Some Naturally occurrlng Patty Aclds

Carbon

siieleton Structure'

12:0 CH, _1CH_›J¡, -.CO0H

14:0 CFLJCHJVCÚCH

16:0 CH,...
C b l "O O , « a0 O

  (  x0/ , A
'  . 
f ,  ç
( a C
< a Í
( >
É >

Hydrocarbon  )

chain < (A)

(a) (b)
Saturated Mixture of saturated and
fatty acids unsaturated fatty acids

(c) (d)
o I n,  a u,  o
C-O/ CÉUH/ (KO-C/ 

«A

l-Stearoyl.  Z-linoleoyi.  3-palmitoyl glycerol. 
a mixed triacylglycerol
15"-” '  * '"'”'¡ "*"""Íiííbí'i-h

ü

151%
Spermaceti
organ
Fatty acids ('55 of total)

100

ã

GS
O

Ȉ
O

lí!  l V; 

Cm and Ch.  Cm and Cn¡ C_,  to C”
saturated unsaluratud satura...
O
| |

CH3 ( CHQ) 14:C: O:CH2:  )28:CH3
dvd;   
Palmitic acid l-Triacontanol

(a)
Storage Mcmbranc llplds (polar)

lipids
(neutral)
Phospholipids Glycolipids
| 
Triacylglycerols Glycetophospholipids Sphix...
lçHgoH

H--zííl--OH CH)
3óHg-o-P-o'
¡¡-| |.. -(›-: (  Rminurilennoyiirit
nun. . ¡ulniiliu- xiii-

 

o
l'l nl l 'l
 *Cll-U-d" ldlí-IHIÍJÍUÍÍHÍÍ) riii
  "mp,  ...
either-linked alkene

H H
'CH2-O-C= C

I
*cH-o- 
3 I u

CH-g O

0=P-O-CH2-CH2-ÉT(CH3)3

à

other-linked alkyl
*CH2-O-CH2-C...
ether-linked alkene

H H
'(|3H2-O-C= C
2cH-o-c 

|  || 
3(|3H2 o
(u)

o=1|>-o-cH2-cH2-1§(cH3›3

'o

Plasmalogen
ether-linked alkyl
1CH2*O-CH2*CH2 

2+H-O-(H3-CH3
30H¡ O
I acetyl ester

O

| 
O= P-O-CH2-CH2-1ÍI(CH3)3

da

Platelet-acti...
Sphingosine
'lI-(7Il= ('ll- n CH,  1~. i. -Clln

- : i
“O Fartyacid

. _ _ _ _ o

hphmgolipid | 

l 579115' T3 l : C H _N_...
l / cHg
_ _ 

0_I| > o CH

(I3H3 (fHg-O 0

CHJ-IÍILCHZ o= c/
CH3

Phosphatidylcholine
I 
: p-O CH OH
CH-z O= C H

Sphingomyelin
000m OH OH

I I
CH-CH-CHgOH

 
   

| |
O
N-Acetylneuraminic acid (sialic acid)
(Neu5Ac)
O M1136¡

AAntism

andem
Phosphohpase A¡

I o

1 .  u

CH2"°_°/ // // // 
O

2 u

? H-OTC -

30112 

-- Phosphohpase A2
Phospholioase C T H O_®
"““...
'í f? 
:: f 
0 cm
v›: ::-| rII'I-~~wvl›«---   Ouunmluntl zanãclimidnmln
l : 

iñ)
: j 
GMS
luI›.4llllII| IlH-I'.  ®_.  T, ...
Polar
head
-NH-CHz-CHz-SO; 

 

Taurocholic acid
(a bile acid)
Phosphatidylinositol
phn-spliuijxlzitinnÉ» 'ZATP

in ¡iliismii
m-nmlirziii-n

'á 2ADP
Phosphatidylinositol 4,5-bisphosphat...
O

II
°H2“°'°/ // // // 
O

Nlembrane H 5 u
plmsphoupid °H'°'C 
A  / 
([312 s 14
Polar ê l'l*. vn›plinli¡: :~. ›uA_
head X...
O

a t»  ; lt-oii

Arachidtmic acid

NSAIDs® 

  “f” O   __, »~. ._›__ F3/ CHÁ*
ou OH  " '   -' 

Prostaglandin E1 '  *T
(...
OH

1130
mc
0
'neslosuamne
? mor-I

C-O

Prednísolone

 

HO

OH

 

Aldosterone

? mon
c-o

O 11,0 on

"aC

Prednisone
CH

| 
CHZ:  C _ CH:  CH2
Isoprene

3
"A7 CH; 
mc éra. .

