東京農業大学

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原子・分子から
生命・生態系を化学する

原子・分子から
生命・生態系を化学する

原子・分子から
生命・生態系を化学する

2022年
Sulforaphane suppresses the activity of sterol regulatory element-binding proteins (SREBPs) by promoting SREBP precursor degradation.
Miyata, S.; Kodaka, M.; Kikuchi, A.; Matsunaga, Y.; Shoji, K.; Kuan, Y.-C.; Iwase, M.; Takeda, K.; Katsuta, R.; Ishigami, K.; Matsumoto, Y.; Suzuki, T.; Yamamoto, Y.; Sato, R.; Inoue, J. Sci. Pep., 12, 8715 (2022). doi: 10.1038/s41598-022-12347-6

Adjacent double branches exist in the branching structure of starch.
Honda, C.; Kaneko, A.; Katsuta, R.; Tokuoka, M. Carbohydr. Res., 519, 108628 (2022). doi: 10.1016/j.carres.2022.108628

Indium(III) bromide-mediated β-selective thioglycosylation of 1,2,4-O-orthoacetylglucose derivatives.
Ikuta, D.; Kumagai, K.; Hagimori, T.; Hirokane, T.; Ikeuchi, K.; Wakamori, S.;  Yamada, H. Carbohydr. Res., 519, 108609 (2022). doi: 10.1016/j.carres.2022.108609

2021年
Sulfoquinovosylglyceryl ether, a new group of ether lipids from lake ball-forming green alga Aegagropilopsis moravica (family Pithophoraceae).
Oku, N.; Hasada, A.; Kimura, K.; Honoki, H.; Katsuta, R.; Yajima, A.; Nukada, T.; Ishigami, K.; Igarashi, Y. Chem. Asian J., 16, 1493-1498 (2021). doi: 10.1002/asia.202100278

Synthesis and DFT-NMR-guided structure revision of cremenolide.
Takeda, K.; Katsuta, R.; Yajima A.; Ishigami, K.; Kuwahara, S.; Nukada, T. Nat. Prod. Res. in press (2021). doi: 10.1080/14786419.2021.2023867

Total synthesis of macaranin B.
Matsumoto, S.; Aoyama, A.; Wakamori, S.; Yamada, H. Biosci. Biotechnol. Biochem., 85, 1937-1944 (2021). doi: 10.1093/bbb/zbab120

Chemical synthesis of small cyclodextrins utilizing bridged pyranose ring.
Wakamori, S. Glycoforum, 24, A5 (2021). doi: 10.32285/glycoforum.24A5

Enantioselective synthesis and stereochemical determination of the highly reduced polyketide ishigamide.
Seo, M.; Du, D.; Katsuyama, Y.; Katsuta, R.; Yajima, A.; Nukada, T.; Ohnishi, Y.; Ishigami. K. Biosci. Biotechnol. Biochem., 85, 148-153 (2021). doi: 10.1093/bbb/zbaa023

Synthesis of both enantiomers of lycoperdic acid, an unusual mushroom-derived amino acid.
Katsuta, R.; Ishiuchi, R.; Kunisawa, M.; Yajima, A.; Ishigami, K.; Nukada, T. Biosci. Biotechnol. Biochem., 85, 154-159 (2021). doi: 10.1093/bbb/zbaa027

Studies on analogs of DAMASCENOLIDE: Part 4. Synthesis and odor evaluation of sulfur-containing analogs of DAMASCENOLIDE.
Miyazawa, Y.; Kawaguchi, K.; Katsuta, R.; Nukada, T.; Ishigami, K. Biosci. Biotechnol. Biochem., 85, 1357-1363 (2021). doi: 10.1093/bbb/zbab032

Studies on analogs of DAMASCENOLIDE: Part 3. Synthesis and odor evaluation of dimethylated, cyclopropanated, and other analogs of DAMASCENOLIDE.
Miyazawa, Y.; Kawaguchi, K.; Katsuta, R.; Nukada, T.; Ishigami, K. Biosci. Biotechnol. Biochem., 85, 756-764 (2021). doi: 10.1093/bbb/zbaa103

