Bioorganic Research on Biologically Active Natural Products towards Development of Agrochemical and Medicinal Lead Compounds

• Project/Area Number: 19580120
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Bioproduction chemistry/Bioorganic chemistry
• Research Institution: Tohoku University
• Principal Investigator: KIYOTA Hiromasa Tohoku University, 大学院・農学研究科, 准教授 (30234397)
• Project Period (FY): 2007 – 2009
• Project Status: Completed (Fiscal Year 2009)
• Budget Amount: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000); Fiscal Year 2009: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000); Fiscal Year 2008: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2007: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
• Keywords: 抗生物質 / 植物毒素 / 海洋天然物 / ジャスモン酸 / タキサンジテルペノイド / 単離構造決定 / 全合成 / 構造活性相関 / 血管新生阻害

Research Abstract

Bioorganic research on biologically active natural products have been achieved. Total synthesis : analogs of polynactin antibiotics, phytotoxin T-beta-L and pyricuols, marine antifeedant pteroenone, plant hormone jasmonic acids, and gizzerosine. Patial synthesis : antibiotics pamamycis, spirofungins and enacyloxins, and anti-angiogenetic cortistatins. Isolation and structure elucidation : enacyloxins, taxanes, limonoids and echinopines.

Research Products

• [Journal Article] Xylocarponoids A and B, Unique C28 Skeleton Limonoids from Xylocarpus granatum (2010)
  • Author(s): C.-H.Huo, ら(9人中9番目)
  • Journal Title: Tetrahedron Letters 51 Pages: 754-757
  • Peer Reviewed
• [Journal Article] Identification of Mesorhizobium loti Gene Responsible for Glycerophosphorylation of Periplasmic Cyclic beta-1,2-Glucans (2010)
  • Author(s): Y.Kawaharada, ら(5人中2番目)
  • Journal Title: FEMS Microbiology Letters 302 Pages: 131-137
  • Peer Reviewed
• [Journal Article] Synthesis and Plant Growth Inhibitory Activity of Both Enantiomers of Pyricuol (2009)
  • Author(s): K. Tanaka, Y. Nakamura, A. Sasaki, R. Ueda, Y. Suzuki, S. Kuwahara, H. Kiyota
  • Journal Title: a Phytotoxin Isolated from Rice Blast Disease Fungus Magnaporthe grisea、Tetrahedron 65巻 Pages: 6115-6122
  • Peer Reviewed
• [Journal Article] The Daphniphyllum Alkaloids (2009)
  • Author(s): M.Dong, ら(5人中5番目)
  • Journal Title: Current Organic Chemistry 13 Pages: 646-682
  • Peer Reviewed
• [Journal Article] Synthesis and Anti-inflammatory Activity of (-)-Epicatechin-3-(3-O-methylgallate) and (+)-Catechin-3-(3-O-methylgallate) (2009)
  • Author(s): T.IIjima, ら(8人中7番目)
  • Journal Title: Chemistry & Biodiversity 6 Pages: 520-526
  • Peer Reviewed
• [Journal Article] Anti-nitric Oxide Production Activity of Isothiocyanates Correlates with Their Polar Surface Area Rather Than Their Lipophilicity (2009)
  • Author(s): T.Noshita, ら(6人中4番目)
  • Journal Title: European Journal Of Medicinal Chemistry 44 Pages: 4931-4936
