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2012 Fiscal Year Final Research Report

Studies on isolation, total synthesis and medicinal chemistryof natural products with regulating activities on memory and pain.

Research Project

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Project/Area Number 22390019
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Drug development chemistry
Research InstitutionChiba University

Principal Investigator

TAKAYAMA Hiromitsu  千葉大学, 大学院・薬学研究院, 教授 (90171561)

Co-Investigator(Kenkyū-buntansha) KOGURE Noriyuki  千葉大学, 大学院・薬学研究院, 助教 (80396689)
Co-Investigator(Renkei-kenkyūsha) HORIE Shunji  城西国際大学, 薬学部, 教授 (50209285)
Project Period (FY) 2010 – 2012
Keywords鎮痛薬 / 脳機能改善薬 / 天然活性物質 / 生物活性物質の探索 / 全合成 / アルカロイト / 構造活性相関
Research Abstract

To develop new analgesics for cancer pain, structure of the lead-compound having Corynanthe-type skeleton was modified, resulting in the creation of new derivatives with potent analgesic activity as well as with stability against microsomal metabolism. Iboga-type indole alkaloids were found to be a new class of antagonist of CB1 receptors. Voacangalactonine, a new alkaloid possessing Iboga structure, was synthesized in an asymmetric manner. To investigate the seeds molecules for development of medicines for dementia, isolation, structure elucidation, and total syntheses of Lycopodium alkaloids were performed.

  • Research Products

    (41 results)

All 2013 2012 2011 2010 Other

All Journal Article (22 results) (of which Peer Reviewed: 22 results) Presentation (12 results) Book (1 results) Remarks (1 results) Patent(Industrial Property Rights) (5 results) (of which Overseas: 2 results)

  • [Journal Article] Aspidosperma-aspidosperma-type Bisindole Alkaloids from2013

    • Author(s)
      M. Kitajima, M. Iwai, N. Kogure, R.Kikura-Hanajiri, Y. Goda, and H. Takayama
    • Journal Title

      Voacanga africana. Tetrahedron

      Volume: 69(2) Pages: 796-801

    • DOI

      DOI:10.1016/j.tet.2012.10.061.

    • Peer Reviewed
  • [Journal Article] Synthesis and Biological Evaluation of 4-Chlorocolchicine Derivatives as Potent Anticancer Agents with Broad Effective Dosage Ranges2012

    • Author(s)
      H. Nishiyama, M. Ono, T. Sugimoto, T.Sasai, N. Asakawa, T. Matsumoto, T. Yaegashi, M. Nagaoka, T. Matsuzaki, N. Kogure, M. Kitajima, and H. Takayama
    • Journal Title

      Med. Chem. Comm

      Volume: 3(12) Pages: 1500-1504

    • DOI

      DOI:10.1039/c2md20250f

    • Peer Reviewed
  • [Journal Article] Asymmetric Total Synthesis of an Iboga-Type Indole Alkaloid, Voacangalactone, Newly Isolated from Voacanga africana2012

    • Author(s)
      M. Harada, K. Asaba, M. Iwai, N.Kogure, M. Kitajima, and H.Takayama
    • Journal Title

      Org. Lett

      Volume: 14(22) Pages: 5800-5803

    • DOI

      DOI:10.1021/ol3027945.

    • Peer Reviewed
  • [Journal Article] Chemical Conversion of Strychnine into Kopsiyunnanine-I, a New Hexacyclic Indole Alkaloid from Yunnan Kopsia arborea2012

    • Author(s)
      N. Kogure, Y. Suzuki, Y. Wu, M.Kitajima, R. Zhang, and H. Takayama
    • Journal Title

      Tetrahedron Lett

      Volume: 53(48) Pages: 6523-6526

    • DOI

      DOI:10.1016/j.tetlet.2012.09.078.

    • Peer Reviewed
  • [Journal Article] Syntheses of Fawcettimine-type Lycopodium Alkaloids Utilizing Pauson-Khand Reaction2012

    • Author(s)
      A. Nakayama, M. Kitajima, and H.Takayama
    • Journal Title

      Synlett

      Volume: 23(14) Pages: 2014-2024

    • DOI

      DOI:10.1055/s-0032-1316680.

