1Chapter16LipidsBroadlydefinedasnaturallyoccurringnon-polarcompoundshavingsimplefunctionalgroups.fattyacids（脂肪酸）Fats/Oils（油脂）Phospholipids（磷脂）Glycolipids（糖脂）Waxes（蜡）Steroids（甾族化合物、甾体化合物）Prostaglandins（前列腺素）Fatsolublevitamins（脂溶性维生素）2I.NomenclatureoffattyacidcommonnamesSystematicnomenclature:twonumericalnomenclaturesystems:1. -Designation:Carbonnumberingstartsfromcarboxylgroup.2.-Designation:Carbonnumberingstartsfrommethylend.Shorthandnomenclature:describestotalnumberofcarbons,numberofdoublebondsandthepositionofthedoublebond(s)inthehydrocarbontail.Section1.Fattyacids:carboxylicacidwithlongchain3SaturatedFattyAcidspalmiticacid,棕榈酸，软脂酸,16:0stearicacid,硬脂酸,18:0-Designation-Designation-Designation-Designation4MonounsaturatedfattyacidsCis9-HexadecenoicAcid(PalmitoleicAcid,棕榈油酸),16:1cis 9-Designation-DesignationCis7-HexadecenoicAcid(PalmitoleicAcid,棕榈油酸),16:1cis 75Cis9-OctadecenoicAcid(oleicacid,油酸),18:1cis 9-Designation-DesignationCis9-OctadecenoicAcid(oleicacid),18:1cis 96linoleicacid,亚油酸,18:2cis9,12PolyunsaturatedFattyAcids-Designation-Designationlinoleicacid,18:2cis6,97-Designation-Designation-linolenicacid,-亚麻酸,18:3cis9,12,15-linolenicacid,18:3cis3,6,9Omega3fattyacidsareconsideredbeneficialforbrainfunction.8-Designation-Designationarachidonicacid,花生四烯酸,20:4cis5,8,11,14arachidonicacid,20:4cis6,9,12,159linoleicacid,-linolenicacidandarachidonicacidareessentialfattyacids（必需脂肪酸）.Essentialfattyacids:essentialinourdietsbecauseourbodiescannotmakethem,yetusethemtomakemanyotherfattyacidsourbodiesmusthave.10Essentialfattyacidsarenecessaryfortheformationofhealthycellmembranes,theproperdevelopmentandfunctioningofthebrainandnervoussystem,andfortheproductionofhormone-likesubstancescalledeicosanoids(廿烷类):thromboxanes(血栓素),leukotrienes(白三烯),prostaglandins(前列腺素类).Whatisimportantisthatessentialfattyacidsareusedtobuildspecializedfatscalled-3and-6fattyacids.11Innature,almostallfattyacidshaveanevennumberofcarbons.Thisisduetothefactthatfattyacidsaresynthesizedstepwisefromacetylbuildingblocks.Unsaturatedfattyacidsalmostalwayshavecisdoublebonds.Transfattyacidsarefoundinavarietyofcookies,chips,andcommercialbakedgoods.Theycanbeproducedwhenoilisusedforfryingfoods.Partialhydrogenationofunsaturatedfattyacidsalsoleadstoproducetransfattyacids.Transfattyacidshaverecentlygainednotorietyasbeingworsewithrespecttoheartdiseasethanevensaturatedfattyacids.1213Trans反反14Inrecentyears,someliteraturesreportedthathighunsaturateddegreefattyacids,suchasEPA(Eicosapentaenoicacid)andDHA(Docosahexaenoicacid)canreducebloodfat,becausetheyincreasetheamountofhighdensitylipoprotein(HDL)anddecreasetheamountoflowdensitylipoprotein(LDL)inplasm.EPA,20:5cis3,6,9,12,15DHA,22:6cis3,6,9,12,15,18JenniferConnelly(詹妮弗康纳利)“OnceUponaTimeinAmerica”(美国往事)16AudreyHepburn(奥黛丽赫本)171819Prostaglandins前列腺素Leukotrienes白三烯cycloxygenase,COX环氧合酶5-Lipoxygenase,LOX5-脂氧化酶COX-1(固有型)，COX-2(诱生型)20尼美舒利（Nimesulide）2011年5月20日，国家食品药品监督管理局（SFDA）决定调整“尼美舒利”临床使用，禁止其用于12岁以下儿童。因该药对中枢神经和肝脏造成损伤的案例时常出现。