  • Peer Reviewed
• [Journal Article] First Synthesis and Absolute Configuration of (-)-Pyriculariol, a Phytotoxin Isolated from Rice Blast Fungus, Magnaporthe grisea. Use of Microwave Irradiation to Control Stille Coupling Reaction Products (2009)
  • Author(s): A.Sasaki, ら(5人中5番目)
  • Journal Title: Tetrahedron Letters 50 Pages: 4637-4638
  • Peer Reviewed
• [Journal Article] Synthesis and Plant Growth Inhibitory Activity of Both Enantiomers of Pyricuol, a Phytotoxin Isolated from Rice Blast Disease Fungus Magnaporthe grisea (2009)
  • Author(s): K.Tanaka, ら(7人中7番目)
  • Journal Title: Tetrahedron 65 Pages: 6115-6122
  • Peer Reviewed
• [Journal Article] Gene Expression Profiles of Differentiating Leukemia Cells Induced by Methyl Jasmonate Largely Share with Those of Cytokinins and Methyl Jasmonate Analogs Induce the Differentiation of Human Leukemia Cells in Primary Culture (2009)
  • Author(s): H.Tsumura, ら(6人中4番目)
  • Journal Title: Leukemia 23 Pages: 753-760
  • Peer Reviewed
• [Journal Article] Chemical and Pharmacological Studies of the Plants from Genus Celastrus (2009)
  • Author(s): X. H. Su, ら(7人中7人目)
  • Journal Title: Chemistry and Biodiversity 6 Pages: 141-161
  • Peer Reviewed
• [Journal Article] Xylomexicanins A and B, New Δ14, 15-Mexicanolides from the Seeds of the Chinese Mangrove Xylocarpus granatum (2009)
  • Author(s): L. R. Shen, ら(10人中8人目)
  • Journal Title: Zeitschrift fuer Narurforshung 64c Pages: 37-42
  • Peer Reviewed
• [Journal Article] Two New 11(15->1)Abeotaxanes with a 2, 20-Epoxy Ring from the Needles of Taxu canadensis (2009)
  • Author(s): M. L. Zhang, ら(10人中9人目)
  • Journal Title: Zeitschrift fuer Narurforshung 64c Pages: 43-49
  • Peer Reviewed
• [Journal Article] New Cytotoxic Phenolic Derivatives from Matured Fruits of Magnolia denudata (2009)
  • Author(s): T. Noshita, ら(5人中2人目)
  • Journal Title: Bioscience, Biotechnology, and Biochemistry 73 Pages: 726-728
  • Peer Reviewed
• [Journal Article] Taxusecone, a Novel Taxane with an Unprecedented 11, 12-Secotaxane Skeleton from Taxus cuspidata (2009)
  • Author(s): S. H. Yu, ら(10人中9人目)
  • Journal Title: Bioscience, Biotechnology, and Biochemistry 73 Pages: 756-758
  • Peer Reviewed
• [Journal Article] (2008)
  • Author(s): Y. Sato, H. Kamiyama, T. Usui, T. Saito, H. Osada, S. Kuwahara, H. Kiyota
  • Journal Title: Biosci.Biotechnol.Biochem. 72巻 Pages: 2292-2297
  • Peer Reviewed
• [Journal Article] (2008)
  • Author(s): A. Miura, S.-y. Takigawa, Y. Furuya, Y. Yokoo, S. Kuwahara, H. Kiyota
  • Journal Title: Eur.J.Org.Chem. Pages: 4955-4962
  • Peer Reviewed
• [Journal Article] (2008)
  • Author(s): M. Dong, B. Cong, S.-H. Yu, F. Sauriol, C.-H. Huo, Q.-W. Shi, Y.-C. Gu, L. O. Zamir, H. Kiyota
  • Journal Title: Org.Lett. 10巻 Pages: 701-704
  • Peer Reviewed
