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Article ; Online: Identification of a novel monocyclic carotenoid and prediction of its biosynthetic genes in Algoriphagus sp. oki45.

Takatani, Naoki / Maoka, Takashi / Sawabe, Tomoo / Beppu, Fumiaki / Hosokawa, Masashi

2024 Volume 108, Issue 1, Page(s) 102

Abstract: Bacteria belonging to the genus Algoriphagus have been isolated from various sources, such as Antarctic sea ice, seawater, and sediment, and some strains are known to produce orange to red pigments. However, the pigment composition and biosynthetic genes ...

Abstract	Bacteria belonging to the genus Algoriphagus have been isolated from various sources, such as Antarctic sea ice, seawater, and sediment, and some strains are known to produce orange to red pigments. However, the pigment composition and biosynthetic genes have not been fully elucidated. A new red-pigmented Algoriphagus sp. strain, oki45, was isolated from the surface of seaweed collected from Senaga-Jima Island, Okinawa, Japan. Genome comparison revealed oki45's average nucleotide identity of less than 95% to its closely related species, Algoriphagus confluentis NBRC 111222
MeSH term(s)	Carotenoids ; Seawater/microbiology ; Bacteria/genetics ; Mixed Function Oxygenases/genetics ; Multigene Family ; Phylogeny ; Fatty Acids/chemistry ; RNA, Ribosomal, 16S/genetics ; DNA, Bacterial/genetics ; Sequence Analysis, DNA ; Bacterial Typing Techniques
Chemical Substances	Carotenoids (36-88-4) ; Mixed Function Oxygenases (EC 1.-) ; Fatty Acids ; RNA, Ribosomal, 16S ; DNA, Bacterial
Language	English
Publishing date	2024-01-11
Publishing country	Germany
Document type	Journal Article
ZDB-ID	392453-1
ISSN	1432-0614 ; 0171-1741 ; 0175-7598
ISSN (online)	1432-0614
ISSN	0171-1741 ; 0175-7598
DOI	10.1007/s00253-023-12995-2
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Article ; Online: Reduction of serum lipid levels in diabetic obese KK-Ay mice using monoalkyldiacylglycerol-rich oil derived from Berryteuthis magister

Kakimoto, Masaki / Takatani, Naoki / Hosokawa, Masashi / Beppu, Fumiaki

Fish Sci. 2023 Mar., v. 89, no. 2 p.243-251

2023

Abstract: Monoalkyldiacylglycerol (MADG), an ether analog of triacylglycerols, is abundant in some marine animals such as deep-sea sharks and echinoderms. The present study aims to investigate the effects of an MADG-rich neutral lipid derived from Berryteuthis ... ...

Abstract	Monoalkyldiacylglycerol (MADG), an ether analog of triacylglycerols, is abundant in some marine animals such as deep-sea sharks and echinoderms. The present study aims to investigate the effects of an MADG-rich neutral lipid derived from Berryteuthis magister (MNB) on the lipid metabolism of diabetic/obese KK-Aʸ mice. Male mice (5 weeks old) were fed soybean oil (control group), MNB, or fish oil (FO) which contain the same amount of EPA and DHA in the form of triacylglycerols. MNB or FO supplementation resulted in a decrease in adipose tissue weights and blood glucose levels compared to the control mice. Interestingly, serum lipid levels in the MNB group were significantly lower than those of the control and FO groups. Although there was no difference in EPA and DHA levels in the tissues between the FO and MNB groups, a decrease in the number of lipoprotein particles was characteristically observed in the mice fed with MNB. Our results suggest that the MADG structure-dependent effect on lipoprotein synthesis and/or secretion partly accounted for the reduced serum lipids in KK-Aʸ mice by dietary MNB. This study advances the understanding of MADG as a nutraceutical and provides insights into the role of ether lipids in lipoprotein metabolism that can contribute to the development of prevention and treatment strategies for hyperlipidemia.
Keywords	adipose tissue ; blood glucose ; blood lipids ; blood serum ; dietary supplements ; fish ; fish oils ; hyperlipidemia ; lipoprotein metabolism ; lipoproteins ; males ; secretion ; soybean oil ; triacylglycerols
Language	English
Dates of publication	2023-03
Size	p. 243-251.
Publishing place	Springer Japan
Document type	Article ; Online
ZDB-ID	1192654-5
ISSN	1444-2906 ; 0919-9268
ISSN (online)	1444-2906
ISSN	0919-9268
DOI	10.1007/s12562-022-01655-5
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Article ; Online: Incorporation of Dietary Arachidonic and Docosatetraenoic Acid into Mouse Brain.