: m: . .

|  .
',  II'.  t
H0: |   _ 7
#Delulllvrlwltellaml
l1'li¡lnu1xl

, a aq» n.  dum

L
H, (7

. ...
Before Vitamin D trczitmqànt

(b)

After 14 nmnths ofxritamin D troatmcnt
_ CN¡
Cns r _. _›:2
í
<>_CH: 
7.?  < XXCH"
/ - g CH3
< cuz,  
oxidationof m"
S alcohol to K
GHz;  (f, 

E

CH3~<__/ 

pCar...
CH¡
(a) Ho |  Hx _ . Hu _ H, 
Vin-min E:  nn . antioxidnnt CH, +C1L-ClL-CH-C¡i, .+CH, -CH, -Cii-C1i, +CH, -CH, -CH-CH= 
CH...
CHe. 
/



l (líHg l CH;  l CHS
|  CHz-E-Cl-lg-CHg-CH-CHg-i-CHg-Cflg-CH-CHg-l-CHg-CHz-êH-CHs
O CHS n n I
113

IIO

CH3

(a...
_ CH3 <|3H3 _ (llHg l C| IH3
:  CH2-CH= C-CH2-HCHg-CHg-CH-CHg_ig-i-CHg-CHg-CH-CHg
l I

(b)
Vitamin K1: a blood-clotting
co...
(c)

Warfarin:  a blood / 
anticoagulant CH
OH | 

cnz-(If-cng
CHgO CH3
l CH3 CH3 CH3

|  l _ o( I | 
01130 CH2-CH= J2-CH2+lCH2-CH= À3-CH2 , ,+CH2-CH= C-CH3
l I

(d)

Ubiquinone:  a mit...
CH3

CH3

n ? H3 ¡ ? H3
,  CHg-CH= C-CH2-H_CH2-CH= C-CH2v), ,
l

(e)

Plastoquínone:  a chloroplast
electron carríer (n = ...
_ ? H3 _ ? H3 _ ? H3
HO+CH2-CH2-CH-CH2+Í_CH2-CH= C-CH2 J, ,+CH3-CH= C-CH3
l l l

(f)

Dolichol:  a sugar carrier
(n =  9-22)
1 "m" ln: : : up-t ¡im!  in

(hlumlun mu NI¡ nnulMuIc-r

u) Wulrl
! lv-n . unnuvvnn-r
(Wcltmáixnu
a. ) lc)
í
Álhunlluax
el...
11 lípidos
11 lípidos
11 lípidos
Próximos SlideShares
Carregando em…5
×

11 lípidos

442 visualizações

Publicada em

Prof. Boniello Vicente
Lehninger. Ed. 4

Publicada em: Educação
0 comentários
0 gostaram
Estatísticas
Notas
  • Seja o primeiro a comentar

  • Seja a primeira pessoa a gostar disto

Sem downloads
Visualizações
Visualizações totais
442
No SlideShare
0
A partir de incorporações
0
Número de incorporações
2
Ações
Compartilhamentos
0
Downloads
5
Comentários
0
Gostaram
0
Incorporações 0
Nenhuma incorporação

