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Maresin information


Maresin 1
Names
Preferred IUPAC name
(4Z,7R,8E,10E,12Z,14S,16Z,19Z)-7,14-Dihydroxydocosa-4,8,10,12,16,19-hexaenoic acid
Identifiers
CAS Number
  • 1268720-28-0 ☒N
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:138249
ChemSpider
  • 29341935
PubChem CID
  • 60201795
UNII
  • M82H7JW4HK checkY
InChI
  • InChI=1S/C22H32O4/c1-2-3-4-5-6-10-15-20(23)16-11-7-8-12-17-21(24)18-13-9-14-19-22(25)26/h3-4,6-13,16-17,20-21,23-24H,2,5,14-15,18-19H2,1H3,(H,25,26)/b4-3-,8-7+,10-6-,13-9-,16-11-,17-12+/t20-,21-/m0/s1
    Key: HLHYXXBCQOUTGK-FHCQLJOMSA-N
  • InChI=1/C22H32O4/c1-2-3-4-5-6-10-15-20(23)16-11-7-8-12-17-21(24)18-13-9-14-19-22(25)26/h3-4,6-13,16-17,20-21,23-24H,2,5,14-15,18-19H2,1H3,(H,25,26)/b4-3-,8-7+,10-6-,13-9-,16-11-,17-12+/t20-,21-/m0/s1
    Key: HLHYXXBCQOUTGK-FHCQLJOMBD
SMILES
  • CC/C=C\C/C=C\C[C@@H](/C=C\C=C\C=C\[C@@H](C/C=C\CCC(=O)O)O)O
Properties
Chemical formula
C22H32O4
Molar mass 360.494 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Maresin 1 (MaR1 or 7R,14S-dihydroxy-4Z,8E,10E,12Z,16Z,19Z-docosahexaenoic acid) is a macrophage-derived mediator of inflammation resolution coined from macrophage mediator in resolving inflammation. Maresin 1, and more recently defined maresins, are 12-lipoxygenase-derived metabolites of the omega-3 fatty acid, docosahexaenoic acid (DHA), that possess potent anti-inflammatory, pro-resolving, protective, and pro-healing properties similar to a variety of other members of the specialized proresolving mediators (SPM) class of polyunsaturated fatty acid (PUFA) metabolites. SPM are dihydroxy, trihydroxy, and epoxy-hydroxy metabolites of long chain PUFA made by certain dioxygenase enzymes viz., cyclooxygenases and lipoxygenases. In addition to the maresins, this class of mediators includes: the 15-lipoxygenase (i.e. ALOX15 and/or possibly ALOX15B)-derived lipoxin A4 and B4 metabolites of the omega 6 fatty acid, arachidonic acid; the cyclooxygenase 2-derived resolvin E series metabolites of the omega 3 fatty acid, eicosapentaenoic acid; certain 15-lipoxygenase-derived resolvin D series metabolites of DHA; certain other 15-lipoxygenase-derived protectin D1 and related metabolites of DHA; and the more recently defined and therefore less fully studied 15-lipoxygenase-derived resolvin Dn-3DPA metabolites of the omega-3 fatty acid n-3 docosapentaenoic acid (n-3 DPA or clupanodonic acid), the cyclooxygenase 2-derived resolvin T metabolites of this clupanodonic acid, and the 15-lipoxygenase-derived products of the N-acetylated fatty acid amide of the DHA metabolite, docosahexaenoyl ethanolamide.[1][2][3][4][5]

  1. ^ Shinohara, M; Mirakaj, V; Serhan, C. N. (2012). "Functional Metabolomics Reveals Novel Active Products in the DHA Metabolome". Frontiers in Immunology. 3: 81. doi:10.3389/fimmu.2012.00081. PMC 3342038. PMID 22566962.
  2. ^ Weylandt, K. H. (2015). "Docosapentaenoic acid derived metabolites and mediators - the new world of lipid mediator medicine in a nutshell". European Journal of Pharmacology. 785: 108–115. doi:10.1016/j.ejphar.2015.11.002. PMID 26546723.
  3. ^ Romano, M; Cianci, E; Simiele, F; Recchiuti, A (2015). "Lipoxins and aspirin-triggered lipoxins in resolution of inflammation". European Journal of Pharmacology. 760: 49–63. doi:10.1016/j.ejphar.2015.03.083. PMID 25895638.
  4. ^ Serhan, C. N.; Chiang, N; Dalli, J; Levy, B. D. (2014). "Lipid mediators in the resolution of inflammation". Cold Spring Harbor Perspectives in Biology. 7 (2): a016311. doi:10.1101/cshperspect.a016311. PMC 4315926. PMID 25359497.
  5. ^ Wang, C. W.; Colas, R. A.; Dalli, J; Arnardottir, H. H.; Nguyen, D; Hasturk, H; Chiang, N; Van Dyke, T. E.; Serhan, C. N. (2015). "Maresin 1 Biosynthesis and Proresolving Anti-infective Functions with Human-Localized Aggressive Periodontitis Leukocytes". Infection and Immunity. 84 (3): 658–65. doi:10.1128/IAI.01131-15. PMC 4771362. PMID 26667839.

