Classification of Fatty Acids and Lipids 200L PDF

Func tionalGr oups Bioche mic almol eculesar ede f i ne dbot hbyt heircarbonske l etonandby structur es calledf unc tionalgr oupst hatusual l yi nvolvebon...

Func tionalGr oups Bioche mic almol eculesar ede f i ne dbot hbyt heircarbonske l etonandby structur es calledf unc tionalgr oupst hatusual l yi nvolvebondsbe twe enc ar bonand ox y g en, carbonandni trog en, car bonandsul fur,andc ar bonandphosphat e groups.I n carbon–c arbonandc arbon–hy drogenbonds, theelectr onsar eshar ed equallybe twe enat oms, andt hebondsar enonpol arandr el ativelyunr eactiv e. Inc arbon–ox y genandc arbon–ni tr og enbonds, t hee lectronsar eshar ed unequal l y ,andt hebondsar epol arandmor ereacti v e.Thus, thepr operties oft hef unc tionalg r oupsusual l yde termi nethetypesofr eact ionst hatoc cur andt hephy siologicr oleoft hemol ec ul e. Func ti onalg roupname sar eof tenincor porat e dintot hec ommonnameofa compound.Fore xampl e ,ake tonemi ghthav eanamet hate ndsi n“ one”like acetone , andt henameofac ompoundt hatcontainsahy droxyl( alcoholor OHg r oup)mi ghte ndi n“ol ”(e.g. , et hanol ).Theac ylgroupi sthepor tionof themol ecul ethatpr ovide sthec ar bony l(–C=O)g roupi nane sterorami de li nkag e.Itisde notedi nanamebyan“ yl”ending.Fore x ampl e,thef atstor es oft hebodyar etriacylgly cerol s.Thr eeac yl(fatt yac id)g roupsar ee ster ified tog ly c erol ,ac ompoundc ont ainingthr eealcoholg roups. Fi g1 1.Majort ypesoff unc tionalg roupsf oundi nbi oche mic alc ompounds ofthehumanbody CL ASSI FICATI ON, PROPERTI ESANDFUNCTI ONSOFL IPI DSANDFATTYACI DS Fatt yAcids Fatt yacidsareusual lystr aightali phat icchai nswithame thy lgroupatone end(cal ledt he-carbon)andac arbox ylgroupattheothe rend.Mostfat ty aci dsinthehumanhav eanevennumbe rofcarbonatoms,usual lybe tween 16and20. Ty pesofFatt yAci ds A.Base donnat ureofhy droc arbonc hai n 1.Saturat edfatt yac i ds Sat urate df at tyaci dshav esi nglebondsbe twe enthecarboni nthechai n.The mostcommonsat urat edf at tyaci dsprese nti nthece llarepal miti caci d(C16) andste aricaci d(C18).  Acet icaci dCH3—COOH  Butyr icaci dCH3(CH2) 2—COOH  Palmit icaci dCH3—(CH2)1 4—COOH  Ste aricaci dCH3—(CH2)1 6—COOH 2.Unsaturatedf attyacids Unsaturatedf attyac i dsc ontai noneormor edoublebonds. Monounsat uratedf att yac idscont ainonedoubl ebondand polyunsaturatedf att yacidsc ont aintwoormor edoubl ebonds.The positi onofadoubl ebondi sdesig natedbyt henumbe rofthecar boni n thedoublebondt hatiscl ose sttot hec arboxy lg r oup.Fore xampl e , olei cac i d,whichc ont ains1 8carbonsandadoubl ebondbe t we en positi on9and1 0i sdesignated1 8:1,9.Thenumbe r18de notesthe numbe rofc arbonat oms, 1(one)de note st henumbe rofdoubl ebonds, and9de not e st hepositi onoft hedoubl ebondbe t we enthe9thand 10thcarbonat oms. a.monounsat urat edMUFA  b.pol yunsat urat ed PUFA B.Base dondi stanc efr om me thy lgr oup Fatt yac i dsarealsoc l assifi edbythedistanceofthedoublebondc losestt o the-end(themethylgroupatthee ndfarthestf romt hec ar boxylgroup). Thusolei cac i disan9f att yacid,andlinole nicacidi san3f at t yaci d. Arachi donicacid,apolyunsatur atedfattyacidwith20carbonsand4doubl e bonds,i san6f att yac i dthatiscomplet e lydescri bedas20:4,5,8, 11, 14  C.Or ient ati onandOc cur renc einnat ure Thedoubl ebondsi nmostnat ur al l yoc curringfatt yac i dsar einthecis conf i gur ati on.Thede signatonc i isme anst hatthehydrogensar eonthesame sideoft hedoubl ebondandt heac ylchainsont heotherside.Intransfatt y ac