Nenhuma nota no slide

11 lípidos

  1. 1. Some Naturally occurrlng Patty Aclds Carbon siieleton Structure' 12:0 CH, _1CH_›J¡, -.CO0H 14:0 CFLJCHJVCÚCH 16:0 CH, ~_lCH¡l¡¡CO0H 18:0 CH3iCH; I¡, _C00H 20:0 cHglcl-kvligâooH 24:0 CH-.1Ci-l¡vl; ;CO0H 16:11.91 CH5iCH_vl; CH= CH(CH¡)vCO0H 1B: 11.3") CH«, lCH¡l_vCH= CH(CH; ).CO0H 1B:2l. i” “l CH; l~JH; l,CH= CHCH¡CH= CH(CHJ)TCOOH 18:31.39 'i “i CH, CH; CI›l-CHCH¡CH- CHCH_. CH= CH(CH; LCOOH 20:41.? " = * “J CH-, lCH¡vI, CH-CHCH: CH- CHCH-_vCH-CHCH-, CH- ciiiciipgcooii Systematlc name' ri lhdmaiic: ›: ': ai: id ri-Tiflrtidrittaviciiit' n: : id riitritzidncnm; ir : acid ri-Cclaói-çzirioic : md ri-Eicosanoic acid rirTetrazosaw-: iin: a: id cís-Q-Hexzxtiecenoiv: and CíSB-Octadecenoic ac id cvs›. cís-9, l Z-Octadecad ie M42 : icld iris , cvs , ais 9, l? , l "ÕCÍEDÓQÇBÍTIG noi-t and '“~'-°= .8.1l. I4~ Common namo Melting (detiiabon) point ('C) Laurie: (11311 44.7 (Latin Jamais, "laurel plant") MVWSÍIC ? ltid 53.9 (Latin Militante. ri utmizqj, gen us) Pislmilir . izjid tÍmÍLl (Latin palma, "palm tree") Slmric ; md 69.13 (Greek srem, "hard fatW Arazhidic acid 76.5 (Latin Anirrhis, legume genusl Lignoceric acid 86.0 (Latin ! igriurng Mood' i cera, 'viafl Palmitoleic acid 0.5 Oleic acid 13.4 (Latin oreum, "oiI"I Linoleii: acid É- (Gri-rk farâ/ SYI_ "ll: ax"l . rLiiizieniziàcld H Àriachizizxii: : . izid 49.5 Solubility at 30 'C (me/ z wlwnt) Water Benaene 0.063 ? ,600 0.024 BM O . fl-DSB 343 0.6034 124 'All ziizids arc- sharan in lhcir ricriioriizcd lorni. A1 pH l, all lrcc lally zicids herit- df¡ icriizcd carboxylailc. Nota: that nurnLic-ririg cl carbon . ãtüriis Inputs . a1 lili: ijzàrlxuiyl C-HLIO” 'The prefix D- indi-: ates the "normal" unhianched structure. For instance, “'dode~r. arir›ic" simply indicates 17 carma atoms. , which could tc . irrdriazcd in a varre! ol brunrlicd lornis; '^r›d'_idi. x“a'›uii: " sçccilics the linear, unbrarichcd lorm. Fcc urisaturalcd latly dCldS, 1h: : configuration ci each ouble ban-d rs indicated. in biological fatty acids the configuration is almost always CLS.
  2. 2. C b l "O O , « a0 O ( x0/ , A ' . f , ç ( a C < a Í ( > É > Hydrocarbon ) chain < (A) (a) (b)
  3. 3. Saturated Mixture of saturated and fatty acids unsaturated fatty acids (c) (d)
  4. 4. o I n, a u, o C-O/ CÉUH/ (KO-C/ «A l-Stearoyl. Z-linoleoyi. 3-palmitoyl glycerol. a mixed triacylglycerol
