Glycosides.ppt

Glycosides Definition Organicnaturalcompoundspresentinalotofplantsandsomeanimals thesecompoundsuponhydrolysisgiveoneormoresugars glycone formandnonsugar aglycone orcalledgenin Solubility glycosidesarewatersolublecompoundsandinsolubleintheorganicsolvents Glyconepart watersoluble insolubleintheorganicsolvents Aglyconepart waterinsoluble solubleintheorganicsolvents Someglycosidessolubleinalcohol Separationbetweenglycosidesparts Glycosidesglycone aglycone HCLG A salt H2O H2O G A H2O G chloroform A WecanseparatethembyusingseparatoryfunnelThebestsolventtoextractaglyconeisEthylacetatebecause A immiscibleinwater B alwayspresentsintheupperlayer NeutralizationbyUsingalkaline Filtration chloroform Hydrolysis HCLdil Note Alcoholandacetonearewatermisciblecompounds sowecan tusethemasorganicsolventsforaglyconeseparation physico chemicalpropertiesofglycosides general Colorless solid amorphous nonvolatile flavonoid yellow anthraquinone redororange GivepositivereactionwithMolisch sandFehling ssolutiontest afterhydrolysis Theyarewatersolublecompounds insolubleinorganicsolventsMostofthemhavebittertaste except populin glycyrrhizin stevioside Cont Odorlessexceptsaponin glycyrrhizin whenaglycosideshasalotofsugarsitssolubilityinwaterdecrease Glycosideshydrolyzedbyusingmineralacidsandtemperatureorbyusingenzymessuchas a EmolsinBitteralmondseeds b MyrosinorMyrosinaseblackmustardseeds c Rhamnaseglycosidescontainingrhamnoseassugarpart Biosynthesisofglycosides O glycosides UTP UridineTriphoshate sugar 1 phoshateUDP sugar ppi Pyrophosphateinorganic UDP sugar acceptor aglycone Acceptor sugar UDP UridylyltransferaseEnzyme GlycosyltransferaseEnzyme GlycosyltransferaseEnzyme Thefunctionortheroleofglycosidesintheplantorganism Convertingtoxicmaterialstononorlesstoxic Transferwaterinsolublesubstancesbyusingmonosaccharide Sourceofenergy sugarreservoir Storingharmfulproductssuchasphenol Regulationforcertainfunctions growth Somehavebeautifulcolours pollenationprocess Cont Someglycosideshaveantibacterialactivity sotheyprotecttheplantsfrombacteriaanddiseases Bitteralmond Amygdalin bacteria HCN hydrolysis kill Eomlsinenzyme Classificationofglycosides Classificationsofglycosidesaccordingtotheirtherapeuticeffects CHFandcardiacmusclesstimulatorssuchas a Digitalisglycosides digoxin digitoxin gitoxin Foxgloveleaves b Ouabain Strophanthusgratusseeds c K strophanthin Strophanthuskombeseeds d ScillarenA BwhichisolatedfromredandwhiteSquillbulbs e Convolloside Convallariamajalis LilyoftheValley Cont Laxativegroupofglycosides a SennosideA B C D Sennaleavesandfruits b CascarosideA B Cascarabark c Frangulinandglucofrangulin Frangulabark d Aloinandbarbaloin AloeveraandAloebarbadensisjuice Cont Localirritantgroup a Sinigrin Blackmusteredseeds Brassicanigra b Sinalbin Whitemusteredseeds Brasicaalba Analgesicsandantipyretics SalicinSalisylicacid WilloworSalixbark Keepingelasticityofbloodvesselslike Rutin Rutoside Bitterorangepeels Lemonpeels Anti inflammatorygroup a Aloinfor1 acne2 pepticulcerb Glycyrrhizin hydrolysis Classificationofglycosidesaccordingtoglyconepart Glucose glucosidegrouplikeinSennoside Rhamnose Rhamnosidelikeinfrangullin Digitoxose Digitoxosidelikeindigoxin GlucoseandRhammnose Glucorhamnoside glucofrangulin Rhamnoseandglucose Rhamnoglucoside Rutin Classificationofglycosidesonthebasisofthelinkagebetweenglyconeandaglyconepart O glycosides intheseglycosidesthesugarpartislinkedwithalcoholicorphenolichydroxylorcarboxylgroup S glycosides intheseglycosidesthesugarattachedtoaSulfuratomofaglyconesuchasinsinigrin N glycosides intheseglycosidesthesugarlinkedwithNitrogenatomof NH2 NH aminogroupofaglyconelikeinnucleosidesDNA RNAC glycosides intheseglycosidesthesugarlinked condensed directlytoCarbonatomofaglyconelikeinaloin N BC glycosidesarenothydrolyzedbyacidsoralkalisorbyenzymesmainly Classificationofglycosidesaccordingtoaglyconepart 1 ifaglyconepartalcohol thisgroupcalledalcoholicgrouplikeSalicin2 ifaglyconepartaldehyde thisgroupcalledaldehydicgr