醫(yī)用有機(jī)化學(xué)-脂類

1Chapter15LipidsBroadlydefinedasnaturallyoccurringnon-polarcompoundshavingsimplefunctionalgroups.fattyacids（脂肪酸）Fats/Oils（油脂）Phospholipids（磷脂）Glycolipids（糖脂）Waxes（蠟）Steroidsandterpenoids（甾族化合物、萜類化合物）Prostaglandins（前列腺素）Fatsolublevitamins（脂溶性維生素）Steroids（甾族化合物）2I.Nomenclatureoffattyacid(P.204):commonnamesSystematicnomenclature:twonumericalnomenclaturesystems1.-Designation:Carbonnumberingstartsfromcarboxylgroup.2.ω-Designation:Carbonnumberingstartsfrommethylend.Shorthandnomenclature:describestotalnumberofcarbons,numberofdoublebondsandthepositionofthedoublebond(s)inthehydrocarbontail.Section1.Fattyacids:carboxylicacidwithlongchain3SaturatedFattyAcidspalmiticacid,棕櫚酸，軟脂酸,16:0stearicacid,硬脂酸,18:0-Designationω-Designation-Designationω-Designation4cis9-OctadecenoicAcid(oleicacid,油酸),18:1cis9-Designationω-Designationcis9-OctadecenoicAcid(oleicacid),18:1cis9MonounsaturatedfattyacidsP.204倒數(shù)第2行至P.205第1行中油酸的縮寫符號(hào)不完整

5linoleicacid,亞油酸,18:2cis9,12PolyunsaturatedFattyAcids-Designationω-Designationlinoleicacid,18:2cis6,96-Designationω-Designation-linolenicacid,-亞麻酸,18:3cis9,12,15-linolenicacid,18:3cis3,6,9Omega3fattyacidsareconsideredbeneficialforbrainfunction.7ω-Designation-Designationarachidonicacid,花生四烯酸,20:4cis5,8,11,14arachidonicacid,20:4cis6,9,12,158必需脂肪酸（essentialfattyacids,EFA）是指人體維持機(jī)體正常代謝不可缺少而自身又不能合成，或合成速度慢無法滿足機(jī)體需要，必須通過食物供給的脂肪酸。必需脂肪酸一般包括亞油酸(linoleicacid,ω-6)、-亞麻酸(-linolenicacid,ω-3)和花生四烯酸(arachidonicacid,ω-6)。亞油酸(linoleicacid,ω-6)和-亞麻酸(-linolenicacid,ω-3)是人體自身無法合成的兩種脂肪酸。arachidonicacid花生四烯酸leukotrienes白三烯

lipoxygenase(脂氧合酶)prostaglandinH2

前列腺素H2

prostaglandins前列腺素thromboxanes血栓素cyclooxygenase(COX,環(huán)氧合酶)PGsynthase(前列腺素合成酶)thromboxanesynthase(TX合成酶)linearpathway(線型途徑)cyclicpathway(環(huán)合途徑)Aspirin阿司匹林//10天然脂肪酸的結(jié)構(gòu)特點(diǎn)：幾乎所有的天然脂肪酸均含偶數(shù)碳原子幾乎所有天然不飽和脂肪酸中碳-碳雙鍵的構(gòu)型為順式構(gòu)型反式脂肪酸（Transfattyacids）的產(chǎn)生途徑：天然脂肪酸被加熱，特別是反復(fù)加熱對(duì)天然脂肪酸進(jìn)行部分氫化反應(yīng)（制備氫化油）1112Trans反13Inrecentyears,someliteraturesreportedthathighunsaturateddegreefattyacids,suchasEPA(Eicosapentaenoicacid)andDHA(Docosahexaenoicacid)canreducebloodfat,becausetheyincreasetheamountofhighdensitylipoprotein(HDL)anddecreasetheamountoflowdensitylipoprotein(LDL)inplasm.EPA,20:5cis3,6,9,12,15