  5. 5. 15"-” ' * '"'”'¡ "*"""Íiííbí'i-h ü 151%
  6. 6. Spermaceti organ
  7. 7. Fatty acids ('55 of total) 100 ã GS O »à O lí! l V; Cm and Ch. Cm and Cn¡ C_, to C” saturated unsaluratud saturated l J l Olive oil, Butter, Beef fat, liquid soft solid hard solid Natural fats at 25 "C
  8. 8. O | | CH3 ( CHQ) 14:C: O:CH2: )28:CH3 dvd; Palmitic acid l-Triacontanol (a)
  9. 9. Storage Mcmbranc llplds (polar) lipids (neutral) Phospholipids Glycolipids | Triacylglycerols Glycetophospholipids Sphixigolipids Sphingolipids í Fatty acid T Patty acid 'd W - - . E . E g e ; e s g_ Fatty acid à Patty acid g0 Fatty acid g Patty acid õ õ' -ã -ã w rn _ Mono- or í Film' acid É poe › Alcohol É po: Choüne oligosuccharide
  10. 10. lçHgoH H--zííl--OH CH) 3óHg-o-P-o'
  11. 11. ¡¡-| |.. -(›-: ( Rminurilennoyiirit nun. . ¡ulniiliu- xiii- o l'l nl l 'l *Cll-U-d" ldlí-IHIÍJÍUÍÍHÍÍ) riii "mp, ÍIlFiI' 'Hifi' ( Clli-O-P-íl- x (l ? In-ml Emup milmlilui nl Nu( ulmr nqnl -plxilipul Num. : uÍ X phÍllphJíilüP : u-icl Pluz-¡ulmlinlyL-Iluumhmilm ›: ii. ... ... I». ... ... ~ -iflh-«YIL-NH; Plwipluilidvkludinc- Flnulim " ("¡-'-c"--N'v'| ›"* plkzqnliuilnlyl-wrim sum. . ou; «lui in_ F00 P'lnx-¡I'I.4Íll| _ll›fÍ_h ml (Ibn ml HH¡ (|75| l'll_i HH OH H u- I' I v Plhl-¡Ilmíllly Ilnm-ÍÍUÍ III_| v›-l| |n i. i1i›H, r› u" H ll -I.5-| Ii-ulinphiiu: bispllnrsplmk- l› ›| H "H HU n_ 'l »Í u (Íanlinhpui Him-¡nlmrulvl- (ÍIL "LWM" Cuull (› Guru_ _o-cu, u o (t›l-4›_4"-R' o l (YlL-n-r-II'
  12. 12. either-linked alkene H H 'CH2-O-C= C I *cH-o- 3 I u CH-g O 0=P-O-CH2-CH2-ÉT(CH3)3 à other-linked alkyl *CH2-O-CH2-CH2 *HÉH-O-E-CHÉ. 3CH2 o acetyl ester Plasmalogen I . O= I|'-O-CH2-CH2-N(CH3). -, o Platelet-activating factor
  13. 13. ether-linked alkene H H '(|3H2-O-C= C 2cH-o-c | || 3(|3H2 o (u) o=1|>-o-cH2-cH2-1§(cH3›3 'o Plasmalogen
  14. 14. ether-linked alkyl 1CH2*O-CH2*CH2 2+H-O-(H3-CH3 30H¡ O I acetyl ester O | O= P-O-CH2-CH2-1ÍI(CH3)3 da Platelet-activating factor
  15. 15. Sphingosine 'lI-(7Il= ('ll- n CH, 1~. i. -Clln - : i “O Fartyacid . _ _ _ _ o hphmgolipid | l 579115' T3 l : C H _N_ , xx x_ -*~. .. '- _/ , x , -. _ . r _xx_ _A 1x_ structure¡ Í xx/ t7/ v/ v/ x/ x/ x/ x/ 'l v/ '. .-/ a/ X Name of sphingolipid Name ofX Formula ofX Cemmide sphnipoin_velixi Phnsphocholixic- (YH. _,OII ¡it/ /Íh O ' Neutral nlycolipids (ilumyylccn-bruaidc u u Í. H('KO, -I_VÍ('PT¡'| IIIÍ(ÍP D"- m" “r _ ; A globomde. IEÍTHSHCChZITIÓÊ Complex Gnngliosidp GM2 oligosncch-iride