• [Journal Article] A new taxane composed of two N-formyl rotamers from Taxus canadensis (2008)
  • Author(s): M. L. Zhang, ら(10人中9人目)
  • Journal Title: Tetrahedron Letters 49 Pages: 3405-3408
  • Peer Reviewed
• [Journal Article] Chemical Studies on Taxus canadensis (2008)
  • Author(s): M. L. Zhang, ら(10人中9人目)
  • Journal Title: Zeitschrift fuer Narurforshung 63b Pages: 1005-1011
  • Peer Reviewed
• [Journal Article] Synthesis of L-Acid (C1-C18) Fragment of Pamamycin-593 and De-N-methylpamamycin-579 (2008)
  • Author(s): A. Miura, ら(6人中6人目)
  • Journal Title: European Journal of Organic Chemistry 2008 Pages: 4955-4962
  • Peer Reviewed
• [Journal Article] Chemical and pharmacological research of the plants in genus Euphorbia (2008)
  • Author(s): Q, W. Shi, ら(3人中3人目)
  • Journal Title: Chemical Reviews 108 Pages: 4295-4327
  • Peer Reviewed
• [Journal Article] Taxpropellane, a Novel Taxane with an Unprecedented Polycyclic Skeleton from the Needles of Taxus canadensis (2008)
  • Author(s): M. L. Zhang, ら(9人中9人目)
  • Journal Title: European Journal of Organic Chemistry 2008 Pages: 5414-5417
  • Peer Reviewed
• [Journal Article] Synthesis and Anti-angiogenic Activity of Cortistatin Analogs (2008)
  • Author(s): Y. Sato, ら(7人中7人目)
  • Journal Title: Bioscience, Biotechnology, and Biochemistry 72 Pages: 2992-2997
  • Peer Reviewed
• [Journal Article] Enzymatic Resolution of (±)-2-Exo-7-syn-7-(1-propynyl) norbornan-2-ol, a Key Synthetic Intermediate for Jasmonoids (2008)
  • Author(s): H. Kiyota, ら(4人中4人目)
  • Journal Title: Zeitschrift fuer Narurforshung 63b Pages: 1441-1442
  • Peer Reviewed
• [Journal Article] Total Synthesis of Natural Products of Microbial Origin (2008)
  • Author(s): H. Kiyota, S. Kuwahara
  • Journal Title: Tohoku J. Agric. Res. 58 Pages: 167-173
• [Journal Article] A Novel Taxane with a Rare 9α, 13α-Oxygen Bridge from Taxus cuspidata Needles (2008)
  • Author(s): M.L. Zhang, ら(8人中8人目)
  • Journal Title: Tetrahedron Lett. 49 Pages: 1180-1183
  • Peer Reviewed
• [Journal Article] Echinopines A and B: Sesquiterpenoids Possessing an Unprecedented Skeleton from Echinps spinosus (2008)
  • Author(s): M. Dong, ら(9人中9人目)
  • Journal Title: Org. Lett. 10 Pages: 701-704
  • Peer Reviewed
• [Journal Article] (2007)
  • Author(s): H. Kiyota, T. Takai, Y. Shimasaki, M. Saitoh, O. Nakayama, T. Takada, S. Kuwahara
  • Journal Title: Synthesis Pages: 2471-2480
  • Peer Reviewed
• [Journal Article] Synthesis of(-)-Tabtoxinine-β-lactam, the Phytotoxin of Tobacco Wildfire Disease (2007)
  • Author(s): H. Kiyota, ら(7人中1人目)
  • Journal Title: Synthesis 2007 Pages: 2471-2480
  • Peer Reviewed
• [Journal Article] Setereochemistry of Enacyloxins 4. Completion of Structure Assignment with(13'R,14'R,15'S)-Configuration of Enacyloxins, a Series of Antibiotics from Frateuria sp. W-315 (2007)
