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Cholesterol Metabolism

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Cholesterol Metabolism Editing File 2 Cholesterol metabolism Color index : Main text IMPORTANT Extra Info Drs Notes RespiratoryCardiovascular Block Block - Biochemistry - Biochemistry Team Team Objectives: Understand the structure and functions of cholesterol. Discuss the regulation of cholesterol homeostasis in the body. Comprehend the important steps of cholesterol synthesis pathway. Identify different levels of regulation of cholesterol synthesis. Discuss the association of hypercholesterolemia with abnormal cholesterol metabolism. Understand the role of statins in the treatment of hypercholesterolemia. Cholesterol Major sources of liver cholesterol ● It’s the most important animal steroid. Dietary cholesterol Cholesterol synthesized because it is the structural component of all cell comes to liver in De novo in extrahepatic tissues membranes form of synthesis in comes to liver in form Chylomicron the liver of HDL(2) اﻟزاﺋد ﻋن ﺣﺎﺟﺗﮭﺎ ﺑﯾﻧﺗﻘل ﻟﻠـ remnants “lipoprotein” liver Functions: Maintains membrane fluidity. Liver plays a 1 Liver central role in because at high temperatures, it stabilizes the membrane and raises its Cholesterol the regulation melting point, whereas at low temperatures it intercalates between the Pool of cholesterol phospholipids and prevents them from clustering together and stiffening. homeostasis 2 Insulating effect on nerve fibres. It's a component of the Myelin sheath “Low level of cholesterol lead to degradation of nerves “ Secretion of Conversion to Free cholesterol Cholesterol is the parent molecule for bile VLDL secreted in the bile bile acids/salts (Very low density lipoprotein ) 3 Excreted by stool ﯾﻧﺗﻘل ﻟﻛل اﻷورﻗﺎﻧز acids and bile salts We need them for digestion and absorption of dietary fat , Steroid hormones e.g cortisol , (1) Vitamin D3 Major routes by which cholesterol leaves the liver ﺑﺎﺧﺗﺻﺎر اﻟﻠﻲ ﯾﮭﻣﻛم ﺗﻌرﻓوﻧﮫ ھﻧﺎ ھو ان اﻟـ cholesterol ﻣﻣﻛن ﯾوﺻل ﻟﻠـ liver ﺑﺛﻼث طرق : ﻣن ﺧﻼل اﻻﻛل او ﻣﻣﻛن (1) cholesterol is not important only for Vit D3 but it’s important for all fat soluble vitamins. اﻟـ Extrahepatic tissues ﺗﺻﻧّﻌﮫ ﺑﻧﻔﺳﮭﺎ او اﺧر طرﯾﻘﮫ ان اﻟـ liver ﺗﺻﻧّﻌﮫ ﺑﻧﻔﺳﮭﺎ This is why we consider HDL a good cholesterol, because it brings all the excess cholesterol (2) from the body to the liver to be metabolized. ﺑﻌدھﺎ ﻟﻣﺎ ﯾوﺻل ﻟـ liver راح ﺗﺗﺧﻠص ﻣﻧﮫ ﺑرﺿو