  16. 16. l / cHg _ _ 0_I| > o CH (I3H3 (fHg-O 0 CHJ-IÍILCHZ o= c/ CH3 Phosphatidylcholine
  17. 17. I : p-O CH OH CH-z O= C H Sphingomyelin
  18. 18. 000m OH OH I I CH-CH-CHgOH | | O N-Acetylneuraminic acid (sialic acid) (Neu5Ac)
  19. 19. O M1136¡ AAntism andem
  20. 20. Phosphohpase A¡ I o 1 . u CH2"°_°/ // // // O 2 u ? H-OTC - 30112 -- Phosphohpase A2 Phospholioase C T H O_® "““--: › 0=1|>-^o H o H o-® Phosphohpase D
  21. 21. 'í f? :: f 0 cm v›: ::-| rII'I-~~wvl›«--- Ouunmluntl zanãclimidnmln l : iñ) : j GMS luI›.4llllII| IlH-I'. ®_. T, .,. .s. .,, ¡¡, id¡. ... .,i. . , Ê l : :i Ccrnmídn Ptmn-phmhnlina Syihlngmiyvdln , ~i. i.~. ›.. v.. »I. -i. .4.. .. a. ... ,¡. .›, ¡¡w. m , ' -¡llIlll| 'I› 'Izxnlilmm- i
  22. 22. Polar head
  23. 23. -NH-CHz-CHz-SO; Taurocholic acid (a bile acid)
  24. 24. Phosphatidylinositol phn-spliuijxlzitinnÉ» 'ZATP in ¡iliismii m-nmlirziii-n 'á 2ADP Phosphatidylinositol 4,5-bisphosphate lllJTlllUllV-HUIÍSIIl1i' __ n20 lllllihpllilllllílhn'l in plílsllhl lll('ll'llJl'. lllI^ _, I"'. _. L-"J/ z/ ""~A Inositol 1,4,5-trisphosphate Diacylglycerol Release of intracellular C212' > Activation of protein kinase C l l l l L i Regulation of other enzymes Regulation of other enzymes (by Ca2+) (by protein phosphorylation)
  25. 25. O II °H2“°'°/ // // // O Nlembrane H 5 u plmsphoupid °H'°'C A / ([312 s 14 Polar ê l'l*. vn›plinli¡: :~. ›uA_ head X SPOUP (a)
  26. 26. O a t» ; lt-oii Arachidtmic acid NSAIDs® “f” O __, »~. ._›__ F3/ CHÁ* ou OH " ' -' Prostaglandin E1 ' *T (PGEIJ OH Thromboxane A2 Eicosanoids (b) , nas 0 É _ 687 7 "l 0 a _ 0 7 7 _zw-cx__§, s=~. _____: ::§~'-~? >. .___ __. .-'~. _›_____, /C_O C
  27. 27. OH 1130 mc 0 'neslosuamne ? mor-I C-O Prednísolone HO OH Aldosterone ? mon c-o O 11,0 on "aC Prednisone
  28. 28. CH | CHZ: C _ CH: CH2 Isoprene 3
  29. 29. "A7 CH; mc éra. . : m: . . | . ', II'. t H0: | _ 7 #Delulllvrlwltellaml l1'li¡lnu1xl , a aq» n. dum L H, (7 . uma &N; ! Zimlm-ldllnú (vilmnlu 0,1 1m: n Lnlivw L W um: n u¡ &dun- HJÍ CIL. “ac »JYHJOH 4311,¡ H0 1 OH 2 l .25-Dí| ¡_Iimu1'lu›lu-. «hifm-l tllí-dihydmlyvlmnaln Dp ta)
  30. 30. Before Vitamin D trczitmqànt (b) After 14 nmnths ofxritamin D troatmcnt