DHA,22:6cis3,6,9,12,15,18

JenniferConnelly(詹妮弗·康納利),

December12,1970“OnceUponaTimeinAmerica”(美國往事)15AudreyHepburn(奧黛麗·赫本)161718Prostaglandins前列腺素Leukotrienes白三烯cycloxygenase,COX環(huán)氧合酶5-Lipoxygenase,LOX5-脂氧化酶COX-1(固有型)，COX-2(誘生型)arachidonicacid花生四烯酸19尼美舒利（Nimesulide）2011年5月20日，國家食品藥品監(jiān)督管理局（SFDA）決定調(diào)整“尼美舒利”臨床使用，禁止其用于12歲以下兒童。因該藥對(duì)中樞神經(jīng)和肝臟造成損傷的案例時(shí)常出現(xiàn)。SelectiveCOX-2inhibitor20Celecoxib(塞來昔布)Celebrex(西樂葆)，1998SpecificCOX-2inhibitorsPfizer,輝瑞Rofecoxib(羅非昔布），1999Vioxx(萬絡(luò)）Merck,默克，默沙東21II.PhysicalpropertiesoffattyacidsMeltingPointsandSolubilityinWaterofFattyAcidsMeltingPointSolubilityinH2O脂肪酸碳鏈長度22C4-8

-C6-4970C81675C10316C12440.55C14540.18C16630.08SaturatedFAm.p.(℃)mg/100mlSolubleinH2OC18700.0423EffectsofDoubleBondsontheMeltingPoints16:06016:1118:06318:11618:2-518:3-1120:07520:4-50F.A.m.p.(℃)飽和與不飽和脂肪酸的物理性質(zhì)相差很大，飽和脂肪酸在室溫下一般呈蠟狀固體，而不飽和脂肪酸在室溫下一般為液態(tài)油狀物。24stearicacid18:0cisoleicacid18:1cis9

transoleicacid18:1trans9

25Saturatedlipids:veryclosepackingofthesidechains,assumeanalmostcrystallinearray.Thekinkthatresultsfromcisdoublebonds,tightpackingoffattyacidchainscannottakeplace.Sincetheinteractionsbetweenthethesearraysarelessextensive,ittakeslessenergytodisruptthem,resultinginalowermeltingpoint.Transfattyacidscanpacksimilarlytosaturatedfattyacids,andthustheyhavemarkedlyhighermeltingpoints.vanderWaalsinteraction262718:2cis6,918:3cis3,6,920:5cis3,6,9,12,1522:6cis3,6,9,12,15,1828Section2.OilsandFats（油脂）Oilsandfatsaretriacylglycerols(三酰甘油，triglycerides,甘油三酯),andtheacylgroupsarecomefromeven-numberedlong-chainacids,whicharecalledfattyacids.Ⅰ.CompositionandStructureliquidformatroomtemperature→oilssolidorsemisolidformatroomtemperature→fats29generalstructureformulaofoilsandfatsIfR1,R2,R3aresamegroup,thetriacylglycerolaresimpleglycerides(單三酰甘油);ifR1,R2,R3aredifferentgroup,thetriacylglycerolaremixedglycerides(混三酰甘油).P.203天然油脂為L構(gòu)型？？30FATS