Yoshinaga, Kazuaki / Ishikawa, Haruna / Beppu, Fumiaki / Gotoh, Naohiro

Journal of agricultural and food chemistry

2021 Volume 69, Issue 8, Page(s) 2457–2461

Abstract: It is essential to analyze the metabolism of dietary polyunsaturated fatty acids in the brain for the research and development of functional foods. In this study, a single dose of 2,2-dideuterium-labeled docosatetraenoic acid ((+2)DTA) or 2,2-dideuterium- ...

Abstract	It is essential to analyze the metabolism of dietary polyunsaturated fatty acids in the brain for the research and development of functional foods. In this study, a single dose of 2,2-dideuterium-labeled docosatetraenoic acid ((+2)DTA) or 2,2-dideuterium-labeled arachidonic acid ((+2)AA) was orally administered to Institute of Cancer Research (ICR) mice and its metabolism in the brain was investigated. In the (+2)DTA group, the (+2)DTA content in the brain was significantly increased at 4, 8, 24, and 96 h compared to 0 h after administration, while in the (+2)AA group, the (+2)AA content was significantly increased at 4, 8, 24, and 96 h compared to 0 h. However, there was no significant difference in the content of (+2)DTA, a metabolite of (+2)AA, among all the groups. These results suggest that dietary (+2)DTA and (+2)AA pass through the blood-brain barrier and dietary (+2)AA is rather stored in the brain than converted to (+2)DTA.
MeSH term(s)	Animals ; Arachidonic Acid ; Brain ; Diet ; Fatty Acids, Unsaturated ; Mice
Chemical Substances	Fatty Acids, Unsaturated ; Arachidonic Acid (27YG812J1I)
Language	English
Publishing date	2021-02-17
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.0c07916
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Article: Preparation of n‐3 Polyunsaturated Phosphatidylglycerol from Salmon Roe Lipids by Phospholipase D and In Vitro Digestion

Chen, Liping / Beppu, Fumiaki / Miyashita, Kazuo / Hosokawa, Masashi

European journal of lipid science and technology. 2020 Feb., v. 122, no. 2

2020

Abstract: Phosphatidylglycerol (PG) is a highly functional phospholipid (PL), which has many physiological functions. However, naturally occurring PG binding n‐3 polyunsaturated fatty acid (n‐3 PUFA) is low in content, resulting in a scarcity of industrial bio‐ ... ...

