研究者詳細 - 菅本　和寛

Two new angular-type pyranocoumarins from the aerial parts of Angelica furcijuga and their synthesis from isoepoxypteryxin 査読あり

Sugamoto K., Sakashita T., Matsumoto T., Hirozawa N.

Phytochemistry Letters 48 1 - 4 2022年1月

担当区分：筆頭著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Phytochemistry Letters

Two new angular-type pyranocoumarins, namely hyuganin G (1) and hyuganin H (2), were isolated from an ethyl acetate extract of the aerial parts of Angelica furcijuga, together with three known angular-type pyranocoumarins, isoepoxypteryxin (3), isopteryxin (4), and hyuganin E (5). Assignment of the 1H and 13C NMR data of 1 and 2 were achieved via analysis of the DEPT, HMQC, and HMBC spectra. The absolute configurations of 1 and 2 were determined by semi-synthesis from 3.

DOI： 10.1016/j.phytol.2022.01.004

Synthesis of chalcones bearing 2-hydroperoxy-3-methyl-3-butenyl or 2-hydroxy-3-methyl-3-butenyl group from prenylated chalcones 査読あり

Sugamoto K., Yoshifuji T., Soejima S., Honda Y.

Synthetic Communications 50 ( 10 ) 1523 - 1527 2020年5月

担当区分：筆頭著者記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：Synthetic Communications

© 2020, © 2020 Taylor & Francis Group, LLC. Chalcones bearing 2-hydroperoxy-3-methyl-3-butenyl or 2-hydroxy-3-methyl-3-butenyl groups, such as xanthoangelol E (1a), xanthoangelol D (2a), psorachalcone A (2 b), xanthohumol D (2c), and related derivatives were first synthesized by using the ene reaction of prenylated chalcones with singlet oxygen.

DOI： 10.1080/00397911.2020.1745242

Synthesis of (2R,6R,10R)- and (2S,6R,10R)-Pristanic Acid Diastereomers 査読あり

Kazuhiro Sugamoto, Ryoya Nishikawa, Tomonori Nakanishi

Letters in Organic Chemistry 22 ( 8 ) 591 - 595 2025年3月

担当区分：筆頭著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

DOI： https://doi.org/10.2174/0115701786370905250228040842

Synthesis and antibacterial activity of chalcones bearing prenyl or geranyl groups from Angelica keiskei 「(共著)」査読あり

Kazuhiro Sugamoto, Yoh-ichi Matsushita, Kana Matsui, Chiaki Kurogi, Takanao Matsui

Tetrahedron 67 5346 - 5359 2011年5月

記述言語：英語掲載種別：研究論文（学術雑誌）

Synthesis of 4-hydroxyderricin and related derivatives「(共著)」査読あり

Kazuhiro Sugamoto, Chiaki Kurogi, Yoh-ichi Matsushita, Takanao Matsui

Tetrahedron Letters 49 6639 - 6641 2008年10月

記述言語：英語掲載種別：研究論文（学術雑誌）

Solvent-Free Oxidative Coupling of 2-Naphthols Catalyzed by Hydrotalcite-Like Compounds in Aerobic Condition 「(共著)」査読あり

Kazuhiro Sugamoto, Yoh-ichi Matsushita, Takanao Matsui

Letters in Organic Chemistry 9 ( 4 ) 263 - 266 2012年5月

記述言語：英語掲載種別：研究論文（学術雑誌）

Microwave-Assisted Beckmann Rearrangement of Aryl Ketoximes Catalyzed by In(OTf))₃　in Ionic Liquid　「(共著)」査読あり

Kazuhiro Sugamoto, Yoh-ichi Matsushita, Takanao Matsui

Synthetic Communications 41 879 - 884 2011年2月

記述言語：英語掲載種別：研究論文（学術雑誌）

身近な素材を用いた中和反応に関する化学実験教材の開発査読あり

菅本和寛, 金丸慎太郎, 三宅琢磨, 矢野康之, 熊川　大輔

九州地区国立大学教育系・文系研究論文集 8 ( 2 ) No.4 2022年3月

担当区分：筆頭著者記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：九州地区国立大学間の連携事業に係る企画委員会リポジトリ部会

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色変わり冷シップ「(共著)」査読あり

菅本和寛，斎藤泰男，松井佳菜，松下洋一

化学と教育 58 ( 9 ) 430 - 430 2010年9月

記述言語：日本語掲載種別：研究論文（学術雑誌）

Selective Extraction of Cd(II) over Zn(II) from Acidic Media with Isooctylthioglycolate 査読あり国際共著

Koga S., Kanemaru S., Sugamoto K., Baba Y., Mumford K.A., Stevens G.W.