SelectiveCOX-2inhibitor21Celecoxib(塞来昔布)Celebrex(西乐葆)，1998SpecificCOX-2inhibitorsPfizer,辉瑞Rofecoxib(罗非昔布），1999Vioxx(万络）Merck,默克，默沙东22II.PhysicalpropertiesoffattyacidsMeltingPointsandSolubilityinWaterofFattyAcidsMeltingPointSolubilityinH2OChainlength23C4-8-C6-4970C81675C10316C12440.55C14540.18C16630.08FattyAcidsm.p.()mg/100mlSolubleinH2OC18700.0424Thephysicalpropertiesofsaturated(nodoublebonds)andunsaturated(oneormoredoublebond)fattyacidsdifferconsiderably.Typically,saturatedfattyacidsarewaxysolidsatroomtemperature,whereasunsaturatedfattyacidsareoilsatthistemperature.25EffectsofDoubleBondsontheMeltingPointsm.pnumbersofdoublebond16:06016:1118:06318:11618:2-518:3-1120:07520:4-50F.A.m.p.()26stearicacid18:0cisoleicacid18:1cis9transoleicacid18:1trans927Saturatedlipids:veryclosepackingofthesidechains,assumeanalmostcrystallinearray.Thekinkthatresultsfromcisdoublebonds,tightpackingoffattyacidchainscannottakeplace.Sincetheinteractionsbetweenthethesearraysarelessextensive,ittakeslessenergytodisruptthem,resultinginalowermeltingpoint.Transfattyacidscanpacksimilarlytosaturatedfattyacids,andthustheyhavemarkedlyhighermeltingpoints.vanderWaalsinteraction282918:2cis6,918:3cis3,6,920:5cis3,6,9,12,1522:6cis3,6,9,12,15,1830Section2.OilsandFatsOilsandfatsaretriacylglycerols(三酰甘油)(triglycerides,甘油三酯),andtheacylgroupsarecomefromeven-numberedlong-chainacids,whicharecalledfattyacids.Customarily,thoseliquidformtriacylglycerolsatroomtemperaturearecalledoils;thesolidformorsemisolidformtriacylglycerolsarecalledfats.Butoilsandfatshavethesamegeneralstructureformulaandhavethesamechemicalproperties.CompositionandStructure31generalstructureformulaofoilsandfatsIfR1,R2,R3aresamegroup,thetriacylglycerolaresimpleglycerides(单三酰甘油单三酰甘油);ifR1,R2,R3aredifferentgroup,thetriacylglycerolaremixedglycerides(混三酰甘油混三酰甘油);.32FATS vs. OILS AnimalsourceFAsmostlysaturatedsolidatRTenergyreservePlantsourceFAsmostlyunsaturatedliquidatRTenergyreserve33Veryconcentratedformofenergy:39kJ/gram(9calories/gram),ourbodiesstoretriglyceridesinfatcellsifweeatextrafoodFatprovides39kJ/gram(protein17andcarbohydrate16kJ/g）3435I.ChemicalProperties1.Saponification(皂化)Saponificationisbase-inducedhydrolysisofanester,usuallyafattyacid.36Thesaltsoflong-chainfattyacidsarecalledsoaps.Thesodiumsaltis“hardsoap,”thegeneralsoapweuseeveryday.Thepotassiumsaltisthe“softsoap.”Adipocere（尸蜡）：Abrown,fatty,waxlikesubstancethatformsondeadanimaltissuesinresponsetomoisture.37Soapman:TheMummyMadeofSoapSmithsoniansNationalMuseumofNaturalHistory10thSt.&ConstitutionAve.NW,Washington,DC38祛痰止咳；开窍通闭；杀虫散结GleditsiasinensisLam皂荚ChineseHoneylocustFruit皂角39hydrophobic(water-hating)hydrophilic(water-loving)40H2OH2OH2OH2OH2OH2OH2OH2OH2OH2OH2OH2OH2OH2OMicelle