likeglucovanillin 3 ifphenolcalledphenolicgrouplikearbutin 4 ifcyanonecalledcyanogenicorcyanophoricorcyanosidelikeamygdalin 5 ifthiocalledglycosidesorisothiocyanateglycosidelikesinigrinorsinalbin S C N SCN 6 anthracene anthraquinoneglycoside sennoside 7 steroid steroidalglycoside cardiac Digoxin8 flavone flavonol flavanone flavonoidglycoside9 triterpenoid saponinglycoside glycyrrhizin melanthin nigellaseeds orginsenoside Mostofglycosidemaybenamedaccordingtotheplantfromwhichtheyisolatedforexample 1 salicin salix 2 cascaroside cascara3 aloin Aloevera4 sennoside senna 5 frangulin frangula6 glycyrrhizin glycyrrhizaAndothers Alwaysglycosidesfoundedintheplantwiththeenzymeswhichhydrolyzedthem Wemustdamagetheseenzymesfirsttoextracttheseglycosidebythefollowingsteps 1 dryingtheplantsfreshinspecialovenat100cfor30minutes 2 boilingthemwithorganicsolventsfor20minutes3 boilingthemwithacetone5minutesN B Ifpresentinthisplanttanninsorresinsweaddleadacetatetoprecipitatethem Classificationofglycosidesaccordingtoaglyconepart 1 phenolicgroupofglycosides SuchasarbutinwhichisolatedfrombearberryleavesUses UTIasantisepticandantibacterial milddiureticDrugs Esoterica cream agespots hydroquinonesolution wethands2 saponingroupofglycosideImportantgroupofglycosideswhichwidelydistributedspeciallyinthehigherplantspartsb Mostofthemareneutralcompounds solubleinwaterinsolubleintheorganicsolvents d Irritantcompoundsformucousmembranese Theyformwithhydrolysisglyconepartwhichusually D glucoseorit sacids glucuronicacid Sapogenin f Theiraqueoussolutionsfromfroths foam onshakinandformemulsionsonshakingandheatingwithoilsandfatsg TheydestroyRBC corpuscles speciallyforfishandcoldbloodedanimalsm Sapogenin Triterpenoid dividedto 1 steroidalSapogenin2 pentacyclicSapogeninExamples licoricerootscontainsaponinglycosidewhichcalledGlycyrrhizinGlycyrrhizinhydrolysisglycyrrheticacid Z M glucyracidSweettaste solutioninH2ObittertasteinsolubleinH2Oexpectorantanti inflammatory GinsengrootsPanaxrootsPanaxquinquefolius panaxginseng containssaponinglycoside ginsenoside panaxoside Triterpenoid steroidalnucleusGinsengrootuses 1 stimulant2 Tonic3 anti stress4 adaptogenicagent Drugs 1 geriatricpharmaton2 gerimax3 polyvit AnthraquinonegroupofglycosidesTheyareanthracenederivatives anthracene isthemainnucleusforanthraquinonecompounds Intheplanttheybiosynthesizedfromacetyl CoAandmalonyl CoA Theyhavecatharticproperty laxativesandpurgativebutsomeofthemhaveanti inflammatoryactivity Withhydrolysistheygiveaglyconepartwhichisdi triortetrahydroxyanthracenederivatives Theyhydrolyzedonlybyacidsorbyenzymes butnothydrolyzedbyalkalines 6 Theyhaveorangeorredcolor mostofthem 7 Solubleinwater insolubleintheorganicsolvents 8 Theyhavebittertasteandslightlycharacteristicodor 9 Anthraquinonemaybefreestatecompounds freefromsugar oranthraquinoneglycoside RelationshipbetweenanthracenederivativesAccordingtolinkagebetweenglyconepartandaglyconepartanthraquinoneglycosidemayclassifiedto 1 C glycoside verystabletohydrolysis 2 O glycoside 3 oandc glycoside AlcoholicgroupofglycosidesSuchas SalicinwhichobtainedfromSalixbark Willowbark Salicinhydrolyzedby 1 Enzymeemolsin2 AcidlikeHCl HNO33 AlkalinesolutionslikeNaOH Theeffectofsalicylicacid Analgesic Anti pyretic Anti coagulant anticlottingagent Anti inflammatoryactivity Rheumatism WartandcornremoverPreventscoloncancer AldehydicgroupofglycosideSuchas Glucovanillinwhichobtainedfrom Vanillabeans fruits Vanillin volatileoilwhichusedasflavoringagent vanillin 1 phenolicgroupvolatileoils2 aldehydegroupofvolatileoils Isothiocyanategroupofglycoside sulfurglycosideorthioglycoside 1 Groupofglycosideswhichcontainssulfur S glycoside 2 Presentinmanycruciferousplants onhydrolysis 3 Theyproduceisothiocynate SCN aglyconeSuchas 1 sinigrinwhichfoundedinBlackMustardseeds2 sinalbinwhichfoundedBrassicaalba WhiteMustardseeds Theseplantscontainalsoenzymemyrosin myrosinase whichhydrolyzetheseglycosides PropertiesofMustardoil 1 Irritantformucousmembrane2 Volatile3 Pungent4 