ﺑﺛﻼث طرق : ﯾﺎ اﻧﮭﺎ ﺗرﺳﻠﮫ ﻟﻸﻋﺿﺎء اﻟﺛﺎﻧﯾﺔ ﻋﻠﻰ ﺷﻛل VLDL أو ﺟزء ﻣﻧﮫ extra info : keep in mind extrahepatic tissues means anything formed outside the liver tissue like* راح ﯾُرﺳل ﻣﺑﺎﺷرة ﻓﻲ اﻟـ bile اﻣﺎ آﺧر طرﯾﻘﺔ أﻧﮭﺎ ﺗﺣوﻟﮫ ﻣﺑﺎﺷرة إﻟﻰ adipose tissue and muscles* bile Cholesterol structure Hydrocarbon “ tail” Cholesterol is made of steroid nucleus that has 4 hydrocarbon fused rings and contain: Hydroxyl group at Double bond Hydrocarbon “tail & 8-10 hydrocarbon C3. between C5 & C6. Free long” at C17 ★ Steroid cholesterol The total number of carbon is 27C. nucleus cholesterol is a type of sterol . all sterols are steroids, (but not all steroids are sterols) Cholesterol Cholesteryl ester has similar structure to cholesterol, but added Fatty acid to the site of hydroxyl group (C3). Hydrocarbon “ tail” Most plasma cholesterol is esterified with a fatty acid. CEs (cholesteryl esters) are not present in Fatty acid membranes Due to absence of the hydrophilic part Steroid (hydroxyl group)& what present in the membrane is free cholesterol ester nucleus cholesteryl Present in small amounts in most cells. More hydrophobic than cholesterol because a fatty acid group was added to it. Cholesteryl ester Cholesterol synthesis Synthesized in all Major sites for synthesis: All carbon atoms Enzymes involved in biosynthesis are partly tissues liver, adrenal cortex, are derived from testes, ovaries and acetyl CoA located in ER and partly (1) intestine (has 2 carbons) in cytoplasm We put the 3 pictures in case if they come as a SAQ , these 3 pictures explained in the next slides اﻟﺳﻼﯾدات اﻟﻠﻲ ﺑﻌدھﺎ ﻣرﯾﺣﮫ ﻟﻠﻌﯾن اﻛﺛر ﻟو ﺗﺑون ﺷرح ، ﺗﻘدرون ﺗرﺟﻌون ﻟﮭﺎﻟﺻور ﻋﺷﺎن ﺗﻌرﻓون byproducts ﻟﻠﻲ طﻠﻌت ودﺧﻠت زي NADPH … اﻟﺦ (1)Even though the enzyme is present in the ER, synthesis only occurs in the cytoplasm, how? Because the catalytic domain of the enzyme that found in the cytoplasm. reversible A helpful video Cholesterol synthesis irreversible 2C 2C ★ Isomerase Acetyl coA Acetyl coA 5C Thiolase DPP coA Transferase IPP ★ HMG CoA synthase is present in both cytosol(cytoplasm) and Acetoacetyl coA Condensation to a 30C 4C 10C compound (squalene) mitochondria of liver: GPP ( which is an opened ring Acetyl coA • Mitochondrial - ketogenesis molecule ) HMG- CoA synthase IPP formation of ketone bodies coA Transferase • Cytosolic – cholesterol synthesis 3-Hydroxy-3-methylglutaryl-CoA 15C FPP • Rate limiting and key step(1) 6C ( HMG CoA ) ★ Squalene • Occurs in cytosol