Structurepolarnonpolar(胶团胶团,胶束胶束)41addheat&agitate.dirtandgreaseHowSoapWorks?42addheat&agitate.43micellesreformspontaneouslyandtrapdirt:dirtissolubleceasemechanicaldisruption.4445DisadvantagesofSoaps:Acidicconditionsconvertssoaptofree,insoluble,fattyacidsDoesntworkwellinhardwater.Thenegativesoapreactswiththepositivelychargedmetalionsandbecomeinsolubleformingthecharacteristicbathtubring.46Similarmicellarspeciesareformedfromdetergents,whicharelong-chainsulfonicacidsalts.Organicdirt(grease)isnotwater-solubleandisnoteasilyremovedwithouttheaidofasoaporadetergent.However,whenadetergentisused,thegreaseisdissolvedbythehydrocarbon-likeinternalportionofthemicellesandmadesolubleinwaterbythepolaracidsaltsoutside.47Thedesigncriteriaforagooddetergentare:(1)alonghydrocarbontailof12to20carbons(2)apolarheadgroupthatdoesnotforminsolublesaltswithCa2+,Mg2+,orFe3+ions.Themostwidelyusedsyntheticdetergentsarethelinearalkylbenzenesulfonates(LAS)SyntheticDetergents:48sodium4-dodecylbenzenesulfonate(ananionicdetergent)dodecylbenzenesulfonate4950DrainCleaners:NaOH+AlOftencontainsodiumhydroxideasasolidorconcentratedliquidNaOHreactswithwaterinthepipetogenerateheatwhichmeltsgreaseNaOHalsoreactswithfatconvertingittosoapwhichcleansouttheremaininggreaseinpipeSomeproductsalsoaddaluminumwhichreactswithNaOHtoformhydrogengaswhichbubblesoutthecloggedareasofthedrainManyliquiddraincleanerscontainNaOClandNaOHBleachdegradeshairtounclogshowerdrains51BiologicalDieselOil(生物柴油)：52Saponificationnumber:Theamount(mg)ofKOHthatcanhydrolyze1goilsandfatscompletely.Wecanusethesaponificationnumbertodeducetheaveragemolecularweightofoilsandfatsapproximately.saponificationnumberaveragemolecularweightcontentoflowmolecularweightoilsandfatslargesmallsmalllargehighlow532.Addition(1)AdditionofhydrogenTheunsaturatedfattyacidsportionofoilsandfatswillbehydrogenizedtobecomesaturatedfattyacids.Whichwillmaketheliquidoilsbecomesolidfats,sothereactionalsocalledindurationofoils(硬化油).Forexample,margarine(人造黄油)ismadebythemethod.5455Partialhydrogenationgivessemi-solidfats,butleadstoisomerizationofthedoublebondstogiveunnaturaltransfattyacidsascomponentsofthetriacylglycerols.56The50WorstInventions(Timemagazine)No.10HydrogenatedOils(28May2010)Timemagazinehasalistofwhatitseditorsconsidertobetheworstinventionsof.57-CaroteneVitaminA1，维生素A1，视黄醇VitaminA258(2)AdditionofiodineIodinenumber:theamountofiodine(g)whichbeabsorbedby100goilsandfats.Iodinenumbercanbeusedtodeducetheunsaturateddegreeofoilsandfats.iodinenumberunsaturateddegreelargesmallhighlow59Saturatedfatscontainsinglecovalentbondsandarecoveredwithhydrogenatoms-lard(猪油).Monounsaturatedarenotcompletelycoveredwithhydrogen-oliveandpeanutoil.Polyunsaturatedfatscontainevenlesshydrogenatoms-saffloweroil(红花油),cornoil.Determinedbythenumberofsingleordoublecovalentbondsinfattyacid.61(3)Rancidity（酸败）a.unsaturatedfattyacids62b.saturatedfattyacids63Acidicnumber:theamount(mg)ofKOHwhichcanneutralizethedissociatedfattyacidsof1goilsandfats.acidicnumberdissociatedfattyacidthedegreeofranciditylargesmallmorelesslargesmall6465SyntheticAntioxidantsButylatedhydroxyanisole(BHA)Butylatedhydroxytoluene(BHT)PropylgallateTertiarybutylhydroquionone(TBHQ)66NaturalAntioxidantsBenefits:HealthimplicationStabilityinfoodsystemLimits:CharacteristicflavorSafetytestrequired67Tocotrienolstocotrienols(生育三烯酚类)TrivialName