LI

PIDS
Wesomet
imest
alkaboutf
atasi
fitwer
eamal
evol
entsubst
ancebent
onourdi et
arydestruction.Inreal
i
ty,fatsareel egantlitt
lemol ecul
es,
eachonemadeoft hreelonghy dr
ocar bont ail
sat t
achedt oal it
tl
e
coathanger-
li
kemol ecul ecall
edglycerol.Liket heotherlarge
biol
ogicalmolecules, t
heyplayessent i
al r
olesi nthebiologyof
humansandot heror ganisms.(Al
so,manyr ecentdietarystudiessee
sugarascausingal otmor ehealt
hpr oblemst hanfat!
)

Fatsar ejustonet ypeof  

lipi
d,acategor yofmol eculesuni t
edbyt heir
i
nabi li
tytomi xwel lwi
t hwater.Lipi
dst endtobehy drophobic,
nonpol ar
, andmadeupmost l
yofhy dr
ocarbonchai ns,thoughther e
aresomev ar
iati
onsont his,
whichwe' llexpl
orebel ow.Thedi ff
erent
varieti
esofl i
pidshav ediffer
entst r
uctures,andcor respondingl
y
diverserolesinor ganisms.Fori nstance,li
pidsstoreener gy,pr
ovide
i
nsul ati
on, makeupcel lmembr anes, f
orm wat er
-repell
entlayerson
l
eav es,andpr ovidebui l
dingblocksf orhormonesl iketestoster
one.

Her
e,we’l
ll
ookingr
eaterdet
ail
atsomeoft hemostimport
antty
pes
ofl
i
pids,
incl
udi
ngfat
sandoils,waxes,
phosphol
i
pids,andst
eroi
ds.

Fat
sandoi
ls
A f
at molecul
econsi stsoftwokindsofparts:agly
cerolbackboneand
thr
eef att
yacidtai
ls.Glyceroli
sasmallorganicmoleculewiththree
hydroxyl(OH)groups,whileafatt
yacidconsistsofalong
hydrocarbonchainattachedtoacarboxylgroup.Atypical
fattyacid
contains12–18car bons,thoughsomemayhav easfewas4oras
manyas36.
Tomakeaf atmol ecule,t
hehydroxy l
gr oupsont hegly cer olbackbone
reactwiththecar boxyl gr
oupsoff att
yaci dsina  dehydr ation
synthesis 
reacti
on.Thi syiel
dsafatmol eculewi t
ht hreef att
yacidt ail
s
boundt othegl ycerolbackboneviaest erlinkages( l
inkagescont aining
anoxy genat om nexttoacar bonyl,orC=O, group).Triglycer i
desmay
containthreeidenticalfat
tyacidtail
s,ort hreediffer
entf attyacidtails
(wit
hdi f
ferentlengthsorpat t
ernsofdoubl ebonds) .
Synthesi
sofatry
acy
lgl
ycerol
mol
eculefrom agl
ycer
olbackboneand
t
hreefatt
yaci
dchai
ns,wit
hther
eleaseofthr
eemolecul
esofwater.
I
magemodi
fi
edf
rom OpenSt
axBi
ology
.

Fatmolecul
esareal
socall
ed 
tr
iacy
lgl
ycer
ols,
or,i
nbloodworkdone
byyourdoct
or,
 t
ri
gly
cer
ides.I
nthehumanbody ,
tri
gly
ceri
desare
 pri
maril
yst or
edinspeci
alizedfatcel
ls,call
edadipocytes,whichmake
upatissueknownasadi poset i
ssue^11star
tsuperscri
pt,1,end
super
script.Whi
lemanyf attyaci
dsaref oundinfatmol ecul
es,some
areal
sof reeint
hebody,andt heyareconsideredat y
peofl ipi
dinthei
r
ownright.

Sat
urat
edandunsat
urat
edf
att
yaci
ds
Asshowni ntheexampleabove,t
hethreef
attyacidtail
sofa
tr
igl
ycer
ideneednotbeidenti
calt
oeachother.Fattyacidchai
nsmay
di
fferi
nlengt
h,aswellasinthei
rdegreeof
 unsaturat
ion.

 I
ftherear eonl
ysi
nglebondsbetweennei ghbor
ingcarbonsint he
hydrocarbonchai
n,afatt
yacidissaidtobe sat
urat
ed.(Thet hingthat
fat
tyacidsaresatur
atedwithi
shy drogen;i
nasaturat
edf at
,asmany
hydrogenatomsaspossi bl
eareattachedtothecar
bonskel eton.)

 Whent hehydrocarbonchainhasadoubl
ebond, t
hefatt
yacidissai
d
tobe 
unsaturated,asitnowhasfewerhydrogens.Ift
herei
sjustone
doubl
ebondi naf att
yacid,i
t’
s 
monounsaturated,whi
leift
hereare
multi
pledoublebonds, i
t’
s 
poly
unsat
urat
ed.

