ジギトキシゲニン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2018/03/03 14:00:27」(JST)
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Digitoxigenin[1]
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Names |
Other names
3-β,14-dihydroxy-5-β,14-β-card-20(22)-enolide
5β-Card-20(22)-enolide, 3β,14-dihydroxy-
Card-20(22)-enolide, 3,14-dihydroxy-, (3β,5β)-
NSC 407806
Δ20:22-3,14,21-Trihydroxynorcholenic acid lactone
cerberigenin
echujetin
evonogenin
thevetigenin
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Identifiers |
CAS Number
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3D model (JSmol)
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Beilstein Reference
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95448 |
ChEMBL |
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ChemSpider |
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ECHA InfoCard |
100.005.095 |
EC Number |
205-603-4 |
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RTECS number |
FH4975000 |
InChI
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InChI=1S/C23H34O4/c1-21-8-5-16(24)12-15(21)3-4-19-18(21)6-9-22(2)17(7-10-23(19,22)26)14-11-20(25)27-13-14/h11,15-19,24,26H,3-10,12-13H2,1-2H3/t15-,16+,17-,18+,19-,21+,22-,23+/m1/s1
Key: XZTUSOXSLKTKJQ-CESUGQOBSA-N
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InChI=1/C23H34O4/c1-21-8-5-16(24)12-15(21)3-4-19-18(21)6-9-22(2)17(7-10-23(19,22)26)14-11-20(25)27-13-14/h11,15-19,24,26H,3-10,12-13H2,1-2H3/t15-,16+,17-,18+,19-,21+,22-,23+/m1/s1
Key: XZTUSOXSLKTKJQ-CESUGQOBBG
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SMILES
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O=C/1OCC(=C\1)\[C@@H]2[C@@]4([C@](O)(CC2)[C@@H]5CC[C@@H]3C[C@@H](O)CC[C@]3(C)[C@H]5CC4)C
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Properties |
Chemical formula
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C23H34O4 |
Molar mass |
374.51 |
Appearance |
solid[citation needed] |
Melting point |
252 to 253 °C (486 to 487 °F; 525 to 526 K) |
Hazards |
Main hazards |
Toxic |
R-phrases (outdated) |
Toxic if swallowed |
S-phrases (outdated) |
In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references |
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Digitoxigenin, a cardenolide, is the aglycone of digitoxin.
Digitoxigenin can be used to prepare actodigin.[2]
In Lednicer's book on steroids, it is made from deoxycholic acid.
References
- ^ http://www.sigmaaldrich.com/catalog/ProductDetail.do?N4=D9404%7CSIGMA&N5=SEARCH_CONCAT_PNO%7CBRAND_KEY&F=SPEC
- ^ Ferland, J. M. (1974). "Synthetic Cardenolides and Related Products. III. Isocardenolides". Canadian Journal of Chemistry. 52 (9): 1652–1661. doi:10.1139/v74-239. ISSN 0008-4042.
English Journal
- Elaeodendron orientale as a source of cytotoxic cardenolides.
- Osorio AA1, López MR2, Jiménez IA1, Moujir LM2, Rodríguez ML1, Bazzocchi IL3.
- Phytochemistry.Phytochemistry.2014 Sep;105:60-7. doi: 10.1016/j.phytochem.2014.06.009. Epub 2014 Jul 7.
- In the present study, we report six cardiac glycosides (1-6) along with four known ones (7-10) isolated from the leaves and fruits of Elaeodendron orientale. Their stereostructures were elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR, and the absolute configuration of 1 wa
- PMID 25014657
- Interaction of digitalis-like compounds with liver uptake transporters NTCP, OATP1B1, and OATP1B3.
- Gozalpour E1, Greupink R, Wortelboer HM, Bilos A, Schreurs M, Russel FG, Koenderink JB.
- Molecular pharmaceutics.Mol Pharm.2014 Jun 2;11(6):1844-55. doi: 10.1021/mp400699p. Epub 2014 May 6.
- Digitalis-like compounds (DLCs) such as digoxin, digitoxin, and ouabain, also known as cardiac glycosides, are among the oldest pharmacological treatments for heart failure. The compounds have a narrow therapeutic window, while at the same time, DLC pharmacokinetics is prone to drug-drug interaction
- PMID 24754247
- Cardenolide glycosides from Elaeodendron australe var. integrifolium.
- Butler MS1, Towerzey L1, Pham NB1, Hyde E1, Wadi SK1, Guymer GP2, Quinn RJ3.
- Phytochemistry.Phytochemistry.2014 Feb;98:160-3. doi: 10.1016/j.phytochem.2013.11.024. Epub 2013 Dec 19.
- Extracts from dried leaf and stems of Elaeodendron australe var. integrifolium (Celastraceae) collected in South East Queensland, Australia, were active in an assay that measured Ca(2+) driven expression of IL-2/luciferase designed to identify inhibitors of the ICRAC channel. Bioassay-guided isolati
- PMID 24361289
Japanese Journal
- Cardenolide Aglycones Inhibit Tumor Necrosis Factor α-Induced Expression of Intercellular Adhesion Molecule-1 at the Translation Step by Blocking Na⁺/K⁺-ATPase
- New Cardenolide Glycosides from the Seeds of Digitalis purpurea and Their Cytotoxic Activity
- Bioscience, biotechnology, and biochemistry 77(6), 1186-1192, 2013-06-23
- NAID 10031184679
- P-68 抗腫瘍活性ステロイド配糖体を構成する糖鎖chacotriose誘導体の合成(ポスター発表の部)