    • Peer Reviewed
  • [Journal Article] New Indole Alkaloids from Melodinus henryi2012

    • Author(s)
      M. Kitajima, S. Ohara, N. Kogure, Y.Wu, R. Zhang, and H. Takayama
    • Journal Title

      Heterocycles

      Volume: 85(8) Pages: 1949-1959

    • Peer Reviewed
  • [Journal Article] Secondary Metabolites from Pandanus simplex2012

    • Author(s)
      M. A. Tan, M. G. Nonato, M. Kitajima, N. Kogure, and H. Takayama
    • Journal Title

      Biochem. Syst. Ecol

      Volume: 40 Pages: 4-5

    • DOI

      DOI:10.1016/j.bse.2011.09.001.

    • Peer Reviewed
  • [Journal Article] Total Synthesis Guided Structure Elucidation of (+)-Psychotetramine2011

    • Author(s)
      K. Foo, T. Newhouse, I. Mori, H.Takayama, and P.l S. Baran
    • Journal Title

      Angew. Chem., Int. Ed

      Volume: 50(12) Pages: 2716-2719

    • DOI

      DOI:10.1002/anie.201008048.

    • Peer Reviewed
  • [Journal Article] Total Synthesis of Dubiusamine C, A Plausible Minor Alkaloid in Pandanus dubius2011

    • Author(s)
      M. A. Tan, N. Kogure, M. Kitajima, and H. Takayama
    • Journal Title

      Phillippine Sci. Lett

      Volume: 4(2) Pages: 98-102

    • Peer Reviewed
  • [Journal Article] Two New Alkaloids from Crinum asiaticum var. sinicum2011

    • Author(s)
      N. Kogure, N. Katsuta, M. Kitajima, and H. Takayama
    • Journal Title

      Chem. Pharm. Bull

      Volume: 59(12) Pages: 1545-1548

    • URL

      https://www.jstage.jst.go.jp/article/cpb/59/12/59_12_1545/_pdf.

    • Peer Reviewed
  • [Journal Article] Asymmetric Total Synthesis of a Pentacyclic Lycopodium Alkaloid, Huperzine-Q. Angew2011

    • Author(s)
      A. Nakayama, N. Kogure, M. Kitajima, and H. Takayama
    • Journal Title

      Chem., Int. Ed.

      Volume: 50(35) Pages: 8025-8028

    • DOI

      DOI:10.1002/anie.201103550.

    • Peer Reviewed
  • [Journal Article] Ten New Fawcettimine-related Alkaloids from Three Species of Lycopodium2011

    • Author(s)
      K. Katakawa, H. Mito, N. Kogure, M.Kitajima, S. Wongseripipatana, M. Arisawa, and H. Takayama
    • Journal Title

      Tetrahedron

      Volume: 67(35) Pages: 6561-6567

    • DOI

      DOI:10.1016/j.tet.2011.05.107.

    • Peer Reviewed
  • [Journal Article] Metacolchicine, A New Colchicinoid from Sandersonia aurantiaca2011

    • Author(s)
      M. Kitajima, A. Tanaka, N. Kogure, and H. Takayama
    • Journal Title

      Heterocycles

      Volume: 83(8) Pages: 1903-1907

    • Peer Reviewed
  • [Journal Article] Design, Synthesis,and Antitumor Activity of4-Halocolchicines and their Pro-drugs Activated by Cathepsin B2011

    • Author(s)
      N. Yasobu, M. Kitajima, N. Kogure, Y.Shishido, T. Matsuzaki, M. Nagaoka, and H. Takayama
    • Journal Title

      ACS Med. Chem. Lett

      Volume: 2(5) Pages: 348-352

    • DOI

      DOI:10.1021/ml100287y.

    • Peer Reviewed
  • [Journal Article] Discovery of Indole Alkaloids with Cannabinoid CB1 Receptor Antagonistic Activity2011

    • Author(s)
      M. Kitajima, M. Iwai, R.Kikura-Hanajiri, Y. Goda, M. Iida, H. Yabushita, and H. Takayama
    • Journal Title

      Bioorg. Med. Chem. Lett

      Volume: 21(7) Pages: 1962-1964

    • DOI

      DOI:10.1016/j.bmcl.2011.02.036.

    • Peer Reviewed
  • [Journal Article] Inhibitory Effect of Iboga-type Indole Alkaloids on Capsaicin-induced Contraction in Isolated Mouse Rectum2011

    • Author(s)
      M. Lo, K. Matsumoto, M. Iwai, K.Tashima, M. Kitajima, S. Horie, and H. Takayama
    • Journal Title

      J. Nat. Med

      Volume: 65(1) Pages: 157-165

    • DOI

      DOI:10.1007/s11418-010-0478-6.

