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Fatty acid desaturase

February 15, 2024

Fatty acid desaturases (also called unsaturases) are a family of enzymes that convert saturated fatty acids into unsaturated fatty acids and polyunsaturated fatty acids. For the common fatty acids of the C18 variety, desaturases convert stearic acid into oleic acid. Other desaturases convert oleic acid into linolenic acid, which is the precursor to alpha-linolenic acid, gamma-linolenic acid, and eicosatrienoic acid.[1]

Fatty acid desaturase, type 1
Identifiers
SymbolFatty_acid_desaturase-1
PfamPF00487
InterProIPR005804
OPM superfamily431
OPM protein4zyo
Available protein structures:
Pfam  structures / ECOD  
PDBRCSB PDB; PDBe; PDBj
PDBsumstructure summary
Fatty acid desaturase, type 2
Identifiers
SymbolFatty_acid_desaturase-2
PfamPF03405
InterProIPR005067
Available protein structures:
Pfam  structures / ECOD  
PDBRCSB PDB; PDBe; PDBj
PDBsumstructure summary

Two subgroups of desaturases are recognized:

  • Delta - indicating that the double bond is created at a fixed position from the carboxyl end of a fatty acid chain. For example, Δ9-desaturase creates a double bond between the ninth and tenth carbon atom from the carboxyl end.
  • Omega - indicating the double bond is created at a fixed position from the methyl end of a fatty acid chain. For instance, ω3 desaturase creates a double bond between the third and fourth carbon atom from the methyl end. In other words, it creates an omega-3 fatty acid.

For example, Δ6 desaturation introduces a double bond between carbons 6 and 7 of linoleic acid (LA C18H32O2; 18:2-n6) and α-linolenic acid (ALA: C18H30O2; 18:3-n3), creating γ-linolenic acid (GLA: C18H30O2,18:3-n6) and stearidonic acid (SDA: C18H28O2; 18:4-n3) respectively.[2]

In the biosynthesis of essential fatty acids, an elongase alternates with various desaturases (for example, Δ6-desaturase) repeatedly inserts an ethyl group, then forms a double bond.

Mechanism and function edit

Desaturases have diiron active sites reminiscent of methane monooxygenase. These enzymes are O2-dependent, consistent with their function as either hydroxylation or oxidative dehydrogenation.[3]

Desaturases produce unsaturated fatty acids. Unsaturated fatty acids help maintain structure and function of membranes. Highly unsaturated fatty acids (HUFAs) are incorporated into phospholipids and participate in cell signaling.[4]

Unsaturated fatty acids and their derived fats increase the fluidity of membranes.[5]

Role in human metabolism edit

Fatty acid desaturase appear in all organisms: for example, bacteria, fungus, plants, animals and humans.[6] Four desaturases occur in humans: Δ9-desaturase, Δ6-desaturase, Δ5-desaturase, and Δ4-desaturase.[4]

Δ9-desaturase, also known as stearoyl-CoA desaturase-1, is used to synthesize oleic acid, a monounsaturated, ubiquitous component of all cells in the human body, and the major fatty acid in mammalian adipose triglycerides, and also used for phospholipid and cholesteryl ester synthesis.[4] Δ9-desaturase produces oleic acid (C18H34O2; 18:1-n9) by desaturating stearic acid (SA: C18H36O2; 18:0), a saturated fatty acid either synthesized in the body from palmitic acid (PA: C16H32O2; 16:0) or ingested directly.

Δ6 and Δ5 desaturases are required for the synthesis of highly unsaturated fatty acids such as eicosopentaenoic and docosahexaenoic acids (synthesized from α-linolenic acid); arachidonic acid and adrenic acid (synthesized from linoleic acid). This is a multi-stage process requiring successive actions by elongase and desaturase enzymes. The genes coding for Δ6 and Δ5 desaturase production have been located on human chromosome 11.[7]

Synthesis of LC-PUFAs in humans and many other eukaryotes starts with:

* Linoleic acid (LA: C18H32O2; 18:2-n6) → Δ6-desaturation → γ-linolenic acid (GLA: C18H30O2; 18:3-n6) → Δ6-specific elongase (introducing two carbons) → dihomo-gamma-linolenic acid DGLA: C20H34O2; 20:3-n6) → Δ5-desaturase → arachidonic acid (AA: C20H32O2; 20:4-n6) → also endocannabinoids.