Abstract	Phosphatidylglycerol (PG) is a highly functional phospholipid (PL), which has many physiological functions. However, naturally occurring PG binding n‐3 polyunsaturated fatty acid (n‐3 PUFA) is low in content, resulting in a scarcity of industrial bio‐resources of n‐3 PUFA enriched PG. The current study investigates the preparation of salmon roe PG (SRPG) from three types of salmon roe lipids and glycerol via phospholipase D (PLD)‐mediated transphosphatidylation. The yields of SRPG obtained from salmon roe total lipid (SRTL) and salmon roe PL (SRPL) are higher than those obtained from purified salmon roe phosphatidylcholine (SRPC) in aqueous system. Following a 24 h reaction with 0.75 U PLD, SRTL, and SRPL yield up to 96.4 mol% and 96.7 mol% SRPG, respectively. In addition, more fatty acids are released from synthesized SRPG via hydrolysis by pancreatic enzymes than from SRPC and soybean PC in in vitro digestion model. Fatty acids at the sn‐2 position of SRPG are completely liberated by 0.04 U of phospholipase A2 (PLA2) during a 6 h reaction, whereas fatty acids of SRPC are partially unhydrolyzed even after a 24 h reaction. Our results suggest that SRPG converted from salmon lipids by PLD is a functional PL with high bioavailability of n‐3 PUFAs. Practical Applications: Phosphatidylglycerol rich in n‐3 PUFAs is prepared from salmon roe lipids (SRPG) catalyzed by PLD. The SRPG yields reach 96.4 mol% and 96.7 mol% of phosphatidylcholine contained in SRTL and SRPL, respectively, in aqueous reaction system. Fatty acids rich in n‐3 PUFAs at sn‐2 position of prepared SRPG are rapidly liberated by PLA2 in an in vitro digestion model.
Keywords	bioavailability ; catalytic activity ; glycerol ; hydrolysis ; in vitro digestion ; omega-3 fatty acids ; phosphatidylcholines ; phospholipase A2 ; phospholipase D ; phospholipases ; polyunsaturated fatty acids ; salmon ; soybeans
Language	English
Dates of publication	2020-02
Publishing place	John Wiley & Sons, Ltd
Document type	Article
Note	JOURNAL ARTICLE
ZDB-ID	2003265-1
ISSN	1438-7697
ISSN	1438-7697
DOI	10.1002/ejlt.201900201
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Article ; Online: Seco-type β-Apocarotenoid Generated by β-Carotene Oxidation Exerts Anti-inflammatory Effects against Activated Macrophages.

Takatani, Naoki / Beppu, Fumiaki / Yamano, Yumiko / Maoka, Takashi / Hosokawa, Masashi

Journal of oleo science

2021 Volume 70, Issue 4, Page(s) 549–558

Abstract: β-Apocarotenoids are the cleavage products of β-carotene. They are found in plants, carotenoid-containing foods, and animal tissues. However, limited information is available regarding the health benefits of β-apocarotenoids. Here, we prepared seco-type ... ...

Abstract	β-Apocarotenoids are the cleavage products of β-carotene. They are found in plants, carotenoid-containing foods, and animal tissues. However, limited information is available regarding the health benefits of β-apocarotenoids. Here, we prepared seco-type β-apocarotenoids through the chemical oxidation of β-carotene and investigated their anti-inflammatory effects against activated macrophages. Oxidation of β-carotene with potassium permanganate produced seco-β-apo-8'-carotenal, in which one end-group formed an "open" β-ring and the other was cleaved at the C-7',8' position. In lipopolysaccharide-stimulated murine macrophage-like RAW264.7 cells, seco-β-apo-8'-carotenal inhibited the secretion and mRNA expression of inflammatory mediators such as nitric oxide, interleukin (IL)-6 and IL-1β, and monocyte chemoattractant protein-1. Furthermore, seco-β-apo-8'-carotenal suppressed phosphorylation of c-Jun N-terminal kinase and the inhibitor of nuclear factor (NF)-κB as well as the nuclear accumulation of NF-κB p65. Notably, since seco-β-apo-8'-carotenal exhibited remarkable anti-inflammatory activity compared with β-apo-8'-carotenal, its anti-inflammatory action could depend on the opened β-ring structure. These results suggest that seco-β-apo-8'-carotenal has high potential for the prevention of inflammation-related diseases.
MeSH term(s)	Animals ; Anti-Inflammatory Agents ; Carotenoids/chemical synthesis ; Carotenoids/chemistry ; Carotenoids/pharmacology ; Chemokine CCL2/genetics ; Chemokine CCL2/metabolism ; Gene Expression/drug effects ; Gene Expression/genetics ; Inflammation/drug therapy ; Inflammation/genetics ; Inflammation Mediators/metabolism ; Interleukin-1beta/genetics ; Interleukin-1beta/metabolism ; Interleukin-6/genetics ; Interleukin-6/metabolism ; Macrophage Activation/drug effects ; Mice ; NF-kappa B/genetics ; NF-kappa B/metabolism ; Nitric Oxide/genetics ; Nitric Oxide/metabolism ; Oxidation-Reduction ; RAW 264.7 Cells ; RNA, Messenger/genetics ; RNA, Messenger/metabolism ; Structure-Activity Relationship ; beta Carotene/chemistry
Chemical Substances	Anti-Inflammatory Agents ; Chemokine CCL2 ; IL1B protein, mouse ; Inflammation Mediators ; Interleukin-1beta ; Interleukin-6 ; NF-kappa B ; RNA, Messenger ; beta-apo-8'-carotenal ; beta Carotene (01YAE03M7J) ; Nitric Oxide (31C4KY9ESH) ; Carotenoids (36-88-4)
Language	English
Publishing date	2021-03-10
Publishing country	Japan
Document type	Journal Article
ZDB-ID	2218264-0
ISSN	1347-3352 ; 1345-8957
ISSN (online)	1347-3352
ISSN	1345-8957
DOI	10.5650/jos.ess20329
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Article ; Online: Application of Partial Hydrogenation for the Generation of Minor Tocochromanol Homologs and Functional Evaluation of Hydrogenated Tocotrienol-rich Vitamin E Oil in Diabetic Obese Mice.