Novel glucoamylase-resistant gluco-oligosaccharides with adjacent α-1, 6 branches at the non-reducing end discovered in Japanese rice wine, sake.
Honda, C.; Katsuta, R.; Yamada, M.; Kojima, Y.; Mamiya, A.; Okada, N.; Kawamura, T.;  Totsuka, A.; Shindo, H.; Hosaka, M.; Tomoo, N.; Tokuoka, M. Carbohydr. Polym., 251, 116993 (2021). doi: 10.1016/j.carbpol.2020.116993 

Disproof of the Proposed Structures of Bradyoxetin, a Putative Bradyrhizobium japonicum Signaling Molecule, and HMCP, a Putative Ralstonia solanacearum Quorum-Sensing Molecule.
Yajima, A.; Katsuta, R.; Shimura, M.; Yoshihara, A.; Saito, T.; Ishigami, K.; Kai, K. Eur. J. Nat. Prod., 84, 495-502 (2021). doi: 10.1021/acs.jnatprod.0c01369

Synthesis and Determination of Absolute Configuration of Zealexin A1, a Sesquiterpenoid Phytoalexin from Zea mays.
Yajima, A.; Shimura, M.; Saito, T.; Katsuta, R.; Ishigami, K.; Huffaker, A.; Schmelz, E. A. Eur. J. Org. Chem., 2021, 1174-1178 (2021). doi: 10.1002/ejoc.202001596

2020年
Analog synthesis of DAMASCENOLIDE, an important aroma component of roses, and their odor properties.
Miyazawaa, Y.; Kawaguchi, K.; Katsuta, R.; Nukada, T.; Ishigami, K. Biosci. Biotechnol. Biochem., 84, 1560-1569 (2020). doi:10.1080/09168451.2020.1753498

Formal synthesis of cochlearol A, a meroterpenoid with renoprotective activity.
Naruse, K.; Katsuta, R.; Yajima, A.; Nukada, T.; Watanabe, H.; Ishigami, K. Tetrahedron Lett., 61, 151845 (2020). doi:10.1016/j.tetlet.2020.151845

Synthesis and stereochemistry of (−)-FE399.
Katsuta, R.; Masada, N.; Kimura,K.; Yajima, A.; Ishigami, K.; Nukada, T. Tetrahedron Lett., 61, 151783 (2020). doi:10.1016/j.tetlet.2020.151783

Synthesis and odour evaluation of double-bond isomers of DAMASCENOLIDE, 4-(4-methylpent-3-en-1-yl)-2(5H)-furanone, which has a citrus-like odour.
Miyazawa, Y.; Ohashi, T.; Kawaguchi, K.; Tanaka, N.; Katsuta, R.; Yajima, A.; Nukada, T.; Ishigami, K. Flavour Fragr. J., 35, 341-349 (2020). doi:10.1002/ffj.3568

Transglycosylation forms novel glycosides ethyl α-maltoside and ethyl α-isomaltoside in sake during the brewing process by α-glucosidase A of Aspergillus oryzae.
Kojima, Y.; Honda, C.; Kobayashi, I.; Katsuta, R.; Matsumura, S.; Wagatsuma, I.; Takehisa, M.; Shindo, H.; Hosaka, M.; Nukada, T.; Tokuoka, M. J. Agric. Food Chem., 68, 1419-1426 (2020). doi:10.1021/acs.jafc.9b06936

2019年
Synthesis of anti-Helicobacter pylori sesquiterpene employing tandem radical cyclization, and determination of the absolute configuration of the natural product.
Ishigami, K.; Kadowaki, K.; Yamada, S.; Aiba, S.; Kawasaki, T.; Katsuta, R.; Yajima, A.; Nukada, T.; Takikawa, H.; Watanabe, H. Tetrahedron, 76, 130834 (2019). doi:10.1016/j.tet.2019.130834