* α-Linolenic acid (ALA: C18H30O2; 18:3-n3) → Δ6-desaturation → stearidonic acid (SDA: C18H28O2; 18:4-n3) and/or → Δ6-specific elongase → eicosatetraenoic acid (ETA: C20H32O2; 20:4-n3) → Δ5-desaturase → eicosapentaenoic acid (EPA: C20H30O2; 20:5-n3).

By a Δ17-desaturase, gamma-linolenic acid (GLA: C18H30O2; 18:3-n6) can be further converted to stearidonic acid (SDA: C18H28O2; 18:4-n3), dihomo-gamma-linolenic acid (DHGLA/DGLA: C20H34O2; 20:3-n6) to eicosatetraenoic acid (ETA: C20H32O2; 20:4-n3; omega-3 arachidonic acid)[8] and arachidonic acid (AA: C20H32O2; 20:4-n6) to eicosapentaenoic acid (EPA: C20H30O2; 20:5-n3), respectively.[2]

* Anandamide (AEA: C22H37NO2; 20:4,n-6) is an N-acylethanolamine resulting from the formal condensation of the carboxyl group of arachidonic acid (AA: C20H32O2; 20:4-n6) with the amino group of ethanolamine (C2H7NO), bind preferably to CB1 receptors.[10]

* 2-Arachidonoylglycerol (2-AG: C23H38O4; 20:4-n6) is an endogenous agonist of the cannabinoid receptors (CB1 and CB2), and the physiological ligand for the cannabinoid CB2 receptor.[11] It is an ester formed from omega-6-arachidonic acid (AA: C20H32O2; 20:4-n6) and glycerol (C3H8O3).[12]

Vertebrates are unable to synthesize polyunsaturated fatty acids because they do not have the necessary fatty acid desaturases to "convert oleic acid (18:1n-9) into linoleic acid (18:2n-6) and α-linolenic acid (18:3n-3)".[7] Linoleic acid (LA) and α-linolenic acid (ALA) are essential for human health and development, and should therefore be consumed by diets, like 15 ml of hemp seed oil, or/and 33 gram of hemp seed protein a day,[13] can provide all the protein, essential fatty acids, and dietary fiber necessary for human survival for one day,[14] as their absence has been found responsible for the development of a wide range of diseases such as metabolic disorders,[15] cardiovascular disorders, inflammatory processes, viral infections, certain types of cancer and autoimmune disorders.[16]

Human fatty acid desaturases include: DEGS1; DEGS2; FADS1; FADS2; FADS3; FADS6; SCD4; SCD5

Classification edit

Δ-desaturases are represented by two distinct families which do not seem to be evolutionarily related.

Family 1 includes Stearoyl-CoA desaturase-1 (SCD) (EC 1.14.19.1).[17]

Family 2 is composed of:

  • Bacterial fatty acid desaturases.
  • Plant stearoyl-acyl-carrier-protein desaturase (EC 1.14.19.1),[18] an enzyme that catalyzes the introduction of a double bond at the delta-9 position of steraoyl-ACP to produce oleoyl-ACP. This enzyme is responsible for the conversion of saturated fatty acids to unsaturated fatty acids in the synthesis of vegetable oils.
  • Cyanobacterial DesA,[19] an enzyme that can introduce a second cis double bond at the delta-12 position of fatty acid bound to membrane glycerolipids. This enzyme is involved in chilling tolerance; the phase transition temperature of lipids of cellular membranes being dependent on the degree of unsaturation of fatty acids of the membrane lipids.

Acyl-CoA dehydrogenases edit

Acyl-CoA dehydrogenases are enzymes that catalyze formation of a double bond between C2 (α) and C3 (β) of the acyl-CoA thioester substrates.[20] Flavin adenine dinucleotide (FAD) is a required co-factor.

