Biosynthesis of DHA-derived SPMs

Molfino A, Amabile MI, Monti M, Muscaritoli M. Omega-3 Polyunsaturated Fatty Acids in Critical Illness: Anti-Inflammatory, Proresolving, or Both? Oxidative Medicine and Cellular Longevity. 2017 Jan;2017(1). doi: 10.1155/2017/5987082.; Serhan CN, Chiang N, Dalli J, Levy BD. Lipid mediators in the resolution of inflammation. Cold Spring Harb Perspect Biol. 2014 Oct 30;7(2):a016311. PMID: 25359497; PMCID: PMC4315926.; Serhan CN, Petasis NA. Resolvins and protectins in inflammation resolution. Chem Rev. 2011 Oct 12;111(10):5922–43. PMID: 21766791; PMCID: PMC3192290.; Kasuga K, Yang R, Porter TF, Agrawal N, Petasis NA, Irimia D, Toner M, Serhan CN. Rapid appearance of resolvin precursors in inflammatory exudates: novel mechanisms in resolution. J Immunol. 2008 Dec 15;181(12):8677–87. PMID: 19050288; PMCID: PMC2664686.; Serhan CN, Hong S, Gronert K, Colgan SP, Devchand PR, Mirick G, Moussignac RL. Resolvins: a family of bioactive products of omega-3 fatty acid transformation circuits initiated by aspirin treatment that counter proinflammation signals. J Exp Med. 2002 Oct 21;196(8):1025–37. PMID: 12391014; PMCID: PMC2194036.

Metabolites

Fe2+

Formula: Fe (55.934939)

CAS ID: 15438-31-0

H+

Formula: H (1.0078246)

CAS ID: 12408-02-5

H2O

Formula: H2O (18.0105642)

CAS ID: 7732-18-5

Magnesium cation

Formula: Mg (23.98505)

CAS ID: 22537-22-0

Oxygen

Formula: O2 (31.98983)

CAS ID: 7782-44-7

Zinc cation

Formula: Zn (63.929145)

CAS ID: 23713-49-7

4S-hydroperoxy-17S-HDHA

Formula: C22H32O5 (376.2249622)

CAS ID:

17R-HpDHA

Formula: C22H32O4 (360.2300472)

CAS ID:

7S,8S-epoxy-17R-HDHA

Formula: C22H30O4 (358.214398)

CAS ID:

NADPH(4-)

Formula: C21H26N7O17P3 (741.0598016)

CAS ID: 53-57-6

NADH(2-)

Formula: C21H27N7O14P2 (663.1091182000001)

CAS ID:

NAD(1-)

Formula: C21H26N7O14P2 (662.1012936000001)

CAS ID: 53-84-9

NADP(3-)

Formula: C21H25N7O17P3 (740.051977)

CAS ID: 53-59-8



Enzyme

EC Number name full name note
1.1.1.-
1.1.1.141 15-hydroxyprostaglandin dehydrogenase (NAD+) (5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprost-5,13-dienoate:NAD+ 15-oxidoreductase
1.1.1.232 15-hydroxyicosatetraenoate dehydrogenase (15S)-15-hydroxy-5,8,11-cis-13-trans-icosatetraenoate:NAD(P)+ 15-oxidoreductase
1.11.1.12 phospholipid-hydroperoxide glutathione peroxidase glutathione:lipid-hydroperoxide oxidoreductase
1.11.1.9 glutathione peroxidase glutathione:hydrogen-peroxide oxidoreductase
1.13.11.12 linoleate 13S-lipoxygenase linoleate:oxygen 13-oxidoreductase
1.13.11.31 arachidonate 12-lipoxygenase arachidonate:oxygen 12-oxidoreductase
1.13.11.33 arachidonate 15-lipoxygenase arachidonate:oxygen 15-oxidoreductase
1.13.11.34 arachidonate 5-lipoxygenase arachidonate:oxygen 5-oxidoreductase
1.14.14.1 unspecific monooxygenase substrate,NADPH-hemoprotein reductase:oxygen oxidoreductase (RH-hydroxylating or -epoxidizing)
1.14.99.1 prostaglandin-endoperoxide synthase (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate,hydrogen-donor:oxygen oxidoreductase
2.5.1.18 glutathione transferase RX:glutathione R-transferase
3.1.3.76 lipid-phosphate phosphatase (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate phosphohydrolase
3.3.2.10 soluble epoxide hydrolase epoxide hydrolase
3.3.2.6 leukotriene-A4 hydrolase (7E,9E,11Z,14Z)-(5S,6S)-5,6-epoxyicosa-7,9,11,14-tetraenoate hydrolase
3.4.11.4 tripeptide aminopeptidase
4.4.1.20 leukotriene-C4 synthase leukotriene-C4 glutathione-lyase (leukotriene-A4-forming)


Proteins

Protein ID name full name