i ds, theac ylc hai nsar eonopposi tesidesoft hedoubl ebond.Mar gari neandt he fatuse di npr e paringFre nc hf ri esar epr obablythemaj orsour csoft e r ans fattyac i dsf oundi nhumans.Tr ansf att yac i dsareproduc e dbyt heche mi c al hydroge nat i onofpol yunsaturatedf att yac idsinveget ableoilsandar enota naturalf oodpr oduct D.Base donl engt hofhy droc arbonc hai n i ).Shortchainf attyaci d2- 6carbonatoms i i ).Me di umc hainfatt yac i d:oc t anoicacid( 8car bons)andde canoi cac id( 10 c ar bons). i i i).Longc hainfatt yac i d16-22c arbons i v).Verylongf att yac i d >24c arbons  E.Base donsour ce( s)/Nut rit ionalc lassi fi cat ion a.Esse nti alf att yac id b.Non-esse nti alf att yac id[ Endog ene ouspol yunsat urat edf att yac id (PUFA)]  Ar achi doni cac idde rivat ive s-Ei cosanoi ds Ar ac hidonat eandsomeot he rC20pol yunsat ur ate df at t yac idsg i v eri set o eicosanoi ds, phy siolog ical l yandphar mac ological lyac ti vec ompounds knownaspr ost agl andi ns( PG) ,thr omboxane s( TX) ,leukot ri e nes( LT),and li poxi ns( LX)Phy siolog i c ally , the yar ec onsi dere dt oac tasl oc alhor mone s (aut oc oids)f unc t ioni ngt hr oug hG- prot ein-li nke dr e cept orst oe li citthei r bioc he mi cale f fec ts. The r ear et hr eeg r oupsofe icosanoi dst hatar esy nthe sizedf romC20 eicosanoi cac i dsde rivedf romt hee ssent ialfattyac i dsl i nol eat eand- li nol enat e,ordi r ec t ly fromdi e taryar ac hidonat eande i cosape ntaenoat e. Ar ac hidonat e,usual lyde r ivedf r omt he2posi t i onofphosphol ipidsint he plasmame mbr anebyt heac tionofphosphol i paseA2, butal sof romt he diet—i sthesubst rat efort hesy nthe sisoft hePG2, TX2se ries( prost anoids) byt hec y clooxy ge nasepat hway ,ort heL T4andL X4se riesbyt he li poxy genase pat hway ,wi tht het wopat hway sc ompe tingfort hear ac hidonat esubst rate. Thee icosanoi ds( includi ngpr ost ag l andi ns[PG] ,thr ombox ane s,and leukot ri e nes) cont r olc e l lularf unc t ioni nr esponset oi njury.The sec ompoundsar eall der ive df romar ac hidoni cac i d, a20- car bonpol yunsat urat edf at tyacidthat i susual lypr e senti nc ell saspar toft heme mbr anel i pidphosphat i dylcholine.Al thoug hal moste veryc e l li nt hebodypr oduc esane i c osanoi di nresponse tot issuei njur y, dif ferentc el lspr oduc edi fferente ic osanoi ds.The eicosanoi dsac tpr incipal lyinpar ac ri neandaut oc r i nef unc tions, affecting thec ellst hatpr oduc et hemort he i rne ighbor i ngc ells.Fore xampl e ,v asc ular endot he l ialc e ll s( c ellsliningt hev esselwal l)sec retet hepr ost ag landinPGI 2 (pr ost ac yclin) , whi c hac tsonne arbysmoot hmusc lec e ll st oc ause vasodi lat i on( ex pansi onoft hebl oodv e ssel). Eicosanoidsarederi vedf romar achi doni cacidandr e tai nitsori gi nal20 carbons(thusthenameei cosanoids).Al lprost aglandi ns,suchas prostacy clin, alsohaveanint ernalri ng.  Cl assi fi cat ionofL ipi ds Fi g.6.Type sofg l yce roli pidsandsphing oli pids.Glyc erol ipi dscontai n gl ycerol ,andsphi ngoli pidscont ainsphi ngosine.Thecat egoryof phospholi pidsov e r lapsbot hglyc er oli pidsandsphi ngoli pids.Thehead groupsincl udec holine,et hanolami ne , seri ne,inosit ol, g l ycerol,and phosphati dylgl ycer ol. Thec arbohydr ate saremonosac charides(whic hmay besulfat ed),ol igosac chari de s, andol i gosaccharideswithbr anche sof Nacety lneur ami nicac i d.P=phosphat e. Fi g7.St ruct uresofthebloodgroupsubst ances.Notethatthe sestruct ures aret hesamee xceptthattpeAhasN- y ac e tylgalact osami ne( GalNAc)atthe