Solvent Extraction Research and Development, Japan 32 ( 1 ) 31 - 41 2025年

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Solvent Extraction Research and Development, Japan

In this study, a new extractant has been developed for mutual separation of Cu(II) / Fe(III) and Cd(II) / Zn(II) from acidic media. These metals are mainly discharged from smelting and refining processes of copper, zinc, and lead. However, the mutual separation of these metals is difficult due to their similar chemical properties. In order to separate these metals, isooctyl thioglycolate (IOTG) which has carbonyl and thiol groups was proposed as a new extractant. Furthermore, 1-dodecanethiol (DOTH) with only a thiol group was used for comparison. We found that IOTG in toluene can selectively separate Cu(II) over Fe(III) and Cd(II) over Zn(II). We paid attention to the selective extraction of Cd(II) with high toxicity and examined the extraction equilibria of Zn(II) and Cd(II) in detail. These extraction equilibria are determined by the conventional slope analysis method from 1 M aqueous ammonium nitrate solution. It was found that the selective extraction of Cd(II) over Zn(II) is due to the formation of the binuclear Cd(II) complexes while Zn(II) is extracted as the mononuclear complex. Furthermore, the stripping of Cd(II) and Zn(II) extracted into the organic phase was achieved using appropriate concentrations of various acids.

DOI： 10.15261/serdj.32.31

Seasonal Variation and Mean Degree of Polymerization of Proanthocyanidin in Leaves and Branches of Rabbiteye Blueberry (Vaccinium virgatum Aiton) 査読あり

Koga Y., Setoguchi Y., Sugamoto K., Goto Y., Hirano T., Kunitake H.

Plants 13 ( 13 ) 2024年7月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Plants

The leaves and branches of rabbiteye blueberry are rich in proanthocyanidins, which are thought to have different physiological activities depending on their structure and degree of polymerization. In this study, we analyzed the constituents of the leaves and branches of rabbiteye blueberry to determine the seasonal variations in polyphenol and proanthocyanidin (PAC) contents as well as their mean degrees of polymerization (mDP). Total PAC content was determined using two methods: The p-dimethylaminocinnamaldehyde (DMACA) method, which measures monomeric PAC, showed an increase from spring to summer in both leaves and branches. On the other hand, using the butanol/HCl method, which measures only polymerized PAC, the PAC content of leaves increased from spring to summer but those of branches remained low throughout the year, showing no significant increase or decrease. Furthermore, analysis of the mDP of PAC showed increases from spring to summer in the leaves of ‘Kunisato 35 gou’. Although the highest value (8.0) was observed in October, values around 4 remained throughout the year in the branches. Since differences in polymerization degree affect absorption in the body and physiological properties such as antioxidant capacity, selecting the appropriate harvest time and plant organs for each purpose is expected to ensure the quality of processed blueberry foods.

DOI： 10.3390/plants13131864

Naturally occurring phytanic acid exerts anti-inflammatory effects in a mouse model of dextran sulfate sodium-induced colitis 査読あり国際共著

Nakanishi T., Suga K., Wakitani S., Yamaguchi K., Sugamoto K., Erickson L., Kawahara S.

European Journal of Lipid Science and Technology 126 ( 4 ) 2024年

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：European Journal of Lipid Science and Technology

Phytanic acid is one of the branched-chain fatty acids in the human diet. Humans incorporate it into their bodies through the ingestion of ruminant meat and milk since these animal products contain the 3RS, 7R, 11R-isomer, as naturally occurring phytanic acid (nPA). Although phytanic acid has been reported to have health-promoting effects such as immunomodulatory effects, these findings were obtained mostly from in vitro cell-based experiments. In this study, the in vivo anti-inflammatory effects of nPA were investigated using a mouse model of dextran sulfate sodium (DSS)-induced colitis. Mice were fed diets containing 0%, 0.05%, or 0.1% nPA for 4 weeks. During the fourth week, acute colitis was induced by administration of a 3% DSS solution. The intake of 0.05% and 0.1% nPA inhibited DSS-induced body weight loss in mice, and showed improvement of histopathological changes in colon epithelium. nPA also inhibited the production of proinflammatory cytokines, especially macrophage-related cytokines such as interleukin-1β in the colon. These results suggest that nPA exerts anti-inflammatory effects under in vivo physiological conditions. Practical application: There is a growing demand for fatty acids possessing distinct nutritional and physical characteristics in the realms of health, nutrition, and food-related applications. The present study demonstrated that a branched-chain fatty acid, phytanic acid, exerts anti-inflammatory activity under not only in vitro but also in vivo conditions, using a commonly used mouse model of human inflammatory bowel disease. Our findings encourage further studies to determine whether phytanic acid elicits beneficial properties in humans, and suggest that phytanic acid enrichment can be a novel product strategy in the food market.

