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Article ; Online: Stereocontrolled total synthesis of Resolvin D4 and 17(

Nshimiyimana, Robert / Glynn, Stephen J / Serhan, Charles N / Petasis, Nicos A

2023 Volume 21, Issue 8, Page(s) 1667–1673

Abstract: The total synthesis of Resolvin D4 and its 17( ...

Abstract	The total synthesis of Resolvin D4 and its 17(
MeSH term(s)	Humans ; Fatty Acids, Unsaturated/chemistry ; Docosahexaenoic Acids ; Inflammation ; Stereoisomerism
Chemical Substances	resolvin D4 ; Fatty Acids, Unsaturated ; Docosahexaenoic Acids (25167-62-8)
Language	English
Publishing date	2023-02-22
Publishing country	England
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	2097583-1
ISSN	1477-0539 ; 1477-0520
ISSN (online)	1477-0539
ISSN	1477-0520
DOI	10.1039/d2ob01697d
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Article ; Online: Infectious neutrophil deployment is regulated by resolvin D4.

Libreros, Stephania / Nshimiyimana, Robert / Lee, Brendon / Serhan, Charles N

Blood

2023 Volume 142, Issue 6, Page(s) 589–606

Abstract: Neutrophils reside in the bone marrow (BM), ready for deployment to sites of injury/infection, initiating inflammation and its resolution. Here, we report that distal infections signal to the BM via resolvins to regulate granulopoiesis and BM neutrophil ... ...

Abstract	Neutrophils reside in the bone marrow (BM), ready for deployment to sites of injury/infection, initiating inflammation and its resolution. Here, we report that distal infections signal to the BM via resolvins to regulate granulopoiesis and BM neutrophil deployment. Emergency granulopoiesis during peritonitis evoked changes in BM resolvin D1 (RvD1) and BM RvD4. We found that leukotriene B4 stimulates neutrophil deployment. RvD1 and RvD4 each limited neutrophilic infiltration to infections, and differently regulated BM myeloid populations: RvD1 increased reparative monocytes, and RvD4 regulated granulocytes. RvD4 disengaged emergency granulopoiesis, prevented excess BM neutrophil deployment, and acted on granulocyte progenitors. RvD4 also stimulated exudate neutrophil, monocyte, and macrophage phagocytosis, and enhanced bacterial clearance. This mediator accelerated both neutrophil apoptosis and clearance by macrophages, thus expediting the resolution phase of inflammation. RvD4 stimulated phosphorylation of ERK1/2 and STAT3 in human BM-aspirate-derived granulocytes. RvD4 in the 1 to 100 nM range stimulated whole-blood neutrophil phagocytosis of Escherichia coli. RvD4 increased BM macrophage efferocytosis of neutrophils. Together, these results demonstrate the novel functions of resolvins in granulopoiesis and neutrophil deployment, contributing to the resolution of infectious inflammation.
MeSH term(s)	Humans ; Neutrophils ; Inflammation ; Phagocytosis ; Fatty Acids, Unsaturated ; Communicable Diseases ; Escherichia coli ; Docosahexaenoic Acids/pharmacology
Chemical Substances	resolvin D4 ; Fatty Acids, Unsaturated ; Docosahexaenoic Acids (25167-62-8)
Language	English
Publishing date	2023-06-07
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	80069-7
ISSN	1528-0020 ; 0006-4971
ISSN (online)	1528-0020
ISSN	0006-4971
DOI	10.1182/blood.2022019145
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Article ; Online: E-series resolvin metabolome, biosynthesis and critical role of stereochemistry of specialized pro-resolving mediators (SPMs) in inflammation-resolution: Preparing SPMs for long COVID-19, human clinical trials, and targeted precision nutrition.

Serhan, Charles N / Libreros, Stephania / Nshimiyimana, Robert

Seminars in immunology

2022 Volume 59, Page(s) 101597

Abstract: The COVID-19 pandemic has raised international awareness of the importance of rigorous scientific evidence and the havoc caused by uncontrolled excessive inflammation. Here we consider the evidence on whether the specialized pro-resolving mediators (SPMs) ...

