MAKABE HIDEFUMI
Academic Assembly School of Science and Technology Institute of Agriculture
Interdisciplinary Cluster for Cutting Edge Research Institute for Biomedical Sciences
Professor
Researcher Information
Educational Background
Research activity information
Paper
- First total synthesis of Inaoside A
Takao, T.; Kawamura, A.*; Makabe, H.*
Asian J. Org. Chem., in press., Dec. 2024, Refereed
Last - Synthesis of prodelphinidin B2 3,3”-digallate using AgOTf mediated self-condensation
Saito, H.; Takahashi, Y.; Kawamura, A.*; Makabe, H.*
Results in Chemistry, 12, 101902, Dec. 2024, Refereed
Last, Corresponding - Inaoside A: new antioxidant phenolic compound from the edible mushroom Laetiporus cremeiporus
Kawamura, A.*; Mizuno, A.; Kurakake, M.; Yamada, A., Makabe, H.*
Heliyon, 10, e24651, Jan. 2024, Refereed
Corresponding - Application of Pd-catalyzed carbonylation followed by spontaneous oxa-Michael addition/diastereoselective reduction of ynone: Synthesis of (+)-goniofufurone
Kameyama, Y.; Makabe, H.*
Tetrahedron Lett., 132, 154827, Nov. 2023, Refereed
Corresponding - Oral administration of procyanidin B2 3,3"-di-O-1 gallate ameliorates experimental autoimmune encephalomyelitis through immunosuppressive effects on CD4+ T cells by regulating glycolysis
Endo, K.; Sawa, T.; Tanaka, Y.; Saiki, T.; Haga, H.; Rizeq, L.; Aso, H.; Isono, M.; Niitsuma, F.; Masaki, A.; Makabe, H.; Tanaka, S.*
Eur. J. Pharm., 954, 175879, Jul. 2023, Refereed - Procyanidin B2 3,3′′-di-O-gallate ameliorates imiquimod-1 induced psoriasis by suppressing TLR7 signaling through the inhibition of endosomal acidification in dendritic cells
Sawa, T.; Endo K.; Nakashima, A.; Tanaka, Y.; Makabe, H.; Tanaka, S.*
International Immunopharmacology, 121, 110444, Jun. 2023, Refereed - Procyanidin B2 3,3″-di-O-gallate suppresses IFN-γ production in CD4+ T cells through the regulation of glutamine influx via direct interaction with ASCT2
Endo, K.; Sawa, T.; Kitamura, H.; Makabe, H.; Tanaka, S.*
International Immunopharmacology, 115, 109617, Dec. 2022, Refereed - Intestinal permeability of agaro-oligosaccharides: Transport across Caco-2 cell monolayers and pharmacokinetics in rats
Shirai, I.; Karasawa, K.; Kodaira, Y.; Iwasaki, Y.; Shigemura, Y.; Makabe, H.; Katayama, S.*
Frontiers in Nutrition, 9, 996607, Aug. 2022, Refereed - Concise Synthesis of Procyanidin B2 3,3”-digallate Using Yb(OTf)3 Mediated Self-Condensation
Tanaka,Y.; Kobayashi, S.; Hattori, Y.; Kawamura, A.; Makabe, H.*
Synlett, 33, 1071-1074, 2022, Refereed
Last, Corresponding - Synthesis of (+)-Muconin via Diastereoselective Oxypalladation
Sugimoto, M.; Nosho, S.; Hikosaka, G.; Hattori, Y.; Umezawa, K.; Kawamura, A.; Makabe, H.*
J. Org. Chem., 86, 4859-4866., Mar. 2021, Refereed - The suppression of IL-17 production from T cells by gallate-type procyanidin is mediated by selectively inhibiting cytokine production from dendritic cells
Endo, K.; Sawa, T.; Matsui, R.; Asami, T.; Tanaka, Y.; Makabe, H.; Tanaka, S.*
Biomedicine & Pharmacotherapy, 137, 111346., Feb. 2021, Refereed - Synthesis of (+)-solenopsin via Pd-catalyzed N-Alkylation and Cyclization
Suzuki, K.; Hattori, Y.; Kawamura, A.; Makabe, H.*
