Informa UK Limited Acta Medica Okayama 1478-6419 36 11 2021 Millifolide A, a dimeric ether of degraded sesquiterpene lactones, inhibited the proliferation of human lung cancer cell line A549 2875 2877 EN Pan-Pan Yu College of Forensic Medicine, Hebei Medical University, Hebei Key Laboratory of Forensic Medicine, Collaborative Innovation Center of Forensic Medical Molecular Identification Feng Yu College of Forensic Medicine, Hebei Medical University, Hebei Key Laboratory of Forensic Medicine, Collaborative Innovation Center of Forensic Medical Molecular Identification Wen-Zhe Li College of Forensic Medicine, Hebei Medical University, Hebei Key Laboratory of Forensic Medicine, Collaborative Innovation Center of Forensic Medical Molecular Identification Si-Ming Wang The Fourth Hospital of Hebei Medical University Chuan Wang Graduate School of Environmental and Life Science, Okayama University Mei Dong Graduate School of Environmental and Life Science, Okayama University Zhi-Yu Ni Graduate School of Environmental and Life Science, Okayama University Yong Li The Fourth Hospital of Hebei Medical University Hiromasa Kiyota Graduate School of Environmental and Life Science, Okayama University The inhibitory effect of three degraded sesquiterpene lactones, iso-seco-tanapartholide, arteludooicinolide A and millifolide A isolated from Achillea millefolium L., on anti-human lung cancer cells was examined using MTT and reporter gene assays. Millifolide A has significant inhibitory effects on the proliferation of human lung cancer cells probably through inducing cell apoptosis. No potential conflict of interest relevant to this article was reported.

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.

岡山大学農学部 Acta Medica Okayama 2186-7755 108 2019 抗リーシュマニア原虫活性物質Ancistrocladinium AとBの合成研究 1 4 EN Hiromasa Kiyota Graduate School of Environmental and Life Science, Okayama University Akihito Saito Graduate School of Agricultural Science, Tohoku University Momoko Takai Graduate School of Agricultural Science, Tohoku University Shigefumi Kuwahara Graduate School of Agricultural Science, Tohoku University Synthetic studies of ancistrocladinium A and B, antileishmanial compounds isolated from a Congolese Ancistrocladus sp., are described. Buchwald‒Hartwig coupling reaction between the dihydroisoquinoline and the naphthyl triflate failed. The main framework of ancistrocladinium A was constructed by 1,2‒addition of the amine to the naphthoquinone in the presence of celium trichloride as a catalyst. On the other hand, 1,4‒addition of the amine to the naphthoquinone proceeded without catalyst to form the framework of B. These products will be valuable leads for antileishmanial agents. 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.

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. Vavricka 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 酵素触媒反応を鍵とする光学活性な香気物質両鏡像体の合成と香気評価 33 38 EN Hiromasa Kiyota Graduate School of Environmental and Life Science, Okayama University Synthesis of both enantiomers of some perfume compounds, and their difference in aroma characteristics are described. Enantiomeric pairs of methyl jasmonate and its 4,5-didehydro congener, principal components of jasmin absolute, were prepared from the corresponding commercially available racemates using lipase-catalyzed optical resolution. The E-value for the reaction is as high as 370. The nature-identical isomers produced superior aroma activity relative to unnatural ones. Racemic lavandulol from a commercial source, was also resolved using several enzymatic transesterifications followed by hydrolysis with PPL. Odor evaluation revealed that the nature-identical isomer should play a key role in lavender oil. Cis-α-irone and cis-γ-irone, used as important violet components for perfumery, were synthesized in optically active forms through fractional crystallization of the diastereomeric salts with α-phenethylamine. The nature-identical irones also had better floral characteristics like ionone. No potential conflict of interest relevant to this article was reported.

John Wiley & Sons, Inc. Acta Medica Okayama 1522-2675 98 5 2015 New Limonoids from the Seeds of Xylocarpus granatum 691 698 EN Yi-Bing Wu Dan Liu Pei-Yu Liu Xue-Mei Yang Man Liao Nan-Nan Lu FranÅoise Sauriol Yu-Cheng Gu Qing-Wen Shi Hiromasa Kiyota Mei Dong Three novel limonoids, 2,3-dideacetylxyloccensin S (1), 30-deacetylxyloccensin W (2), and 7-hydroxy-21β-methoxy-3-oxo-24,25,26,27-tetranortirucalla-1,14-diene-23(21)-lactone (3), were isolated from the seeds of the Chinese mangrove, Xylocarpus granatum. The structures were elucidated on the basis of 1D- and 2D-NMR (including 1H- and 13C-NMR, DEPT, 1H,1H-COSY, HSQC, HMBC, and NOESY) data and confirmed by HR-MS. No potential conflict of interest relevant to this article was reported.