Beppu, Fumiaki / Sakuma, Aimi / Kasatani, Satoshi / Aoki, Yoshinori / Gotoh, Naohiro

Journal of oleo science

2021 Volume 70, Issue 1, Page(s) 103–112

Abstract: Recent research has identified minor homologs of vitamin E with one or two double bonds in the side-chain, namely tocomonoenol (T1) and tocodienol (T2), in natural products. We first explored the effectiveness of partial hydrogenation for generating ... ...

Abstract	Recent research has identified minor homologs of vitamin E with one or two double bonds in the side-chain, namely tocomonoenol (T1) and tocodienol (T2), in natural products. We first explored the effectiveness of partial hydrogenation for generating minor tocochromanols from tocotrienol (T3). During hydrogenation with pure α-T3 as a substrate, the side-chain was partially saturated in a time-dependent manner, and a large amount of α-T1 and α-T2 was obtained. To investigate the beneficial effects of the hydrogenated product, we fed diabetic obese KK-A
MeSH term(s)	Animals ; Cholesterol, HDL/blood ; Diabetes Mellitus/drug therapy ; Diabetes Mellitus/metabolism ; Glucose/metabolism ; Hydrogenation ; Hyperglycemia/drug therapy ; Hyperglycemia/metabolism ; Lipid Metabolism/drug effects ; Male ; Mice, Inbred Strains ; Obesity/drug therapy ; Obesity/metabolism ; Structure-Activity Relationship ; Time Factors ; Tocotrienols/administration & dosage ; Tocotrienols/chemistry ; Tocotrienols/pharmacology ; Vitamin E/administration & dosage ; Vitamin E/chemistry ; Vitamin E/pharmacology ; Mice
Chemical Substances	Cholesterol, HDL ; Tocotrienols ; Vitamin E (1406-18-4) ; Glucose (IY9XDZ35W2)
Language	English
Publishing date	2021-01-11
Publishing country	Japan
Document type	Journal Article
ZDB-ID	2218264-0
ISSN	1347-3352 ; 1345-8957
ISSN (online)	1347-3352
ISSN	1345-8957
DOI	10.5650/jos.ess20233
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Article ; Online: Preparation of Apoastaxanthinals and Evaluation of Their Anti-inflammatory Action against Lipopolysaccharide-Stimulated Macrophages and Adipocytes.

Takatani, Naoki / Beppu, Fumiaki / Yamano, Yumiko / Maoka, Takashi / Miyashita, Kazuo / Hosokawa, Masashi

ACS omega

2022 Volume 7, Issue 26, Page(s) 22341–22350

Abstract: Apocarotenoids are carotenoid derivatives in which the polyene chain is ... ...