vs.OILS

AnimalsourceFA’smostlysaturatedsolidatRTenergyreservePlantsourceFA’smostlyunsaturatedliquidatRTenergyreserve31Veryconcentratedformofenergy:39kJ/gram(9calories/gram),ourbodiesstoretriglyceridesinfatcellsifweeatextrafoodFatprovides39kJ/gram(protein17andcarbohydrate16kJ/g）3233I.ChemicalProperties1.Saponification(皂化)34Thesaltsoflong-chainfattyacidsarecalledsoaps.Thesodiumsaltis“hardsoap,”thegeneralsoapweuseeveryday.Thepotassiumsaltisthe“softsoap.”Adipocere（尸蠟）：Abrown,fatty,waxlikesubstancethatformsondeadanimaltissuesinresponsetomoisture.35Soapman:TheMummyMadeofSoapSmithsonian'sNationalMuseumofNaturalHistory10thSt.&ConstitutionAve.NW,Washington,DC36祛痰止咳；開竅通閉；殺蟲散結(jié)GleditsiasinensisLam皂莢ChineseHoneylocustFruit皂角37hydrophobic(water-hating)hydrophilic(water-loving)38H2OH2OH2OH2OH2OH2OH2OH2OH2OH2OH2OH2OH2OH2OMicelleStructurepolarnonpolar(膠團(tuán),膠束)39addheat&agitate.....dirtandgreaseHowSoapWorks?40addheat&agitate.....41micellesreformspontaneouslyandtrapdirt:dirtis‘soluble’ceasemechanicaldisruption....42DisadvantagesofSoaps:Acidicconditionsconvertssoaptofree,insoluble,fattyacidsDoesn’tworkwellinhardwater.Thenegativesoapreactswiththepositivelychargedmetalionsandbecomeinsolubleformingthecharacteristicbathtubring.43Similarmicellarspeciesareformedfromdetergents,whicharelong-chainsulfonicacidsalts.Organicdirt(grease)isnotwater-solubleandisnoteasilyremovedwithouttheaidofasoaporadetergent.However,whenadetergentisused,thegreaseisdissolvedbythehydrocarbon-likeinternalportionofthemicellesandmadesolubleinwaterbythepolaracidsaltsoutside.44Thedesigncriteriaforagooddetergentare:(1)alonghydrocarbontailof12to20carbons(2)apolarheadgroupthatdoesnotforminsolublesaltswithCa2+,Mg2+,orFe3+ions.Themostwidelyusedsyntheticdetergentsarethelinearalkylbenzenesulfonates(LAS)SyntheticDetergents:45sodium4-dodecylbenzenesulfonate(ananionicdetergent)dodecylbenzenesulfonate4647DrainCleaners:NaOH+AlOftencontainsodiumhydroxideasasolidorconcentratedliquidNaOHreactswithwaterinthepipetogenerateheatwhichmeltsgreaseNaOHalsoreactswithfatconvertingittosoapwhichcleansouttheremaininggreaseinpipeSomeproductsalsoaddaluminumwhichreactswithNaOHtoformhydrogengaswhichbubblesoutthecloggedareasofthedrainManyliquiddraincleanerscontainNaOClandNaOHBleachdegradeshairtounclogshowerdrains48BiologicalDieselOil(生物柴油)：4950Saponificationnumber:Theamount(mg)ofKOHthatcanhydrolyze1goilsandfatscompletely.(P.205)Wecanusethesaponificationnumbertodeducetheaveragemolecularweightofoilsandfatsapproximately.saponificationnumberaveragemolecularweightcontentoflowmolecularweightoilsandfatslargesmallsmalllargehighlow512.Addition(1)AdditionofhydrogenTheunsaturatedfattyacidsportionofoilsandfatswillbehydrogenizedtobecomesaturatedfattyacids.Whichwillmaketheliquidoilsbecomesolidfats,sothereactionalsocalledindurationofoils(硬化油).Forexample,margarine(人造黃油)ismadebythemethod.5253Partialhydrogenationgivessemi-solidfats,butleadstoisomerizationofthedoublebondstogiveunnatural"trans"fattyacidsascomponentsofthetriacylglycerols.54The50WorstInventions(Timemagazine)No.10HydrogenatedOils(28May2010)Timemagazinehasalistofwhatitseditorsconsidertobetheworstinventionsof.55-Carotene（-胡蘿卜素）VitaminA1，維生素A1，視黃醇VitaminA2P.218P.19556β-胡蘿卜素?cái)z食過度會(huì)造成胡蘿卜素沉著癥（Carotenodermia）。它對(duì)人體無害，但會(huì)表現(xiàn)為皮膚的橙色色素沉著。57(2)AdditionofiodineIodinenumber:theamountofiodine(g)whichbeabsorbedby100goilsandfats.(P.206)Iodinenumbercanbeusedtodeducetheunsaturateddegreeofoilsandfats.iodinenumberunsaturateddegreelargesmallhighlow58Saturatedfatscontainsinglecovalentbondsandarecoveredwithhydrogenatoms----lard(豬油).Monounsaturatedarenotcompletelycoveredwithhydrogen----oliveandpeanutoil.Polyunsaturatedfatscontainevenlesshydrogenatoms----saffloweroil(紅花油),cornoil.Determinedbythenumberofsingleordoublecovalentbondsinfattyacid.60(3)Rancidity（酸敗）a.unsaturatedfattyacids61b.saturatedfattyacidsP.157酮式分解酸式分解62Acidicnumber:theamount(mg)ofKOHwhichcanneutralizethedissociatedfattyacidsof1goilsandfats.acidicnumberdissociatedfattyacidthedegreeofranciditylargesmallmorelesslargesmall6364SyntheticAntioxidantsButylatedhydroxyanisole(BHA)Butylatedhydroxytoluene(BHT)二丁基羥基甲苯丁基羥基茴香醚65包括中國在內(nèi)的很多國家規(guī)定BHA、BHT、TBHQ、PG禁用于嬰兒食品Propylgallate(PG)Tertiarybutylhydroquionone(TBHQ)沒食子酸丙酯叔丁基對(duì)苯二酚麥樂雞：TBHQ含量為0.02%今麥郎方便面67NaturalAntioxidantsBenefits:HealthimplicationStabilityinfoodsystemLimits:CharacteristicflavorSafetytestrequired 68Tocotrienolstocotrienols(生育三烯酚類)