CharacteristicodorTheusesofMustardseeds counterirritantrubefacient condiment emeticinlargedoses Drug Acneaidsoap AgisTreatmentofAcne Sinapine alkaloids alkaloidalaminegroup protoalkaloidpropertiesofAcrinylisothiocynate 1 Lessirritantthanallylisothiocynate 2 Lessvolatile 3 Odorless 4 Pungent UsesofwhitemustardseedsCondiment carminative counterirritant emetic OrganicsulfurdrugsGarliccloves CharacteristicodorofGarlicAllicin yellowliquidresponsiblefortheodorofGarlic Uses 1 Anti bacterial2 Anti hyperlipidemicactivityHDL3 anti histaminic4 anti coagulant5 Immunesystemstimulant Coatedtabletandcapsulesstomachacidinactivatesalliinaseenzyme CyanogenicglycosidesGroupglycosideswhichwidelydistributedbetweenthemembersofRosaceaefamily TheygavewithhydrolysisHCN Hydrocyanicacid Theyderivedfromnitrileofmandelicacid Cyanosideslike Amygdalin a Bitteralmondseeds b Apricotsseeds c Plumsseeds d Peachesseeds 2 Prunasin presentinWildCherrybark Prunussertina Linmarin LinseedsTheplantscontainenzymeemolsinwhichproduceduringhydrolysistwoenzymes1 Amygdalasehydro Amygdalin 2 Prunasehydro Prunasin FlavonoidsLargegroupofglycosideswhichwidelydistributedintheplantskingdomandinallplantsparts leaves roots rhizomes fruitspeels Variouscolorsinflowers yellow orange red purple Theyarebenzo gama pyronederivatives Theirchemicalstructurebasedon C6C3C6 ThegeneralusesofFlavonoidsandFlavonoidglycosides IncreaseelasticityofbloodvesselsspeciallyRutinandhesperidinwhichknownasvitamin p AntiinflammatoryactivitylikeTaxifolin AntispasmodicactivitylikeThymeandsageflavonoids Cytostaticactivity ClassificationofFlavonoidsaccordingtothemainnucleus C G Cardiacglycosides groupofglycosideswhichhaspowerfulactiononcardiacmuscles cardiacmusclestimulant C Gglyconepartconsistofone two threemonosaccharideunitsormoresimilarordifferentAglyconeparthassteroidalnucleuscyclopentanoperhudrophenanthreneB glyconepartofC GalwaysattachedatC 3positionofaglyconepartclassification1 cardenolide onedoublebond lactonering Hasfivememberlactonering unsaturated attachedatC17Bpositionofsteroidalnucleus 2 Bufadienolide containtwodoublebonds lactonering Hassixmember unsaturated lactoneringattachedatC 17alpha position WhatisimportantforactivityofC G 1 ThepresenceofhydroxylgroupinC14positionmakestheglycosideveryactiveandgivesrapidactioninthebody butifwechangeitto H groupthedrugwillbeinactiveorlessactive 2 ThepresenceofAlpha BetaunsaturatedlactoneringincreasestheactivityofC G butifwemakeitsaturatedtheC Gwillloseitsactivity 3 TheringjunctionsCis Trans Cismakethenucleusverystablesomoreactive 4 ThesugarpartincreasesabsorptionanddistributionofC GinthebodyS P Glucose Rhamnose Cymarose Digitoxose ExamplesofCardenolides1 DigitalisglycosidesDigoxinDigitoxinGitoxin 2 StrophanthusgratusC G Oubain 3 StrophanthusKombeglycoside K strophanthin BufadienolideexampleSquillbulbglycosideScillaren Chemicaltests 1 KellerKilianitest C G CH3COOH H2SO4 FeCl3brown2 Legaltest C G pyridinesodiumnitroprussideRedtopinkcolour Uses 1 CHF2 arrhythmias GeneralpropertiesofC G 1 Amorphouspowder2 bittertaste3 sol InH2O4 Insol InOrg solvents5 Verytoxiccompounds6 Odorlessdig Bindspecificantibody Tannins Complexnaturalorganiccompounds polyphenolic polyhydroxybenzoicacidderivativesorFlavanolderivatives Widelydistributedinthenature leaves barks immaturefruitsbut theydisappearduringripeningprocess Theyprotecttheplantsfromherbivorousanimals insects bacteriaandothersspeciallyduringgrowth likeinnewleaveswhichcontainhighpercentageoftannins Someofthemhavelowmolecularweightbut mostofthemhaveverylargemolecularweight Physico chemicalproperties Theyformcolloidalsolutionswithwater Noncrystallinesubstances Theiraqueoussolutionisacidic Theyhavesharppuckeringtaste Theyhaveastringentproperty Theyprecipitatedby alkaloids gelatin saltsofheavymetals proteins enzymes Tanninsareclassifiedinto Truetannins hydrolysable non hydrolysable 2 Pseudotannins Classificationoftannins Truetannins Hydrolysablegroup 1 Hydrolyzedbyacidsorenzymes Tannase 2 Theyareestersofasugar D glucose withoneo