Abstract	Apocarotenoids are carotenoid derivatives in which the polyene chain is cleaved
Language	English
Publishing date	2022-06-22
Publishing country	United States
Document type	Journal Article
ISSN	2470-1343
ISSN (online)	2470-1343
DOI	10.1021/acsomega.2c01164
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Article ; Online: Identification and tissue distribution of fucoxanthinol and amarouciaxanthin A fatty acid esters in fucoxanthin-fed mice.

Takatani, Naoki / Sakimura, Kana / Nagata, Kodai / Beppu, Fumiaki / Yamano, Yumiko / Maoka, Takashi / Hosokawa, Masashi

Food chemistry

2022 Volume 410, Page(s) 135318

Abstract: Administered carotenoid fatty acid esters are thought to be hydrolyzed to their free forms and absorbed into the body, and information on the tissue distribution of carotenoid fatty acid esters has been limited. Fucoxanthin, a marine carotenoid, exhibits ...

Abstract	Administered carotenoid fatty acid esters are thought to be hydrolyzed to their free forms and absorbed into the body, and information on the tissue distribution of carotenoid fatty acid esters has been limited. Fucoxanthin, a marine carotenoid, exhibits various health benefits, including anti-diabetic and anti-obesity effects. However, fucoxanthin metabolism in mammals remains unclear. Herein, we investigated the fatty acid esters of fucoxanthin metabolites, fucoxanthinol and amarouciaxanthin A, in the tissues of male C57BL/6J mice fed a fucoxanthin-containing diet for one week. Fucoxanthinol and amarouciaxanthin A-3-esters accumulated abundantly in the liver and epididymal white adipose tissue, respectively. These esters were less detectable in the serum and other tissues. Therefore, it is suggested that fucoxanthinol and amarouciaxanthin A are partially acylated in the liver and epididymal white adipose tissue after being transported through the body as their free forms. This study presents a novel carotenoid metabolic pathway in mammals.
MeSH term(s)	Mice ; Male ; Animals ; Tissue Distribution ; Mice, Inbred C57BL ; Carotenoids ; Mammals
Chemical Substances	amarouciaxanthin A (100667-78-5) ; fucoxanthin (06O0TC0VSM) ; fucoxanthinol (7176-02-5) ; Carotenoids (36-88-4)
Language	English
Publishing date	2022-12-28
Publishing country	England
Document type	Journal Article
ZDB-ID	243123-3
ISSN	1873-7072 ; 0308-8146
ISSN (online)	1873-7072
ISSN	0308-8146
DOI	10.1016/j.foodchem.2022.135318
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Article: Monocaprin Enhances Bioavailability of Fucoxanthin in Diabetic/Obese KK-Ay Mice

Nagata, Kodai / Takatani, Naoki / Beppu, Fumiaki / Abe, Aya / Tominaga, Etsuko / Fukuhara, Tomohisa / Ozeki, Makoto / Hosokawa, Masashi

Marine drugs. 2022 July 07, v. 20, no. 7

2022

Abstract: Fucoxanthin is a marine carotenoid found in brown seaweeds and several microalgae. It has been reported that fucoxanthin has health benefits such as anti-obesity and anti-diabetic effects. To facilitate fucoxanthin applications in the food industry, it ... ...

