词条 | Apocynin |
释义 |
| Watchedfields = changed | verifiedrevid = 443394610 | ImageFile=Acetovanillone.svg | ImageSize=150px | PIN = 1-(4-Hydroxy-3-methoxyphenyl)ethan-1-one | OtherNames=1-(4-Hydroxy-3-methoxyphenyl)ethanone 4-Hydroxy-3-methoxyacetophenone Acetovanillone |Section1={{Chembox Identifiers | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C11380 | InChI = 1/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3 | InChIKey = DFYRUELUNQRZTB-UHFFFAOYAW | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = DFYRUELUNQRZTB-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo=498-02-2 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 21106900 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 346919 | PubChem=2214 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = B6J7B9UDTR | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 2781 | SMILES = Oc1ccc(cc1OC)C(C)=O }} |Section2={{Chembox Properties | Formula = C9H10O3 | MolarMass = 166.17 g/mol | Appearance= | Density= | MeltingPtC=115 | BoilingPtC= 295-300 | Solubility= |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = }} Apocynin, also known as acetovanillone, is a natural organic compound structurally related to vanillin. It has been isolated from a variety of plant sources and is being studied for its variety of pharmacological properties. HistoryApocynin was first described by Oswald Schmiedeberg, a German pharmacologist, in 1883 and was first isolated by Horace Finnemore,[1] in 1908,from the root of Canadian hemp (Apocynum cannabinum).[2] At the time, this plant was already used for its known effectiveness against edema and heart problems. In 1971, apocynin was also isolated from Picrorhiza kurroa, a small plant that grows at high altitudes in the western Himalayas. P. kurroa was used for ages as a treatment for liver and heart problems, jaundice, and asthma. In 1990, Simons et al. isolated apocynin to a pharmacologically useful level using an actively guided isolation procedure. Apocynin’s observed anti-inflammatory capabilities proved to be a result of its ability to selectively prevent the formation of free radicals, oxygen ions, and peroxides in the body. Apocynin has since been extensively studied to help determine its disease-fighting capabilities and applications.{{citation needed|date=January 2016}} Physical propertiesApocynin is a solid with a melting point of 115 °C and the faint odor of vanilla. It is soluble in hot water, alcohol, benzene, chloroform, and ether.{{citation needed|date=January 2016}} Mode of actionNADPH oxidase is an enzyme that effectively reduces O2 to superoxide (O2–•), which can be used by the immune system to kill bacteria and fungi. Apocynin is an inhibitor of NADPH oxidase activity and thus is effective in preventing the production of the superoxide in human white blood cells or neutrophilic granulocytes. It does not however obstruct the phagocytic or other defense roles of granulocytes. Due to the selectivity of its inhibition, apocynin can be widely used as an inhibitor of NADPH oxidase without interfering in other aspects of the immune system.{{citation needed|date=January 2016}} Apocynin was used to determine whether ionic activation due to proton flux across the membrane of renal medulla cells was coupled to NADPH oxidase production of superoxide. Apocynin was introduced to the cells and completely blocked the production of superoxide, and was a key component in determining that the proton outflow was responsible for the activation of NADPH oxidase.[3] The mechanism of action of apocynin is not understood yet. In the experimental studies, apocynin is shown to dimerize and form diapocynin.[4] Although, diapocynin seems to have beneficial effect in reducing reactive oxygen species and anti-inflammatory properties, it is still yet to be shown as biologically relevant molecule.[5] Biotransformation of apocynin predominantly leads to glycosylated form of apocynin. Another molecule that is shown to form under experimental conditions is nitroapocynin.[6] Potential use in medical treatments{{medical citations needed|section|date=January 2017}}
Clinical trials
