11. Lípidos isoprenoides
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Transcript of 11. Lípidos isoprenoides
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11. Lípidos isoprenoides
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Lípidos isoprenoides
Formados por aposición de unidades isoprenoides:
H3CC
CH3
CHCH3
HO CHO
Colesterol
11-cis retinal
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Unión cabeza-cola
Unión cola-cola
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C5 Monoprenoides HemiterpenosC10 Diprenoides MonoterpenosC15 Triprenoides SesquiterpenosC20 Tetraprenoides Diterpenos
C30 Hexaprenoides TriterpenosC40 Octaprenoides Tetraterpenos
Lípidos isoprenoides: nomenclatura
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H2CC
CH2
CH2CH2OHCH2OH
CH2OH
CH2OH
Isopentenol
Geraniol
Farnesol
Escualeno
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Esteroides
Compuestos hexaprenoides estructurados en unsistema polialicíclico, ciclopentano perhidrofenantreno
- Esteroles o alcoholes esteroideos- Calciferoles o vitaminas D- Ácidos biliares- Esteroides hormonales, que incluyen:
- Glucocorticoides- Mineralocorticoides- Gestágenos- Estrógenos- Andrógenos
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HOH
12
345
67
89
10
11121314 15
1617
18
19
20
2122
23
24
2526
27
Numeración
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HHO
Colestanol
CH3
H
A B
CH3
H
Serieallo
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HOH
Coprostanol
CH3
H
A B
CH3
HSerienormal
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HOColesterol
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CH2
Colecalciferol
CH2
OH
25-hidroxicolecalciferol
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CH2
OH
HO
1,25 dihidroxicolecalciferol
Colesterol
7-dehidrocolesterol
Colecalciferol
25-hidroxicolecalciferol
1,25-dihidroxicolecalciferol
Luz ultravioleta
Estímulo transcripcional desíntesis de transportador
intestinal de calcio
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COO-
HOHHO
OH
CO
HHO OH
OHNH CH2 COO
-
CO
HHO OH
OHNH CH2 CH2 S
O
O
O-
Ác.cólico
Ác.taurocólico
Ác.glicocólico
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Ácido cólico(visto por la cara polar)
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C O
CH2OH
O
HO OH
O
C O
CH2OH
CHO
HO
Cortisol
Aldosterona
Glucocorticoides
Mineralocorticoides
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Progesterona
C O
O
CH3
Gestágenos
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OH
HO 17- estradiol
Estrógenos
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O
OH
Testosterona
Andrógenos
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Terpenos
Compuestos poliprenoides no esteroideos, que incluyen:
- Retinoides o vitaminas A- Tocoferoles o vitaminas E- Naftoquinonas o vitaminas K
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CH2OH
Retinol
-caroteno
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CHO
CHO11-cis retinal
todo-trans retinal
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HCN
CHCO
HNHC
OCNH
CH
NHOC
HCHN
CO
R
R
R
Uniónretinal-opsina
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11-cis retinal
Opsina
Rodopsina (11-cis)
Rodopsina*
todo-trans retinal
Opsina
h
(cuanto de luz)
Retinalisomerasa
El ciclo visual, 1
Impulsonervioso
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Rodopsina* + Transducina + cGMPfosfodiesterasa
cGMP (canaliónico abierto)
5’-GMP (canaliónico cerrado)
Impulsonervioso
El ciclo visual, 2
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-tocoferol
O
CH3
H3C
HO
CH3
3
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Radical librelipídico, L*
Radical libreoxigenado, L-O-O*
O2
Lípidointacto, L
HidroperóxidoL-O-O-H
Enranciamiento
Peroxidación encadena de lípidos
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Naftoquinona
O
O
CH3
n
O
O
CH3
Menadiona
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O
OH
CH2
OOO
OH
Dicumarol
COO-
HC COO-
CH2
HC NH3+
COO-
Ác. -carboxiglutámico
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O P
O
O-
O-16
Dolicol fosfato