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Article: Transformation of Prostaglandin D2 to 11‐Dehydro Thromboxane B2 by Baeyer‐Villiger Oxidation

Nakashima, Fumie / Schneider, Claus

Lipids. 2020 Jan., v. 55, no. 1

2020

Abstract: Prostaglandin D₂ is one of five chief prostanoids formed in the cyclooxygenase pathway of arachidonic acid oxidation. Except for a single oxygen atom, PGD₂ is structurally identical to 11‐dehydro thromboxane B₂ (11d‐TxB₂), a urinary metabolite of the pro‐ ...

Abstract	Prostaglandin D₂ is one of five chief prostanoids formed in the cyclooxygenase pathway of arachidonic acid oxidation. Except for a single oxygen atom, PGD₂ is structurally identical to 11‐dehydro thromboxane B₂ (11d‐TxB₂), a urinary metabolite of the pro‐aggregatory platelet activator, thromboxane A₂. The close structural relationship suggested that one might be transformed to the other. Accordingly, we tested whether the cyclopentanone of PGD₂ can be expanded to the δ‐lactone of 11d‐TxB₂ in a Baeyer‐Villiger oxidation. Oxidation of PGD₂ with two standard oxidants showed that 11d‐TxB₂ was formed only with H₂O₂ but not with peracetic acid. Byproducts of the H₂O₂‐mediated oxidation were hydroperoxide derivatives and isomers of PGD₂. Chemical oxidation of PGD₂ to 11d‐TxB₂ may be a model for an equivalent enzymatic transformation, suggesting a possible link in the metabolism of PGD₂ and thromboxane A₂.
Keywords	arachidonic acid ; metabolism ; metabolites ; models ; oxidation ; oxygen ; peracetic acid ; prostaglandin synthase ; prostaglandins ; thromboxanes
Language	English
Dates of publication	2020-01
Size	p. 73-78.
Publishing place	John Wiley & Sons, Inc.
Document type	Article
Note	JOURNAL ARTICLE
ZDB-ID	241539-2
ISSN	1558-9307 ; 0024-4201
ISSN (online)	1558-9307
ISSN	0024-4201
DOI	10.1002/lipd.12206
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Article ; Online: Transformation of Prostaglandin D

Nakashima, Fumie / Schneider, Claus

Lipids

2019 Volume 55, Issue 1, Page(s) 73–78

Abstract: Prostaglandin ... ...

Abstract	Prostaglandin D
MeSH term(s)	Chromatography, High Pressure Liquid ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Molecular Structure ; Oxidation-Reduction ; Prostaglandin D2/chemistry ; Thromboxane B2/analogs & derivatives ; Thromboxane B2/chemistry
Chemical Substances	Thromboxane B2 (54397-85-2) ; 11-dehydro-thromboxane B2 (67910-12-7) ; Prostaglandin D2 (RXY07S6CZ2)
Language	English
Publishing date	2019-12-12
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	241539-2
ISSN	1558-9307 ; 0024-4201
ISSN (online)	1558-9307
ISSN	0024-4201
DOI	10.1002/lipd.12206
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Article ; Online: Eriodictyol and thymonin act as GPR35 agonists.

Nakashima, Fumie / Qi Loh, Wei / Wakabayashi, Mayuka / Shimomura, Sayako / Hattori, Hiroyuki / Kita, Masaki / Inoue, Asuka / Uchida, Koji / Shibata, Takahiro

Bioscience, biotechnology, and biochemistry

2023 Volume 87, Issue 12, Page(s) 1514–1522

Abstract: Although herbs and spices have been used in traditional medicine for more than a century owing to their health benefits, the associated underlying mechanism is still not clear. Since the G protein-coupled receptor 35 (GPR35) has been linked to exert ... ...