TrivialName ChemicalName R1 R2 R3-Tocotrienol 5,7,8-Trimethyltocotrienol CH3 CH3 CH3-Tocotrienol 5,8-Dimethyltocotrienol CH3 H CH3-Tocotrienol 7,8-Dimethyltocotrienol H CH3 CH3-Tocotrienol 8-Methyltocotrienol H H CH369VitaminE,Tocopherol(生育酚)d--tocopherolismosteffectiveP.195抗壞血酸棕櫚酸酯AscorbicPalmitate抗壞血酸，維生素CL-AscorbicAcid(VC)異抗壞血酸ErythorbicAcid較安全的嬰兒食品抗氧化劑71TeaEpicatechinEpigallocatechin表兒茶素,茶丹寧I(-)-表沒食子兒茶素72Section3PhospholipidsⅠ.Phospholipidsphospholipidsphosphoglycerides(甘油磷脂)sphingomyelins(鞘磷脂)1.Phosphoglycerides:thederivativesofphosphatidicacidphosphatidicacidR(磷脂酸)*73GlycerolIfthesecondaryhydroxylgroupofglyceroltotheleftofC-2inFisherProjection,thecarbonaboveC-2isC-1andthebelowC-3Theuseofthisstereospecificnumbering(立體專一編號(hào))isindicatedbytheprefix“Sn”beforethesystematicnameofthecompound74Sn-Glycero-1-PhosphateSn-Glycero-3-Phosphate75Inphosphatidate:fattyacidsareesterifiedtohydroxylsonC1andC2theC3hydroxylisesterifiedtoPi.phosphatidate76Inmostphosphoglycerides(glycerophospholipids),

PiisinturnesterifiedtoOHofapolar

headgroup(X),e.g.:serine（絲氨酸

）,choline,ethanolamine,glycerol,orinositol(肌醇).The2fattyacidstendtobenon-identical.Theymaydifferinlengthand/orthepresence/absenceofdoublebonds.phosphoglycerides77Representativephosphoglycerides:phosphatidylcholine

（磷脂酰膽堿）Lecithin（卵磷脂，PC）cholineAbundantinbrainandnervetissuesFirstfoundineggyolk78Phosphatidylethanolamine（磷脂酰乙醇胺）-Cephalin（-腦磷脂，PE）ethanolamine79卵磷脂（Lecithin）溶于乙醇、乙醚和氯仿；-腦磷脂（

-Cephalin）能溶于乙醚，但不能溶于冷的乙醇。利用此溶解度差異，可將卵磷脂和-腦磷脂分離開。80phosphatidylserine(磷脂酰絲氨酸)serineP.20815-281Eachglycerophospholipidincludesapolarregion:glycerol,carbonyloffattyacids,Pi,andthepolarheadgroup(X),2non-polarhydrocarbontailsoffattyacids(R,R’).Itisanamphipathicmolecule.

polar

non-polar

"kink"duetodoublebond

82Thethreemostcommonfamiliesofmembraneglycerophospholipidsare:Phosphatidylethanolamine（-腦磷脂）