FPP HMG- CoA reductase coA synthase • HMG CoA reductase is an ER membrane enzyme with catalytic Mevalonic acid 30C Squalene unit hanging in the cytosol 6C The enzyme is present in ER but Cyclization of squalene to ★ Squalene the site of action ( catalytic Kinase 30C lanosterol(2) HMG CoA reductase monooxygenase unit ) hanging in cytosol. Lanosterol This step is not 5- Pyrophosphomevalonate 30C 6C (First sterol) Synthesis of 27-Carbon important cholesterol (defect in this leads to Smith-Lemli- decarboxylase Multiple steps Opitz Syndrome “SLOS” ) There is an enzyme that has Production of a 5-carbon unit Isopentenyl pyrophosphate to transfer the double bond patent sterol for all sterols, and the building between C7&C8 to C5&C6, if 27C Cholesterol block of cholesterol the enzyme is absent that 5C5C (IPP) lead to SLOS because the lanosterol didn’t not get (1) step that regulates the whole pathway, which is an irreversible and slow step, and is the target for inhibitors. converted to cholesterol. (2) to form a ring ( the first sterol that is made in the body ). 2 x Acetyl CoA Summary of the pathway In order for you to gain a better understanding Thiolase CoA ﻓﻲ اﻟﺑداﯾﺔ ﺑﻧﺣﺗﺎج ﯾﻛون ﻋﻧدﻧﺎ اﺛﻧﯾن Acetyl coA ﯾﻧدﻣﺟون ﻣﻊ ﺑﻌض ﺑﻌدﯾن ﻧﺣذف CoA ﻣن وﺣدة ﻣﻧﮭم ﺑﻣﺳﺎﻋدة إﻧزاﯾم اﺳﻣﮫ (Thiolase) ﻓﺑﺳﺑب اﻧدﻣﺎﺟﮭم ﺑﯾﺗﻛون ﻋﻧدﻧﺎ ﻣرﻛب ﺟدﯾد اﺳﻣﮫ Acetoacetyl coA ﺑﻌدھﺎ ﺑرﺿو ﺑﻧﺿﯾف Acetyl coA ﺛﺎﻟث وﺑﻧﺣذف ﻣﻧﮫ اﻟـ CoA ﺑﻣﺳﺎﻋدة إﻧزاﯾم اﺳﻣﮫ HMG-COA (HMG-coA synthase) وﺑﯾﺗﻛون ﻋﻧدﻧﺎ ﻣرﻛب ﻣﮭم ﺟدًا اﺳﻣﮫ HMG coA ﺑﻌدھﺎ ﺑﯾﺟﯾﻧﺎ إﻧزاﯾم اﺳﻣﮫ (HMG-coA reductase) ﻣﺎ راح ﯾﺿﯾف synthase Will be explained in ﺷﻲء ﻣﺛل اﻹﻧزاﯾﻣز اﻟﻠﻲ ﻗﺑﻠﮫ ﻷن وظﯾﻔﺗﮫ ﻓﻘط ﯾﻐﯾر اﻟﻣﺟﻣوﻋﺔ اﻟوظﯾﻔﯾﺔ وﯾﺣذف coA وﺑﯾﻛون ﻋﻧدﻧﺎ ﻣرﻛب اﺳﻣﮫ (the next slides .. (Mevalonic acid ﺣﺎﻟﯾًﺎ ﺻﺎر ﻋﻧدﻧﺎ اﻷﺳﯾد ھذا اﻟﻠﻲ ﻋدد اﻟﻛرﺑون ﻓﯾﮫ 6 ﺑﯾﺻﯾر ﻟﮫ ﻛم ﺧطوه ﻋﻠﻰ اﻷﻏﻠب ﻣﺎ ﯾﮭﻣﻛم ﺗﻌرﻓوﻧﮭﺎ ( راح ﯾﻧﺿﺎف ﻓوﺳﻔﺎت وﯾﺻﯾراﺳﻣﮫ Pyrophosphomevalonate ﻋن طرﯾق اﻧزاﯾم kinase وﺑﻌدھﺎ ﺑﻧﺷﯾل ﻣﻧﮫ CO2 ﻋن طرﯾق اﻧزاﯾم decarboxylase) اﻟﻠﻲ ﯾﮭﻣﻛم ﺗﻌرﻓوﻧﮫ أﻧﮫ ﺑﯾﺗﻛون ﻋﻧدﻧﺎ ﻣرﻛب ﺟدﯾد ﻋدد اﻟﻛرﺑون ﻓﯾﮫ 5 واﺳﻣﮫ (IPP) ﺑﻌدھﺎ ﻣن ﺧﻼل Isomerase راح ﯾﺗﺣول إﻟﻰ (DPP) ﻋدد اﻟﻛرﺑون ﻣﺎ ﺗﻐﯾر ﻟﻠﺣﯾن 5 ﻷن اﻷﯾزوﻣﯾرﯾز ﻓﻘط ﻏﯾر HMG-COA ﺷﻛﻠﮫ ﻣﺎ أﺿﺎف ﻟﮫ ﺷﻲء. reductase اﻟﻣراﺣل اﻟﺟﺎﯾﺔ ﻛﻠﮭﺎ ﻋﺑﺎرة ﻋن إﻧدﻣﺎج ﻣرﻛﺑﺎت ﻣﻊ ﺑﻌض ﻋﺷﺎن ﯾﻧﺗﺞ ﻟﻧﺎ اﻟﻛوﻟﯾﺳﺗرول ﻓﻲ اﻟﻧﮭﺎﯾﺔ، اﺣﻔظوھم ﻛذا ﻛﺄﻧﮭم ﻣﻌﺎدﻻت: DPP(C5) + IPP (C5) = GPP(C10).. The enzyme: Transferase Isomerase GPP (C10) + IPP(C5) = FPP(C15).. The enzyme: Transferase FPP (C15) + FPP (C15) = Squalene (C30).. The enzyme is: Squalene synthase