Thedoubl ebondsi nunsaturatedfattyacids,

li
keotherty
pesofdouble
bonds, canexistineithera ci
s ora tr
ans confi
gur
ati
on.In
the ci
s confi
gur at
ion,thetwohy drogensassociat
edwi t
hthebondare
ont hesamesi de,whil
ei na t
rans 
conf i
gurati
on,t
heyareonopposite
sides(seebel ow).A cis 
doublebondgener at
esakinkorbendinthe
fatt
yaci d,afeaturethathasi mportantconsequencesforthebehav
ior
offats.
 Saturat
edfat
tyaci
dexample:stear
icaci
d(st
raightshape)
.
Unsat
uratedfat
tyaci
dexamples:ci
solei
cacid(ci
s doubl
ebond, bent
chai
n),
transol
eicaci
d(t
rans 
doubl
ebond,
str
aightchai
n).
I
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edi
t:OpenSt
axBi
ology
.

Saturat
edfattyacidstai
lsar estr
aight,sof
atmol ecul
eswithfully
saturat
edtail
scanpackt i
ght l
yagainstoneanother.Thi
stightpacking
resul
tsinfatsthataresoli
datr oom temperature(havearelat
ively
highmelti
ngpoi nt
).Forinstance,mostofthef atinbutt
eri
ssat urat
ed
fat^
22squared.

I
ncont
rast
,ci
  s-
unsat
urat
edf
att
yaci
dtai
l
sar
ebentduet
o
the cis doublebond.Thi smakesithardf
orfatmoleculeswit
honeor
mor e cis-unsaturatedfat
tyacidt
ail
stopackti
ght
ly.So, f
atswit
h
unsat uratedt ai
lstendtobeliqui
datroom t
emperature(havea
rel
at i
v elylowmel ti
ngpoint)–theyarewhatwecommonl ycal
loil
s.
Fori nstance, ol
iveoili
smost l
ymadeupofunsaturated
fats^22squar ed.

Tr
ansf
ats
Atthispoint
,youmaybenot i
cingthatI’
veleftsomethingout
:Idi
dn’
t
sayany t
hingaboutunsaturat
edf at
swi t
h t
rans doubl
ebondsinthei
r
fatt
yacidtail
s,or
 t
rans 
fats.Tr
  ans f
atsarerareinnature,
butar
e
readil
yproducedinanindustri
alprocedurecalledpar
tial
hydrogenati
on.

Inthi sprocess, hydrogengasi spassedt hroughoi ls(mademost ly

of cis-unsaturatedf ats),
conv ert
ingsome–butnotal l–oft hedouble
bondst osinglebonds.Thegoal ofpar t
ialhy drogenat i
oni stogi v
ethe
oil
ssomeoft hedesi rablepropertiesofsat ur atedfats,suchassol i
dit
y
atr oom t emper ature,butanuni ntendedconsequencei sthatsomeof
the cis doublebondschangeconf igurati
onandbecome  trans double
bonds^ 33cubed. Trans-unsaturatedf att
yaci dscanpackmor et i
ghtl
y
andar emor el i
kelyt obesol i
datr oom t emper atur
e.Somet ypesof
shor tening,forexampl e,contai
nahi ghfractionof t
 rans fats^33cubed.

Part
ialhydrogenati
onand t
rans 
fatsmightseem l
ikeagoodwayt o
getabut t
er-l
i
kesubstanceatoil
-l
ikepri
ces.Unfor
tunatel
y,
 t
rans 
fats
haveturnedouttohav ever
ynegat i
veeff
ectsonhumanheal th.
Becauseofast rongli
nkbetween tr
ans 
fatsandcoronaryheart
disease,
t heU.S.FoodandDr ugAdmi nist
rati
on(FDA)recentl
yissued
abanon  trans 
fatsi
nfoods,wi t
hat hree-
yeardeadl
ineforcompanies
toremov e tr
ans f
atsfr
om theirproducts^
44star
tsuperscr
ipt
,4,end
superscr
ipt .

Omegaf
att
yaci
ds
Anotherclassoff at
tyacidsthatdeser vesmenti
onincl
udes
the 
omega- 3 and omega-6 f
attyacids.Therearedif
fer
entt
ypesof
omega-3andomega- 6fatt
yaci ds,butall
ofthem ar
emadef rom t
wo
basi
cpr ecursorforms:alpha-l
inoleni
cacid(ALA)foromega-3sand
l
inol
eicacid( LA)foromega- 6s.