Phosphatidylserine（磷脂酰絲氨酸）Phosphatidylcholine（卵磷脂）ThesearenotsinglecompoundbutratherfamiliesofmoleculesthathavethesamepolarheadgroupbutdifferentfattyacylchainsesterifiedatC-1andC-2oftheglycerolbackbone.832.Sphingomyelin(神經(jīng)磷脂,鞘磷脂):Majorcomponentofmyelinsheaths(髓鞘)thatsurroundnervecellsABCDA:sphingol（sphingosine,鞘氨醇）,B:fattyacid,C:phosphoricacid,D:choline,A+B:ceramide（神經(jīng)酰胺）84Foundinthemyelinsheath（髓鞘）ConstituentsofplantandanimalcellmembranesAbundantinbrainandnervetissue,ascoatingaroundnervefibers.85Sphingomyelinscontainphosphocholineorphosphoethanolamineastheirpolarheadgroup.Althoughtheydifferchemicallyfromphosphatidylcholineandphosphatidylethanolamine(twoglycerophospholipids),theirconformationsandchargedistributionsarequitesimilar.SphingomyelinPhosphatidylcholine86PhosphoglycerideMembranesPhosphoglyceridescomprisethemajorlipidcomponentofcellmembranesNonpolartailsaggregateinthecenterofabilayerIonicheadisexposedtosolvent87脂質(zhì)體88(脂質(zhì)體)89909192PermeabilitypropertiesofphospholipidmembranesGases O2,CO2,NOSmall,uncharged ethanolpolarmoleculesWater H2OLarge,uncharged glucosepolarmoleculesIons Na+,K+,Mg2+,Ca2+ Cl-,HCO3-,HPO42-Charged aminoacids,nucleotides,polarmolecules sugarphosphatesHydrophobic steroidhormonesmolecules93Lipidsandmembranefluidity(P.209)Thefluidityofalipidbilayerdependson:(1)composition(2)temperatureFattyacylchainsinlipidmembranescanexistinanordered,rigidstateorinadisorderedfluidstate94MembranefluidityisdependentonlipidfluidityLipidfluidityisdependenton:C-CchainlengthandthenumberofC=Cbonds.Cis-doublebondsandshorthydrocarbonchainsincreasefluidityTheratiooflecithin(卵磷脂)andsphingomyelin(鞘磷脂),moresphingomyelindecreasefluiditybecausetheviscosityofsphingomyelinishighthanlecithin’s.95Section4Steroids（甾族化合物，甾體）Ⅰ.StructureandNumberingSteroidsarecommonlyfoundinnatureandareconsideredimportantprimarilybecauseoftheirpowerfulbiologicalactivities.Theyoftenfunctionasregulatorsofhumanbiology.Manynaturallyoccurringsteroidshavebeenconstructedinthelaboratoryandnumerous“unnatural”steroidshavebeencreatedaswell.9612345678910111213141516171819Allsteroidssharethefour-ringskeletonofthemoleculeshownabove.TheringsaredesignatedA,B,CandD,andnumberedasshownabove.Usually,steroidshaveaxialmethylgroups(angularmethylgroups，角甲基)attachedtoC(10)andC(13),andoftencarryanoxygenatomatC(3)andacarbonchainatC(17).甾災(zāi)*******97Therearetwokindsofnaturalsteroids.Oneis5-steroids(5系，別系),anotheroneis5-steroids(5系，正系).Allnaturalsteroids’BandCring,CandDringaretransringfusions.ThedifferenceisthefusionofAandBring.IfAandBringistransringfusion(eefusion),,theyare5-steroids;ifAandBringiscisringfusion(eafusion),theyare5-steroids.5-steroidsaremorecommonthan5-steroids.985-steroidsSubstituentspointeitherdown(dashedbond,a)orup(solidbond,b)991005-steroids1015-steroids1025-steroids1031045-steroids1055-steroids106II.FunctionsofSteroidsInhumansashormones,steroidsarechemicalmessengerssecretedbyglandsandcarriedthroughthebloodstreamtotargettissuesAlsowidelydistributedascholesterol107(1)MaleSexHormonesTestosteroneandandrosteronearethetwomostimportantmalesexhormones,orandrogensAndrostenedioneisaprecursorTestosterone睪酮，睪丸素Androsterone雄甾酮Androstenedione雄烯二酮1.SexhormonesQuestion:Testosteroneis5-steroidor5-steroid?