 

See also edit

N-acylethanolamine (NAE)

References edit

  1. ^ Jiao J, Zhang Y (May 2013). "Transgenic biosynthesis of polyunsaturated fatty acids: a sustainable biochemical engineering approach for making essential fatty acids in plants and animals". Chemical Reviews. 113 (5): 3799–3814. doi:10.1021/cr300007p. PMID 23421688.
  2. ^ a b Abedi E, Sahari MA (September 2014). "Long-chain polyunsaturated fatty acid sources and evaluation of their nutritional and functional properties". Food Science & Nutrition. 2 (5): 443–463. doi:10.1002/fsn3.121. PMC 4237475. PMID 25473503.
  3. ^ Wallar BJ, Lipscomb JD (November 1996). "Dioxygen Activation by Enzymes Containing Binuclear Non-Heme Iron Clusters". Chemical Reviews. 96 (7): 2625–2658. doi:10.1021/cr9500489. PMID 11848839.
  4. ^ a b c Nakamura MT, Nara TY (2004). "Structure, function, and dietary regulation of Δ6, Δ5, and Δ9 desaturases". Annual Review of Nutrition. 24: 345–376. doi:10.1146/annurev.nutr.24.121803.063211. PMID 15189125.
  5. ^ Alberts B, Johnson A, Lewis J, Raff M, Roberts K, Walter P (2002). "The Fluidity of a Lipid Bilayer Depends on Its Composition". Molecular Biology of the Cell (4th ed.). New York: Garland Science. p. 588. ISBN 978-0-8153-3218-3.
  6. ^ Los DA, Murata N (October 1998). "Structure and expression of fatty acid desaturases". Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism. 1394 (1): 3–15. doi:10.1016/S0005-2760(98)00091-5. PMID 9767077.
  7. ^ a b Hastings N, Agaba M, Tocher DR, Leaver MJ, Dick JR, Sargent JR, Teale AJ (December 2001). "A vertebrate fatty acid desaturase with Delta 5 and Delta 6 activities". Proceedings of the National Academy of Sciences of the United States of America. 98 (25): 14304–14309. Bibcode:2001PNAS...9814304H. doi:10.1073/pnas.251516598. PMC 64677. PMID 11724940.
  8. ^ "8,11,14,17-Eicosatetraenoic acid". PubChem. U.S. National Library of Medicine. Retrieved 2022-11-27.
  9. ^ Berger A, Crozier G, Bisogno T, Cavaliere P, Innis S, Di Marzo V (May 2001). "Anandamide and diet: inclusion of dietary arachidonate and docosahexaenoate leads to increased brain levels of the corresponding N-acylethanolamines in piglets". Proceedings of the National Academy of Sciences of the United States of America. 98 (11): 6402–6406. Bibcode:2001PNAS...98.6402B. doi:10.1073/pnas.101119098. PMC 33480. PMID 11353819.
  10. ^ "Anandamide". PubChem. U.S. National Library of Medicine. Retrieved 2022-11-28.