Abstract	The COVID-19 pandemic has raised international awareness of the importance of rigorous scientific evidence and the havoc caused by uncontrolled excessive inflammation. Here we consider the evidence on whether the specialized pro-resolving mediators (SPMs) are ready to meet this challenge as well as targeted metabololipidomics of the resolution-inflammation metabolomes. Specific stereochemical mechanisms in the biosynthesis of SPMs from omega-3 essential fatty acids give rise to unique local-acting lipid mediators. SPMs possess stereochemically defined potent bioactive structures that are high-affinity ligands for cognate G protein-coupled surface receptors that evoke the cellular responses required for efficient resolution of acute inflammation. The SPMs biosynthesized from the major omega-3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) are coined Resolvins (resolution phase interaction products; E series and D-series), Protectins and Maresins (macrophage mediators in resolving inflammation). Their biosynthesis and stereochemical assignments are established and confirmed (>1,441 resolvin publications in PubMed.gov) as well as their functional roles on innate immune cells and adaptive immune cells (both lymphocyte T-cell subsets and B-cells). The resolution of a protective acute inflammatory response is governed mainly by phagocytes that actively clear apoptotic cells, debris, blood clots and pathogens. These resolution phase functions of the acute inflammatory response are enhanced by SPMs, which together prepare the inflammatory loci for homeostasis and stimulate tissue regeneration via activating stem cells and the biosynthesis of novel cys-SPMs (e.g. MCTRs, PCTRs and RCTRs). These cys-SPMs also activate regeneration, are organ protective and stimulate resolution of local inflammation. Herein, we review the biosynthesis and functions of the E-series resolvins, namely resolvin E1 (the first n-3 resolvin identified), resolvin E2, resolvin E3 and resolvin E4 biosynthesized from their precursor eicosapentaenoic acid (EPA), and the critical role of total organic synthesis in confirming SPM complete stereochemistry, establishing their potent functions in resolution of inflammation, and novel structures. The physical properties of each biologically derived SPM, i.e., ultra-violet (UV) absorbance, chromatographic behavior, and tandem mass spectrometry (MS
MeSH term(s)	Animals ; Humans ; COVID-19 ; Docosahexaenoic Acids/therapeutic use ; Eicosapentaenoic Acid/therapeutic use ; Inflammation ; Inflammation Mediators/metabolism ; Metabolome ; Pandemics ; Post-Acute COVID-19 Syndrome ; Clinical Trials as Topic
Chemical Substances	Docosahexaenoic Acids (25167-62-8) ; Eicosapentaenoic Acid (AAN7QOV9EA) ; Inflammation Mediators
Language	English
Publishing date	2022-02-16
Publishing country	England
Document type	Journal Article ; Review ; Research Support, N.I.H., Extramural
ZDB-ID	1018141-6
ISSN	1096-3618 ; 1044-5323
ISSN (online)	1096-3618
ISSN	1044-5323
DOI	10.1016/j.smim.2022.101597
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Article ; Online: Metabolization of Resolvin E4 by ω-Oxidation in Human Neutrophils: Synthesis and Biological Evaluation of 20-Hydroxy-Resolvin E4 (20-OH-RvE4).

Reinertsen, Amalie Føreid / Libreros, Stephania / Nshimiyimana, Robert / Serhan, Charles Nicholas / Hansen, Trond Vidar

ACS pharmacology & translational science

2023 Volume 6, Issue 12, Page(s) 1898–1908

Abstract: Resolvin E4 (RvE4) belongs to the resolvin family of specialized pro-resolving mediators (SPMs). The resolvins are endogenously formed mediators with both potent pro-resolving and anti-inflammatory biological activities and have attracted considerable ... ...