（麝香味）1081096mgandrostenoneand1mgandrosterone（雄甾酮)androstenone,雄甾烯酮豬烯酮110Dihydrotestosterone,DHTTestosterone,T二氫睪丸酮P.213重要的雄性激素有睪酮、雄酮和雄烯二酮，其中睪酮的活性最高。111Through5-alphareductase,testosteroneisconvertedtoahormone4Xaspotent,dihydrotestosterone.DHTbindstoreceptorsmuchmoreavidlythantestosterone.5-alphareductaseispresentinhighamountsintissuesoftheprostate,skin,scalp(頭皮),liver,andcentralnervoussystem.112Finasteride（非那雄胺），Proscar（保列治）

Finasterideisa4-azasteroid.It’sainhibitorof5-reductase.Whichcanbeusedtotreatbenignprostatichyperplasia(BPH，良性前列腺增生,Proscar,保列治,5mg),alopecia(脫發(fā),Propecia,保法止,1mg)andacne（痤瘡）.113保列治，5mg*10片，約66元，1mg/1.3RMB保法止，1mg*28片，約258元，1mg/9.2RMB114(2)FemaleSexHormonesEstroneandestradiolarethetwomostimportantfemalesexhormones,orestrogensProgesteroneisthemostimportantprogestin,steroidsthatfunctioninpregnancyEstrone雌酮Estrodiol雌二醇Estriol雌三醇Activity:0.310.1115Estrodiol雌二醇EstradiolValerate戊酸雌二醇116117Progesteroneisthemostimportantprogestin,steroidsthatfunctioninpregnancy.Progesterone(Progestin)，孕酮,黃體酮118SomethingMore:Mifepristone(Ru486)米非司酮，含珠停,息隱Medroxyprogesterone甲孕酮,安宮黃體酮September23,1988119MifepristoneisinventedbyRoussel-UclafCompanyinFrance.Whichisaantigestagen,caninduceabortionintheearlystageofpregnancy.Low-doseMifepristonealsousedinemergencycontraception.TheFoodandDrugAdministration’s(FDA)approvaloftheearlyoptionpill(RU-486ormifepristone)wasamilestoneforU.S.women.120121WichitaabortionproviderGeorgeTiller（喬治·蒂勒）shottodeathatWichitachurch(May31,2009)122米索前列醇，MisoprostolderivativeofPGE1123Levonorgestrel,LNG左炔諾孕酮（毓婷）Usedinemergencycontraception0.75mgLNG/片2片裝1.5mgLNG/片1片裝124Levonorgestrel,LNG左炔諾孕酮Ethinylestradiol,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（來不了）May,2007NoMore

Periods!127Norethisterone,炔諾酮0.625mgethinylestradiol,炔雌醇0.035mg復(fù)方炔諾酮口服避孕片1號(hào)+MegestrolAcetate醋酸甲地孕酮,1mgethinylestradiol,炔雌醇0.035mg復(fù)方酸酸甲地孕酮口服避孕片2號(hào)+128++Norethisterone炔諾酮0.312mgEthinylestradiol炔雌醇0.035mgMegestrolAcetate醋酸甲地孕酮,0.5mg口服避孕片0號(hào)129Norgestrel,18-甲基炔諾酮ethinylestradiol,炔雌醇+復(fù)方18-甲基炔諾酮12mg3mg短效0.3mg0.03mg長效130DextronorgestrelLevonorgestrel(+)-Norgestrel;L-Norgestrel(-)-Norgestrel;D-Norgestrel131CyproteroneAcetate醋酸環(huán)丙孕酮,2mgEthinylestradiol,炔雌醇0.035mg+達(dá)英-35Diane-35132Anabolicsteroids(促蛋白合成甾類,同化激素):Anyhormonalsubstance,chemicallyandpharmacologically,relatedtotestosteronethatpromotesmusclegrowth(DEA,DrugEnforcementAdministration).Increasedskeletalmusclemass,bonedensity,hemoglobin,nitrogenretentionandproteinsynthesis.133DianabolStanozolol大力補(bǔ)康力龍Thesetwocompoundsaresyntheticanabolichormones,canusedasmedicine,alsocanusedasperformance-enhancementinathleticsports.134孫英杰王德顯2005年10月十運(yùn)會(huì)135BenJohnsonset100mworldrecord(9.83)at1987WorldChampionshipsCarlLewis136BenJohnsonbeatCarlLewis9.79to9.92intheMen's100mFinalsintheSeoulOlympics(1988).137138Anabolic–“building”,increasedskeletalmusclemass,bonedensity,hemoglobin,nitrogenretentionandproteinsynthesis.Androgenic–androgensaresexhormonesthatcaninducemaletraits(e.g.growthofsexorgans,increasedbodyhair,libido,skinoil,andchangeinvoice).Anabolic/Androgenicsteroids(AAS)seektomaximizetheanaboliceffectswhileminimizingtheandrogeniceffects.Theratiooftheseanabolic/androgeniceffectsiscalledthetherapeuticindex（治療指數(shù)）.Testosteroneisthebaselineat1.139Tetrahydrogestrinone(四氫孕三烯酮,THG,BalcoLab)GestrinoneTrenbolone