DOI： 10.1002/ejlt.202300165

Separation and Recovery of Sc(III) and Y(III) from Aqueous Acidic Media with N-Lauroylsarcosine 査読あり

MATSUMOTO Marina, KANEMARU Shintaro, BABA Yoshinari, SUGAMOTO Kazuhiro

Solvent Extraction Research and Development, Japan 30 ( 1 ) 71 - 79 2023年4月

担当区分：最終著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：日本溶媒抽出学会

In this study, the selective extraction and mutual separation of Sc(III) and Y(III) from Ni(II), Co(II) and Mn(II) in acidic media were performed with N-lauroylsarcosine (NLS) in toluene. The experimental results were quantitatively analyzed using the conventional slope analysis method. This method reasonably elucidated reasonably the extraction equilibrium formulation of these metals with LNS. Isostearic acid with only a carboxylic acid group in the molecule extracted Sc(III) and Y(III) in a higher pH region compared with that with LNS having amide and carboxylic acid moieties. Therefore, we found that the amide group included in the molecule structure of NLS plays an important role to extract these metals. Mutual separation of Sc(III) and Y(III) was carried out by a one-step extraction using NLS from Ni(II), Co(II) and Mn(II) in acidic media. Sc(III) is more strongly extracted than Y(III) with NLS, and the separation factor of the metals is quite high at 4.68×103. Furthermore, the stripping of Sc(III) and Y(III) extracted into the organic phase was achieved using appropriate concentrations of various acids.

DOI： 10.15261/serdj.30.71

Selective extraction equilibria of Sc(III), Y(III), Fe(III) and Al(III) from acidic media with toluene mixture of deep eutectic solvent (DES) composed of TOPO and isostearic acid 査読あり

Ushizaki S., Kanemaru S., Baba Y., Sugamoto K.

Analytical Sciences 39 ( 4 ) 473 - 481 2023年4月

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：Analytical Sciences

A deep eutectic solvent (DES) composed of isostearic acid and TOPO was newly found out and investigated for selective recovery of scandium. The four elements used in this study are scandium, iron, yttrium, and aluminum. It was difficult to separate the four elements owing to the overlap of extraction behavior when isostearic acid or TOPO alone in toluene was used, respectively. However, scandium was able to be selectively extracted from other metals using DES prepared by 1:1 mol ratio of isostearic acid and TOPO without toluene. In DES consisting of isostearic acid and TOPO, synergistic and blocking effects with three extractants acted on the extraction selectivity for scandium. Both effects are proved also from the fact that scandium was easily stripped with diluted acidic solutions such as 2 M HCl and H2SO4. Thus, DES extracted selectively scandium and back-extraction was easily achieved. In order to elucidate these phenomena above, the extraction equilibria of Sc(III) using DES dissolved in toluene was investigated in detail. The extraction mechanism of scandium by DES in toluene indicates that the extracted chemical species vary with pH, and that trivalent scandium is extracted by forming stable metal complexes with DESs consisting of five molecules of isostearic acid and five molecules of TOPO. Graphical abstract: [Figure not available: see fulltext.].

DOI： 10.1007/s44211-022-00234-z

Blueberry stem extract and stem active components prevent blue light-emitting diode light-induced retinal photoreceptor cell damage in vitro 査読あり

Ogawa K., Urata K., Suzuki Y., Sugamoto K., Goto Y., Nakayama T., Nishiyama K., Kunitake H., Yamasaki M.

Bioscience, biotechnology, and biochemistry 87 ( 4 ) 378 - 388 2023年3月

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：Bioscience, biotechnology, and biochemistry

Blue light causes retinal damage that can lead to ocular diseases such as age-related macular degeneration. In this study, we determined the protective effect of blueberry stem extract (BStEx) and active components on blue light-emitting diode (LED) light-induced retinal photoreceptor cell damage in vitro. Photoreceptor cells cultured in the presence of BStEx or components were exposed to blue light to induce cell damage. BStEx, fractions of BStEx containing proanthocyanidins, chlorogenic acid, catechin, and epicatechin prevented the cell damage and/or inhibited the generation of reactive oxygen species (ROS). Furthermore, BStEx reduced apoptosis and cell death, and inhibited the phosphorylation of p38 mitogen-activated protein kinase and c-Jun N-terminal kinase leading to cellular apoptosis induced by blue light exposure. These findings suggest that BStEx and components exert a protective effect against blue light-induced photoreceptor cell damage through the inhibition of MAPK phosphorylation and ROS production.