Biosci. Biotecnol. Biochem., 85, 223-227., Feb. 2021, Refereed - Procyanidin B2 gallate regulates TNF-α production from T cells through inhibiting glycolytic activity via mTOR-HIF-1 pathway
Endo, K.; Matsui, R.; Sugiyama. M.; Asami, T.; Inaba, C.; Kobayashi, S.; Makabe, H.; Tanaka, S.*
Biochem. Pharm., 177, 113952, Jun. 2020, Refereed - Identification and characterization of oligomeric proanthocyanidins with significant anti-cancer activity in adzuki beans (Vigna angularis)
Kawahara, S.; Ishihara, C.; Matsumoto, K.; Senga, S.; Kawaguchi, K.; Yamamoto, A.; Suwannachot, J.; Hamauzu, Y.; Makabe, H.*; Fujii, H.*
Heliyon, 5, e02610, 24 Oct. 2019, Refereed - Synthesis of (+)-goniopypyrone and (+)-goniotriol using Pd-catalyzed carbonylation
Miyazawa, Y.; Oda-Tanaka, A.; Makabe, H.*
Tetrahedron Lett., 60, 151039, Sep. 2019, Refereed - Isolation and characterization of a novel oligomeric proanthocyanidin with significant anti-cancer activities from grape stems (Vitis vinifera)
Kawahara, S.; Toda, K.; Matsumoto, K.; Ishihara, C.; Nonobe, S.; Matsunaga, C.; Gomi, K. Y.; Senga, S.; Kawaguchi, K.; Yamamoto, A.; Suwannachot, J.; Noda, R.; Kobayashi, S.; Hamauzu, Y.; Makabe, H.*; Fujii, H.*
SCIENTIFIC REPORTS, 9, 12046-12053, Aug. 2019, Refereed - Adzuki bean (Vigna angularis) extract reduces amyloid-β aggregation and corrects cognitive impairment in Drosophila models of Alzheimer’s disease
Miyazaki, H.; Okamoto, Y.; Watanabe, T.; Katayama, S.; Kawahara, S.; Makabe, H.; Fujii, H.; Yonekura, S.*
NUTRITION RESEARCH AND PRACTICE, 13, 64-69, Feb. 2019, Refereed - Synthesis of (+)-altholactone, (+)-7-epi-altholactone, (-)-etharvensin, and (-)-almuheptolide-A using Pd-catalyzed carbonylation
Miyazawa, Y.; Hattori, Y.; Makabe, H.*
Tetrahedron Lett., 59, 4024-4027, Nov. 2018, Refereed - Synthesis of epigallocatechin trimer, (epigallocatechin)2-epicatechin, and (epigallocatechin)2-catechin via a Lewis acid mediated one-pot condensation and their antitumor activities in prostate cancer cells
Ichikawa,M.; Yamamoto,S.; Ishihara,C.; Nonobe, S.; Hattori, Y.; Umezawa, K.; Fujii, H*.;Makabe, H.*
Tetrahedron, 74, 3534-3542, Jul. 2018, Refereed - Kale supplementation up-regulates HSP70 and suppresses cognitivedecline in a mouse model of accelerated senescence
Kushimoto, S.; Uchibori, Y.; Yanai, S.; Suto, Y.; Kobayashi, H.; Makabe, H.; Nakamura, S.; Katayama, S.*
Journal of Functional Foods, 44, 292-298, May 2018, Refereed - An asymmetric synthesis of (+)-monomorine I
Asai, M.; Takemoto, Y.; Deguchi, A.; Hattori, Y.; Makabe, H.*
Tetrahedron: Asymmetry, 28, 1582-1586, Nov. 2017, Refereed - Epicatechin oligomers longer than trimers have anti-cancer activities, but not the catechin counterparts
Takanashi, K.; Suda, M.; Matsumoto, K.; Ishihara, C.; Toda, K,; Kawaguchi, K.; Senga, S.; Kobayashi, N.; Ichikawa, M.; Katoh, M.; Hattori, Y.; Kawahara, S. –i.; Umezawa, K.; Fujii, H*.; Makabe, H.*
SCIENTIFIC REPORTS, 7, 7791, 10 Aug. 2017, Refereed - Synthesis of (-)-isosolenopsin using Diasereoselective Aminopalladation
Takemoto, Y.; Hattori, Y.; Makabe, H*
Heterocycles, 94(2), 286-296, Feb. 2017, Refereed - Procyanidin B2 Gallates Inhibit IFN-γ and IL-17 Production in T cells by Suppressing T-bet and RORγt Expression
Tanaka, S.*; Furuya, K,;Yamamoto, K.; K. Yamada, K.; Ichikawa, M.; Suda, M.; Makabe, H.