去甲雄三烯醇酮140DualsprintworldchampionKelliWhiteWednesday,May19,2004,AmericansprinterKelliWhiteacceptedatwo-yearbanforTHGuse.141Montgomeryranaworld-best9.78secondsinthe100minParisinSeptember2002.MarionJonesTimMontgomery142hammerthrowerJohnMcEwen.143Androisavailableoverthecounter(OTC)!!Androstenedione(Andro)AndrostenediolDehydroepiandrosterone(DHEA)SteroidPrecursors/Prohormones脫氫表雄酮144145PositivesideeffectsofAAS:Enhancedmusclemass/strengthEnhancedbloodvolumeandhemoglobinconcentrationEnhancedbonedensityandstrengthHastenedhealingofmuscularinjuriesDecreasedbodyfatIncreasedimmuneresponseElevatedmood146ClinicalApplications:Bonemetabolismconditions–osteoporosis(骨質(zhì)疏松癥)Testosteronedeficiencyconditions–malehypogonadism,andropause（男性更年期）syndromeCardiovascularconditions–reducesanginapectoris（心絞痛）,coronaryarterydisease（冠心?。〢IDS–reducesAIDSwasting147Generallysideeffectsofanabolicsteroidusemayincludejaundice(黃疸)andliverdamage,hypertension,acne,fluidretention

heartenlargement,euphoria(異常欣快),improvedself-esteem,moodswings,depression,paranoia(妄想狂)andaggression.Effectsspecifictofemalesmayincludeanincreaseinfacialandbodyhair,menstrualproblems,andpermanentdeepeningofthevoice,foetaldamageandclitoralenlargement.SideEffectsofanabolicsteroid:148鄒春蘭1492.AdrenocorticalHormones(腎上腺皮質(zhì)激素)Adrenocorticalsteroids:secretedbytheadrenalglandsneartheupperendofeachkidney.(1)Mineralocorticoids（鹽皮質(zhì)激素）:controltissueswellingbyregulatingcellularsaltbalance.aldosterone

醛固酮P.214倒數(shù)第1、2行的描述錯(cuò)誤150(2)Glucocorticoids（糖皮質(zhì)激素）:regulationofglucosemetabolismandinthecontrolofinflammation.cortisonecortisol可的松氫化可的松151PhilipHench亨奇TadeusReichstein萊希斯坦因EdwardKendall肯德爾TheNobelPrizeinPhysiologyorMedicine(1950)152SomethingMore:FluocinoloneAcetonideAcetateThismedicineisasyntheticglucocorticoid.sodiumretention鈉潴留醋酸氟輕松，膚輕松153Dexamethasoneacetate,醋酸地塞米松154Beclomethasonedipropionate二丙酸倍氯米松TheBeclomethasonedipropionatecanbeusedtoantiallergicrhinitisandasthma.155156DoctorsinHongkonguseRibavirinandglucocorticoids(Prednisolone,Methylprednisolone)totreatSARS(SeriousAcuteRespiratorySyndrome)(atypicalpneumonia)Ribavirin，利巴韋林，三氮唑核苷，病毒唑157Prednisolone(潑尼松龍,氫化潑尼松,強(qiáng)的松龍)Methylprednisolone(甲潑尼龍,甲基強(qiáng)的松龍)158Reductioningrowthinchildren.Muscleweakness,especiallyoftheshouldermusclesandthighs.Rarely,avascularnecrosisofthefemoralhead(destructionofthehipjoint).Diabetescanbeprecipitatedoraggravated.Increaseincirculatingbloodfat(triglycerides).Redistributionofbodyfat:moonface,buffalohumpandtruncalobesity.Sideeffectsofglucocorticoids159RedistributionofFatinGlucocorticoidExcessCentralobesityseeninCushing’sSyndrome（庫欣綜合征）(GlucocorticoidExcess)160Buffalohump161moonface1623.Cholesterol(Cholesterin)Cholesterolwasfoundin1770.Ithas8chiralca