DOI： 10.1093/bbb/zbad001

In vitro characterization of anti-inflammatory activities of 3RS, 7R, 11R-phytanic acid 査読あり国際共著

Nakanishi T, Izumi M, Suzuki R, Yamaguchi K, Sugamoto K, Erickson L, Kawahara S

The Journal of dairy research 90 ( 1 ) 1 - 8 2023年2月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Journal of Dairy Research

The aim of the research described here was to investigate the in vitro immunomodulatory effects of 3RS, 7R, 11R-phytanic acid (3RS-PHY) from the perspective of efficacy against autoimmune diseases. 3RS-PHY is a milk component with strong agonist activity at the peroxisome proliferator activated receptor (PPAR). As PPAR is a therapeutic target for several human diseases, 3RS-PHY intake may have possible health benefits. Recently, we chemically synthesized a preparation of 3RS-PHY and demonstrated that 3RS-PHY inhibited T-cell production of interferon (IFN)-γ. However, the overall immunomodulatory effects were not evaluated. In this study, mouse splenocytes, purified T-cells and B-cells were stimulated by mitogens and incubated with 3RS-PHY, followed by evaluation of cytokine and antibody production. A macrophage-like cell line J774.1 was also incubated with 3RS-PHY to evaluate nitric oxide production. 3RS-PHY decreased mRNA levels not only of IFN-γ but also of interleukin (IL)-2, IL-10 and IL-17A in splenocytes and similar effects were confirmed at the protein level. In addition, 3RS-PHY had a direct action on T-cells with preferential inhibitory effects on Th1 and Th17 cytokines such as IFN-γ and IL-17A. Furthermore, 3RS-PHY suppressed antibody secretion by B-cells and nitric oxide production by J774.1 almost completely, indicating that 3RS-PHY is a bioactive fatty acid with anti-inflammatory properties. These findings encourage further investigations, including in vivo experiments, to evaluate whether 3RS-PHY actually shows the potential to prevent autoimmune diseases, and provide basic information to produce milk and dairy products with an increased 3RS-PHY concentration.

DOI： 10.1017/S0022029923000146

Grifola gargal水抽出物に含まれるヌクレオシドの組成

菅野友美, 菅本和寛, 亀井一郎, 三宅義明

日本きのこ学会誌 30 ( 4 ) 150 - 154 2023年1月

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：日本きのこ学会

本研究では，アンニンコウから芳香族化合物を単離し，新たな機能性を探索することを目的とした．HPLC分析によりアンニンコウ水抽出物に特徴的なピークが検出されたため，精製・単離し，NMRなどを用いて構造決定したところ，血小板凝集阻害効果のあるアデノシンと同定された．17種のキノコ粉末水抽出からアデノシン含量を測定した結果，ヒラタケが最も高い含量を示した．アデノシン以外のヌクレオシド（シチジン，ウリジン，グアノシン，チミジン）についても同定・定量した結果，それぞれの含量はきのこの種類，部位などで異なることが明らかとなった．

DOI： 10.24465/msb.30.4_150

Blueberry Leaf Extract Prevents Lacrimal Hyposecretion in Sjögren's Syndrome-like Model of Non-obese Diabetic Mice. 査読あり

Ogawa K, Urata K, Maeda S, Ohno Y, Satoh K, Yamada Y, Suzuki Y, Koga Y, Sugamoto K, Kawaguchi M, Kunitake H, Nishiyama K, Goto YO, Nakayama T, Yamasaki M

In vivo (Athens, Greece) 37 ( 1 ) 149 - 162 2023年1月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：In Vivo

Background/Aim: This study evaluated the effect of blueberry leaf hot water extract (BLEx) on Sjögren's syndrome (SS)-like lacrimal hyposecretion in male non-obese diabetic (NOD) mice. Materials and Methods: NOD or BALB/c mice were fed 1% BLEx or control (AIN-93G) for 2 weeks from the age of 4 to 6 weeks. Pilocarpine-induced tear volume was measured using a phenol red-impregnated thread. The lacrimal glands were evaluated histologically by H&E staining. The IL-1β and TNF-α levels in the lacrimal gland tissue were measured by ELISA. The mRNA expression levels of secretion-related proteins were measured by real-time PCR. LC3 I/II and arginase 1 expression levels were measured by western blot. Results: After feeding with BLEx, pilocarpine-induced tear secretion in NOD mice was increased. In contrast, the mRNA expression levels of the cholinergic muscarinic M3 receptor, aquaporin 5, and ion channels related to lacrimal secretion were not changed by BLEx administration. In addition, the protein expression of arginase 1, which was recently reported to be involved in tear hyposecretion in NOD mice, was also not improved by BLEx administration. Although infiltration in the lacrimal gland of NOD mice was not decreased, the levels of TNF-α and the autophagy-related protein LC3 were significantly suppressed by BLEx treatment. Conclusion: BLEx treatment may ameliorate lacrimal hyposecretion in NOD mice by delaying the progression of autoimmune disease by suppressing autophagy in lacrimal glands.

DOI： 10.21873/invivo.13064