Abstract	Resolvin E4 (RvE4) belongs to the resolvin family of specialized pro-resolving mediators (SPMs). The resolvins are endogenously formed mediators with both potent pro-resolving and anti-inflammatory biological activities and have attracted considerable attention in both inflammation research and drug discovery. Hence, further metabolism of the resolvins is of interest. Gaining knowledge about the structure-function of further metabolites of the resolvins is important due to their interest in drug-discovery efforts. For the first time, the total synthesis and biological evaluations of the ω-20 hydroxylated metabolite of RvE4, named herein 20-OH-RvE4, are presented. RvE4 was converted to 20-OH-RvE4 by human polymorphonuclear leukocytes. LC-MS/MS analysis and UV spectrophotometry reveal that the synthetic 20-OH-RvE4 matched RvE4-converted product 20-OH-RvE4 by human neutrophils. Cellular studies have revealed that RvE4 is formed from eicosapentaenoic acid in physiologic hypoxia by human neutrophils and macrophages, and we herein established that 20-OH-RvE4 is a secondary metabolite formed by the ω-oxidation of RvE4 in human neutrophils. A direct comparison of the biological actions between RvE4 and its metabolic product suggested that 20-OH-RvE4 displayed reduced bioactions in stimulating the efferocytosis of human senescent erythrocytes by human M2-like macrophages. At concentrations down to 0.1 nM, RvE4 increased macrophage erythrophagocytosis, an important pro-resolving function that was diminished due to metabolic transformation. The results provided herein contribute to a novel molecular insight on the further local metabolization of RvE4, the newest member among the SPM superfamily.
Language	English
Publishing date	2023-11-20
Publishing country	United States
Document type	Journal Article
ISSN	2575-9108
ISSN (online)	2575-9108
DOI	10.1021/acsptsci.3c00201
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Article: First stereoselective total synthesis of 4(S),5(S)-oxido-17(S)-hydroxy-6(E),8(E),10(Z),13(Z),15(E),19(Z)-docosahexaenoic acid, the biosynthetic precursor of resolvins D3 and D4

Nshimiyimana, Robert / Lam, Ting Fung / Aggarwal, Shubhangi / Serhan, Charles N. / Petasis, Nicos A.

RSC advances. 2022 Apr. 19, v. 12, no. 19

2022

Abstract: The first total convergent synthesis of 4(S),5(S)-oxido-17(S)-hydroxy-6(E),8(E),10(Z),13(Z),15(E),19(Z)-docosahexaenoic acid (1) is described. The reported synthesis led to confirmation of the native epoxydocosahexaenoic acid as the biosynthetic ... ...

Abstract	The first total convergent synthesis of 4(S),5(S)-oxido-17(S)-hydroxy-6(E),8(E),10(Z),13(Z),15(E),19(Z)-docosahexaenoic acid (1) is described. The reported synthesis led to confirmation of the native epoxydocosahexaenoic acid as the biosynthetic precursor of lipid mediators resolvin D3 and resolvin D4. These potent enzymatic products of docosahexaenoic acid (DHA) are important signaling molecules in the resolution of inflammation. A stereocontrolled and chiral pool-based synthetic strategy was employed, with key features including epoxide transposition under basic conditions to form the oxirane ring, and a cis-selective Wittig reaction to secure the target docosahexaenoate backbone.
Keywords	biosynthesis ; chemical reactions ; docosahexaenoic acid ; ethylene oxide ; inflammation ; stereoselectivity
Language	English
Dates of publication	2022-0419
Size	p. 11613-11618.
Publishing place	The Royal Society of Chemistry
Document type	Article
ISSN	2046-2069
DOI	10.1039/d2ra01537d
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Article ; Online: First stereoselective total synthesis of 4(

Nshimiyimana, Robert / Lam, Ting Fung / Aggarwal, Shubhangi / Serhan, Charles N / Petasis, Nicos A

RSC advances

2022 Volume 12, Issue 19, Page(s) 11613–11618

Abstract: The first total convergent synthesis of 4( ...

Abstract	The first total convergent synthesis of 4(
Language	English
Publishing date	2022-04-19
Publishing country	England
Document type	Journal Article
ISSN	2046-2069
ISSN (online)	2046-2069
DOI	10.1039/d2ra01537d
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Article ; Online: Stereochemistry and functions of the new cysteinyl-resolvin, 4S,5R-RCTR1, in efferocytosis and erythrophagocytosis of human senescent erythrocytes.