  11. ^ Sugiura T, Kondo S, Kishimoto S, Miyashita T, Nakane S, Kodaka T, et al. (January 2000). "Evidence that 2-arachidonoylglycerol but not N-palmitoylethanolamine or anandamide is the physiological ligand for the cannabinoid CB2 receptor. Comparison of the agonistic activities of various cannabinoid receptor ligands in HL-60 cells". The Journal of Biological Chemistry. 275 (1): 605–612. doi:10.1074/jbc.275.1.605. PMID 10617657.
  12. ^ "2-Arachidonoylglycerol". PubChem. U.S. National Library of Medicine. Retrieved 2022-11-28.
  13. ^ Galasso I, Russo R, Mapelli S, Ponzoni E, Brambilla IM, Battelli G, Reggiani R (2016-05-20). "Variability in Seed Traits in a Collection of Cannabis sativa L. Genotypes". Frontiers in Plant Science. 7: 688. doi:10.3389/fpls.2016.00688. PMC 4873519. PMID 27242881.
  14. ^ "Hemp Seed Protein". Innvista. Retrieved 2022-11-28.
  15. ^ Charytoniuk T, Zywno H, Berk K, Bzdega W, Kolakowski A, Chabowski A, Konstantynowicz-Nowicka K (March 2022). "The Endocannabinoid System and Physical Activity-A Robust Duo in the Novel Therapeutic Approach against Metabolic Disorders". International Journal of Molecular Sciences. 23 (6): 3083. doi:10.3390/ijms23063083. PMC 8948925. PMID 35328503.
  16. ^ Guil-Guerrero JL, Rincón-Cervera MÁ, Venegas-Venegas E (2010). "Gamma‐linolenic and stearidonic acids: Purification and upgrading of C18‐PUFA oils". European Journal of Lipid Science and Technology. 112 (10): 1068–1081. doi:10.1002/ejlt.200900294. ISSN 1438-7697.
  17. ^ Kaestner KH, Ntambi JM, Kelly Jr TJ, Lane MD (September 1989). "Differentiation-induced gene expression in 3T3-L1 preadipocytes. A second differentially expressed gene encoding stearoyl-CoA desaturase" (PDF). The Journal of Biological Chemistry. 264 (25): 14755–61. doi:10.1016/S0021-9258(18)63763-9. PMID 2570068.
  18. ^ Shanklin J, Somerville C (March 1991). "Stearoyl-acyl-carrier-protein desaturase from higher plants is structurally unrelated to the animal and fungal homologs". Proceedings of the National Academy of Sciences of the United States of America. 88 (6): 2510–4. Bibcode:1991PNAS...88.2510S. doi:10.1073/pnas.88.6.2510. PMC 51262. PMID 2006187.
  19. ^ Wada H, Gombos Z, Murata N (September 1990). "Enhancement of chilling tolerance of a cyanobacterium by genetic manipulation of fatty acid desaturation". Nature. 347 (6289): 200–3. Bibcode:1990Natur.347..200W. doi:10.1038/347200a0. PMID 2118597. S2CID 4326551.
  20. ^ Thorpe C, Kim JJ (June 1995). "Structure and mechanism of action of the acyl-CoA dehydrogenases". FASEB Journal. 9 (9): 718–25. doi:10.1096/fasebj.9.9.7601336. PMID 7601336. S2CID 42549744.
This article incorporates text from the public domain Pfam and InterPro: IPR005067