Transcriptional regulators involved in responses to volatile organic compounds in plants.
Nagashima, A.; Higaki, T.; Koeduka, T.; Ishigami, K.; Hosokawa, S.; Watanabe, H.; Matsui, K.; Hasezawa, S.; Touhara, K. J. Biol. Chem., 294, 2256-2266 (2019). doi:10.1074/jbc.RA118.005843

Synthesis and odour evaluation of novel sulfur-containing cyclic acetals.
Miyazawa, Y.; Masuda, Y.; Ohmori, Y.; Katsuta, R.; Nukada, T.; Ishigami, K. Flavour Fragr. J., 34, 43-51 (2019). doi:10.1002/ffj.3478

2018年
Enantioselective Total Synthesis of (+)-Anthecularin.
Yusuke, O.; Okada, S.; Mori, Na.; Ishigami, K.; Watanabe, H. Organic Lett., 20, 3888-3891 (2018). doi:10.1021/acs.orglett.8b01467

Nitro-Mannich reaction and intramolecular 1,3-dipolar cycloaddition route to acylpyrrolidinones: Synthesis of a tetramic acid and (+)-laccarin.
Katsuta, R.; Ichijo, H.; Oouchi, G.; Yajima, A.; Ishigami, K.; Nukada, T. Tetrahedron Lett., 59, 2352-2355 (2018). doi:10.1016/j.tetlet.2018.05.014

Structural revision of glabramycin by synthetic and computational approaches.
Ishigami, K. Kagaku to Seibutsu, 56, 240-241 (2018). doi:10.1271/kagakutoseibutsu.56.240

Synthesis and stereochemistry of JBIR-81, a peptide enamide derived from aspergilli.
Katsuta, R.; Toyoda, M.; Yajima, A.; Ishigami, K.; Nukada, T. Tetrahedron Lett., 59, 1010-1013 (2018). doi:10.1016/j.tetlet.2018.01.080

2017年
First total synthesis of glabramycin B and revision of its relative configuration.
Yamamoto, M.; Ishigami, K.; Watanabe, H. Tetrahedron, 73, 3271-3280 (2017). doi:10.1016/j.tet.2017.04.061

Synthesis and stereochemistry of decarestrictines H and J.
Katsuta, R.; Masada, N.; Shimodaira, Y.; Ueda, S.; Yajima, A.; Nukada, T. Tetrahedron, 73, 1733-1739 (2017). doi:10.1016/j.tet.2017.02.023

Structural Insights into the CotB2-Catalyzed Cyclization of Geranylgeranyl Diphosphate to the Diterpene Cyclooctat-9-en-7-ol.
Tomita, T.; Kim, S-Y.; Teramoto, K.; Meguro, A.; Ozaki, T.; Yoshida, A.; Motoyoshi, Y.; Mori, N.; Ishigami, K.; Watanabe, H.; Nishiyama, M.; Kuzuyama, T. ACS Chem. Biol., 12, 1621–1628 (2017). doi:10.1021/acschembio.7b00154

2016年
Prediction of the structure of a novel amylopectin-based Cd-associated molecule in the stem of common reed grown in the presence of Cd.
Higuchi, K.; Ito, N.; Nukada, T. Biosci. Biotechnol. Biochem., 80, 1960-1965 (2016). doi:10.1080/09168451.2016.1194184

Synthesis and absolute configuration of formosusin A, a specific inhibitor of mammalian DNA polymerase b.
Yajima, A.; Iizuka, Y.; Katsuta, R.; Nukada, T. Tetrahedron Lett., 57, 2012-2015 (2016). doi:10.1016/j.tetlet.2016.03.094

Stereoselective synthesis of (±)-urechitol A employing [4+3] cycloaddition.
Sumiya, T.; Ishigami, K.; Watanabe, H. Tetrahedron, 72, 6982-6987 (2016). doi:10.1016/j.tet.2016.09.026

