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2008 Fiscal Year Final Research Report

Synthesis of the Selective Nuclear Receptor LXRa Agonist, Riccardins and Development of Anti-arteriosclerosis Drug

Research Project

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Project/Area Number 18590113
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

FUKUYAMA Yoshiyasu  Tokushima Bunri University, 薬学部, 教授 (70208990)

Co-Investigator(Kenkyū-buntansha) ASAKAWA Yoshinori  徳島文理大学, 薬学部, 教授 (50033874)
Project Period (FY) 2006 – 2008
Keywordsリカルデイン / パラジウム触媒 / 核内受容体 / コレステロール代謝 / 天然物合成 / 大環状ビスビベンジル / LXRα アゴニスト / 鈴木・宮浦反応
Research Abstract

研究成果の概要:大環状ビスビベンジル化合物リカルデイン C はコレステロールのセンサー蛋白である核内レセプター LXRα の特異的アゴニスト活性を有する天然物として知られ、新しい抗コレステロール薬への展開が期待されている。リカルデイン Cの効率的合成法の開発と、活性発現に必要な構造因子を明らかにする目的で合成研究を行い、その合成に成功した。さらに、7 種の誘導体を調製し、アゴニスト活性を検討した結果、リカルデイン C のみにLXRα特異的アゴニスト活性が発現したが、他の誘導体には全く活性が認められなかった。

  • Research Products

    (29 results)

All 2009 2008 2007 2006

All Journal Article (22 results) (of which Peer Reviewed: 22 results) Presentation (3 results) Book (1 results) Patent(Industrial Property Rights) (3 results)

  • [Journal Article] The First Synthesis of Neovibsanin B2009

    • Author(s)
      H. Imagawa, H. Saijo, T. Kurisaki, M. Kubo, Y. Fukuyama, M. Nishizawa
    • Journal Title

      Org. Lett. 11

      Pages: 1253-1255

    • Peer Reviewed
  • [Journal Article] Sweet and Bitter Constituents of Wilbrandia species2009

    • Author(s)
      M. Ochi, K. Moriyama, K. Ohmae, Y. Fukuyama, K. Nihei, I. Kubo
    • Journal Title

      Food Chemistry 115

      Pages: 61-65

    • Peer Reviewed
  • [Journal Article] Total Synthesis of Pseudodehydrothyrsiferol2009

    • Author(s)
      H. Hioki, M. Motosue, Y. Mizutani, A. Noda, K. Shnimoda, M. Kubo, K. Harada, Y. Fukuyama, M. Kodama
    • Journal Title

      Org. Lett., 11

      Pages: 579-582

    • Peer Reviewed
  • [Journal Article] Synthesis of Riccardin C and Its Seven Analogues: the Role of Their Phenolic Hydroxy Groups as LXRα Receptor Agonists2009

    • Author(s)
      H. Hioki, N. Shima, K. Kawaguchi, K. Harada, M. Kubo, T. Esumi, T. Mogami, T. Hashimoto, Y. Asakawa, Y. Fukuyama
    • Journal Title

      Bioorg. Med. Chem. Lett. 19

      Pages: 746-749

    • Peer Reviewed
  • [Journal Article] Novel NGF-Potentiating Diterpenoids from a Brazilian Medicinal Plant, Ptychopetalum olacoides2009

    • Author(s)
      W. Tang, H. Hioki, K. Harada, M. Kubo, Y. Fukuyama
    • Journal Title

      Bioorg. Med. Chem. Lett. 19

      Pages: 890-894

    • Peer Reviewed
  • [Journal Article] Acetal-Bearing Rearranged Vibsane-type Diterpenoids from Viburnum awabuki2009

    • Author(s)
      M. Kubo, Y. Minoshima, A. Arimoto, H. Minami, K. Harada, H. Hioki, Y. Fukuyama
    • Journal Title

      Heterocycles 77

      Pages: 539-546

    • Peer Reviewed
  • [Journal Article] Efficient Construction of a Chiral All-carbon Quaternary Center by Asymmetric 1,4-addittion and Its Application to Total Synthesis of (+)-Bakuchiol2008

    • Author(s)
      T. Esumi, H. Shimizu, A. Kashiyama, C. Sasaki, M. Toyota, Y. Fukuyama
    • Journal Title

      Tetrahedron Lett. 49

      Pages: 6846-6849

    • Peer Reviewed
  • [Journal Article] Clerodane Diterpenoids with NGF-Potentiating Activity from Ptychopetalum olacoides2008

    • Author(s)
      W. Tang, H. Hioki, K. Harada, M. Kubo, Y. Fukuyama
    • Journal Title

