Oxford University Press (OUP) Acta Medica Okayama 1347-6947 85 1 2021 Synthesis of (12R,13S)-pyriculariol and (12R,13S)-dihydropyriculariol revealed that the rice blast fungus, Pyricularia oryzae, produces these phytotoxins as racemates 134 142 EN Yuta Nagashima Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University Ayaka Sasaki Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University Ryoya Hiraoka Graduate School of Environmental and Life Science, Okayama University Yuko Onoda Graduate School of Environmental and Life Science, Okayama University Koji Tanaka Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University Zi-Yi Wang Graduate School of Environmental and Life Science, Okayama University Atsuki Kuwana Graduate School of Environmental and Life Science, Okayama University Yuki Sato Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University Yuji Suzuki Laboratory of Plant Nutrition and Function, Graduate School of Agricultural Science, Tohoku University Minoru Izumi Graduate School of Environmental and Life Science, Okayama University Shigefumi Kuwahara Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University Manabu Nukina Professor Emeritus, Yamagata University Hiromasa Kiyota Graduate School of Environmental and Life Science, Okayama University Synthesis of assumed natural (12R,13S)-enantiomers of pyriculariol (1) and dihydropyriculariol (2), phytotoxins isolated from rice blast disease fungus, Pyricularia oryzae, was achieved using Wittig reaction or microwave-assisted Stille coupling reaction as the key step. The synthesis revealed that the natural 1 and 2 are racemates. Foliar application test on a rice leaf indicated that both the salicylaldehyde core and side chain were necessary for phytotoxic activity. The fungus is found to produce optically active phytotoxins when incubated with rotary shaker, but racemic ones when cultured using an aerated jar fermenter. No potential conflict of interest relevant to this article was reported.

Nature Publishing Group Acta Medica Okayama 2045-2322 7 1 2017 Synthesis of Sulfo-Sialic Acid Analogues: Potent Neuraminidase Inhibitors in Regards to Anomeric Functionality 8239 EN Christopher J. Vavrick Graduate School of Environmental and Life Science, Okayama University Chiaki Muto Graduate School of Environmental and Life Science, Okayama University Tomohisa Hasunuma Graduate School of Science, Technology and Innovation, Kobe University Yoshinobu Kimura Graduate School of Environmental and Life Science, Okayama University Michihiro Araki Graduate School of Science, Technology and Innovation, Kobe University Yan Wu CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences George F. Gao CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences Hiroshi Ohrui Yokohama College of Pharmacy Minoru Izumi Graduate School of Environmental and Life Science, Okayama University Hiromasa Kiyota Graduate School of Environmental and Life Science, Okayama University The design, synthesis and application of N-acetylneuraminic acid-derived compounds bearing anomeric sulfo functional groups are described. These novel compounds, which we refer to as sulfo-sialic acid analogues, include 2-decarboxy-2-deoxy-2-sulfo-N-acetylneuraminic acid and its 4-deoxy-3,4-dehydrogenated pseudoglycal. While 2-decarboxy-2-deoxy-2-sulfo-N-acetylneuraminic acid contains no further modifications of the 2-deoxy-pyranose ring, it is still a more potent inhibitor of avian-origin H5N1 neuraminidase (NA) and drug-resistant His275Tyr NA as compared to the oxocarbenium ion transition state analogue 2,3-dehydro-2-deoxy-N-acetylneuraminic acid. The sulfo-sialic acid analogues described in this report are also more potent inhibitors of influenza NA (up to 40-fold) and bacterial NA (up to 8.5-fold) relative to the corresponding anomeric phosphonic acids. These results confirm that this novel anomeric sulfo modification offers great potential to improve the potency of next-generation NA inhibitors including covalent inhibitors. No potential conflict of interest relevant to this article was reported.

