サリシン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/07/17 06:06:14」(JST)
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Salicin[1]
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Names |
IUPAC name
(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3, 4,5-triol
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Other names
Salicin; D-(−)-Salicin; Salicoside; 2-(Hydroxymethyl)phenyl
-β-D-glucopyranoside
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Identifiers |
CAS Number
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138-52-3 Y |
ChemSpider |
388601 N |
Jmol 3D model |
Interactive image |
KEGG |
C01451 N |
PubChem |
439503 |
RTECS number |
LZ5901700 |
UNII |
4649620TBZ Y |
InChI
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InChI=1/C13H18O7/c14/h1-4,9-18H,5-6H2
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SMILES
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c1ccc(c(c1)CO)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
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Properties |
Chemical formula
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C13H18O7 |
Molar mass |
286.28 g·mol−1 |
Melting point |
197 to 200 °C (387 to 392 °F; 470 to 473 K) |
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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Salicin is an alcoholic β-glucoside. Salicin is produced in (and named after) willow (Salix) bark and acts as an anti-inflammatory agent in the human body.[2] Salicin is also commonly found in the bark of Populus species, and the leaves of willows and poplars. It is also found in castoreum, which was used as an analgesic, anti-inflammatory, and antipyretic. The activity of castoreum has been credited to the accumulation of salicin from willow trees in the beaver's diet, which is transformed to salicylic acid and has an action very similar to aspirin.[3] Salicin was the historical origin aspirin[4] and is chemically related to it. When consumed, the acetalic ether bridge is broken down. The two parts of the molecule, glucose and salicyl alcohol, then are metabolized separately. By oxidizing the alcohol function the aromatic part finally is metabolized to salicylic acid. Salicin tastes bitter like quinine.[5] Alkaline cleavage of the glucoside populin produces benzoate and salicin.[6]
Mild side effects are standard, with rare occurrences of nausea, vomiting, rash, dizziness and breathing problems. Overdose from high quantities of salicin can be toxic, damaging kidneys, causing stomach ulcers, diarrhea, bleeding or digestive discomfort. Some people may be allergic or sensitive to salicylates and suffer reactions similar to those produced by aspirin. People should not take salicin if they have asthma, diabetes, gout, gastritis, hemophilia, stomach ulcers; also contraindicated are children under 16, and pregnant and breastfeeding women.[7][8]
References
- ^ Merck Index, 11th Edition, 8293
- ^ Uchytil, RJ (1991). "Salix drummondiana". Fire Effects Information System,. Online. U.S. Department of Agriculture, Forest Service, Rocky Mountain Research Station, Fire Sciences Laboratory (Producer). Retrieved 2006-07-19.
- ^ Stephen Pincock (28 March 2005). "The quest for pain relief: how much have we improved on the past?". Retrieved 2007-06-17.
- ^ "History of Aspirin". About.com Inventors. Retrieved 2016-06-15.
- ^ Daniells, S (2006-10-09). "Symrise explores cheaper alternatives in bitter-maskers". www.foodnavigator.com. Retrieved 2007-12-13.
- ^ Richtmyer, Nelson K.; Yeakel, Eleanor H. (1934). "The Structure of Populin". Journal of the American Chemical Society 56 (11): 2495–2497. doi:10.1021/ja01326a090. ISSN 0002-7863.