February 15, 2024
fatty, acid, desaturase, also, called, unsaturases, family, enzymes, that, convert, saturated, fatty, acids, into, unsaturated, fatty, acids, polyunsaturated, fatty, acids, common, fatty, acids, variety, desaturases, convert, stearic, acid, into, oleic, acid, . Fatty acid desaturases also called unsaturases are a family of enzymes that convert saturated fatty acids into unsaturated fatty acids and polyunsaturated fatty acids For the common fatty acids of the C18 variety desaturases convert stearic acid into oleic acid Other desaturases convert oleic acid into linolenic acid which is the precursor to alpha linolenic acid gamma linolenic acid and eicosatrienoic acid 1 Fatty acid desaturase type 1IdentifiersSymbolFatty acid desaturase 1PfamPF00487InterProIPR005804OPM superfamily431OPM protein4zyoAvailable protein structures Pfam structures ECOD PDBRCSB PDB PDBe PDBjPDBsumstructure summaryFatty acid desaturase type 2IdentifiersSymbolFatty acid desaturase 2PfamPF03405InterProIPR005067Available protein structures Pfam structures ECOD PDBRCSB PDB PDBe PDBjPDBsumstructure summaryTwo subgroups of desaturases are recognized Delta indicating that the double bond is created at a fixed position from the carboxyl end of a fatty acid chain For example D9 desaturase creates a double bond between the ninth and tenth carbon atom from the carboxyl end Omega indicating the double bond is created at a fixed position from the methyl end of a fatty acid chain For instance w3 desaturase creates a double bond between the third and fourth carbon atom from the methyl end In other words it creates an omega 3 fatty acid For example D6 desaturation introduces a double bond between carbons 6 and 7 of linoleic acid LA C18H32O2 18 2 n6 and a linolenic acid ALA C18H30O2 18 3 n3 creating g linolenic acid GLA C18H30O2 18 3 n6 and stearidonic acid SDA C18H28O2 18 4 n3 respectively 2 In the biosynthesis of essential fatty acids an elongase alternates with various desaturases for example D6 desaturase repeatedly inserts an ethyl group then forms a double bond Contents 1 Mechanism and function 2 Role in human metabolism 3 Classification 4 Acyl CoA dehydrogenases 5 See also 6 ReferencesMechanism and function editDesaturases have diiron active sites reminiscent of methane monooxygenase These enzymes are O2 dependent consistent with their function as either hydroxylation or oxidative dehydrogenation 3 Desaturases produce unsaturated fatty acids Unsaturated fatty acids help maintain structure and function of membranes Highly unsaturated fatty acids HUFAs are incorporated into phospholipids and participate in cell signaling 4 Unsaturated fatty acids and their derived fats increase the fluidity of membranes 5 Role in human metabolism editFatty acid desaturase appear in all organisms for example bacteria fungus plants animals and humans 6 Four desaturases occur in humans D9 desaturase D6 desaturase D5 desaturase and D4 desaturase 4 D9 desaturase also known as stearoyl CoA desaturase 1 is used to synthesize oleic acid a monounsaturated ubiquitous component of all cells in the human body and the major fatty acid in mammalian adipose triglycerides and also used for phospholipid and cholesteryl ester synthesis 4 D9 desaturase produces oleic acid C18H34O2 18 1 n9 by desaturating stearic acid SA C18H36O2 18 0 a saturated fatty acid either synthesized in the body from palmitic acid PA C16H32O2 16 0 or ingested directly D6 and D5 desaturases are required for the synthesis of highly unsaturated fatty acids such as eicosopentaenoic and docosahexaenoic acids synthesized from a linolenic acid arachidonic acid and adrenic acid synthesized from linoleic acid This is a multi stage process requiring successive actions by elongase and desaturase enzymes The genes coding for D6 and D5 desaturase production have been located on human chromosome 11 7 Synthesis of LC PUFAs in humans and many other eukaryotes starts with Linoleic acid LA C18H32O2 18 2 n6 D6 desaturation g linolenic acid GLA C18H30O2 18 3 n6 D6 specific elongase introducing two carbons dihomo gamma linolenic acid DGLA C20H34O2 20 3 n6 D5 