岡山大学農学部 Acta Medica Okayama 2186-7755 106 2017 半強制的な反復学習による基礎科目の徹底教育 1 3 EN Minoru Izumi Graduate School of Environmental and life Science, Okayama University Yoshiyuki Murata Graduate School of Environmental and life Science, Okayama University 　We employ the methodology of “Compulsory Repetitive Learning” to improve student learning and performance in fundamental subjects. It is a challenge for many universities to intrinsically motivate students and it is a demanding issue that a large part of students do not sufficiently do homework. Here, we let students solve the problems associated with the teaching immediately following each lecture. Through the usage of “Compulsory Repetitive Learning”, each student as well as the subject teacher(s) could monitor and evaluate the quality of student learning and performance. No potential conflict of interest relevant to this article was reported.

Japan Society for Bioscience, Biotechnology, and Agrochemistry Acta Medica Okayama 0916-8451 71 4 2007 Three antinematodal diterpenes from Euphorbia kansui 1086 1089 EN Jian-Xiao Shi Zhi-Xuan Li Teruhiko Nitoda Minoru Izumi Hiroshi Kanzaki Naomichi Baba Kazuyoshi Kawazu Shuhei Nakajima Three compounds, 20-O-acetyl-[3-O-(2'E,4'Z)-deca-dienoyl]-ingenol (1), 20-O-acetyl-[5-O-(2'E,4'Z)-decadienoyl]-ingenol (2) and 3-O-(2'E,4'Z)-decadienoylingenol (3), were isolated from Euphorbia kansui under the bioassay-guided method. Each compound showed the same antinematodal activity against the nematode, Bursaphelenchus xylophilus, at a minimum effective dose (MED) of 5 mu g/cotton ball. No potential conflict of interest relevant to this article was reported.

Japan Society for Bioscience, Biotechnology, and Agrochemistry Acta Medica Okayama 0916-8451 71 3 2007 Glucosylation of Sucrose Laurate with Cyclodextrin Glucanotransferase 826 829 EN Katsuhide Okada Haisuo Zhao Minoru Izumi Shuhei Nakajima Naomichi Baba Sucrose monolauroyl esters were found to serve as substrates for cyclodextrin glucanotransferase (CGTase)-catalyzed transglucosidation reactions, affording new sucrose esters that have an additional 1-3 glucose residues on the pyranose ring of the sucrose moiety in the ester. No potential conflict of interest relevant to this article was reported.

Japan Society for Bioscience, Biotechnology, and Agrochemistry Acta Medica Okayama 0916-8451 71 4 2007 Synthesis of lipid derivatives of pyrrole polyamide and their biological activity 1078 1082 EN Masahiko Yamamoto Changjin Zhu Lui Yi Zheng Rong Yoshie Miura Minoru Izumi Shuhei Nakajima Ken-ichi Tanamoto Sakayu Shimizu Naomichi Baba Novel fatty acyl and phospholipid derivatives of pyrrole polyamide were synthesized. Their cytotoxicity against a cancer cell line of MT-4 cells and those infected by human immunodeficiency virus (HIV) was examined. Although no anti-HIV activity was found, their cytotoxicitty against the cancer cells was significantly enhanced by introducing a lipophilic group into the pyrrole polyamide. No potential conflict of interest relevant to this article was reported.

岡山大学農学部 Acta Medica Okayama 0474-0254 94 1 2005 アルキン型リンカーを用いた糖鎖固相合成--薗頭反応による高反応部位の選択 81 84 EN Minoru Izumi Two new alkyne-type linkers having alkynylmethyloxy moieties were elaborated for solid-phase synthesis of oligosaccharide. A propargyl glycoside-type linker between a sugar residue and a solid support was formed by the Sonogashira reaction of a propargyl glycoside with polymer-supported iodobenzene. A propargyl ester-type linker was also constructed by the same reaction of a 4-(proparygyloxycarbonyl)benzyl glycoside with the latter. Both linkers are stable against acids such as TFA but can be readily cleaved with this acid after conversion to the corresponding alkyne-cobalt complex by treatment with Co2(CO)8. The latter ester linker is generally advantageous in that mild cleavage liberates a proceed only at spatially reactive sites on the solid support where the reagent accesses readily, so that the subsequent reactions including glycosylation on solid phase proceeded smoothly to result in high total yields of the desired oligosaccharides. No potential conflict of interest relevant to this article was reported.