  • Author(s): H. Furukawa, ら(7人中2人目)
  • Journal Title: Chem. Biodivers. 4 Pages: 1601-1604
  • Peer Reviewed
• [Journal Article] A New Metabolite with a New Substituted Pattern from the Seeds of the Chinese Yew, Taxusmairei (2007)
  • Author(s): C.H. Huo, ら(6人中6人目)
  • Journal Title: Chem. Biodivers. 4 Pages: 84-88
  • Peer Reviewed
• [Journal Article] Canataxpropellane, a Novel Taxane with a Unique Polycyclic Carbon Skeleton(Tricyclotaxane)from the Needles of Taxus canadensis (2007)
  • Author(s): C.H. Huo, ら(6人中6人目)
  • Journal Title: Tetrahedron Lett. 48 Pages: 2721-2724
  • Peer Reviewed
• [Journal Article] Structural Determination of a New 2(3->20)Abeotaxane with an Unusual13 β-Substitution Pattern and a New 6/8/6-Ring Taxane from Taxus cuspidata (2007)
  • Author(s): C.H. Huo, ら(8人中8人目))
  • Journal Title: Magn. Reson. Chem. 45 Pages: 527-530
  • Peer Reviewed
• [Journal Article] New 14-Hydroxy-taxane and 2α,20-Epoxy-11(15->1)abeotaxane from the Needles of Taxus canadensis (2007)
  • Author(s): Q.W. Shi, ら(8人中8人目)
  • Journal Title: Biosci. Biotechnol. Biochem. 77 Pages: 1777-1780
  • Peer Reviewed
• [Journal Article] Chemical Constituents of the Plants in Genus Laggera (2007)
  • Author(s): X.C. Li, ら(4人中4人目)
  • Journal Title: Chem. Biodivers. 4 Pages: 105-111
  • Peer Reviewed
• [Journal Article] Structures and Biological Properties of the Chemical Constituents from the Genus Wedelia (2007)
  • Author(s): X. Li, ら(5人中5人目)
  • Journal Title: Chem. Biodivers. 4 Pages: 823-836
  • Peer Reviewed
• [Journal Article] Two New Taxanes from Taxus canadensis (2007)
  • Author(s): C.H. Huo, ら(7人中7人目)
  • Journal Title: Biochem. Syst. Ecol. 35 Pages: 909-913
  • Peer Reviewed
• [Journal Article] Three New Taxanes with 10-Alkoxy Group from the Heartwood of Taxus cuspidata (2007)
  • Author(s): M. Dong, ら(8人中8人目)
  • Journal Title: Biosci. Biotechnol. Biochem. 70 Pages: 2087-2090
  • Peer Reviewed
• [Journal Article] 7,8 β-Dihydroponasterone A, a New Phytoecdysteroid from the Needles of the Japanese Yew, Taxus cuspidata (2007)
  • Author(s): Q.W. Shi, ら(7人中7人目)
  • Journal Title: J. Braz. Chem. Soc. 18 Pages: 1081-1084
  • Peer Reviewed
• [Journal Article] A New Taxol Analogue from the Leaves of Taxus cuspidate (2007)
  • Author(s): C.H. Huo, ら(6人中6人目)
  • Journal Title: Biochem. Syst. Ecol. 35 Pages: 704-708
  • Peer Reviewed
• [Presentation] 血管新生阻害物質cortistatin類の合成化学的研究 (2010)
  • Author(s): 佐藤勇気, ら(4人中4番目)
  • Organizer: 日本農芸化学会2010年度大会
  • Place of Presentation: 東京
  • Year and Date: 2010-03-28
• [Presentation] 抗生物質enacyloxin類のC9'-C23'部分の合成研究 (2010)
  • Author(s): 五十嵐渉, ら(7人中7番目)
  • Organizer: 日本農芸化学会2010年度大会
  • Place of Presentation: 東京
  • Year and Date: 2010-03-28
• [Presentation] サリチルアルデヒド型イネいもち病菌毒素類の全合成研究 (2009)
