-beta-guaiacylglyceryl) ether
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English Journal
- Isolation of a new β-carboline alkaloid from aerial parts of Triclisia sacleuxii and its antibacterial and cytotoxicity effects.
- Samita F1, Ochieng CO1, Owuor PO1, Manguro LO1, Midiwo JO2.
- Natural product research.Nat Prod Res.2017 Mar;31(5):529-536. doi: 10.1080/14786419.2016.1201666. Epub 2016 Jul 3.
- A new β-carboline alkaloid named sacleuximine A (1) together with known compounds palmatine (2), isotetrandrine (3), trans-N-feruloyltyramine (4), trans-N-caffeoyltyramine (5), yangambin (6), syringaresinol (7), sesamin (8), (+) epi-quercitol (9), 4-hydroxybenzaldehyde (10), β-sitosterol (11), que
- PMID 27373319
- Magnetic solid-phase extraction based on graphene oxide for the determination of lignans in sesame oil.
- Wu L1, Yu L2, Ding X3, Li P4, Dai X1, Chen X2, Zhou H5, Bai Y5, Ding J6.
- Food chemistry.Food Chem.2017 Feb 15;217:320-5. doi: 10.1016/j.foodchem.2016.08.109. Epub 2016 Aug 29.
- Graphene oxide was fabricated by a simple method and applied to magnetic solid-phase extraction. In a pretreatment procedure before the sesamol, sesamin and sesamolin in sesame oil were detected by high performance liquid chromatography. Several parameters affecting the extraction efficiency were in
- PMID 27664640
- Differential and directional estrogenic signaling pathways induced by enterolignans and their precursors.
- Zhu Y1,2, Kawaguchi K1, Kiyama R1.
- PloS one.PLoS One.2017 Feb 2;12(2):e0171390. doi: 10.1371/journal.pone.0171390. eCollection 2017.
- Mammalian lignans or enterolignans are metabolites of plant lignans, an important category of phytochemicals. Although they are known to be associated with estrogenic activity, cell signaling pathways leading to specific cell functions, and especially the differences among lignans, have not been exp
- PMID 28152041
Japanese Journal
- sesamin、asarinin (episesamin)の光学純度測定法の確立と細辛sesaminに光学異性体混在の証明
- 松本 恵実,牧岡 富広,山本 諭志,柳瀬 笑子,中塚 進一
- 日本食品化学学会誌 21(1), 37-41, 2014-04-25
- … Sesamin and asarinin are important components of Asiasari Radix, and it is reported that their stereochemistry is l-form. … On the contrary, the stereochemistry of sesamin and episesamin from sesame are reported as d-form. … As a result, we clarified that asarinin from Asiasari Radix existed as only l-form, and sesamin and episesamin from sesame existed as only d-form. …
- NAID 110009810363
- sesamin, asarinin (episesamin)の光学純度測定法の確立と細辛sesaminに光学異性体混在の証明
- Combined effect of sesamin and soybean phospholipid on hepatic fatty acid metabolism in rats
- Ide Takashi
- Journal of Clinical Biochemistry and Nutrition 54(3), 210-218, 2014
- … We studied the combined effect of sesamin (1:1 mixture of sesamin and episesamine) and soybean phospholipid on lipid metabolism in rats. … Male rats were fed diets supplemented with 0 or 2 g/kg sesamin, and containing 0 or 50 g/kg soybean phospholipid, for 19 days. … Sesamin and soybean phospholipid decreased serum triacylglycerol concentrations and the combination of these compounds further decreased the parameter in an additive fashion. …
- NAID 130004466751
Related Links
- サントリーセサミンEXの公式サイト。セサミンEXは、40代以降の若々しさを応援するエイジングサプリメントです。ゴマの健康成分セサミンに関する研究成果をはじめ、セサミンの歴史、ご愛飲者のお声など、輝く年の重ね方をご紹介します。
- セサミンEXは、ゴマ約1000粒分の健康成分セサミンを1粒に凝縮。セサミンに、ビタミンEと美容にうれしい成分トコトリエノールをプラスした自信作です。自然の恵みを生かす技術と科学的根拠に裏付けられたサントリーウエルネスオンラインの ...
Related Pictures
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参考
- http://en.wikipedia.org/wiki/Sesamin