Nshimiyimana, Robert / Libreros, Stephania / Simard, Mélissa / Chiang, Nan / Rodriguez, Ana R / Spur, Bernd W / Haeggström, Jesper Z / Serhan, Charles N

American journal of hematology

2023 Volume 98, Issue 7, Page(s) 1000–1016

Abstract: Specialized pro-resolving lipid mediators play key functions in the resolution of the acute inflammatory response. Herein, we elucidate the stereochemical structure of the new 4S,5R-RCTR1, a cysteinyl-resolvin, recently uncovered in human leukocytes ... ...

Abstract	Specialized pro-resolving lipid mediators play key functions in the resolution of the acute inflammatory response. Herein, we elucidate the stereochemical structure of the new 4S,5R-RCTR1, a cysteinyl-resolvin, recently uncovered in human leukocytes incubated with a 4S,5S-epoxy-resolvin intermediate, using liquid chromatography-tandem mass spectrometry (LC-MS/MS) and ultra-violet (UV) spectrophotometry. With this approach, the physical properties of the new mediator prepared by total organic synthesis were matched to enzymatically produced biogenic material. In addition, we confirmed the potent biological actions of 4S,5R-RCTR1 with human M2-like macrophage phagocytosis of live bacteria, efferocytosis of apoptotic neutrophils, and erythrophagocytosis of senescent human red blood cells in a concentration-dependent manner from 0.1 to 10 nM. Taken together, these results establish the complete stereochemistry of 4S,5R-RCTR1 as 5R-glutathionyl-4S,17S-dihydroxy-6E,8E,10Z,13Z,15E,19Z-docosahexaenoic acid and give evidence of its novel bioactivities in human phagocyte responses. Moreover, they confirm and extend the stereoselective functions of the 4S,5R-RCTR1 with isolated human phagocytes of interest in the resolution of inflammation.
MeSH term(s)	Humans ; Chromatography, Liquid ; Tandem Mass Spectrometry ; Phagocytosis ; Inflammation ; Macrophages ; Lymphohistiocytosis, Hemophagocytic
Language	English
Publishing date	2023-05-04
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
ZDB-ID	196767-8
ISSN	1096-8652 ; 0361-8609
ISSN (online)	1096-8652
ISSN	0361-8609
DOI	10.1002/ajh.26932
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Article: First total synthesis of 4(R),17(R)-Resolvin D6 stereoisomer, a potent neuroprotective docosanoid

Nshimiyimana, Robert / Fung Lam, Ting / Aggarwal, Shubhangi / G. Bazan, Nicolas / Bazan, Haydee E.P. / Petasis, Nicos A.

Tetrahedron letters. 2022 Sept. 14, v. 106

2022

Abstract: The first total synthesis of a novel neuroprotective Resolvin D6 enantiomer, 4(R),17(R)-Resolvin D6, is described. Resolvin D6 is a lipid mediator derived from docosahexaenoic acid (DHA, C22:6, ω-3) with anti-inflammatory properties. Key synthetic ... ...

Abstract	The first total synthesis of a novel neuroprotective Resolvin D6 enantiomer, 4(R),17(R)-Resolvin D6, is described. Resolvin D6 is a lipid mediator derived from docosahexaenoic acid (DHA, C22:6, ω-3) with anti-inflammatory properties. Key synthetic features include the use of a MacMillan enantioselective organocatalytic α-oxidation of aldehydes in conjunction with a chiral pool-based approach to generate chiral synthons, a 1,4‑enyne unit as a linchpin, as well as a (Z)-selective Wittig coupling to assemble the Resolvin D6 core carbon skeleton.
Keywords	carbon ; catalytic activity ; docosahexaenoic acid ; enantiomers ; enantioselectivity
Language	English
Dates of publication	2022-0914
Publishing place	Elsevier Ltd
Document type	Article
ZDB-ID	204287-3
ISSN	1873-3581 ; 0040-4039
ISSN (online)	1873-3581
ISSN	0040-4039
DOI	10.1016/j.tetlet.2022.154091
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Article ; Online: Human leukocytes selectively convert 4

Shay, Ashley E / Nshimiyimana, Robert / Samuelsson, Bengt / Petasis, Nicos A / Haeggström, Jesper Z / Serhan, Charles N

Proceedings of the National Academy of Sciences of the United States of America

2021 Volume 118, Issue 51

Abstract: Human phagocytes have key functions in the resolution of inflammation. Here, we assessed the role of the proposed ... ...