Abstract	Fucoxanthin is a marine carotenoid found in brown seaweeds and several microalgae. It has been reported that fucoxanthin has health benefits such as anti-obesity and anti-diabetic effects. To facilitate fucoxanthin applications in the food industry, it is important to improve its low bioavailability. We attempted the combined feeding of fucoxanthin-containing seaweed oil (SO) and monocaprin in a powder diet and analyzed the fucoxanthin metabolite contents in the liver, small intestine and serum of diabetic/obese KK-Aʸ mice. After 4 weeks of feeding with the experimental diets, the serum fucoxanthinol concentrations of the mice fed 0.2% SO and 0.5% monocaprin were higher than those of the 0.2% SO-fed mice. Furthermore, fucoxanthinol accumulation in the liver and small intestine tended to increase in a combination diet of 0.2% SO and 0.125–0.5% monocaprin compared with a diet of 0.2% SO alone, although amarouciaxanthin A accumulation was not different among the 0.2% SO-fed groups. These results suggest that a combination of monocaprin with fucoxanthin-containing SO is an effective treatment for improving the bioavailability of fucoxanthin.
Keywords	bioavailability ; blood serum ; carotenoids ; food industry ; liver ; macroalgae ; metabolites ; microalgae ; oils ; small intestine
Language	English
Dates of publication	2022-0707
Publishing place	Multidisciplinary Digital Publishing Institute
Document type	Article
ZDB-ID	2175190-0
ISSN	1660-3397
ISSN	1660-3397
DOI	10.3390/md20070446
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Article: n-3 Polyunsaturated fatty acid-enriched phosphatidylglycerol suppresses inflammation in RAW264.7 cells through Nrf2 activation via alteration of fatty acids in cellular phospholipids

Chen, Liping / Beppu, Fumiaki / Takatani, Naoki / Miyashita, Kazuo / Hosokawa, Masashi

Fisheries science. 2021 Sept., v. 87, no. 5

2021

Abstract: Phosphatidylglycerol (PG) is a naturally occurring phospholipid. The immunomodulatory activity of PG has been reported to be dependent on its fatty acid composition. In this study, the anti-inflammatory effect of n-3 polyunsaturated fatty acid-enriched ... ...

Abstract	Phosphatidylglycerol (PG) is a naturally occurring phospholipid. The immunomodulatory activity of PG has been reported to be dependent on its fatty acid composition. In this study, the anti-inflammatory effect of n-3 polyunsaturated fatty acid-enriched PG (n-3 PUFA-PG) was investigated on macrophage-like RAW264.7 cells stimulated by lipopolysaccharide (LPS). n-3 PUFA-PG binding eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) significantly suppressed interleukin-6, interleukin-1β and nitric oxide production by RAW264.7 cells. Notably, the suppressive effect of n-3 PUFA-PG on inflammatory factor production was more potent compared to n-3 PUFA-phosphatidylcholine (PC) and soybean PG. n-3 PUFA-PG treatment markedly increased EPA and DHA in intracellular PC and phosphatidylethanolamine and decreased 18:1n-9 through downregulation of fatty acid synthase and stearoyl-CoA desaturase mRNA expression compared to n-3 PUFA-PC treatment. Furthermore, n-3 PUFA-PG enhanced nuclear factor erythroid E2-related factor (Nrf2) levels in the nucleus and increased heme oxygenase-1 mRNA expression. N-acetyl-L-cysteine, which is an inhibitor against Nrf-2 activation, alleviated the induction of HO-1 mRNA and anti-inflammatory effect of n-3 PUFA-PG. These data suggest that n-3 PUFA-PG exhibits anti-inflammatory effects on LPS-stimulated RAW264.7 cells through Nrf2 activation by altering cellular fatty acids.
Keywords	acetylcysteine ; anti-inflammatory activity ; docosahexaenoic acid ; eicosapentaenoic acid ; fatty acid composition ; fatty-acid synthase ; gene expression ; heme oxygenase (biliverdin-producing) ; immunomodulators ; inflammation ; interleukin-6 ; lipopolysaccharides ; nitric oxide ; phosphatidylethanolamines ; soybeans ; stearoyl-CoA desaturase
Language	English
Dates of publication	2021-09
Size	p. 727-737.
Publishing place	Springer Japan
Document type	Article
ZDB-ID	1192654-5
ISSN	1444-2906 ; 0919-9268
ISSN (online)	1444-2906
ISSN	0919-9268
DOI	10.1007/s12562-021-01542-5
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