nonreduci ngend,ty peBhasg al actose(Gal), andt ypeOhasne it her.Ris ei the rapr otei northelipi dc e ramide.Eachant ige nicdet e rmi nantisboxed. Fuc_f uc ose;GlNAc_N- c acet ylg lucosamine ;Gal_galac t ose Func tionsofL ipi ds 1.Nut ri ti on- prov idet ast e,ar omaandpal atabi li tyt othef ood  Enhanc edabsopt ionoff at- sol ubl evi tami ns; ADEK  Vit aminAi sasubstr ateforrhodopsi npi gme nti nther eti na, thus enhanc evi si onespe cial lyindarkne ss  Vi tami nAst imul atee pit hel isat ion, thuse nhanc ehe ali ngpr oce ss  Vi tami nAse rvease xog ene ousant iox idant  Vi tami nD,pr omotecal ciumabsorpt ioni ntheg ast roi nte sti nalt rac t, he ncefac ili tatebonemi ne r ali zat ion  Vi tami nEse rveasapot entant iox idante spe cial ly- toc ophe rol   Vi tami nK, -c arbox ylat ionofv itami nk-de pende ntc lot ti ngf act ors 2.Prot ect ive-c onf erprot ecti onandc ushi oni nge ffe ctt oint ernalor gansl ike hear t,ki dneyandmese nter y 3.Ther malinsul atorvi adepositi onoff atsintheadi poset issue sand subcut ane oust i ssue sregul atebodyt emperat ure 4.Ele ctri cali nsul ator -my e li nshe athpr ote ctt heax onande nhanc e propagati onofimpulse s 5.Ene rgygene r at ion- thr oughtr iac y l gly cerol, provi defatsf oradi posest ore s andmobil izat ionofthesest oresforgene r at ionofene rgy 6.Generati onandtransmissi onofne ur otransmit ter sviac holeste ryle ste r thathydroly sist oreleasephosphat idyl choli netoprovi dechol inefort he generat ionofacety lcholi ne 7.Prov ideme tabol icf ueldur ingpr olong edf ast ingandst arv ati onv ia l ipol ysi s 8.Chol est erolse rveasapr ecur sorf orst eroi dhor mone ssy nthe sis 9.Chol est eroli sapre cursorf orbil eac idsanditssal t,par ti ci pat ein emulsi fi cat ion off atsandbil ir ubi nmetabol ism 10.Chole ster olse r v easapr ec ur sorinthesy nt he si sofc ort icosteroi dsi nthe adrenalcort exoft headrenalgl and.Thr oughthispathway , cholester olhe lps tomaintainfl uidande le ctrol ytes,cardiovascularsyste mande nergy substrat ehome ostasi s.Theyprepar ethebodyt owi t hstande f fe c tsofall kindsofnoxious(poisonousorhar mf ul)sti mul iandstress 1 1.Ar achi doni cac idsi samake rofc ell ularandt issuei njur y/damag e 12.Arachi doni caci dde r ivat ive s-e icosanoidsareaut ocoi dsand proinfl ammatorythatpart ici pat eintissueinj uryandhomeostasi s 1 3.Phosphog lye crol sar ecompone ntsofsur fac tantt hatpr eve ntal veol ar c oll apse 14.Glyc olipidsser vei nint erce llul arcommunic ationandit s ol igosaccharide sconf ercel lrecogni ti onf actorsasintheABObl ood gr oupingsy stem 1 5.Transport ation:theplasmalipoprotei ntransportplasmal ipidsin c irc ulati onsandt ransferthemtope ri pheralti ssuesforutil ization.Makes t hemsolublethuspre ve ntpolyme r izat ion..Byformingv e siclespar t ici pat es i nvesi culartr anspor tofmol ec ules 1 5.Mai ntai nfl uidi tyandi nte gri tyofpl asmame mbr ane 16.Gl obosi des( cer emi deol igosac char ide s)ar ecompone ntofe ryt hroc yte me mbrane 1 7.Gangl iosi des,c ont ri butetost abil it yofpar anodalj unc tionandi on c hannelcl uster sinmyel inat ednerv ef i bre s 18.Cardiolipin-t womol ecul esofphosphatidi cacidli nkedwi t hg l ycer olfor m diphosphat idylg lyc erolorcardi oli pinisamaj orcompone ntof mitochondr ialmembrane.It sdefi ci e ncyorabsentle adt omitochondri al dysfunctionandsubse quentl yheartfai lur e,hypothyr oidismandsomet ype s ofmy opat hies. 19.Essenti alf at t yaci ds( li nol eicandli nol enicaci ds)ar epr ecur sorf or arachidoni cacidswhi chi ntur npr oduc eprostag ladi ns