International Immunopharmacology, 44, 87-96, Jan. 2017, Refereed - Synthesis of Prodelphinidin Trimer Isolated from Cistus albidus and Its Growth Inhibitory Activity Against Human Prostate Cancer Cell Lines
Mori, M.; Matsumoto, K.; Ishihara, C.; Kawaguchi, K.; Kawahara, S. -i.; Hattori, Y.; Fujii, H.;* Makabe, H.*
Heterocycles, 92(10), 1822-1831, Oct. 2016, Refereed - Concise Synthesis of Cinnamtannin A2 from Dimeric Epicatechin Electrophile and Nucleophile Prepared by Zn(OTf)2 Mediated Self-Condensation
Ichikawa, M.; Takanashi, K.; Suda, M.; Hattori, Y.; Kawahara, S.-i.; Fujii, H.; Makabe, H*.
Synthesis, 48, 1525-1532, May 2016, Refereed - Synthesis of Decytospolide A, B and Their C-3-epimers Using Stereoselective Oxypalladation
Kurogome, Y.; Hattori, Y.; Makabe, H.*
Synthesis, 48, 765-771, Mar. 2016, Refereed - Divergent Synthesis of 2,6-Disubstituted Piperidine Alkaroid, (+)-Spectaline by Palladium-Catalyzed Cyclization
Katsuyama, M.; Furuta, M.;Kobayashi, K.; Teruya, K.; Makabe, H.; Akaji, K.; Hattori, Y.*
Heterocycles, 91(5), 959-969, May 2015, Refereed - Syntheses of a pyrrolidine analog of a tetrahydrofuran containing acetogenin, cis-solamin
Onishi, K.; Sakurai, H.; Kobayashi, K.; Makabe, H.; Teruya, K.; Akaji, K.; Hattori, Y.*
Heterocycles, 91(3), 573-582, Mar. 2015, Refereed - Syntheses of procyanidin B2and B3 gallatederivatives using equimolar condensation mediated by Yb(OTf)3 and their antitumor activities
Suda, M.; Katoh, M.; Toda, K.; Matsumoto, K.; Kawaguchi, K.; Kawahara, S-i.; Hattori, Y.; Fujii, H.*; Makabe, H.*
Bioorg. Med. Chem. Lett., 23(17), 4935-4939, 01 Sep. 2013 - “Enzymatic synthesis of novel phenol acid rutinosides using rutinase and their antiviral activity in vitro”
Katayama, S.; Ohno, F.; Yamauchi,Y.; Kato, M.; Makabe, H.; Nakamura, S.*
J. Agric. Food Chem., 61, 9617-9622, 2013, Refereed - Synthesis of Procyanidin B1, B2, and B4 and Their Anti-inflammatory Activity
Katoh, M.; Oizumi, Y.; Mohri, Y.; Hirota, M.; Makabe, H.*
Lett. Org. Chem., 9(4), 233-238, 2012, Refereed - バイレンシ科アセトゲニン類の合成とミトコンドリアcomplexIに対する阻害活性
服部恭尚,今野博行,三芳秀人,真壁秀文*
有機合成化学協会誌, 69(2), 159-168, 2011, Refereed - Synthesis of solamin type mono-THF acetogenins using cross-metathesis
Konno, H*.; Makabe, H.; Hattori, Y.; Nosaka,K.; Akaji, K.