Cucumis sativus secretes 4′-ketoriboflavin under iron-deficient conditions.
Satoh, J.; Koshino, H.; Sekino, K.; Ito, S.; Katsuta, R.; Takeda, K.; Yoshimura, E.; Shinmachi, F.; Kawasaki, S.; Niimura, Y.; Nukada, T. Biosci. Biotechnol. Biochem., 80, 363-367 (2016). doi:10.1080/09168451.2015.1095070

Amino-group carrier-protein-mediated secondary metabolite biosynthesis in Streptomyces.
Hasebe, F.; Matsuda, K.; Shiraishi, T.; Futamura, Y.; Nakano, T.; Tomita, T.; Ishigami, K.; Taka, H.; Mineki, R.; Fujimura, T.; Osada, Y.; Kuzuyama, T.; Nishiyama, M. Nat. Chem. Biol., 12, 967–972 (2016). doi:10.1038/nchembio.2181

2015年
Stereoselective synthesis of (–)-decarestrictine G.
Katsuta, R.; Fujikawa, S.; Yajima, A.; Nukada, T. Tetrahedron, 71, 3428-3432 (2015). doi:10.1016/j.tet.2015.03.082

Synthesis and revision of the relative configuration of glabramycin B.
Ishigami, K,; Yamamoto, M.; Watanabe, H. Tetrahedron Lett., 56, 6290-6293 (2015). doi:10.1016/j.tetlet.2015.09.149

キラリティーを有する天然生理活性物質の合成研究.
Ishigami, K.; Kato, T.; Wakamori, S.; Kageji, H.; Watanabe, H. Annual Report 2014 (Cryogenic Research Center, The University of Tokyo), 6, 39-44 (2015).

Synthesis of marine oxylipin topsentolide A1 and its stereoisomers, and determination of the absolute configuration of the natural product.
Ishigami, K.; Kobayashi, M.; Takagi, M.; Shin-ya, K.; Watanabe, H. Tetrahedron, 71, 8436-8443 (2015). doi:10.1016/j.tet.2015.09.013

Synthesis of (±)-(Z)-2β-hydroxy-14-hydro-β-santalol employing tandem radical cyclization.
Ishigami, K.; Yamada, S.; Watanabe, H. Tetrahedron Lett., 56, 5816-5819 (2015). doi:10.1016/j.tetlet.2015.09.011

2014年
Computational Chemistry on Chemical Glycosylations.
Satoh, H.; Nukada, T. Trends Glycosci. Glyc., 147, 11-27 (2014). doi:10.4052/tigg.26.11

Total synthesis of epicoccamides A and D via olefin cross-methathesis.
Yajima, A.; Kawajiri, A.; Mori, A.; Katsuta, R.; Nukada, T. Tetrahedron Lett., 55, 4350-4354 (2014). doi:10.1016/j.tetlet.2014.06.040

Concise syntheses and biological activities of ganomycin I and fornicin A.
Yajima, A.; Urao, S.; Katsuta, R.; Nukada, T. Eur. J. Org. Chem., 2014, 731-738 (2014). doi:10.1002/ejoc.201301269

2013年
Syntheses of 5′-O-desmethylterphenyllin and related p-terphenyls and their inhibitory activity of TNF-α release from RBL-2H3 cells.
Yajima, A.; Urao, S.; Yoshioka, S.; Abe, N.; Katsuta, R.; Nukada, T. Tetrahedron Lett., 54, 4986-4989 (2013). doi:10.1016/j.tetlet.2013.07.062

Total synthesis of virgineone aglycone and stereochemical assignment of natural virgineone.
Yajima, A.; Ida, C.; Taniguchi, K.; Murata, S.; Katsuta, R.; Nukada, T. Tetrahedron Lett., 54, 2497-2501 (2013). doi:10.1016/j.tetlet.2013.03.006

Synthesis of the core framework of the proposed structure of sargafuran.
Katsuta, R.; Aoki, K.; Yajima, A.; Nukada, T. Tetrahedron Lett., 54, 347-350 (2013). doi:10.1016/j.tetlet.2012.11.052