  • Author(s): 佐々木郁香, 田中功二, 中村葉子, 上田留美, 貫名学, 桑原重文, 鈴木雄二, 清田洋正
  • Organizer: 香料・テルペンおよび精油化学に関する討論会
  • Place of Presentation: 奈良
  • Year and Date: 2009-11-07
• [Presentation] サリチルアルデヒド型イネいもち病菌毒素類の全合成研究 (2009)
  • Author(s): 佐々木郁香, ら(8人中8番目)
  • Organizer: 香料・テルペン及び精油化学に関する討論会
  • Place of Presentation: 奈良
  • Year and Date: 2009-11-07
• [Presentation] シクロプロパン環を有する香気物質の創製 (2009)
  • Author(s): 清田洋正, ら(9人中9番目)
  • Organizer: 香料・テルペン及び精油化学に関する討論会
  • Place of Presentation: 奈良
  • Year and Date: 2009-11-07
• [Presentation] 血管新生阻害物質cortistatin類モデル化合物の合成研究 (2009)
  • Author(s): 佐藤勇気、桑原重文、清田洋正
  • Organizer: 日本農芸化学会東北支部大会
  • Place of Presentation: 岩手
  • Year and Date: 2009-10-31
• [Presentation] 新規四環性セスキテルペノイドechinopine類の合成研究 (2009)
  • Author(s): 長島優太, ら(5人中5番目)
  • Organizer: 日本農芸化学会東北支部大会
  • Place of Presentation: 岩手
  • Year and Date: 2009-10-31
• [Presentation] 抗腫瘍活性物質 maoecrystal Vの合成研究 (2009)
  • Author(s): 浅尾洋樹, 島崎泰治, 佐々木郁香, 桑原重文, 清田洋正
  • Organizer: 日本農芸化学会2009年度大会
  • Place of Presentation: 福岡
  • Year and Date: 2009-03-29
• [Presentation] 抗腫瘍活性物質maoecrystal Vの合成研究 (2009)
  • Author(s): 浅尾洋樹, ら(6人中6人目)
  • Organizer: 日本農芸化学会2009年度大会
  • Place of Presentation: 福岡マリンメッセ福岡
  • Year and Date: 2009-03-29
• [Presentation] イネいもち病菌毒素pyriculariol及び生合成関連物質の合成研究 (2009)
  • Author(s): 佐々木郁香, ら(5人中5人目)
  • Organizer: 日本農芸化学会2009年度大会
  • Place of Presentation: 福岡マリンメッセ福岡
  • Year and Date: 2009-03-29
• [Presentation] Ancistrocladinium Aの合成研究 (2009)
  • Author(s): 高井桃子, ら(3人中3人目)
  • Organizer: 日本農芸化学会2009年度大会
  • Place of Presentation: 福岡マリンメッセ福岡
  • Year and Date: 2009-03-29
• [Presentation] 抗生物質 enacyloxin 類のC9'-C23' 部分の合成研究 (2009)
  • Author(s): 五十嵐渉, 星川浩輝, 古川博之, 八尾坂学, 山田てい子, 桑原重文, 清田洋正
  • Organizer: 日本農芸化学会2010年度大会
  • Place of Presentation: 東京
  • Year and Date: 2009-03-28
• [Presentation] 新規骨格植物成分echinopine類の合成研究 (2009)
  • Author(s): 田中功二, ら(4人中3人目)
  • Organizer: 日本農薬学会第34回大会
  • Place of Presentation: 東京東京大学
  • Year and Date: 2009-03-19
• [Presentation] イネいもち病菌毒素 pyricuol 及び関連化合物の合成研究 (2008)
  • Author(s): 田中功二, 佐々木郁香, 中村葉子, 桑原重文, 清田洋正
  • Organizer: 有機合成シンポジウム
  • Place of Presentation: 東京
  • Year and Date: 2008-11-08
• [Presentation] イネいもち病菌毒素pyricuol及び関連物質の合成研究 (2008)
  • Author(s): 田中功二, ら(5人中5人目)
  • Organizer: 有機合成シンポジウム(第94回)
  • Place of Presentation: 東京早稲田大学
  • Year and Date: 2008-11-08
• [Presentation] イネいもち病菌毒素pyricuol及び関連物質の合成研究 (2008)
  • Author(s): 田中功二, ら(5人中5人目)
  • Organizer: 農薬デザイン研究会(第23回)
  • Place of Presentation: 東京大手町サンホール
  • Year and Date: 2008-11-06
• [Presentation] 抗腫瘍物質maocrvstal Vの合成研究 (2008)
  • Author(s): 浅尾洋樹, ら(4人中4人目)
  • Organizer: 農薬デザイン研究会(第23回)
  • Place of Presentation: 東京大手町サンホール
  • Year and Date: 2008-11-06
• [Presentation] 血管新生阻害物質cortistatin類アナログ化合物の合成研究 (2008)
  • Author(s): 佐藤勇気, ら(3人中3人目)
  • Organizer: 農薬デザイン研究会(第23回)