Tetrahedron, 66(40), 7946-7953, 2010, Refereed - Daedalin A, a Metabolite of Daedalia dickinsii, Inhibits Melanin Synthesis in an in vitro Human Skin Model
Morimura, K.,Hiramatsu, K.; Yamazaki, C., Hattori, Y., Makabe, H., Hirota, M.*
Biosci. Biotechnol. Biochem., 73(3), 627-632, 2009, Refereed - Synthesis of (-)-Epicatechin 3-(3"-O-Methylgallate) and (+)-Catechin 3-(3"-O-Methylgallate) and Their Anti-infalammatory Activity
Iijima, T.; Mohri, Y.; Hattori, Y.; Kashima, A.; Kamo, T.; Hirota, M.; Kiyota, H.; Makabe, H.*
Chem. Biodivers., 6(4), 520-526, 2009, Refereed - Current Topics of Organic and Biological Chemistry of Annonaceous Acetogenins and Their Synthetic Mimics
Makabe, H.*; Konno, H.; Miyoshi, H.*
Current Drug Discovery Technologies, 5(3), 213-229, 2008, Refereed - Total synthesis of cis-solamin A, a mono-tetrahydrofuran acetogenin isolated from Annona muricata
Konno, H.*; Okuno, Y.; Makabe, H.; Nosaka, K.; Onishi, A.; Abe, Y.; Sugimoto, A.; Akaji, K.
Tetrahedron Lett., 49, 782-785, 2008, Refereed - Stimulation conditions for spore germination of Agaricus blazei
Mahmud, M. A.; Ohno, S.; Fukuda, M.*; Yamada, A.; Hattori, Y.; Makabe, H.
Mushuroom Science and Biotechnology, 16(2), 87-92, 2008, Refereed - Synthesis of Pyranicin and Its Inhibitory Action with Bovine Heart Mitochondrial Complex I
Hattori, Y.; Furuhata, S.; Okajima, M.; Konno, H.; Abe, M.; Miyoshi, H.; Goto, T.; Makabe, H.*
Org. Lett., 10, 717-720, 2008, Refereed - DynamicFunction of the Spacer Region of Acetogenins in the Inhibition of Bovine Mitochondrial NADH-Ubiquinone Oxidoreductase (Complex I)
Abe, M.; Kubo, A.; Yamamoto, S.; Hatoh, Y.; Murai, M.; Hattori, Y.; Makabe, H.; Nishioka, T.; Miyoshi, H.*
Biochemistry, 47(23), 6257-6263, 2008, Refereed - Synthesis of pyranicin and its deoxygenated analogues and their inhibitory action with bovine heart mitochondrial complex I
Furuhata, S.;Hattori, Y.; Okajima, M.; Konno, H.; Abe, M.; Miyoshi, H.; Goto, T.; Makabe, H.*
Tetrahedron, 64, 7695-7703, 2008, Refereed - Taxpropellane: A Novel Taxane with an Unprecedented Polycyclic Skeleton from the Needles of Taxus canadensis
Zhang, M. L; Dong, M.; Huo, C. -H.; Li, L. -G.; Sauriol, F.; Shi, Q.-W.*; Gu,Y. -C.; Makabe, H.; Kiyota, H.
Eur. J. Org. Chem., 5414-5417, 2008, Refereed - Synthesis of Annonaceous Acetogenins from Muricatacin
Makabe, H.
Biosci. Biotechnol. Biochem., 71, 2367-2374, 2007 - Synthesis, determination of the absolute configuration oftonkinelin, and inhibitoryaction with bovine heart mitochondrial complex I
Hattori, Y., Konno, H., Abe, M., Miyoshi, T. Goto, T., Makabe, H.*
Bioorg. Med. Chem., 15, 3026-3031, 2007 - Total synthesis of miraziridine A and identification of its major reaction site for cathepsin B
Konno, H.*; Kubo, K.; Makabe, H.; Toshiro,E.; Hinoda, N.; Nosaka, K.; Akaji, K.