  31. 31. _ CN¡ Cns r _. _›:2 í <>_CH: 7.? < XXCH" / - g CH3 < cuz, oxidationof m" S alcohol to K GHz; (f, E CH3~<__/ pCarotene (n) , 7 aldehyde u V2 S-CIL. Cílr/ < É _ñcnzon H/ Cxo Vitamin A¡ l l-cis-Retinal íretiuoln «visual pigmenti» (b) (c) oxidation . . . o¡ awehyde Reuncnc acid › to my (d) . z/ / ' CH: z xx “ _ CH, visible Cn** , f light '< “g, GHz¡ *pu '> cuz. f, n/ Ko all-trans-Retinal (e) Homional signal tu epithelial cells N euronal signal to brain
  32. 32. CH¡ (a) Ho | Hx _ . Hu _ H, Vin-min E: nn . antioxidnnt CH, +C1L-ClL-CH-C¡i, .+CH, -CH, -Cii-C1i, +CH, -CH, -CH-CH= CH, o CH: : ' ' ' (b) Vitamin mnbimddmcin¡ - CH* H* . _ n" . H* <›Í¡¡d(¡r| pÍ1_f”I)Ql)D01lz-J : CPL-CH -CH, +', CH¡-CH H-CH, «¡+CH-, «-CH-, H-CHx O (c) Warfaràu: .a blood xlunmaagulant CH H . CHuMHJ O (d) CPLO cn: Lüquínoac: a mitothandrinl ¡ H1 _H_ , HW clvctrun cmrrirr (cocnlymc Q) ' . _ ' n ' (II 4-8¡ CHJO , CH. -Clí-C-Cllg+'. CHg-CH : -CH, ,LH-Clig-CÍÍ-C-CH; u n (e) Plusioquinone: :I thlumpln-xl c-loctmn cnrricrü¡ 4-8¡ CHu HK _ CH: : Cm-CHJ-CHH-Ícm-CH _cm rg+cn, -ca= Í:-cní. I I (D Duluchnl: a sugar riu-net 1 _XNA u . É": 1 'HJ ín 9-22¡ HO-i-CHg-CH¡ H-CHg-HCHg-CH- H¡ ', ,+CH-¡-CH -CHa Í Í Í
  33. 33. CHe. / l (líHg l CH; l CHS | CHz-E-Cl-lg-CHg-CH-CHg-i-CHg-Cflg-CH-CHg-l-CHg-CHz-êH-CHs O CHS n n I 113 IIO CH3 (a) Vitamin E: an antioxidant
  34. 34. _ CH3 <|3H3 _ (llHg l C| IH3 : CH2-CH= C-CH2-HCHg-CHg-CH-CHg_ig-i-CHg-CHg-CH-CHg l I (b) Vitamin K1: a blood-clotting cofactor (phylloquínone)
  35. 35. (c) Warfarin: a blood / anticoagulant CH OH | cnz-(If-cng
  36. 36. CHgO CH3 l CH3 CH3 CH3 | l _ o( I | 01130 CH2-CH= J2-CH2+lCH2-CH= À3-CH2 , ,+CH2-CH= C-CH3 l I (d) Ubiquinone: a mitochondrial electron carrier (coenzyme Q) (n. = 4-8)
  37. 37. CH3 CH3 n ? H3 ¡ ? H3 , CHg-CH= C-CH2-H_CH2-CH= C-CH2v), , l (e) Plastoquínone: a chloroplast electron carríer (n = 4-8) ? H3
  38. 38. _ ? H3 _ ? H3 _ ? H3 HO+CH2-CH2-CH-CH2+Í_CH2-CH= C-CH2 J, ,+CH3-CH= C-CH3 l l l (f) Dolichol: a sugar carrier (n = 9-22)
  39. 39. 1 "m" ln: : : up-t ¡im! in (hlumlun mu NI¡ nnulMuIc-r u) Wulrl ! lv-n . unnuvvnn-r (Wcltmáixnu a. ) lc) í Álhunlluax el¡ nnllulnvfrnplly _ 'Ihhnhy z duuxulnçmqnln) Nc-ulml Pular Chamar¡ lnpirl; hpidn lípíuh. (d) cí Hllnwlluu nul Pau), m''| nmchyl »atur- F5. (u) (l) v"" 551m5' H &Kll-¡nvrlim mou-w r! .nmmtcgnnphy | ¡.¡. ,;. | rhmm-n I : cm php' N¡ m. , um JUULJL Iílulinln (inu- Pnun-nlnnínnv

×