2012年
Total synthesis of (±)-lysidicin A.
Ogura, Y.; Ishigami, K.; Watanabe, H. Tetrahedron, 68, 1723-1728 (2012). doi:10.1016/j.tet.2011.12.062

Determination of strain-specific wall teichoic acid structures in Lactobacillus plantarum reveals diverse α-d-glucosyl substitutions and high structural uniformity of the repeating units.
Tomita, S.; Furihata, K.; Tanaka, N.; Satoh, E.; Nukada, T.; Okada, S. Microbiol., 158, 2712-2723 (2012). doi:10.1099/mic.0.060913-0

Synthetic study of versipelostatin A: Synthesis of the spirotetronate unit starting from pulegone.
Katsuta, R.; Arai, K.; Yajima, A.; Nukada, T. Synlett, 23, 397-400 (2012). doi:10.1055/s-0031-1290204

Structure-activity relationship of alpha hormones, the mating factors of phytopathogen Phytophthora.
Molli, S. D., Qi, J.; Yajima, A.; Shikai, K.; Imaoka, T.; Nukada, T.; Yabuta, G.; Ojika, M. Bioorg. Med. Chem., 20, 681-686 (2012). doi:10.1016/j.bmc.2011.12.015

Synthesis of two osteoclast-forming suppressors, demethylincisterol A3 and and chaxine A.
Yajima, A.; Kagohara, Y.; Shikai, K.; Katsuta, R.; Nukada, T. Tetrahedron, 68, 1729-1735 (2012). doi:10.1016/j.tet.2011.12.057

2011年
Syntheses of the four stereoisomers of Phytophthora mating hormone α2 and a concise synthesis of mating hormone α1.
Yajima, A.; Toda, K.; Molli, S. D.; Ojika, M.; Nukada, T. Tetrahedron, 67, 8887-8894 (2011). doi:10.1016/j.tet.2011.09.066

Synthesis of aspergillide A via proline-catalyzed trans-to-cis isomerization of a substituted tetrahydropyran.
Nagasawa, T.; Nukada, T.; Kuwahara, S. Tetrahedron, 67, 2882-2888 (2011). doi:10.1016/j.tet.2011.02.061

Synthesis of (±)-cyclic dehypoxanthine futalosine, the biosynthetic intermediate in an alternative biosynthetic pathway for menaquinones.
Yajima, A.; Kouno, S.; Dairi, T.; Mogi, M.; Katsuta, R.; Seto, H.; Nukada, T. Tetrahedron Lett., 52, 4934-4937 (2011). doi:10.1016/j.tetlet.2011.07.061

The second Phytophthora mating hormone defines interspecies biosynthetic crosstalk.
Ojika, M.; Molli, S. D.; Kanazawa, H.; Yajima, A.; Toda, K.; Nukada, T.; Mao, H.; Murata, R.; Asano, T.; Qi, J.; Sakagami, Y. Nat. Chem. Biol., 7, 591-593 (2011). doi:10.1038/nchembio.617

Stereocontrolled total synthesis of (±)-3β-hydroxy-9β-pimara-7,15-diene, a putative biosynthetic intermediate of momilactones.
Yajima, A.; Toda, K.; Okada, K.; Yamane, H.; Yamamoto, M.; Hasegawa, M.; Katsuta, R.; Nukada, T. Tetrahedron Lett., 52, 3212-3215 (2011). doi:10.1016/j.tetlet.2011.04.044

2010年
Synthesis of (2RS,8R,10R)-YM-193221 and an Improved Approach to Tyroscherin, Bioactive Natural Compounds from Pseudallescheria sp.
Katsuta, R.; Yajima, A.; Ishigami, K.; Nukada, T.; Watanabe, H. Biosci. Biotechnol. Biochem., 74, 2056-2059 (2010). doi:10.1271/bbb.100361