Tetrahedron, 63, 9502-9513, 2007 - A refined method for determining the absolute configuration of the 3-hydroxy-3-methylglutaryl group
Hattori, Y., Horikawa, K., Makabe, H., Hirai, N., Hirota, M., Kamo, T.*
Tetrahedron: Asymmetry, 18, 1183-1186, 2007 - An efficient synthesis of procyanidins. Rare earth metal Lewis acid catalyzed equimolar condensation of catechin and epicatechin
Mohri, Y., Sagehashi, M., Yamada, T., Hattori, Y., Morimura, K., Kamo, T., Hirota, M., Makabe, H.*
TetrahedronLett., 48, 5891-5894, 2007 - A Tyrosinase Inhibitor, Daedalin A, from the Mycelial Culture of Daedalea dickinsi
Morimura, K., Yamazaki, C., Hattori, Y., Makabe, H., Kamo, T., Hirota,M.*
Biosci. Biotechnol. Biochem., 71, 2837-2840, 2007 - Synthesis of murisolin, (15R, 16R, 19R, 20S)-murisolin A, and (15R, 16R, 19S, 20S)-16,19-cis-murisolin and their inhibitory action with bovine heart mitochondrial complex I
Hattori,Y; Kimura, Y; Moroda, A; Konno, H; Abe, M; Miyoshi, H; Goto, T; Makabe, H.*
CHEMISTRY-AN ASIAN JOURNAL, 1(6), 894-904, 2006 - A Novel Hydrogen Transfer Hydroalumination of Alkenes withTriisobutylaluminum Catalyzed by Pd and Other Late Transition Metal Complexes
Gagneur, S.; Makabe, H.; Negishi, E.*
Tetrahedron Lett., 42(2), 785-787, Jan. 2001 - Intermolecular trapping of acylpalladium and related acylmetal derivatives with active C-H compounds
Negishi, E.*; Liou, S. -Y.; Xu, C.; Shimoyama, I.; Makabe, H.
J. Mol. Cat. (A), 143, 279-286, Jan. 1999 - Hydrogen Transfer Hydrozirconation of Alkenes with i-BuZrCp2Cl Catalyzed by Lewis-Acidic Metal Compounds Containing Al, Zn, Si, Ag, and Pd
Makabe, H.; Negishi, E.*
Eur. J. Org. Chem., 969-971, 1999 - Catalytic Generation and Trapping Acylmetals Containing Ni and Cu with Enolates
Negishi, E.*; Makabe, H.; Shimoyama, I.; Wu, G.; Zhang, Y.
Tetrahedron, 54(2), 1095-1106, Jan. 1998 - Total Synthesis of (+)-4-Deoxygigantecin
Makabe, H.; Tanaka, A.*; Oritani, T.
Tetrahedron, 54, 6329-6340, 1998 - Total Synthesis of (+)-4-Deoxygigantecin
Makabe, H.; Tanaka, A.*; Oritani, T.
Tetrahedron Lett., 38(24), 4247-4250, Jun. 1997 - Total Synthesis of (8’R)-,and (8’S)-Corrosoline
Makabe, H.; Tanimoto, H.; Tanaka, A.*; Oritani, T.
Heterocycles, 43(10), 2229-2248, Oct. 1996 - Total Synthesis of (15S, 16R, 19S, 20R, 34S)-Diepomuricanin
Konno, H.; Makabe, H.; Tanaka, A.*; Oritani, T.
Tetrahedron Lett., 37(30), 5393-5396, Aug. 1996 - Synthesis of Two Possible Diastereoisomers of the Epoxy Lactone Proposed for an Annonaceous Acetogenins, Epoxyrollin A
Konno, H.; Makabe, H.; Tanaka, A.*; Oritani, T.
Tetrahedron, 52(28), 9399-9408, Jul. 1996 - Syntehsis of Squamostanal-A
Konno, H.; Makabe, H.; Tanaka, A.*; Oritani, T.