ChemicalNameR1R2R3-Tocotrienol5,7,8-TrimethyltocotrienolCH3CH3CH3-Tocotrienol5,8-DimethyltocotrienolCH3HCH3-Tocotrienol7,8-DimethyltocotrienolHCH3CH3-Tocotrienol8-MethyltocotrienolHHCH368VitaminE,Tocopherol(生育酚)d-tocopherolismosteffective69TeaEpicatechinEpigallocatechin表儿茶素,茶丹宁I(-)-表没食子儿茶素70AscorbicAcidandRelatedCompoundsL-AscorbicAcid(VitaminC)ErythorbicAcidAscorbicPalmitate抗坏血酸，维生素C异抗坏血酸71Section3PhospholipidsandGlycolipids.Phospholipidsphospholipidsphosphoglycerides(甘油磷脂)sphingomyelins(鞘磷脂)1.Phosphoglycerides:thederivativesofphosphatidicacidphosphatidic acidR(磷脂酸)72GlycerolIfthesecondaryhydroxylgroupofglyceroltotheleftofC-2inFisherProjection,thecarbonaboveC-2isC-1andthebelowC-3Theuseofthisstereospecificnumbering(立体专一编号)isindicatedbytheprefix“Sn”beforethesystematicnameofthecompound73Sn-Glycero-1-PhosphateSn-Glycero-3-Phosphate74Inphosphatidate:fattyacidsareesterifiedtohydroxylsonC1andC2theC3hydroxylisesterifiedtoPi.phosphatidate75Inmostphosphoglycerides(glycerophospholipids),PiisinturnesterifiedtoOHofapolarheadgroup(X),e.g.:serine（丝氨酸（丝氨酸）,choline,ethanolamine,glycerol,orinositol(肌醇肌醇).The2fattyacidstendtobenon-identical.Theymaydifferinlengthand/orthepresence/absenceofdoublebonds.phosphoglycerides76Phosphatidylcholine,withcholineaspolarheadgroup,isanexampleofaglycerophospholipid.Itisacommonmembranelipid.Phosphatidylcholine(磷脂酰胆碱，卵磷脂)77Phosphatidylinositol,withinositolaspolarheadgroup,isanotherglycerophospholipid.Inadditiontobeingamembranelipid,phosphatidylinositolhasrolesincellsignaling.Phosphatidylinositol(磷脂酰肌醇)78Eachglycerophospholipidincludesapolarregion:glycerol,carbonyloffattyacids,Pi,andthepolarheadgroup(X),2non-polarhydrocarbontailsoffattyacids(R,R).Itisanamphipathicmolecule.polarnon-polarkinkduetodoublebond79Representativephosphoglycerides:phosphatidylcholine,Lecithin（卵磷脂，PC）cholineAbundantinbrainandnervetissuesFirstfoundineggyolk80phosphatidylethanolamine,-Cephalin（-脑磷脂，PE）ethanolamine81Lecithincanbedissolvedinalcohol,etherandchloroform.-Cephalincanbedissolvedinether,butcannotbedissolvedincoldalcohol.82phosphatidylserine(磷脂酰丝氨酸)serine83Thethreemostcommonfamiliesofmembraneglycerophospholipidsare:phosphatidylethanolaminephosphatidylserinephosphatidylcholineThesearenotsinglecompoundsbutratherfamiliesofmoleculesthathavethesamepolarheadgroupbutdifferentfattyacylchainsesterifiedatC-1andC-2oftheglycerolbackbone.84PhosphoglycerideMembranesPhosphoglyceridescomprisethemajorlipidcomponentofcellmembranesNonpolartailsaggregateinthecenterofabilayerIonicheadisexposedtosolvent852.Sphingomyelin(神经磷脂,鞘磷脂):Majorcomponentofmyelinsheaths(髓鞘)thatsurroundnervecellsABCDA:sphingol（sphingosine,鞘氨醇）,B:fattyacid,C:phosphoricacid,D:choline,A+B:ceramide（神经酰胺）86FoundinthemyelinsheathConstituentsofplantandanimalcellmembranesAbundantinbrainandnervetissue,ascoatingaroundnervefibers.87Sphingomyelinscontainphosphocholineorphosphoethanolamineastheirpolarheadgroup.Althoughtheydifferchemicallyfromphosphatidylcholineandphosphatidylethanolamine(twoglycerophospholipids),theirconformationsandchargedistributionsarequitesimilar.SphingomyelinPhosphatidylcholine88Niemann-Pickdisease（尼曼匹克症）isageneticdefectinsphingomyelindegradation.CausesSphingomyelinaccumulationinbrain,spleenandliver.Causesmentalretardation(精神发育迟缓).Childrendiebyage3or4.89脂质体909192PermeabilitypropertiesofphospholipidmembranesGasesO2,CO2,NOSmall,unchargedethanolpolarmoleculesWaterH2OLarge,unchargedglucosepolarmoleculesIonsNa+,K+,Mg2+,Ca2+Cl-,HCO3-,HPO42-Chargedaminoacids,nucleotides,polarmoleculessugarphosphatesHydrophobicsteroidhormonesmolecules93(脂质体)9495LipidsandmembranefluidityThefluidityofalipidbilayerdependson:compositiontemperatureFattyacylchainsinlipidmembranescanexistinanordered,rigidstateorinadisorderedfluidstateThischangeofstateiscalledaphasetransition(相变相变)andthetemperatureatwhichitoccursisthemeltingtemperatureortransitiontemperature(afreezingpoint),Tm.Membranephospholipidsnormallyhavetransitiontemperaturesbelow12C.9697MembranefluidityisdependentonlipidfluidityLipidfluidityisdependenton:C-CchainlengthandthenumberofC=Cbonds.Cis-doublebondsandshorthydrocarbonchainsincreasefluiditybecausethehydrocarbonchainsdontpackaswellaslongsaturatedhydrocarbonchains.Theratiooflecithin(卵磷脂)andsphingomyelin(鞘磷脂),moresphingomyelindecreasefluiditybecausetheviscosityofsphingomyelinishighthanlecithins.Itisanimportantbiologicalfeatureofmembranesbecauseitallowsinteractionofproteinsembeddedwithinthebilayer.98.Glycolipid(cerebroside)糖脂（脑苷脂）containsonemonosaccharideresidueattachedtoC-1ofceramide(神经酰胺)GlucoseandgalactosearecommonCanhaveupto3moremonosaccharideresiduesattachedtosugaronC1AbundantinnervetissueUpto15%ofmyelinsheathmadeupofcerebrosides99-galactocerebroside(-半乳糖脑苷脂)100Section4Steroids（甾族化合物，甾体）.StructureandNumberingSteroidsarecommonlyfoundinnatureandareconsideredimportantprimarilybecauseoftheirpowerfulbiologicalactivities.Theyoftenfunctionasregulatorsofhumanbiology.Manynaturallyoccurringsteroidshavebeenconstructedinthelaboratoryandnumerous“unnatural”steroidshavebeencreatedaswell.10112345678910111213141516171819Allsteroidssharethefour-ringskeletonofthemoleculeshownabove.TheringsaredesignatedA,B,CandD,andnumberedasshownabove.Usually,steroidshaveaxialmethylgroups(angularmethylgroups，角甲基)attachedtoC(10)andC(13),andoftencarryanoxygenatomatC(3)andacarbonchainatC(17).甾災災*102Therearetwokindsofnaturalsteroids.Oneis5-steroids(5系，别系),anotheroneis5-steroids(5系，正系).AllnaturalsteroidsBandCring,CandDringaretransringfusions.ThedifferenceisthefusionofAandBring.IfAandBringistransringfusion(eefusion),theyare5-steroids;ifAandBringiscisringfusion(eafusion),theyare5-steroids.5-steroidsaremorecommonthan5-steroids.1035-steroidsSubstituentspointeitherdown(dashedbond,)orup(solidbond,)1041055-steroids1065-steroids1075-steroids1081095-steroids1105-steroids111II.FunctionsofSteroidsInhumansashormones,steroidsarechemicalmessengerssecretedbyglandsandcarriedthroughthebloodstreamtotargettissuesAlsowidelydistributedascholesterol112(1)MaleSexHormonesTestosteroneandandrosteronearethetwomostimportantmalesexhormones,orandrogensAndrostenedioneisaprecursorTestosterone睾酮，睾丸素Androsterone雄甾酮Androstenedione雄烯二酮1.SexhormonesQuestion:Testosteroneis5-steroidor5-steroid?