Abstract	Although herbs and spices have been used in traditional medicine for more than a century owing to their health benefits, the associated underlying mechanism is still not clear. Since the G protein-coupled receptor 35 (GPR35) has been linked to exert various antioxidant and anti-inflammatory effects, we screened 19 different herbs and spices for possible GPR35 agonist(s) to understand the GPR35-dependent functions of herbs and spices. Among the screened extracts, the ethyl acetate extract of thyme exhibited a remarkable GPR35 agonistic activity. Activity-guided separations allowed us to identify 2 polyphenolic phytochemicals, eriodictyol and thymonin, acting as GPR35 agonists. Both eriodictyol and thymonin showed a potent and specific agonist activity toward GPR35 with half maximal effective concentration values of 5.48 and 8.41 µm, respectively. These findings indicate that these phytochemicals may have beneficial health effects upon GPR35 activation.
MeSH term(s)	Flavanones/pharmacology ; Spices ; Antioxidants ; Receptors, G-Protein-Coupled
Chemical Substances	eriodictyol (Q520486B8Y) ; Flavanones ; Antioxidants ; Receptors, G-Protein-Coupled
Language	English
Publishing date	2023-09-04
Publishing country	England
Document type	Journal Article
ZDB-ID	1106450-x
ISSN	1347-6947 ; 0916-8451
ISSN (online)	1347-6947
ISSN	0916-8451
DOI	10.1093/bbb/zbad125
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Article ; Online: A unique mechanism for thiolation of serum albumins by disulphide molecules.

Nakashima, Fumie / Shibata, Takahiro / Uchida, Koji

Journal of biochemistry

2019 Volume 167, Issue 2, Page(s) 165–171

Abstract: Protein S-thiolation is a reversible oxidative modification that serves as an oxidative regulatory mechanism for certain enzymes and binding proteins with reactive cysteine residues. It is generally believed that the thiolation occurs at free sulphydryl ... ...

Abstract	Protein S-thiolation is a reversible oxidative modification that serves as an oxidative regulatory mechanism for certain enzymes and binding proteins with reactive cysteine residues. It is generally believed that the thiolation occurs at free sulphydryl group of cysteine residues. Meanwhile, despite the fact that disulphide linkages, serving structural and energetic roles in proteins, are stable and inert to oxidative modification, a recent study shows that the thiolation could also occur at protein disulphide linkages when human serum albumin (HSA) was treated with disulphide molecules, such as cystine and homocystine. A chain reaction mechanism has been proposed for the thiolation at disulphide linkages, in which free cysteine (Cys34) is involved in the reaction with disulphide molecules to form free thiols (cysteine or homocysteine) that further react with protein disulphide linkages to form the thiolated cysteine residues in the protein. This review focuses on the recent finding of this unique chain reaction mechanism of protein thiolation.
MeSH term(s)	Animals ; Disulfides/chemistry ; Disulfides/metabolism ; Humans ; Serum Albumin/chemistry ; Serum Albumin/metabolism ; Sulfhydryl Compounds/chemistry ; Sulfhydryl Compounds/metabolism
Chemical Substances	Disulfides ; Serum Albumin ; Sulfhydryl Compounds
Language	English
Publishing date	2019-10-09
Publishing country	England
Document type	Journal Article ; Review
ZDB-ID	218073-x
ISSN	1756-2651 ; 0021-924X
ISSN (online)	1756-2651
ISSN	0021-924X
DOI	10.1093/jb/mvz084
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Article ; Online: Sodium sulfite causes gastric mucosal cell death by inducing oxidative stress.

Oshimo, Moeri / Nakashima, Fumie / Kai, Kenji / Matsui, Hirofumi / Shibata, Takahiro / Akagawa, Mitsugu

Free radical research

2021 Volume 55, Issue 6, Page(s) 731–743

Abstract: Sulfites are commonly used as a preservative and antioxidant additives in the food industry. Sulfites are absorbed by the gastrointestinal tract and distributed essentially to all body tissues. Although sulfites have been believed to be safe food ... ...

Abstract	Sulfites are commonly used as a preservative and antioxidant additives in the food industry. Sulfites are absorbed by the gastrointestinal tract and distributed essentially to all body tissues. Although sulfites have been believed to be safe food additives, some studies have shown that they exhibit adverse effects in various tissues. In this study, we examined the cytotoxic effect of sodium sulfite (Na
MeSH term(s)	Animals ; Cell Death/physiology ; Oxidative Stress/physiology ; Rats ; Stomach/cytology ; Stomach/drug effects ; Stomach/metabolism ; Sulfites/adverse effects
Chemical Substances	Sulfites ; sodium sulfite (VTK01UQK3G)
Language	English
Publishing date	2021-06-21
Publishing country	England
Document type	Journal Article
ZDB-ID	1194130-3
ISSN	1029-2470 ; 1071-5762
ISSN (online)	1029-2470
ISSN	1071-5762
DOI	10.1080/10715762.2021.1937620
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Article ; Online: The 5-lipoxygenase/cyclooxygenase-2 cross-over metabolite, hemiketal E

Nakashima, Fumie / Giménez-Bastida, Juan A / Luis, Paula B / Presley, Sai H / Boer, Robert E / Chiusa, Manuel / Shibata, Takahiro / Sulikowski, Gary A / Pozzi, Ambra / Schneider, Claus

The Journal of biological chemistry

2023 Volume 299, Issue 4, Page(s) 103050

Abstract: Consecutive oxygenation of arachidonic acid by 5-lipoxygenase and cyclooxygenase-2 yields the hemiketal eicosanoids, ... ...