Biosci. Biotechnol. Biochem., 60(3), 526-527, Mar. 1996 - Synthesis of Two Possible Diastereoisomers of the Epoxy Lactone Proposed for Epoxyrollin A
Konno, H.; Makabe, H.; Tanaka, A.*; Oritani, T.
Biosci. Biotechnol. Biochem., 59(12), 2355-2357, Dec. 1995 - Total Synthesis of Solamin and Reticulatacin
Makabe, H.; Tanaka, A.*; Oritani, T.
J. Chem. Soc. Perkin Trans. 1, 1975-1981, 1994 - Synthesis of (-)-Muricatacin
Makabe, H.; Tanaka, A.*; Oritani, T.
Biosci. Biotechnol. Biochem., 57(6), 1028-1029, Jun. 1993
MISC
- ヒアリの毒性成分とその作用
真壁秀文
化学と生物, 56(7), 513-515, Jul. 2018, Refereed - プロアントシアニジンオリゴマーの生物活性
真壁秀文,河原誠一,藤井博
化学と生物, 54(9), Sep. 2016, Refereed - Winners of CASMI2013: Automated Tools and Challenge Data
Nishioka, T.*; Kasama, T.; Kinumi, T.; Makabe, H.; Matsuda, F.; Miura, D.; Miyashita, M.;Nakamura, T.; Tanaka, K.; Yamamoto, A.
Mass Spectrometry, 3, S0039, Sep. 2014 - Synthetic studies on miraziridine A, a cysteine protease inhibitor isolated from Theonella aff. mirabilis
Konno, H.*; Kubo, K.; Makabe, H.; Nosaka, K.; Akaji, K.
Peptide Science, 43, 37-38, 2007 - Synthetic studies of tokaramide A and miraziridine A isolated from marine sponge Theonella aff. mirabilis
Konno, H.*; Kubo, K.; Makabe, H.; Fujii, N.; Nosaka, K.; Akaji, K.
Peptide Science, 42, 47-50, 2006 - 研究小集会報告 「根岸英一先生講演会」
真壁秀文
日本農芸化学会誌, 75(10), 49-50, Oct. 2001
Books and other publications
- Frontiers in Natural Product Chemistry 3
Hattori, Y.; Makabe, H.*, Joint work, The Biological Activities and Synthesis of 2,6-Disubstituted Piperidinols
182-206 Jun. 2017, RefereedStudies in Natural Products Chemistry, Atta-Ur-Rahman Eds 48
Makabe, H.*, Studies on prodelphinidins: isolation, synthesis, and their biological activities
ELSEVIER SCIENCE PUBLISHERS - AMSTERDAM, 323-346 Jun. 2016Studies in Natural Products Chemistry, Atta-Ur-Rahman Eds 42
Makabe, H., Recent progress of the synthesis of 2,6-disubstituted hydroxypiperidine alkaloids
ELSEVIER SCIENCE PUBLISHERS - AMSTERDAM, 353-371 2014, RefereedTea in Health and Disease Prevention, Academic Press
Makabe, H., (-)-Epicatechin 3-(3”-O-methylgallate) and (+)-catechin 3-(3”-O-methylgallate), and Their anti-inflammatory activity
Elsevier, Victor R. Preedy Eds., 1215-1222 2012, Refereedみすずかる信濃の健康志向食品、9章昆虫食の時代がやってくる!
信大大学院機能性食料開発学専攻編, Joint work
郷土出版社, 158-168頁 Sep. 2003Reactions of Acylpalladium Derivativeswith Enolates and Related Amphiliphilic Reactions, Handbook of Organopalladium Chemistry, VI.2.3
Negishi, E.*; Makabe, H., Joint work
Wiley-VCH, 2455-2471頁 Jul. 2002Palladium-Catalyzed Hydrometallation, Handbook of Organopalladium Chemistry, VII.4
Makabe, H.; Negishi, E.*, Joint work
Wiley-VCH, 2789-2823頁 Jul. 2002