References1. ^{{cite web |title=Acetovanillone |url=https://books.google.com/books?id=zl3yCAAAQBAJ&pg=PA410 |pages=410–1 }} in {{cite book |first1=George |last1=de Stevens |first2=F. F. |last2=Nord |chapter=Natural Phenylpropane Derivatives |chapterurl=https://books.google.com/books?id=zl3yCAAAQBAJ&pg=PA392 |pages=392–427 |doi=10.1007/978-3-642-64958-5_10 |editor1-first=K. |editor1-last=Paech |editor2-first=M. V. |editor2-last=Tracey |year=1955 |title=Moderne Methoden der Pflanzenanalyse / Modern Methods of Plant Analysis |publisher=Springer-Verlag Berlin Heidelberg |isbn=978-3-642-64958-5 }} 2. ^{{cite journal |last=Horace |first=Finnemore |title=The Constituents of Canadian Hemp. Part I. Apocynin |journal=Journal of the Chemical Society |year=1908 |volume=93 |issue=2 |pages=1513–9 |url=https://books.google.com/books?id=S982AAAAYAAJ&pg=PA1513 |accessdate=10 April 2014 |doi=10.1039/ct9089301513 }} 3. ^{{cite journal |vauthors=Li N, Zhang G, Yi FX, Zou AP, Li PL |title=Activation of NAD(P)H oxidase by outward movements of H+ ions in renal medullary thick ascending limb of Henle |journal=American Journal of Physiology. Renal Physiology |volume=289 |issue=5 |pages=F1048–56 |year=2005 |pmid=15972387 |doi=10.1152/ajprenal.00416.2004 }} 4. ^{{cite journal |last1=Luchtefeld |first1=Ron |last2=Dasari |first2=Mina S. |last3=Richards |first3=Kristy M. |last4=Alt |first4=Mikaela L. |last5=Crawford |first5=Clark F. P. |last6=Schleiden |first6=Amanda |last7=Ingram |first7=Jai |last8=Hamidou |first8=Abdel Aziz Amadou |last9=Williams |first9=Angela |last10=Chernovitz |first10=Patricia A. |last11=Sun |first11=Grace Y. |last12=Luo |first12=Rensheng |last13=Smith |first13=Robert E. |title=Synthesis of Diapocynin |journal=Journal of Chemical Education |volume=85 |issue=3 |year=2008 |pages=411 |bibcode=2008JChEd..85..411D |doi=10.1021/ed085p411 }} 5. ^{{cite journal |vauthors=Chandasana H, Chhonker YS, Bala V, Prasad YD, Chaitanya TK, Sharma VL, Bhatta RS |title=Pharmacokinetic, bioavailability, metabolism and plasma protein binding evaluation of NADPH-oxidase inhibitor apocynin using LC-MS/MS |journal=Journal of Chromatography B |volume=985 |issue= |pages=180–8 |year=2015 |pmid=25682338 |doi=10.1016/j.jchromb.2015.01.025 }} 6. ^{{cite journal |vauthors=Babu S, Raghavamenon AC, Fronczek FR, Uppu RM |title=4-Hydr-oxy-3-meth-oxy-5-nitro-aceto-phenone (5-nitro-apocynin) |journal=Acta Crystallographica E |volume=65 |issue=Pt 9 |pages=o2292–3 |year=2009 |pmid=21577684 |pmc=2969931 |doi=10.1107/S160053680903390X }} 7. ^{{cite journal |vauthors='T Hart BA, Simons JM, Knaan-Shanzer S, Bakker NP, Labadie RP |title=Antiarthritic activity of the newly developed neutrophil oxidative burst antagonist apocynin |journal=Free Radical Biology & Medicine |volume=9 |issue=2 |pages=127–31 |year=1990 |pmid=2172098 |id={{INIST|19326251}} |doi=10.1016/0891-5849(90)90115-Y }} 8. ^{{cite journal |last1=Palmen |first1=M.J.H.J. |last2=Beukelman |first2=C.J. |last3=Mooij |first3=R.G.M. |last4=Pena A.S. |last5=van Rees |first5=E.P. |title=Anti-inflammatory effect of apocynin, a plant-derived NADPH oxidase antagonist, in acute experimental colitis |journal=The Netherlands Journal of Medicine |volume=47 |issue=2 |year=1995 |pages=41 |url=http://www.ingentaconnect.com/content/els/03002977/1995/00000047/00000002/art97052 }} 9. ^1 {{cite journal |vauthors=Van den Worm E, Beukelman CJ, Van den Berg AJ, Kroes BH, Labadie RP, Van Dijk H |title=Effects of methoxylation of apocynin and analogs on the inhibition of reactive oxygen species production by stimulated human neutrophils |journal=European Journal of Pharmacology |volume=433 |issue=2–3 |pages=225–30 |year=2001 |pmid=11755156 |doi=10.1016/S0014-2999(01)01516-3 }} 10. ^{{cite journal |vauthors=Harraz MM, Marden JJ, Zhou W, Zhang Y, Williams A, Sharov VS, Nelson K, Luo M, Paulson H, Schöneich C, Engelhardt JF |title=SOD1 mutations disrupt redox-sensitive Rac regulation of NADPH oxidase in a familial ALS model |journal=The Journal of Clinical Investigation |volume=118 |issue=2 |pages=659–70 |year=2008 |pmid=18219391 |pmc=2213375 |doi=10.1172/JCI34060 }} 11. ^{{cite journal |vauthors=Stefanska J, Sarniak A, Wlodarczyk A, Sokolowska M, Pniewska E, Doniec Z, Nowak D, Pawliczak R |title=Apocynin reduces reactive oxygen species concentrations in exhaled breath condensate in asthmatics |journal=Experimental Lung Research |volume=38 |issue=2 |pages=90–9 |year=2012 |pmid=22296407 |doi=10.3109/01902148.2011.649823 }} 12. ^{{ClinicalTrialsGov|NCT01402297|Hydrogen Peroxide and Nitrite Reduction in Exhaled Breath Condensate of COPD Patients}} 4 : O-Methylated natural phenols|Vanilloids|Aromatic ketones|Catechols |
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