- ^ http://umm.edu/health/medical/altmed/herb/willow-bark
- ^ http://www.heart-health-guide.com/salicin.html
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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Salicylates
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- Salicylic acid
- Aspirin
- Aloxiprin
- Methyl salicylate
- Magnesium salicylate
- Ethyl salicylate
- Bismuth subsalicylate
- Sodium salicylate
- Salicylamide
- Salicin
- Benorilate
- Salsalate
- Ethenzamide
- Diflunisal
- Trolamine salicylate
- Homosalate
- Salicylmethylecgonine
- Octyl salicylate
- Aluminon
- Benzyl salicylate
- Copper aspirinate
- Potassium salicylate
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Prostanoid signaling
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Receptor
(ligands) |
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Enzyme
(inhibitors) |
COX (PTGS) |
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PGD2 synthase |
- Retinoids
- Selenium (selenium tetrachloride, sodium selenite, selenium disulfide)
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PGE synthase |
HQL-79
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PGF synthase |
Bimatoprost
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PGI2 synthase |
Tranylcypromine
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TXA synthase |
- Camonagrel
- Dazmegrel
- Dazoxiben
- Furegrelate
- Isbogrel
- Midazogrel
- Nafagrel
- Nicogrelate
- Ozagrel
- Picotamide
- Pirmagrel
- Ridogrel
- Rolafagrel
- Samixogrel
- Terbogrel
- U63557A
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Others |
- Precursors: Linoleic acid
- γ-Linolenic acid (gamolenic acid)
- Dihomo-γ-linolenic acid
- Diacylglycerol
- Arachidonic acid
- Prostaglandin G2
- Prostaglandin H2
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See also: Leukotrienergics
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English Journal
- Origin and Differential Selection of Allelic Variation at TAS2R16 Associated with Salicin Bitter Taste Sensitivity in Africa.
- Campbell MC, Ranciaro A, Zinshteyn D, Rawlings-Goss R, Hirbo J, Thompson S, Woldemeskel D, Froment A, Rucker JB, Omar SA, Bodo JM, Nyambo T, Belay G, Drayna D, Breslin PA, Tishkoff SA.Author information Department of Genetics, University of Pennsylvania.AbstractBitter taste perception influences human nutrition and health, and the genetic variation underlying this trait may play a role in disease susceptibility. To better understand the genetic architecture and patterns of phenotypic variability of bitter taste perception, we sequenced a 996 bp region, encompassing the coding exon of TAS2R16, a bitter taste receptor gene, in 595 individuals from 74 African populations and in 94 non-Africans from 11 populations. We also performed genotype-phenotype association analyses of threshold levels of sensitivity to salicin, a bitter anti-inflammatory compound, in 296 individuals from Central and East Africa. In addition, we characterized TAS2R16 mutants in vitro to investigate the effects of polymorphic loci identified at this locus on receptor function. Here, we report striking signatures of positive selection, including significant Fay and Wu's H statistics predominantly in East Africa, indicating strong local adaptation and greater genetic structure among African populations than expected under neutrality. Furthermore, we observed a "star-like" phylogeny for haplotypes with the derived allele at polymorphic site 516 associated with increased bitter taste perception that is consistent with a model of selection for "high-sensitivity" variation. In contrast, haplotypes carrying the "low-sensitivity" ancestral allele at site 516 showed evidence of strong purifying selection. We also demonstrated, for the first time, the functional effect of nonsynonymous variation at site 516 on salicin phenotypic variance in vivo in diverse Africans and showed that most other nonsynonymous substitutions have weak or no effect on cell surface expression in vitro, suggesting that one main polymorphism at TAS2R16 influences salicin recognition. Additionally, we detected geographic differences in levels of bitter taste perception in Africa not previously reported and infer an East African origin for high salicin sensitivity in human populations.
- Molecular biology and evolution.Mol Biol Evol.2013 Dec 9. [Epub ahead of print]
- Bitter taste perception influences human nutrition and health, and the genetic variation underlying this trait may play a role in disease susceptibility. To better understand the genetic architecture and patterns of phenotypic variability of bitter taste perception, we sequenced a 996 bp region, enc
- PMID 24177185
- Willow bark extract increases antioxidant enzymes and reduces oxidative stress through activation of Nrf2 in vascular endothelial cells and Caenorhabditis elegans.