Spliceostatin A blocks angiogenesis by inhibiting global gene expression including VEGF.
Furumai, R.; Uchida, K.; Komi, Y.; Yoneyama, M.; Ishigami, K.; Watanabe, H.; Kojima, S.; Yoshida, M. Cancer Sci., 101, 2483-2489 (2010). doi:10.1111/j.1349-7006.2010.01686.x

Determination of the absolute configuration of marine oxylipin topsentolide A1 by the synthesis of the enantiomer of the natural product.
Kobayashi, M.; Ishigami, K.; Watanabe, H. Tetrahedron Lett., 51, 2762-2764 (2010). doi:10.1016/j.tetlet.2010.03.071

Determination of the absolute configuration of nodulisporacid A by the concise synthesis of four stereoisomers via three-component reaction and one-pot construction of the framework.
Sumiya, T.; Ishigami, K.; Watanabe, H. Tetrahedron Lett., 51, 2765-2767 (2010). doi:10.1016/j.tetlet.2010.03.064

Stereoselective Total Synthsis of (±)-Urechitol A.
Sumiya, T.; Ishigami, K.; Watanabe,H. Angew. Chem. Int. Ed., 49, 5527-5528 (2010). doi:10.1002/anie.201002505

Comparison of components and synthesis genes of cell wall teichoic acid among Lactobacillus plantarum strains.
Tomita, S.; Irisawa, T.; Tanaka, N.; Nukada, T.; Satoh, E.; Uchimura, T.; Okada, S. Biosci. Biotechnol. Biochem., 74, 928-933 (2010). doi:10.1271/bbb.90736

Synthesis of a proposed structure for the diffusible extracellular factor of Xanthomonas campestris pv. campestris.
Yajima, A.; Imai, N.; Poplawsky, A. R.; Nukada, T.; Yabuta, G. Tetrahedron Lett., 51, 2074-2077 (2010). doi:10.1016/j.tetlet.2010.02.088

2009年
Enantioselective synthesis of phomallenic acid C by In- and Pd-mediated anti-SN2' coupling.
Kato, T.; Ishigami, K.; Akasaka, K.; Watanabe, H. Tetrahedron, 65, 6953-6958(2009). doi.10.1016/j.tet.2009.06.054

Synthetic Studies of Natural 10-Membered Lactones, Mueggelone, Microcarpalide, and Sch 642305, Which Have Interesting Bioactivities.
Ishigami, K. Biosci. Biotechnol. Biochem., 73, 971-979 (2009). doi:10.1271/bbb.80877

Structures of two monomeric units of teichoic acid prepared from the cell wall of Lactobacillus plantarum NRIC 1068.
Tomita, S.; Furihata, K.; Nukada, T.; Satoh, E.; Uchimura, T.; Okada, S. Biosci. Biotechnol. Biochem., 73, 530-535 (2009). doi:10.1271/bbb.80582

A simple synthesis of four stereoisomers of roseoside and their inhibitory activity on leukotriene release from mice bone marrow-derived cultured mast cells.
Yajima, A.; Oono, Y.; Nakagawa, R.; Nukada, T.; Yabuta, G. Bioorg. Med. Chem., 17, 189-194 (2009). doi: 10.1016/j.bmc.2008.11.002

Synthesis and structure revision of tyroscherin, and bioactivities of its stereoisomers against IGF-1-dependent tumor cells.
Ishigami, K.; Katsuta, R.; Shibata, C.; Hayakawa, Y.: Watanabe, H.; Kitahara, T. Tetrahedron, 65, 3629-3638 (2009). doi:10.1016/j.tet.2009.03.003

2008年
Synthesis and Structure Revision of Tyroscherin, a Growth Inhibitor of IGF-1-dependent Tumor Cells. Katsuta, R.; Shibata, C.; Ishigami, K.; Watanabe, H.; Kitahara, T. Tetrahedron Lett., 49, 7042-7045 (2008). doi:10.1016/j.tetlet.2008.09.141

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