（麝香味）113Dihydrotestosterone,DHTTestosterone,T二氢睾丸酮114Through5-alphareductase,testosteroneisconvertedtoahormone4Xaspotent,dihydrotestosterone.DHTbindstoreceptorsmuchmoreavidlythantestosterone.5-alphareductaseispresentinhighamountsintissuesoftheprostate,skin,scalp(头皮),liver,andcentralnervoussystem.115Proscar,Finasteride，Finasterideisa4-azasteroid.Itsainhibitorof5-reductase.Whichcanbeusedtotreatbenignprostatichyperplasia(BPH，良性前列腺增生,Proscar,保列治,5mg),alopecia(losehair,Propecia,保法止,1mg)andacne.116保列治，5mg*10片，约66元，1mg/1.3RMB保法止，1mg*28片，约258元，1mg/9.2RMB117(2)FemaleSexHormonesEstroneandestradiolarethetwomostimportantfemalesexhormones,orestrogensProgesteroneisthemostimportantprogestin,steroidsthatfunctioninpregnancyEstroneEstrodiolEstriolActivity:0.310.1118Progesteroneisthemostimportantprogestin,steroidsthatfunctioninpregnancy.Progesterone(Progestin)，孕酮,黄体酮119SomethingMore:Mifepristone(Ru486)米非司酮，含珠停,息隐Medroxyprogesterone甲孕酮,安宫黄体酮September23,1988120MifepristoneisinventedbyRoussel-UclafCompanyinFrance.Whichisaantigestagen,caninduceabortionintheearlystageofpregnancy.Low-doseMifepristonealsousedinemergencycontraception.121122WichitaabortionproviderGeorgeTiller（乔治蒂勒）shottodeathatWichitachurch(May31,2009)123米索前列醇，MisoprostolderivativeofPGE1124Levonorgestrel,左炔诺孕酮（毓婷）Usedinemergencycontraceptionethinylestradiol,炔雌醇125SEASONALE(levonorgestrel/ethinylestradioltablets)0.15mg/0.03mg(levonorgestrel/ethinylestradioltablets)0.15mg/0.03mgand(ethinylestradioltablets)0.01mgSEASONIQUE季信、季事September,2003July,2006126Lybrel(levonorgestrel/ethinylestradioltablets)0.09mg/0.02mg（来不了）（来不了）May,2007NoMorePeriods!127Anabolicsteroids(促蛋白合成甾类,同化激素):Anyhormonalsubstance,chemicallyandpharmacologically,relatedtotestosteronethatpromotesmusclegrowth(DEA,DrugEnforcementAdministration).Increasedskeletalmusclemass,bonedensity,hemoglobin,nitrogenretentionandproteinsynthesis.128DianabolStanozolol大力补康力龙Thesetwocompoundsaresyntheticanabolichormones,canusedasmedicine,alsocanusedasperformance-enhancementinathleticsports.129孙英杰王德显2005年10月十运会130BenJohnsonset100mworldrecord(9.83)at1987WorldChampionshipsCarlLewis131BenJohnsonbeatCarlLewis9.79to9.92intheMens100mFinalsintheSeoulOlympics(1988).132133Anabolic“building”,increasedskeletalmusclemass,bonedensity,hemoglobin,nitrogenretentionandproteinsynthesis.Androgenicandrogensaresexhormonesthatcaninducemaletraits(e.g.growthofsexorgans,increasedbodyhair,libido,skinoil,andchangeinvoice).Anabolic/Androgenicsteroids(AAS)seektomaximizetheanaboliceffectswhileminimizingtheandrogeniceffects.Theratiooftheseanabolic/androgeniceffectsiscalledthetherapeuticindex（治疗指数）（治疗指数）.Testosteroneisthebaselineat1.134Tetrahydrogestrinone(四氢孕三烯酮,THG,BalcoLab)GestrinoneTrenbolone去甲雄三烯醇酮135Tetrahydrogestrinone(THG)isaspeciallydesignedperformance-enhancingdrug(anabolicsteroid)modifiedtotrytoavoiddetectionduetomorerigoroustestingTHGschemicalstructureislikethecompoundstrenboloneandgestrinone,bothofwhicharebannedforathleticusebyinternationalsportsfederationsundertheanabolicagentscategory.TheWorldAnti-DopingAgency(WADA)listsprohibitedsubstancesundereightcategories:stimulants,narcotics,cannabinoids,anabolicagents,peptidehormones,beta-2agonists,agentswithanti-oestrogenicactivity,andmaskingagents.Italsolistsseveralprohibitedperformance-enhancementmethods,suchasoxygenenhancementandgenedoping.136DualsprintworldchampionKelliWhiteWednesday,May19,2004,AmericansprinterKelliWhiteacceptedatwo-yearbanforTHGuse.137Montgomeryranaworld-best9.78secondsinthe100minParisinSeptember2002.MarionJonesTimMontgomery138hammerthrowerJohnMcEwen.139Androisavailableoverthecounter(OTC)!Androstenedione(Andro)AndrostenediolDehydroepiandrosterone(DHEA)SteroidPrecursors/Prohormones脱氢表雄酮140141PositivesideeffectsofAAS:Enhancedmusclemass/strengthEnhancedbloodvolumeandhemoglobinconcentrationEnhancedbonedensityandstrengthHastenedhealingofmuscularinjuriesDecreasedbodyfatIncreasedimmuneresponseElevatedmood142ClinicalApplications:Bonemetabolismconditionsosteoporosis(骨质疏松症)Testosteronedeficiencyconditionsmalehypogonadism,andropause（男性更年期）syndromeCardiovascularconditionsreducesanginapectoris（心绞痛）,coronaryarterydisease（冠心病）AIDSreducesAIDSwasting143Generallysideeffectsofanabolicsteroidusemayincludejaundice(黄疸)andliverdamage,hypertension,acne,fluidretentionheartenlargement,euphoria(异常欣快),improvedself-esteem,moodswings,depression,paranoia(妄想狂)andaggression.Effectsspecifictofemalesmayincludeanincreaseinfacialandbodyhair,menstrualproblems,andpermanentdeepeningofthevoice,foetaldamageandclitoralenlargement.SideEffectsofanabolicsteroid:144邹春兰145Effectsspecifictomalesmayincludethedevelopmentofbreasttissue,infertility,baldness,libidoreductionandbenignprostateenlargement.146Girlsareabusingsteroidstoo,expertssay（CNN,April25,2005）Teenshopingtoloseweightfacedangeroushealth.AnalarmingnumberofAmericangirls,someasyoungas9,areusingbodybuildingsteroidsnotnecessarilytogetanedgeontheplayingfield,buttogetthetoned,sculptedlookofmodelsandmoviestars,expertssay.Overall,uptoabout5percentofhighschoolgirlsand7percentofmiddle-schoolgirlsadmittryinganabolicsteroidsatleastonce,withuseofrisingsteadilysince1991,variousgovernmentanduniversitystudieshaveshown.1471482.AdrenocorticalHormones(肾上腺皮质激素肾上腺皮质激素)Adrenocorticalsteroids:secretedbytheadrenalglandsneartheupperendofeachkidney.(1)Mineralocorticoids（盐皮质激素）:controltissueswellingbyregulatingcellularsaltbalance.aldosterone醛固酮醛固酮149(2)Glucocorticoids（糖皮质激素）:regulationofglucosemetabolismandinthecontrolofinflammation.cortisonecortisol可的松氢化可的松150PhilipHench亨奇TadeusReichstein莱希斯坦因EdwardKendall肯德尔TheNobelPrizeinPhysiologyorMedicine(1950)151SomethingMore:FluocinoloneAcetonideAcetateThismedicineisasyntheticglucocorticoid.sodiumretention152Dexamethasoneacetate,醋酸地塞米松153Beclomethasonedipropionate二丙酸倍氯米松TheBeclomethasonedipropionatecanbeusedtoantiallergicrhinitisandasthma.154155DoctorsinHongkonguseRibavirinandglucocorticoids(Prednisolone,Methylprednisolone)totreatSARS(SeriousAcuteRespiratorySyndrome)(atypicalpneumonia)Ribavirin，利巴韦林，三氮唑核苷，病毒唑156Prednisolone(泼尼松龙,氢化泼尼松,强的松龙)Methylprednisolone(甲泼尼龙,甲基强的松龙)157Reductioningrowthinchildren.Muscleweakness,especiallyoftheshouldermusclesandthighs.Rarely,avascularnecrosisofthefemoralhead(destructionofthehipjoint).Diabetescanbeprecipitatedoraggravated.Increaseincirculatingbloodfat(triglycerides).Redistributionofbodyfat:moonface,buffalohumpandtruncalobesity.Sideeffectsofglucocorticoids158RedistributionofFatinGlucocorticoidExcessCentralobesityseeninCushingsSyndrome(GlucocorticoidExcess)159Buffalohump160moonface1613.Cholesterol(Cholesterin)Cholesterolwasfoundin1770.Ithas8chiralcarbonatoms.Thecontentinhumanbodyis250g/75kgman.Thepresenceofthehydroxylgroupmakescholesterolamphipathic.*162163Cholesteroldecreasesmembranefluidityandbroadensthetemperaturerangeofmeltingofmembranesbyinterferingwiththeorderlypackingoflipidfattyacidsidechains.164CholesterolReducespermeabilityDecreasesfluidity,butincreasesfluidityatcooltemperaturesHydrophobiclipidLocatedwithinlipidbilayercholesteroldecreasesfluiditybecauseitrestrictsthemovementofthehydrocarbonchains.165Cholesterolistheprecursortoavarietyofsteroidhormones.孕烯醇酮孕酮166167ultravioletVitaminD37-dehydrocholesterolultravioletergosterol麦角甾醇VitaminD2168VitaminD3(cholecalciferol)isproducedintheskinwhen7-dehydrocholesterolisexposedtoUVradiation.VitaminD3isthenfurthertransformedintoahormonethatregulatescalciumuptakeandutilization.Rickets，佝偻病169-Sitosterol，-谷固醇，-谷甾醇Cholesterol-sitosterolreducesbloodlevelsofcholesterol,andissometimesusedintreatinghypercholesterolemia（高胆固醇血症）1703.CholicacidCholicacidglycocholicacidDeoxycholicacid(taurine牛磺酸)Taurocholicacid171Bileacids(salts)aregooddetergents.Theyaidindigestionbydissolvingfatsinthesmallintestineandallowingabsorptionintotheblood.172Prostaglandins:C20carboxylicacidsthatcontaina5-memberringandhavetwolongsidechainsOriginallyisolatedfromseminalfluid,sotheywereatfirstthoughttooriginateintheprostategland.Allarederivedfromarachidonicacid.Allhave20carbons.Section3Prostaglandinsarachidonicacid,20:4cis6,9,12,15173174175RepresentativeStructures176Biologicaleffects：ResponsibleforbloodclottingLowerbloodpressureStimulationofsmoothmusclesStimulateuterinecontractionsduringchildbirthRegulationofsteroidproductionInhibitionofgastricsecretionInhibitionofhormone-sensitivelipasesInhibition/stimulationofplateaggregationRegulationofnervetransmissionSensitizationtopainMediationofinflammatoryresponse(炎症反应)177Section4WaxesWaxesareestersoflong-chainsaturatedandunsaturatedfattyacids(C14toC36)withlong-chainalcohols(C16toC30).Waxestypicallyhavefairlyhighmeltingpoints,espeicallywhencomparedtotriacylglycerols.Naturalprotectivelayerinfruits,vegetables,etcCertainskinglandsofvertebratessecretewaxestoprotecthairandskinandkeepitpliable,lubricated,andwaterproof.Usedasenergysourcebyplankton（浮游生物）.178Spermaceti,鲸蜡Beeswax,蜂蜡whitewax,insectwax,Chinesewax,白蜡,虫蜡