desaturase arachidonic acid AA C20H32O2 20 4 n6 also endocannabinoids a Linolenic acid ALA C18H30O2 18 3 n3 D6 desaturation stearidonic acid SDA C18H28O2 18 4 n3 and or D6 specific elongase eicosatetraenoic acid ETA C20H32O2 20 4 n3 D5 desaturase eicosapentaenoic acid EPA C20H30O2 20 5 n3 By a D17 desaturase gamma linolenic acid GLA C18H30O2 18 3 n6 can be further converted to stearidonic acid SDA C18H28O2 18 4 n3 dihomo gamma linolenic acid DHGLA DGLA C20H34O2 20 3 n6 to eicosatetraenoic acid ETA C20H32O2 20 4 n3 omega 3 arachidonic acid 8 and arachidonic acid AA C20H32O2 20 4 n6 to eicosapentaenoic acid EPA C20H30O2 20 5 n3 respectively 2 Fatty acids with at least 20 carbons C20 and three double bonds 20 3 bind to CB1 receptors 9 Arachidonic acid AA is also the catalyst to the formation of the two main endocannabinoids anandamide AEA and 2 arachidonoylglycerol 2 AG Anandamide AEA C22H37NO2 20 4 n 6 is an N acylethanolamine resulting from the formal condensation of the carboxyl group of arachidonic acid AA C20H32O2 20 4 n6 with the amino group of ethanolamine C2H7NO bind preferably to CB1 receptors 10 2 Arachidonoylglycerol 2 AG C23H38O4 20 4 n6 is an endogenous agonist of the cannabinoid receptors CB1 and CB2 and the physiological ligand for the cannabinoid CB2 receptor 11 It is an ester formed from omega 6 arachidonic acid AA C20H32O2 20 4 n6 and glycerol C3H8O3 12 Vertebrates are unable to synthesize polyunsaturated fatty acids because they do not have the necessary fatty acid desaturases to convert oleic acid 18 1n 9 into linoleic acid 18 2n 6 and a linolenic acid 18 3n 3 7 Linoleic acid LA and a linolenic acid ALA are essential for human health and development and should therefore be consumed by diets like 15 ml of hemp seed oil or and 33 gram of hemp seed protein a day 13 can provide all the protein essential fatty acids and dietary fiber necessary for human survival for one day 14 as their absence has been found responsible for the development of a wide range of diseases such as metabolic disorders 15 cardiovascular disorders inflammatory processes viral infections certain types of cancer and autoimmune disorders 16 Human fatty acid desaturases include DEGS1 DEGS2 FADS1 FADS2 FADS3 FADS6 SCD4 SCD5Classification editD desaturases are represented by two distinct families which do not seem to be evolutionarily related Family 1 includes Stearoyl CoA desaturase 1 SCD EC 1 14 19 1 17 Family 2 is composed of Bacterial fatty acid desaturases Plant stearoyl acyl carrier protein desaturase EC 1 14 19 1 18 an enzyme that catalyzes the introduction of a double bond at the delta 9 position of steraoyl ACP to produce oleoyl ACP This enzyme is responsible for the conversion of saturated fatty acids to unsaturated fatty acids in the synthesis of vegetable oils Cyanobacterial DesA 19 an enzyme that can introduce a second cis double bond at the delta 12 position of fatty acid bound to membrane glycerolipids This enzyme is involved in chilling tolerance the phase transition temperature of lipids of cellular membranes being dependent on the degree of unsaturation of fatty acids of the membrane lipids Acyl CoA dehydrogenases editAcyl CoA dehydrogenases are enzymes that catalyze formation of a double bond between C2 a and C3 b of the acyl CoA thioester substrates 20 Flavin adenine dinucleotide FAD is a required co factor nbsp See also editN acylethanolamine NAE References edit Jiao J Zhang Y May 2013 Transgenic biosynthesis of polyunsaturated fatty acids a sustainable biochemical engineering approach for making essential fatty acids in plants and animals Chemical Reviews 113 5 3799 3814 doi 10 1021 cr300007p PMID 23421688 a b Abedi E Sahari MA September 2014 Long chain polyunsaturated fatty acid sources and evaluation of their nutritional and functional properties Food Science amp Nutrition 2 5 443 463 doi 10 1002 fsn3 121 PMC 4237475 PMID 25473503 Wallar BJ Lipscomb JD November 1996 Dioxygen Activation by Enzymes Containing Binuclear Non Heme Iron Clusters Chemical Reviews 96 7 2625 2658 doi 10 1021 cr9500489 PMID 11848839 a b c Nakamura MT Nara TY 2004 Structure function