    • Peer Reviewed
  • [Journal Article] Seven New Monoterpenoid Indole Alkaloids from Gelsemium elegans2011

    • Author(s)
      Y. Yamada, M. Kitajima, N. Kogure, S.Wongseripipatana, and H. Takayama
    • Journal Title

      Chem. Asian J.

      Volume: 6(1) Pages: 166-173

    • DOI

      DOI:10.1002/asia.201000538.

    • Peer Reviewed
  • [Journal Article] 生物活性リコポジウムアルカロイドの探索と不斉合成2010

    • Author(s)
      高山廣光
    • Journal Title

      有合化

      Volume: 68(5) Pages: 457-469

    • Peer Reviewed
  • [Journal Article] Isolation of Pandamarilactonine-H from the Roots of Pandanus amaryllifolius and Synthesis of epi-Pandamarilactonine-H2010

    • Author(s)
      M. A. Tan, M. Kitajima, N. Kogure, M.G. Nonato, and H. Takayama
    • Journal Title

      J. Nat. Prod

      Volume: 73(8) Pages: 1453-1455

    • DOI

      DOI:10.1021/np1003998.

    • Peer Reviewed
  • [Journal Article] New Oxindole andIndole Alkaloids from Gelsemium rankinii2010

    • Author(s)
      M. Kitajima, H. Kobayashi, N. Kogure, and H. Takayama
    • Journal Title

      Tetrahedron

      Volume: 66(32) Pages: 5987-5992

    • DOI

      DOI:10.1016/j.tet.2010.06.032.

    • Peer Reviewed
  • [Journal Article] New Pyrrolidine Alkaloids from the Roots of Pandanus amaryllifolius2010

    • Author(s)
      M. A. Tan, M. Kitajima, N. Kogure, M.G. Nonato, and H. Takayama
    • Journal Title

      Tetrahedron Lett

      Volume: 51(31) Pages: 4143-4146

    • DOI

      DOI:10.1016/j.tetlet.2010.05.150.

    • Peer Reviewed
  • [Journal Article] Two New Aspidosperma Indole Alkaloids from Yunnan Kopsia arborea2010

    • Author(s)
      Y. Wu, M. Kitajima, N. Kogure, Y.Wang, R. Zhang, and H. Takayama
    • Journal Title

      Chem. Pharm. Bull

      Volume: 58(7) Pages: 961-963

    • URL

      https://www.jstage.jst.go.jp/article/cpb/58/7/58_7_961/_pdf.

    • Peer Reviewed
  • [Presentation] 新規骨格LycopodiumアルカロイドLycoposerramine-Rの不斉全合成研究2013

    • Author(s)
      石田寛明,木村真也,小暮紀行,北島満里子,高山廣光
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Year and Date
      2013-03-30
  • [Presentation] アルカロイドの探索と全合成研究から得られるもの2012

    • Author(s)
      高山廣光
    • Organizer
      第47回天然物化学談話会
    • Place of Presentation
      熊本
    • Year and Date
      2012-07-04
  • [Presentation] 有機合成化学の醍醐味-戦略的アプローチの最前線-2012

    • Author(s)
      高山廣光
    • Organizer
      生物活性アルカロイドの探索から全合成へ.そして創薬研究へ.平成24年度前期(春期)有機合成化学講習会
    • Place of Presentation
      東京
    • Year and Date
      2012-06-21
  • [Presentation] Pauson-Khand反応を基盤としたFawcettimineの不斉全合成研究2012

    • Author(s)
      中山淳,小暮紀行,北島満里子,高山廣光
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Year and Date
      2012-03-31
  • [Presentation] 栃木県産Lycopodiumserratum含有アルカロイドの成分探索2012

    • Author(s)
      池城沙耶子,北島満里子,小暮紀行,片川和明,高山廣光
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Year and Date
      2012-03-30
  • [Presentation] 生物活性アルカロイドの探索と全合成2012

    • Author(s)
      高山廣光
    • Organizer
      有機合成2月セミナー「有機合成のニュートレンド2012」
    • Place of Presentation
      大阪
    • Year and Date
      2012-02-03
  • [Presentation] Synthetic Study of Lycoposerramine-R, A Novel Skeletal Type of Lycopodium Alkaloids2011