Abstract	Consecutive oxygenation of arachidonic acid by 5-lipoxygenase and cyclooxygenase-2 yields the hemiketal eicosanoids, HKE
MeSH term(s)	Mice ; Humans ; Animals ; Cyclooxygenase 2/metabolism ; Arachidonic Acid ; Vascular Endothelial Growth Factor Receptor-2/metabolism ; Arachidonate 5-Lipoxygenase ; Vascular Endothelial Growth Factor A/metabolism ; Neovascularization, Physiologic ; Human Umbilical Vein Endothelial Cells/metabolism ; Angiogenesis Inhibitors/pharmacology ; Cell Movement ; Cell Proliferation
Chemical Substances	Cyclooxygenase 2 (EC 1.14.99.1) ; Arachidonic Acid (27YG812J1I) ; Vascular Endothelial Growth Factor Receptor-2 (EC 2.7.10.1) ; Arachidonate 5-Lipoxygenase (EC 1.13.11.34) ; Vascular Endothelial Growth Factor A ; Angiogenesis Inhibitors
Language	English
Publishing date	2023-02-21
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	2997-x
ISSN	1083-351X ; 0021-9258
ISSN (online)	1083-351X
ISSN	0021-9258
DOI	10.1016/j.jbc.2023.103050
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Article ; Online: Biosynthetic Crossover of 5-Lipoxygenase and Cyclooxygenase-2 Yields 5-Hydroxy-PGE

Nakashima, Fumie / Suzuki, Takashi / Gordon, Odaine N / Golding, Dominic / Okuno, Toshiaki / Giménez-Bastida, Juan A / Yokomizo, Takehiko / Schneider, Claus

JACS Au

2021 Volume 1, Issue 9, Page(s) 1380–1388

Abstract: The biosynthetic crossover of 5-lipoxygenase (5-LOX) and cyclooxygenase-2 (COX-2) enzymatic activities is a productive pathway to convert arachidonic acid into unique eicosanoids. Here, we show that COX-2 catalysis with 5-LOX derived 5-hydroxy- ... ...

Abstract	The biosynthetic crossover of 5-lipoxygenase (5-LOX) and cyclooxygenase-2 (COX-2) enzymatic activities is a productive pathway to convert arachidonic acid into unique eicosanoids. Here, we show that COX-2 catalysis with 5-LOX derived 5-hydroxy-eicosatetraenoic acid yields the endoperoxide 5-hydroxy-PGH
Language	English
Publishing date	2021-08-04
Publishing country	United States
Document type	Journal Article
ISSN	2691-3704
ISSN (online)	2691-3704
DOI	10.1021/jacsau.1c00177
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Article: A Dual Perspective of the Action of Lysine on Soybean Oil Oxidation Process Obtained by Combining

Martin-Rubio, Ana S / Sopelana, Patricia / Nakashima, Fumie / Shibata, Takahiro / Uchida, Koji / Guillén, María D

Antioxidants (Basel, Switzerland)

2019 Volume 8, Issue 9

Abstract: Little is still known about both the effect of amino acids on the oxidation course of edible oils and the modifications that the former may undergo during this process. Bearing this in mind, the objective of this work was to study the evolution of a ... ...

Abstract	Little is still known about both the effect of amino acids on the oxidation course of edible oils and the modifications that the former may undergo during this process. Bearing this in mind, the objective of this work was to study the evolution of a system consisting of soybean oil with 2% of l-lysine under heating at 70 °C and stirring conditions, analyzing how the co-oxidation of the oil and of the amino acid affects their respective evolutions, and trying to obtain information about the action mechanism of lysine on soybean oil oxidation. The study of the oil progress by
Language	English
Publishing date	2019-08-21
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2704216-9
ISSN	2076-3921
ISSN	2076-3921
DOI	10.3390/antiox8090326
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Article ; Online: Mechanistic Differences in the Inhibition of NF-κB by Turmeric and Its Curcuminoid Constituents.