and dietary regulation of D6 D5 and D9 desaturases Annual Review of Nutrition 24 345 376 doi 10 1146 annurev nutr 24 121803 063211 PMID 15189125 Alberts B Johnson A Lewis J Raff M Roberts K Walter P 2002 The Fluidity of a Lipid Bilayer Depends on Its Composition Molecular Biology of the Cell 4th ed New York Garland Science p 588 ISBN 978 0 8153 3218 3 Los DA Murata N October 1998 Structure and expression of fatty acid desaturases Biochimica et Biophysica Acta BBA Lipids and Lipid Metabolism 1394 1 3 15 doi 10 1016 S0005 2760 98 00091 5 PMID 9767077 a b Hastings N Agaba M Tocher DR Leaver MJ Dick JR Sargent JR Teale AJ December 2001 A vertebrate fatty acid desaturase with Delta 5 and Delta 6 activities Proceedings of the National Academy of Sciences of the United States of America 98 25 14304 14309 Bibcode 2001PNAS 9814304H doi 10 1073 pnas 251516598 PMC 64677 PMID 11724940 8 11 14 17 Eicosatetraenoic acid PubChem U S National Library of Medicine Retrieved 2022 11 27 Berger A Crozier G Bisogno T Cavaliere P Innis S Di Marzo V May 2001 Anandamide and diet inclusion of dietary arachidonate and docosahexaenoate leads to increased brain levels of the corresponding N acylethanolamines in piglets Proceedings of the National Academy of Sciences of the United States of America 98 11 6402 6406 Bibcode 2001PNAS 98 6402B doi 10 1073 pnas 101119098 PMC 33480 PMID 11353819 Anandamide PubChem U S National Library of Medicine Retrieved 2022 11 28 Sugiura T Kondo S Kishimoto S Miyashita T Nakane S Kodaka T et al January 2000 Evidence that 2 arachidonoylglycerol but not N palmitoylethanolamine or anandamide is the physiological ligand for the cannabinoid CB2 receptor Comparison of the agonistic activities of various cannabinoid receptor ligands in HL 60 cells The Journal of Biological Chemistry 275 1 605 612 doi 10 1074 jbc 275 1 605 PMID 10617657 2 Arachidonoylglycerol PubChem U S National Library of Medicine Retrieved 2022 11 28 Galasso I Russo R Mapelli S Ponzoni E Brambilla IM Battelli G Reggiani R 2016 05 20 Variability in Seed Traits in a Collection of Cannabis sativa L Genotypes Frontiers in Plant Science 7 688 doi 10 3389 fpls 2016 00688 PMC 4873519 PMID 27242881 Hemp Seed Protein Innvista Retrieved 2022 11 28 Charytoniuk T Zywno H Berk K Bzdega W Kolakowski A Chabowski A Konstantynowicz Nowicka K March 2022 The Endocannabinoid System and Physical Activity A Robust Duo in the Novel Therapeutic Approach against Metabolic Disorders International Journal of Molecular Sciences 23 6 3083 doi 10 3390 ijms23063083 PMC 8948925 PMID 35328503 Guil Guerrero JL Rincon Cervera MA Venegas Venegas E 2010 Gamma linolenic and stearidonic acids Purification and upgrading of C18 PUFA oils European Journal of Lipid Science and Technology 112 10 1068 1081 doi 10 1002 ejlt 200900294 ISSN 1438 7697 Kaestner KH Ntambi JM Kelly Jr TJ Lane MD September 1989 Differentiation induced gene expression in 3T3 L1 preadipocytes A second differentially expressed gene encoding stearoyl CoA desaturase PDF The Journal of Biological Chemistry 264 25 14755 61 doi 10 1016 S0021 9258 18 63763 9 PMID 2570068 Shanklin J Somerville C March 1991 Stearoyl acyl carrier protein desaturase from higher plants is structurally unrelated to the animal and fungal homologs Proceedings of the National Academy of Sciences of the United States of America 88 6 2510 4 Bibcode 1991PNAS 88 2510S doi 10 1073 pnas 88 6 2510 PMC 51262 PMID 2006187 Wada H Gombos Z Murata N September 1990 Enhancement of chilling tolerance of a cyanobacterium by genetic manipulation of fatty acid desaturation Nature 347 6289 200 3 Bibcode 1990Natur 347 200W doi 10 1038 347200a0 PMID 2118597 S2CID 4326551 Thorpe C Kim JJ June 1995 Structure and mechanism of action of the acyl CoA dehydrogenases FASEB Journal 9 9 718 25 doi 10 1096 fasebj 9 9 7601336 PMID 7601336 S2CID 42549744 This article incorporates text from the public domain Pfam and InterPro IPR005067 Retrieved from https en wikipedia org w index php title Fatty acid desaturase amp oldid 1171234762, wikipedia, wiki, book, books, library,

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