Thehumanbodyneedst hesemolecul
es( andthei
rderi
vati
ves) ,
but
can'
tsynthesizeeitherALAorLAi tsel
f^55st
artsuper
scri
pt,5,end
super
script.Accordingly
,ALAandLAar eclassi
fi
edas essent
ialf at
ty
aci
ds andmustbeobt ai
nedf r
om aperson’sdiet
.Somef i
sh,suchas
sal
mon, andsomeseeds, suchaschiaandf l
ax,aregoodsour cesof
omega-3f att
yacids.

Omega- 3andomega- 6fat

tyacidshaveatleasttwo ci
s-unsat
urat
ed
bonds,whichgivesthem acur
v edshape.ALA,shownbel ow,isqui
te
bentbutisn’
tthemostextremeexampl e–DHA, anomega- 3fat
tyaci
d
madef rom ALAbytheformationofadditi
onaldoublebonds,has
si
x ci
s-unsatur
atedbondsandi scur
ledupalmosti nacircl
e! 
[
Whatmakesaf
att
yaci
domega-
3oromega-
6?]
I
mageofal
pha-
li
nol
eicaci
d(ALA),showingit
scur
ledshapeduet
oit
s
t
hr ci
ee  s 
doublebonds.
I
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edi
t:OpenSt
axBi
ology
.

Omega- 3andomega- 6f att

yacidspl ayanumberofdi ff
erentrolesin
thebody .Theyareprecursors(st
artingmat eri
al)forthesynthesisofa
numberofi mportantsignali
ngmol ecules,incl
udingonest hatregul
ate
i
nf l
ammat ionandmood.Omega- 3f attyacidsinparti
cularmayr educe
ther i
skofsuddendeat hfrom heartattacks,decreasetri
glyceri
desin
theblood,lowerbloodpressure,andpr eventthef or
mat i
onofbl ood
clots.

Rol
eoff
ats
Fat
shav
erecei
vedal
otofbadpubl
i
cit
y,andi
t’
str
uet
hateat
ingl
arge
amountsoffr
iedfoodsandother“f
att
y ”f
oodscanleadtoweightgai
n
andcausehealt
hproblems.However,
fatsareessent
ial
tothebody
andhaveanumberofi mport
antfunct
ions.

Fori
nstance,manyvi
tami
nsarefat-
solubl
e,meani
ngthattheymust
beassociat
edwithf
atmolecul
esinordertobeeff
ect
ivel
yabsorbed
bythebody.Fatsalsoprovideaneff
ici
entwayt ostor
eenergyover
l
ongtimeperiods,sincetheycont
ainov ert
wiceasmuchener gyper
gram ascar
bohy dr
ates,andtheyaddit
ional
lyprov
ideinsul
ati
onfort
he
body.

Likeall
theotherl
argebiol
ogical
molecules,
fatsi
ntheri
ghtamounts
arenecessarytokeepyourbody(andthebodiesofot
herorgani
sms)
funct
ioningcor
rectl
y.

Waxes
Waxesar eanot herbi
ologicallyi
mpor tantcategoryoflipi
ds.Wax
coversthefeathersofsomeaquat i
cbi r
dsandt hel eafsurf
acesof
somepl ant
s, whereit
shy drophobi c(water-
repell
ing)properti
es
preventwaterf r
om st
ickingt o,orsoakinginto,t
hesur face.Thisi
s
whywat erbeadsupont hel eavesofmanypl ants,andwhybi rdsdon’
t
getsoakedt hroughwheni tr ai
ns.
 I
mageofshi
nyl
eafsur
facecov
eredwi
thwax.
I
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edi
t:OpenSt
axBi
ology
.

Structur
allyspeaki
ng,waxestypi
call
ycontainlongf
attyaci
dchai ns
connectedt oalcohol
sbyesterli
nkages,
althoughwaxespr oducedby
plantsoftenhav epl
ainhydr
ocarbonsmixedinaswel l
^66st
art
superscri
pt ,
6,endsuperscr
ipt
.

Phosphol
ipi
ds
Whatkeepst hewater
ygoo(cyt
osol)insi
deofyourcel
lsfr
om spi
l
li
ng
out
?Cellsaresurr
oundedbyastructurecal
ledt
heplasmamembr ane,
whi
chser vesasabarri
erbet
weenthei nsi
deofthecel
landit
s
sur
roundings.

Speci
ali
zedl
i
pidscal
l
ed 
phosphol
ipi
ds 
aremaj
orcomponent
soft
he
plasmamembr ane.Likef ats,theyaret ypical
lycomposedoff at
tyacid
chainsattachedt oabackboneofgl ycerol.I
nsteadhav i
ngt hreefatty
acidtail
s,howev er,phosphol ipidsgener all
yhav ej
ustt wo, andt he
thir
dcarbonoft heglycerol backbonei soccupi edbyamodi f
ied
phosphategr oup.Di f
ferentphosphol i
pidshav edifferentmodi fi
erson
thephosphat egr oup,withchol i
ne(ani t
rogen-containingcompound)
andser i
ne( anami noaci d)bei ngcommonexampl es.Di f
ferent
modi f
ier
sgi vephosphol ipidsdi ff
erentpr oper
tiesandr olesi nacel l
.