Edwards, Rebecca L / Luis, Paula B / Nakashima, Fumie / Kunihiro, Andrew G / Presley, Sai-Han / Funk, Janet L / Schneider, Claus

Journal of agricultural and food chemistry

2020 Volume 68, Issue 22, Page(s) 6154–6160

Abstract: Turmeric extract, a mixture of curcumin and its demethoxy (DMC) and bisdemethoxy (BDMC) isomers, is used as an anti-inflammatory preparation in traditional Asian medicine. Curcumin is considered to be the major bioactive compound in turmeric but less is ... ...

Abstract	Turmeric extract, a mixture of curcumin and its demethoxy (DMC) and bisdemethoxy (BDMC) isomers, is used as an anti-inflammatory preparation in traditional Asian medicine. Curcumin is considered to be the major bioactive compound in turmeric but less is known about the relative anti-inflammatory potency and mechanism of the other components, their mixture, or the reduced in vivo metabolites. We quantified inhibition of the NF-κB pathway in cells, adduction to a peptide mimicking IκB kinase β, and the role of cellular glutathione as a scavenger of electrophilic curcuminoid oxidation products, suggested to be the active metabolites. Turmeric extracts (IC
MeSH term(s)	Animals ; Cell Line ; Curcuma/chemistry ; Curcumin/chemistry ; Curcumin/pharmacology ; Diarylheptanoids/chemistry ; Diarylheptanoids/pharmacology ; Humans ; Kinetics ; NF-kappa B/antagonists & inhibitors ; NF-kappa B/metabolism ; Oxidation-Reduction/drug effects ; Plant Extracts/chemistry ; Plant Extracts/pharmacology
Chemical Substances	Diarylheptanoids ; NF-kappa B ; Plant Extracts ; turmeric extract (856YO1Z64F) ; Curcumin (IT942ZTH98)
Language	English
Publishing date	2020-05-20
Publishing country	United States
Document type	Journal Article
ZDB-ID	241619-0
ISSN	1520-5118 ; 0021-8561
ISSN (online)	1520-5118
ISSN	0021-8561
DOI	10.1021/acs.jafc.0c02607
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Article: A Dual Perspective of the Action of Lysine on Soybean Oil Oxidation Process Obtained by Combining <sup>1</sup>H NMR and LC–MS: Antioxidant Effect and Generation of Lysine–Aldehyde Adducts

Martin-Rubio, Ana S / Sopelana, Patricia / Nakashima, Fumie / Shibata, Takahiro / Uchida, Koji / Guillén, María D

Antioxidants. 2019 Aug. 21, v. 8, no. 9

2019

Abstract	Little is still known about both the effect of amino acids on the oxidation course of edible oils and the modifications that the former may undergo during this process. Bearing this in mind, the objective of this work was to study the evolution of a system consisting of soybean oil with 2% of l-lysine under heating at 70 °C and stirring conditions, analyzing how the co-oxidation of the oil and of the amino acid affects their respective evolutions, and trying to obtain information about the action mechanism of lysine on soybean oil oxidation. The study of the oil progress by 1H Nuclear Magnetic Resonance (1H NMR) showed that the presence of lysine noticeably delays oil degradation and oxidation products generation in comparison with a reference oil without lysine. Regarding lysine evolution, the analysis by 1H NMR and Liquid Chromatography–Mass Spectrometry of a series of aqueous extracts obtained from the oil containing lysine over time revealed the formation of lysine adducts, most of them at the ε position, with n-alkanals, malondialdehyde, (E)-2-alkenals, and toxic oxygenated α β-unsaturated aldehydes. However, this latter finding does not seem enough to explain the antioxidant action of lysine.
Keywords	antioxidant activity ; cooking fats and oils ; liquid chromatography ; lysine ; malondialdehyde ; mass spectrometry ; nuclear magnetic resonance spectroscopy ; oxidation ; soybean oil ; toxicity
Language	English
Dates of publication	2019-0821
Publishing place	Multidisciplinary Digital Publishing Institute
Document type	Article
ZDB-ID	2704216-9
ISSN	2076-3921
ISSN	2076-3921
DOI	10.3390/antiox8090326
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