Dimethylallyl pyrophosphate Then Dimethylallyl pyrophosphate + isopentenyl pyrophosphate ﻟﻛن ﻓﻲ ھﺎﻟﺣﺎﻟﺔ اﻟـ Squalene ﺑﯾﻛون linar وأﺣﻧﺎ ﻧﺣﺗﺎﺟﮫ ﯾﻛون rings ﻓﺑﻧﺳوي ﻟﮫ Cyclization ﻣن ﺧﻼل إﻧزاﯾم اﺳﻣﮫ Transferase Squalane monoxygenase وﺑﺗﻐﯾر اﺳم اﻟﻣرﻛب وﺑﯾﺻﯾر Lanosterol وھذا ﯾﻌﺗﺑر أول ﺳﺗﯾرول ﯾﺗﻛون ﻟﻛن ﻣو ھو اﻟطﺑﯾﻌﻲ اﻟﻠﻲ ﻧﺣﺗﺎﺟﮫ ﻷن ﻋدد اﻟﻛرﺑون ﻓﯾﮫ 30 وﻟو ﺑﻘﻰ ھذا ﺑﺟﺳﻣﻧﺎ وﻣﺎ ﺗﺣول إﻟﻰ ﻛوﻟﯾﺳﺗرول ﻓراح ﯾﺳﺑب ﻟﻧﺎ ﻣرض اﺳﻣﮫ (SLOS) ﻓﻌﺷﺎن ﻛذا ﺿروري ﯾﺗﺣول Geranyl pyrophosphate Then ﻟﻛن ﺣﻧﺎ ﻣﺎ ﯾﮭﻣﻧﺎ ﻧﻌرف ﺧطوات اﻟﺗﺣول اﻟﻣﮭم ﺑﺎﻷﺧﯾر ﺑﯾﺗﻛون ﻋﻧدﻧﺎ اﻟﻛوﻟﺳﺗرول اﻟطﺑﯾﻌﻲ اﻟﻠﻲ ﻋدد اﻟﻛرﺑون ﻓﯾﮫ Geranyl pyrophosphate + isopentenyl pyrophosphate 27 اﻟﺧطوات اﻻوﻟﻰ ﻟﯾن ال pyrophosphomevalonate ﻋﻠﯾﻛم ﺗﺣﻔظوﻧﮭﺎ ﺑس ﻋﺷﺎن ﺗﺣﻔظون ال sequence of products ﺑﻌدھﺎ ﻋﻧدﻛم ھﺎﻟـ mnemonics Transferase ”I Don't Get it why Fatimah Stole Lama's Coat or I Do Get Frightened Stealing Luxurious“ I = isopentenyl pyrophosphate Farnesyl pyrophosphate D = Dimethylallyl pyrophosphate Then 2 x Farnesyl pyrophosphate G = Geranyl pyrophosphate F = Farnesyl pyrophosphate Squalene S = Squalene synthase Squalane Squalene monoxygenase Lanosterol Cholesterol L = Lanosterol Multistep Finally we arrived C = Cholesterol ★ extra explanation Summary of the pathway In order for you to gain a better understanding In tables Reaction 1 ★ Reaction 2 ★ Reaction 3 Reactant 2 Acetyl coA Reactant Acetoacetyl coA + Reactant HMG CoA Acetyl coA Product Acetoacetyl coA Product Mevalonic acid Product HMG CoA Enzyme Thiolase Enzyme HMG- CoA reductase Enzyme HMG- CoA synthase Action Join 2 Acetyl coA Action Join them together and together and remove Action Join them together and remove CoA CoA remove CoA Byproduct Use 2NADPH + 2H+ and Byproduct COA Byproduct COA produce NADP+ Reaction 4 ★ Reaction 5 Reaction 6 Reactant IPP Reactant Mevalonic acid Reactant 5- Pyrophosphomevalonate Product Dimethylallyl Product 5- Pyrophosphomevalonate Product Isopentenyl pyrophosphate (DPP) pyrophosphate (IPP) Enzyme Kinase Enzyme Isomerase Enzyme decarboxylase Action Add 2 phosphate groups Action Change the structure of to it the molecule Action Remove CO2 group Consume 2 ATP Byproduct - Consume 1 ATP ★ extra explanation Summary of the pathway In order for you to gain a better understanding In tables … contd Reaction 7 Reaction 8 ★ Reaction 9 Reactant DPP + IPP Reactant GPP + IPP Reactant 2 FPP Product Squalene Product Geranyl pyrophosphate Product Farnesyl pyrophosphate
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