and 16 Related for: Maresin information

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Maresin

Last Update:

Maresin 1 (MaR1 or 7R,14S-dihydroxy-4Z,8E,10E,12Z,16Z,19Z-docosahexaenoic acid) is a macrophage-derived mediator of inflammation resolution coined from...

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Docosapentaenoic acid

Last Update:

Neuroprotectin), and three maresins (MaR1n-3, MaR2n-3, and MaR3n-3; see Specialized proresolving mediators § n-3 DPA-derived maresins and Maresin). Docosapentaenoic...

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Inflammation

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anti-inflammatory specialized proresolving mediators, i.e. lipoxins, resolvins, maresins, and neuroprotectins Downregulation of pro-inflammatory molecules, such...

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C22H32O4

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may refer to: Iloprost, a drug used to treat blood vessels constriction Maresin, a macrophage-derived mediator of inflammation Protectin D1, a specialized...

Word Count : 69

Aspirin

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aspirin-triggered lipoxins, aspirin-triggered resolvins, and aspirin-triggered maresins. These mediators possess potent anti-inflammatory activity. It is proposed...

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TRPV1

Last Update:

Resolvin E1 (RvE1), RvD2 (see resolvins), neuroprotectin D1 (NPD1), and maresin 1 (Mar1) are metabolites of the omega 3 fatty acids, eicosapentaenoic acid...

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Resolvin

Last Update:

; Levy, B. D. (2015). "DHA- and EPA-derived resolvins, protectins, and maresins in airway inflammation". European Journal of Pharmacology. 785: 144–155...

Word Count : 1310

ALOX12

Last Update:

acid (i.e. 13,14-e-maresin) This is further metabolized to 7R,14S-dihydroxy-4Z,8E,10E,12Z,16Z,19Z-docosahexaenoic acid (i.e. Maresin 1), by an unidentified...

Word Count : 3928

TRPA1

Last Update:

future drug development. Resolvin D1 (RvD1) and RvD2 (see resolvins) and maresin 1 are metabolites of the omega 3 fatty acid, docosahexaenoic acid. They...

Word Count : 4044

Efferocytosis

Last Update:

Resolvin E's; docosahexaenoic acid which is metabolized to the resolvin D's, maresins, and neuroprotectins; and n-3 docosapentaenoic acid which is metabolized...

Word Count : 678

Lipoxin

Last Update:

distinguishes them from other SPMs such as the resolvins, neuroprotectins, and maresins, which are metabolites of the omega 3 fatty acids, eicosapentaenoic acid...

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Docosanoid

Last Update:

protectins: PD1n-3 and PD2n-3. DHA-derived maresins: MaR1, MaR2, 7-epi-Mar1, Mar-L1, and Mar-L2. n-3 DPA-derived maresins: Mar1n-3, Mar2n-3, and Mar3n-3. These...

Word Count : 1125

Nutritional immunology

Last Update:

promote production of protective mediators such as resolvins, protectins and maresins. Micronutrients are a group of nutrients, usually in smaller amounts, that...

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Protectin D1

Last Update:

Serhan CN, Dalli J, Colas RA, Winkler JW, Chiang N (2015). "Protectins and maresins: New pro-resolving families of mediators in acute inflammation and resolution...

Word Count : 2846

Undurti Narasimha Das

Last Update:

(link) Undurti Narasimha Das (2013). "Lipoxins, resolvins, protectins, maresins and nitrolipids, and their clinical implications with specific reference...

Word Count : 2416

Formyl peptide receptor 2

Last Update:

Duvall MG, Levy BD (2015). "DHA- and EPA-derived resolvins, protectins, and maresins in airway inflammation". European Journal of Pharmacology. 785: 144–55...

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