    • Author(s)
      S. Kimura, N. Kogure, M. Kitajima, and H. Takayama
    • Organizer
      8th AFMC International Medicinal Chemistry Symposium (AIMECS11)
    • Place of Presentation
      Tokyo
    • Year and Date
      2011-12-30
  • [Presentation] Synthetic Studies of Fawcettimine-type Lycopodium Alkaloids, Potential Seed Molecules for Drug Development2011

    • Author(s)
      A. Nakayama, N. Kogure, M. Kitajima,and H. Takayama
    • Organizer
      8th AFMC International Medicinal Chemistry Symposium (AIMECS11)
    • Place of Presentation
      Tokyo
    • Year and Date
      2011-12-30
  • [Presentation] 生物活性アルカロイドの探索と全合成2011

    • Author(s)
      高山廣光
    • Organizer
      理研シンポジウム第6回有機合成化学のフロンティア
    • Place of Presentation
      和光
    • Year and Date
      2011-07-01
  • [Presentation] Fawcettimine型リコポジウムアルカロイドHuperzine-Qの不斉全合成2011

    • Author(s)
      中山淳,小暮紀行,北島満里子,高山廣光
    • Organizer
      第99回有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2011-06-15
  • [Presentation] Pauson-Khand反応を基盤としたfawcettimine型リコポジウムアルカロイド類の不斉全合成研究2010

    • Author(s)
      中山淳,小暮紀行,北島満里子,高山廣光
    • Organizer
      第36回反応と合成の進歩シンポジウム
    • Place of Presentation
      名古屋
    • Year and Date
      2010-11-01
  • [Presentation] Investigation and Syntheses of Novel Analgesic Indole Alkaloids in Rubiaceous Medicinal Plants2010

    • Author(s)
      H. Takayama
    • Organizer
      The 1^<st> Joint Symposium on Pharmaceutical Sciences between College of Pharmacy, Seoul National University and Graduate School ofPharmaceutical Sciences, Chiba University - Cutting-Edge Research on Natural Products -
    • Place of Presentation
      Chiba
    • Year and Date
      2010-08-27
  • [Book] Lycopodium Alkaloids: Isolation and Asymmetric Synthesis. Topics in Current Chemistry, "Alkaloid Synthesis"2012

    • Author(s)
      Mariko Kitajima and Hiromitsu Takayama
    • Total Pages
      1-32
    • Publisher
      ed. by H.-J. Knolker, Springer
  • [Remarks]

    • URL

      http://www.p.chiba-u.ac.jp/lab/seitai/index.html

  • [Patent(Industrial Property Rights)] Indole Alkaloid Derivatives Having Opioid Receptor Antagonistic Effect, and Therapeutic Compositions and Methods Relating to Same.発 明 者 : H. Takayama, M. Kitajima, K. Matsumoto, S. Horie2012

    • Industrial Property Rights Holder
      千葉大学他
    • Industrial Property Number
      PCT Int. Appl、US 8,247,428 B2
    • Filing Date
      2012-08-21
    • Overseas
  • [Patent(Industrial Property Rights)] Compound Having Activity ofBlocking NMDA Receptor Channel, and Pharmaceutical Agent Using the Same.2011

    • Industrial Property Rights Holder
      千葉大学
    • Industrial Property Number
      2012514異議申立てがなかった、EP2039354
    • Filing Date
      2011-06-29
    • Overseas
  • [Patent(Industrial Property Rights)] ボアカンガアフリカーナより得られるカンナビノイド受容体薬およびその利用2011

    • Inventor(s)
      合田幸広, 花尻瑠理, 高山廣 光, 他
    • Industrial Property Rights Holder
      千葉大学 他
    • Industrial Property Number
      特開、JP2011121895
    • Filing Date
      2011-06-23
  • [Patent(Industrial Property Rights)] Colchicine Derivatives2011

    • Inventor(s)
      H. Takayama et al.
    • Industrial Property Rights Holder
      千葉大学 他
    • Industrial Property Number
      PCT Int. Appl、WO 2011021397
    • Filing Date
      2011-02-24
  • [Patent(Industrial Property Rights)] コルヒチン誘導体2010

    • Inventor(s)
      高山廣光,, 他
    • Industrial Property Rights Holder
      千葉大学 他
    • Industrial Property Number
      出願、PCT/JP2010/005136
    • Filing Date
      2010-08-20

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Published: 2014-08-29  

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