MedKoo Biosciences/Betulinic acid/200160/500mg

Synonym:ALS357;ALS357;ALS-357;Mairin.

IUPAC/ChemicalName:(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylicacid

InChiKey:QGJZLNKBHJESQX-FZFNOLFKSA-N

InChiCode:InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1

SMILESCode:O=C([C@]1(CC[C@H]2C(C)=C)[C@@]2([H])[C@@]3([H])CC[C@]4([H])[C@@]5(C)CC[C@H](O)C(C)(C)[C@]5([H])CC[C@@]4(C)[C@]3(C)CC1)O

TechnicalData

AdditionalInformation

Betulinicacidisanaturallyoccurringpentacyclictriterpenoidwhichhasanti-retroviral,anti-malarial,andanti-inflammatoryproperties,aswellasamorerecentlydiscoveredpotentialasananticanceragent,byinhibitionoftopoisomerase. Itisfoundinthebarkofseveralspeciesofplants,principallythewhitebirch(Betulapubescens) fromwhichitgetsitsname,butalsotheBertree(Ziziphusmauritiana),selfheal(Prunellavulgaris),thetropicalcarnivorousplantsTriphyophyllumpeltatumandAncistrocladusheyneanus,Diospyrosleucomelasamemberofthepersimmonfamily,Tetraceraboiviniana,thejambul(Syzygiumformosanum), floweringquince(Chaenomelessinensis),Rosemary,andPulsatillachinensis.see:http://en.wikipedia.org/wiki/Betulinic_acid.
  
 

References

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3:LiY,HeK,HuangY,ZhengD,GaoC,CuiL,JinYH.Betulininducesmitochondrialcytochromecreleaseassociatedapoptosisinhumancancercells.MolCarcinog.2010Jul;49(7):630-40.PubMedPMID:20564340.

4:EichenmüllerM,HemmerleinB,vonSchweinitzD,KapplerR.BetulinicacidinducesapoptosisandinhibitshedgehogsignallinginrhaBDomyosarcoma.BrJCancer.2010Jun29;103(1):43-51.Epub2010Jun1.PubMedPMID:20517313;PubMedCentralPMCID:PMC2905279.

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6:AhmadFB,GhaffariMoghaddamM,BasriM,AbdulRahmanMB.Anticanceractivityof3-O-acylatedbetulinicacidderivativesobtainedbyenzymaticsynthesis.BiosciBiotechnolBiochem.2010;74(5):1025-9.Epub2010May7.PubMedPMID:20460723.

7:KommeraH,KaluderovićGN,DittrichS,KalbitzJ,DrägerB,MuellerT,PaschkeR.Carbamatederivativesofbetulinicacidandbetulinwithselectivecytotoxicactivity.BioorgMedChemLett.2010Jun1;20(11):3409-12.Epub2010Apr18.PubMedPMID:20451375.

8:ChadalapakaG,JutooruI,BurghardtR,SafeS.Drugsthattargetspecificityproteinsdownregulateepidermalgrowthfactorreceptorinbladdercancercells.MolCancerRes.2010May;8(5):739-50.Epub2010Apr20.PubMedPMID:20407012;PubMedCentralPMCID:PMC2872686.

9:daSilveiraCV,TrevisanMT,RiosJB,ErbenG,HaubnerR,PfundsteinB,OwenRW.Secondaryplantsubstancesinvariousextractsoftheleaves,fruits,stemandbarkofCaraipadensifoliaMart.FoodChemToxicol.2010Jun;48(6):1597-606.Epub2010Mar27.PubMedPMID:20347919.

10:Eder-CzembirekC,ErovicBM,CzembirekC,BrunnerM,SelzerE,PötterR,ThurnherD.BetulinicAcidaRADIosensitizerinHeadandNeckSquamousCellCarcinomaCellLines.StrahlentherOnkol.2010Feb22.[Epubaheadofprint]PubMedPMID:20339825.