エスクロシド
- 関
- esculin
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/07/12 20:27:42」(JST)
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Not to be confused with aescin, a saponin also found in horse chestnut.
Aesculin
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| Names |
| IUPAC name
7-hydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy- 6-(hydroxymethyl)-2-tetrahydropyranyl]oxy}-2-chromenone
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Other names
Esculetin 6-β-D-glucoside
6,7-dihydroxycoumarin 6-β-D-glucoside
6,7-dihydroxychromen-2-one 6-β-D-glucoside |
| Identifiers |
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CAS Number
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531-75-9 Y |
| ChEMBL |
ChEMBL482581 Y |
| ChemSpider |
4444765 Y |
| Jmol 3D model |
Interactive image |
| PubChem |
5281417 |
| UNII |
1Y1L18LQAF Y |
InChI
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InChI=1S/C15H16O9/c16-5-10-12(19)13(20)14(21)15(24-10)23-9-3-6-1-2-11(18)22-8(6)4-7(9)17/h1-4,10,12-17,19-21H,5H2/t10-,12-,13+,14-,15-/m1/s1 Y
Key: XHCADAYNFIFUHF-TVKJYDDYSA-N Y
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InChI=1/C15H16O9/c16-5-10-12(19)13(20)14(21)15(24-10)23-9-3-6-1-2-11(18)22-8(6)4-7(9)17/h1-4,10,12-17,19-21H,5H2/t10-,12-,13+,14-,15-/m1/s1
Key: XHCADAYNFIFUHF-TVKJYDDYBL
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SMILES
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O=C/3Oc2c(cc(O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)c(O)c2)\C=C\3
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| Properties |
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Chemical formula
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C15H16O9 |
| Molar mass |
340.282 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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| Y verify (what is YN ?) |
| Infobox references |
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Aesculin, also rendered Æsculin or Esculin, is a coumarin glucoside that naturally occurs in the horse chestnut (Aesculus hippocastanum),[1] California Buckeye (Aesculus californica),[2] Prickly Box (Bursaria spinosa) and in daphnin (the dark green resin of Daphne mezereum). It is also found in dandelion coffee.
Contents
- 1 Medical uses
- 2 Aesculin hydrolysis test
- 3 Warnings
- 4 Notes
- 5 References
Medical uses
As medication, Aesculin is sometimes used as a vasoprotective agent.[3]
Aesculin is also used in a microbiology laboratory to aid in the identification of bacterial species (especially Enterococci and Listeria). In fact, all strains of Group D Streptococci hydrolyze æsculin in 40% bile.
Aesculin hydrolysis test
Aesculin is incorporated into agar with ferric citrate and bile salts (bile aesculin agar).[4] Hydrolysis of the aesculin forms aesculetin (6,7-dihydroxycoumarin) and glucose. The aesculetin forms dark brown or black complexes with ferric citrate, allowing the test to be read.
The bile aesculin agar is streaked and incubated at 37 °C for 24 hours. The presence of a dark brown or black halo indicates that the test is positive. A positive test can occur with Enterococcus, Aerococcus and Leuconostoc. Aesculin will fluoresce under long wave ultraviolet light (360 nm): hydrolysis of aesculin results in loss of this fluorescence.
Enterococcus will often flag positive within four hours of the agar being inoculated.
UV visible spectrum of esculin with a maximum of absorbance at 346 nm
Warnings
Aesculin ingest can produce stomachache, spasms, diarrhea, disorientation, even death at high doses.[citation needed]
Notes
- ^ Plant poisons: Aesculin
- ^ C. Michael Hogan, 2008
- ^ Esculin. Drugs.com. Retrieved 11 June 2016.
- ^ National Standard Methods (UK)
References
- Plant poisons: Aesculin
- National Standard Methods MSOP 48 (Bile aesculin agar) and BSOPTP 2 (Aesculin hydrolysis test (UK)).
- C. Michael Hogan (2008) California Buckeye: Aesculus californica, GlobalTwitcher.com, N. Stromberg ed.
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Glycosides
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| Bond |
- O-glycosidic bond
- N-glycosidic bond
- S-glycosidic bond
- C-glycosidic bond
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| Geometry |
- α-Glycoside
- β-Glycoside
- 1,4-Glycoside
- 1,6-Glycoside
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| Glycone |
- Fructoside
- Galactoside
- Glucoside
- Glucuronide
- Rhamnoside
- Riboside
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| Aglycone |
- Alcoholic glycoside
- Cardiac glycoside
- Bufadienolide
- Cardenolide
- Cyanogenic glycoside
- Glycosylamine
- Phenolic glycoside
- Anthraquinone glycoside
- Coumarin glycoside
- Flavonoid glycoside
- Saponin
- Steviol glycoside
- Thioglycoside
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Types of coumarins
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| Aglycones |
- Aesculetin
- Ferujol
- Umbelliferone
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O-Methylated
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- Fraxetin
- Herniarin (7-O-Methylumbelliferone)
- Osthol
- Scopoletin (6-Methoxyumbelliferone)
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| glycosides |
- Aesculin (Esculetin 6-O-glucoside)
- Fraxin (Fraxetin glucoside)
- Skimmin (Umbelliferone 7-O-glucoside)
- Scopolin
- Umbelliferone 7-apiosylglucoside
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| derivatives |
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Furanocoumarins
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Aglycones
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- Angelicin
- Marmesin
- Psoralen
- Vaginol
- Xanthotoxol (8-Hydroxypsoralen)
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O-Methylated
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- Bergapten (5-methoxypsoralen)
- Isopimpinellin (5,8-Dimethoxypsoralene)
- Methoxsalen (8-Methoxypsoralen)
- Trioxsalen (2,5,9-Trimethylpsoralen)
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Furanocoumarin glycosides
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- Apterin (vaginol glucoside)
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Meroterpene furanocoumarin ether
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- Auraptene
- Bergamottin
- Imperatorin
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| Oligomers |
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| Synthetic |
- Acenocoumarol
- Coumatetralyl
- Ensaculin
- Ethyl biscoumacetate
- 4-Hydroxycoumarins
- Hymecromone
- Phenprocoumon
- Warfarin
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English Journal
- Enterococcus in surface waters from the Des Moines River (Iowa) watershed: location, persistence and vancomycin resistance.
- Larsen B, Essmann MK, Geletta S, Duff B.Sourcea University Research, Des Moines University , 3200 Grand Avenue , Ryan Hall 209 , Des Moines , 50312 , USA.
- International journal of environmental health research.Int J Environ Health Res.2012 Aug;22(4):305-16. Epub 2011 Nov 30.
- The object of this study was to quantify vancomycin-resistant enterococci in surface water from Central Iowa obtained from April 2007 to August 2007. Water from established sampling sites in four watersheds was plated on bile-esculin agar. Presumptively identified enterococci were categorized as "ab
- PMID 22128914
- Identification of amino acids important for substrate specificity in sucrose transporters using gene shuffling.
- Reinders A, Sun Y, Karvonen KL, Ward JM.SourceUniversity of Minnesota, United States.
- The Journal of biological chemistry.J Biol Chem.2012 Jul 17. [Epub ahead of print]
- Plant sucrose transporters (SUTs) are H+-coupled uptake transporters. Type I and II (SUTs) are phylogenetically related but have different substrate specificities. Type I SUTs transport sucrose, maltose and a wide range of natural and synthetic α- and β-glucosides. Type II SUTs are more selective
- PMID 22807445
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