St
ructureofaphospholipid, showinghydrophobi
cf att
yacidtail
sand
hydrophi
li
chead( i
ncludingest erli
nkages,gl
ycerolbackbone,
phosphategroup,andat tachedRgr ouponphosphat egr oup)
.A
bil
ayeredmembr aneconsi sti
ngofphospholipi
dsar r
angedi ntwo
l
ayers,witht
heirheadspoi ntingoutandt hei
rtai
lssandwichedinthe
mi ddl e,
isalsoshown.
I
magemodi
fi
edf
rom OpenSt
axBi
ology
.
Aphosphol ipidisan amphi pat hi
c mol ecule,meani ngi thasa
hydr ophobicpar tandahy drophili
cpar t.Thef attyacidchai nsar e
hydr ophobicanddonoti nteractwithwat er,
wher east hephosphat e-
cont aininggroupi shydrophilic(becauseofi t
schar ge)andi nteracts
readi l
ywi t
hwat er.Inamembr ane, phosphol i
pidsar ear rangedintoa
struct urecall
edabi lay
er, wit
ht heirphosphat eheadsf acingthewat er
andt heirt
ailspointi
ngtowar dst hei nside(abov e).Thi sorganizati
on
prev entsthehy drophobict ai
lsf r
om comi ngintocont actwiththe
wat er, makingitalow-ener gy,stablear rangement .

Ifadr opofphosphol i
pidsispl acedinwat er,i
tmayspont aneously
for
m aspher e-
shapedst ructureknownasa  micelle,i
nwhi chthe
hydrophili
cphosphat eheadsf acetheout si
deandt hefatt
yaci dsface
theinteri
orofthisstructure.Format i
onofmi celleisanener getical
ly
favoredbecausei tsequest er
st hehy dr
ophobicf attyacidtai
ls,
all
owi ngthehydrophili
cphosphat eheadgr oupt oinsteadinteractwit
h
thesur r
oundingwat er^{
7,8} 8s
7, tartsuperscr
ipt,7,comma, 8,end
superscript
. 
[
Mor
edet
ail
s]

St
eroi
ds
Steroi
ds areanot herclassoflipidmol ecules,identi
fiablebytheir
str
uctureoff ourfusedr i
ngs.Al t
hought heydonotr esembl et heother
l
ipidsstr
uct ural
ly,ster
oidsareincludedi nlipidcategor ybecausethey
arealsohy drophobi candinsol
ubl einwat er.Allster
oi dshavef our
l
inkedcar bonr i
ngsandsev er
al ofthem, li
kechol esterol,al
sohav ea
shorttai
l.Manyst eroi
dsalsohav ean–OHf uncti
onal groupat t
ached
atapar t
icularsit
e, asshownf orchol ester
ol below;suchst eroidsare
al
socl
assi
fi
edasal
cohol
s,andar
ethuscal
l
edst
erol
s.

Examplesofster
oids:
cholest
erol
andcorti
sol
.Bothhavethe
char
acter
ist
icstr
uctur
eoffourfusedhy
drocar
bonrings.
I
magecr
edi
t:OpenSt
axBi
ology
.

[
Ster
eochemi
str
yofchol
est
erol
]

Cholester
ol, themostcommonst eroid,i
smai nl
ysy nt
hesizedint he
l
iverandist hepr ecur
sortomanyst eroidhormones.Thesei ncludet he
sexhor monest est
oster
oneandest radi
ol,whi
char esecretedbyt he
gonads( t
est esandov ari
es).Cholesterolal
soservesast hestar t
ing
materialf
orot heri
mportantmolecul esinthebody,incl
udingv i
taminD
andbileacids, whichaidinthedigest i
onandabsor pti
onoff at
sf rom
diet
arysources.I t’
salsoakeycomponentofcel lmembr anes,alter
ing
t
hei
rfl
uidi
tyanddy
nami
cs.

Ofcour se,cholest
eroli
salsofoundinthebloodstr
eam,andblood
l
evelsofchol ester
olarewhatweof tenhearaboutatthedoct
or’
s
of
ficeori nnewsr eport
s.Cholest
eroli
nthebloodcanhav eboth
pr
ot ecti
veeffects(i
nitshi
gh-densi
ty,orHDL,form)andnegati
ve
ef
fect s(i
nitslow-densi
ty,
orLDL, f
orm)oncar di
ovascul
arheal
th.