Abstract	Human phagocytes have key functions in the resolution of inflammation. Here, we assessed the role of the proposed 4
MeSH term(s)	Cells, Cultured ; Fatty Acids, Unsaturated/metabolism ; Granuloma ; Humans ; Leukocytes/metabolism ; Macrophages/metabolism
Chemical Substances	Fatty Acids, Unsaturated ; resolvin D3 ; resolvin D4
Language	English
Publishing date	2021-12-15
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	209104-5
ISSN	1091-6490 ; 0027-8424
ISSN (online)	1091-6490
ISSN	0027-8424
DOI	10.1073/pnas.2116559118
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Article ; Online: A newly synthesized 17-epi-NeuroProtectin D1/17-epi-Protectin D1: Authentication and functional regulation of Inflammation-Resolution.

Hamidzadeh, Kajal / Westcott, Jodi / Wourms, Nicholas / Shay, Ashley E / Panigrahy, Anand / Martin, Michael J / Nshimiyimana, Robert / Serhan, Charles N

Biochemical pharmacology

2022 Volume 203, Page(s) 115181

Abstract: The production of specialized pro-resolving mediators (SPMs) during the resolution phase in the inflammatory milieu is key to orchestrating the resolution of the acute inflammatory response. 17-epi-neuroprotectin D1/17-epi-protectin D1 (17-epi-NPD1/17- ... ...

Abstract	The production of specialized pro-resolving mediators (SPMs) during the resolution phase in the inflammatory milieu is key to orchestrating the resolution of the acute inflammatory response. 17-epi-neuroprotectin D1/17-epi-protectin D1 (17-epi-NPD1/17-epi-PD1: 10R,17R-dihydroxy-4Z,7Z,11E,13E,15Z,19Z-docosahexaenoic acid) is an SPM of the protectin family, biosynthesized from docosahexaenoic acid (DHA), that exhibits both potent anti-inflammatory and neuroprotective functions. Here, we carried out a new commercial-scale synthesis of 17-epi-NPD1/17-epi-PD1 that enabled the authentication and confirmation of its potent bioactions in vivo and determination of its ability to activate human leukocyte phagocytosis. We provide evidence that this new synthetic 17-epi-NPD1/17-epi-PD1 statistically significantly increases human macrophage uptake of E. coli in vitro and confirm that it limits neutrophilic infiltration in vivo in a murine model of peritonitis. The physical properties of the new synthetic 17-epi-NPD1/17-epi-PD1, namely its ultra-violet absorbance, chromatography, and tandem mass spectrometry fragmentation pattern, matched those of the originally synthesized 17-epi-NPD1/17-epi-PD1. In addition, we verified the structure and complete stereochemical assignment of this new synthetic 17-epi-NPD1/17-epi-PD1 using nuclear magnetic resonance (NMR) spectroscopy. Together, these results authenticate this 17-epi-NPD1/17-epi-PD1 for its structure and potent pro-resolving functions.
MeSH term(s)	Animals ; Docosahexaenoic Acids/chemistry ; Escherichia coli ; Humans ; Inflammation ; Macrophages ; Mice
Chemical Substances	protectin D1 ; Docosahexaenoic Acids (25167-62-8)
Language	English
Publishing date	2022-07-16
Publishing country	England
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	208787-x
ISSN	1873-2968 ; 0006-2952
ISSN (online)	1873-2968
ISSN	0006-2952
DOI	10.1016/j.bcp.2022.115181
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