  • Place of Presentation: 東京大手町サンホール
  • Year and Date: 2008-11-06
• [Presentation] 血管新生阻害物質cortistatin類モデル化合物の合成研究 (2008)
  • Author(s): 佐藤勇気, ら(3人中3人目)
  • Organizer: 第143回日本農芸化学会東北支部大会
  • Place of Presentation: 弘前弘前大学
  • Year and Date: 2008-10-18
• [Presentation] 抗生物質enacyloxin類のポリオール(C9'-C23')部分の合成研究 (2008)
  • Author(s): 星川浩輝, ら(5人中5人目)
  • Organizer: 第143回日本農芸化学会東北支部大会
  • Place of Presentation: 弘前弘前大学
  • Year and Date: 2008-10-18
• [Presentation] イネいもち病菌毒素pyriculariolの全合成 (2008)
  • Author(s): 佐々木郁香, ら(5人中5人目)
  • Organizer: 日本農芸化学会東北支部大会(第143回)
  • Place of Presentation: 弘前弘前大学
  • Year and Date: 2008-10-11
• [Presentation] 血管新生阻害活性物質 cortistatin 類アナログの合成と生物活性 (2007)
  • Author(s): 佐藤勇気, 神山洋, 長田裕之, 桑原重文, 清田洋正
  • Organizer: 日本農芸化学会東北支部大会
  • Place of Presentation: 仙台
  • Year and Date: 2007-11-10
• [Presentation] 血管新生阻害活性物質cortistatin類アナログの合成と生物活性 (2007)
  • Author(s): 佐藤, ら(5人中5人目)
  • Organizer: 第142回日本農芸化学会東北支部大会
  • Place of Presentation: 仙台
  • Year and Date: 2007-11-10
• [Presentation] Maoecrystal Vの合成研究 (2007)
  • Author(s): 浅尾, ら(4人中4人目)
  • Organizer: 第142回日本農芸化学会東北支部大会
  • Place of Presentation: 仙台
  • Year and Date: 2007-11-10
• [Presentation] イネいもち病菌毒素pyricuolの全合成 (2007)
  • Author(s): 田中, ら(6人中6人目)
  • Organizer: 第142回日本農芸化学会東北支部大会
  • Place of Presentation: 仙台
  • Year and Date: 2007-11-10
• [Presentation] エナンチオ・ディフェレンシャル分子ブローブ法によるジャスモン酸配糖体型就眠物質受容体の生物有機化学 (2007)
  • Author(s): 中村, ら(5人中4人目)
  • Organizer: 第49回天然有機化合物討論会
  • Place of Presentation: 札幌
  • Year and Date: 2007-09-19
• [Presentation] イネいもち病菌毒素pyricuolの天然型光学活性体の合成研究 (2007)
  • Author(s): 田中, ら(4人中4人目)
  • Organizer: 第42回天然物化学談話会
  • Place of Presentation: 仙台
  • Year and Date: 2007-07-12
• [Book] Natural Products : Chemistry, Biochemistry and Pharmacology (2009)
  • Author(s): M. Dong, ら(5人中5人目)
  • Publisher: Narosa
• [Book] Natural Products : Chemistry, Biochemistry and Pharmacology (2009)
  • Author(s): X. H. Su, ら(5人中5人目)
  • Publisher: Narosa
• [Book] Natural Products : Chemistry, Biochemistry and Pharmacology (2008)
  • Author(s): X.-H. Su, M. Dong, Q.-W. Shi, Y.-C. Gu, H. Kiyota
  • Publisher: Narosa 社
• [Book] Natural Products : Chemistry, Biochemistry and Pharmacology (2008)
  • Author(s): M. Dong, M.-L. Zhang, Q.-W. Shi, Y.-C. Gu, H. Kiyota
  • Publisher: Narosa 社
• [Book] Chemistry of Natural Products : Recent Trends and Developments (2007)
  • Author(s): Y.-F. Wang, Q.-W. Shi, H. Kiyota
  • Publisher: Research Signpost 社
• [Book] Chemistry of Natural Products: Recent Trends and Developments (2007)
  • Author(s): Q. W. Shi
  • Publisher: Research Signpost
• [Remarks]
  • URL: http://www.agri.tohoku.ac.jp/yuuki/00kiyo/res/resJ.html
• [Remarks]
  • URL: http://www.agri.tohoku.ac.jp/yuuki/OOkiyo/res/resJ.html
• [Remarks]
  • URL: http://www.agri.tohoku.ac.jp/yuuki/00kiyo/res/resJ.html