- Ishikado A, Sono Y, Matsumoto M, Robida-Stubbs S, Okuno A, Goto M, King GL, Keith Blackwell T, Makino T.Author information R&D Department, Sunstar Inc., Osaka 569-1195, Japan.AbstractWillow bark extract (WBE) is listed in the European Pharmacopoeia and has been traditionally used for treating fever, pain, and inflammation. Recent studies have demonstrated its clinical usefulness. This study investigated the antioxidative effects of WBE in human umbilical vein endothelial cells (HUVECs) and Caenorhabditis elegans. WBE prevented oxidative-stress-induced cytotoxicity of HUVECs and death of C. elegans. WBE dose-dependently increased mRNA and protein expression levels of the nuclear factor erythroid 2-related factor 2 (Nrf2) target genes heme oxygenase-1, γ-glutamylcysteine ligase modifier and catalytic subunits, and p62 and intracellular glutathione (GSH) in HUVECs. In the nematode C. elegans, WBE increased the expression of the gcs-1::green fluorescent protein reporter, a well-characterized target of the Nrf2 ortholog SKN-1, in a manner that was SKN-1-dependent. WBE increased intranuclear expression and DNA binding of Nrf2 and the activity of an antioxidant response element (ARE) reporter plasmid in HUVECs. WBE-induced expression of Nrf2-regulated genes and increased GSH levels in HUVECs were reduced by Nrf2 and p38 small interfering (si) RNAs and by the p38-specific inhibitor SB203580. Nrf2 siRNA reduced the cytoprotective effect of WBE against oxidative stress in HUVECs. Salicin, a major anti-inflammatory ingredient of WBE, failed to activate ARE-luciferase activity, whereas a salicin-free WBE fraction showed intensive activity. WBE induced antioxidant enzymes and prevented oxidative stress through activation of Nrf2 independent of salicin, providing a new potential explanation for the clinical usefulness of WBE.
- Free radical biology & medicine.Free Radic Biol Med.2013 Dec;65:1506-15. doi: 10.1016/j.freeradbiomed.2012.12.006. Epub 2012 Dec 28.
- Willow bark extract (WBE) is listed in the European Pharmacopoeia and has been traditionally used for treating fever, pain, and inflammation. Recent studies have demonstrated its clinical usefulness. This study investigated the antioxidative effects of WBE in human umbilical vein endothelial cells (
- PMID 23277146
- A commercialized dietary supplement alleviates joint pain in community adults: a double-blind, placebo-controlled community trial.
- Nieman DC, Shanely RA, Luo B, Dew D, Meaney MP, Sha W.Author information Appalachian State University, Human Performance Lab, North Carolina Research Campus, 600 Laureate Way, Kannapolis, NC 28081, USA. niemandc@appstate.edu.AbstractBACKGROUND: The purpose of this study was to assess the effect of 8-weeks ingestion of a commercialized joint pain dietary supplement (InstaflexTM Joint Support, Direct Digital, Charlotte, NC) compared to placebo on joint pain, stiffness, and function in adults with self-reported joint pain. InstaflexTM is a joint pain supplement containing glucosamine sulfate, methylsufonlylmethane (MSM), white willow bark extract (15% salicin), ginger root concentrate, boswella serrata extract (65% boswellic acid), turmeric root extract, cayenne, and hyaluronic acid.
- Nutrition journal.Nutr J.2013 Nov 25;12(1):154. doi: 10.1186/1475-2891-12-154.
- BACKGROUND: The purpose of this study was to assess the effect of 8-weeks ingestion of a commercialized joint pain dietary supplement (InstaflexTM Joint Support, Direct Digital, Charlotte, NC) compared to placebo on joint pain, stiffness, and function in adults with self-reported joint pain. Instafl
- PMID 24274358
Japanese Journal
- 今井 啓雄,鈴木 南美
- 生物物理 53(4), 194-197, 2013
- In mammals, bitter taste is mediated by TAS2Rs, which belong to the large family of seven transmembrane G protein-coupled receptors. Since TAS2Rs are directly involved in the interaction between mamma …
- NAID 130003362500
- A new acidophilic fungus Teratosphaeria acidotherma (Capnodiales, Ascomycota) from a hot spring
- Yamazaki Atsushi,Toyama Kyoko,Nakagiri Akira
- Mycoscience 51(6), 443-455, 2010-11-25
- … populi </I>by the ability to ferment glucose and to assimilate L-sorbose, sucrose, maltose, α-methyl-D-glucoside, and salicin. …
- NAID 10027671801
Related Links
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- salicin [sal′ə sin] salicin definition by Webster's New World noun a bitter, white, crystalline or powdery glucoside, HOCHCHOCHO, obtained from the bark of certain poplars and willows, and used as a reagent Origin: French salicine; from Classical Latin ...
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