      J. Nat. Prod. 71

      Pages: 1760-1763

    • Peer Reviewed
  • [Journal Article] Solid-phase Combinatorial Synthesis of 2-Arylquinazolines and 2-Arylquinazolines by an 4-Alkoxyaniline Linker2008

    • Author(s)
      H, Hioki, K. Matsushita, M. Kubo, K. Harada, M. Kodama, Y. Fukuyama
    • Journal Title

      J. Comb. Chem. 10, (5)

      Pages: 620-623

    • Peer Reviewed
  • [Journal Article] Two New Sesquiterpenoids and Two New Prenylated Phenylpropanoids from Illicium fargesii, and Neuroprotective Activity of Macranthol2008

    • Author(s)
      M. Moriyama, J.-M. Huang, C.-S. Yang, M. Kubo, K. Harada, H. Hioki, Y. Fukuyama
    • Journal Title

      Chem. Pharm. Bull. 56

      Pages: 1201-1204

    • Peer Reviewed
  • [Journal Article] Synthesis of (-)-Talaumidin, a Neurotrophic 2,5-Diaryl-3,4-dimethyl Tetrahydrofuran Lignan, and Its Stereosiomers2008

    • Author(s)
      Y. Fukuyama, K. Harada, T. Esumi, D. Hojyo, Y. Kujime, N. Kubo, M. Kubo, H. Hioki
    • Journal Title

      Heterocycles 76, 1

      Pages: 551-567

    • Peer Reviewed
  • [Journal Article] Synthetic Studies toward Neovibsanins A and B: Construction of the Neovibsanin Core Utilizing Palladium(0)-catalyzed Carbonylative Cyclization with Carbon Monoxide2008

    • Author(s)
      T. Esumi, M. Zhao, T. Kawakami, M. Fukumoto, M. Toyota, Y. Fukuyama
    • Journal Title

      Tetrahedron Lett. 49

      Pages: 2692-2696

    • Peer Reviewed
  • [Journal Article] Antioxidative Phenylpropanoidsubstituted Epicatechins from Trichilia catigua2007

    • Author(s)
      W. Tang, H. Hioki, K. Harada, M. Kubo, Y. Fukuyama
    • Journal Title

      J. Nat. Prod. 70

      Pages: 2010-2013

    • Peer Reviewed
  • [Journal Article] Solid-phase Combinatorial Synthesis of Benzothiazoles, Benzimidazoles and Benzoxazoles Using a Traceless Linker2007

    • Author(s)
      H, Hioki, K. Matsushita, M. Kubo, K. Harada, M. Kodama, Y. Fukuyama
    • Journal Title

      Tetrahedron 63

      Pages: 11315-11324

    • Peer Reviewed
  • [Journal Article] An Efficient Synthesis of the CD rings Model for Merrilactone A2007

    • Author(s)
      K. Harada, H. Ito, H. Hioki, Y. Fukuyama
    • Journal Title

      Tetrahedron Lett. 48

      Pages: 6105-6108

    • Peer Reviewed
  • [Journal Article] Total Synthesis and Bioactivity of an Unnatural Enantiomer of Merrilactone A: Development of an Enantioselective Desymmerization Strategy2007

    • Author(s)
      M. Inoue, N. Lee, T. Sato, M. Hirama, M. Moriyama, Y. Fukuyama
    • Journal Title

      J. Org. Chem. 72

      Pages: 3065-3075

    • Peer Reviewed
  • [Journal Article] Structure and Neurotrophic Activity of Novel Sesqui-neolignans from the Pericarps of Illicium fargesii2007

    • Author(s)
      M. Moriyama, Jian-Mei Huang, Chun-Shu Yang, H. Hioki, K. Harada, M. Kubo, Y. Fukuyama
    • Journal Title

      Tetrahedron 63

      Pages: 4243-4249

    • Peer Reviewed
  • [Journal Article] Two Diterpene Rhamnosides, Mimosasides B and C, from Mimosa hostilis2006

    • Author(s)
      A. Ohsaki, R. Yokoyama, H. Miyatake, Y. Fukuyama
    • Journal Title

      Chem. Pharm. Bull. 54,

      Pages: 1728-1729

    • Peer Reviewed
  • [Journal Article] Neovibsanin F and its Congeners, Rearranged Vibsane-type Diterpenes from Viburnum suspesnsiom2006

    • Author(s)
      Y. Fukuyama, H. Fujii, M. Kubo, H. Minami, H. Takahashi
    • Journal Title

      J. Nat. Prod. 69

      Pages: 1098-1100

    • Peer Reviewed
  • [Journal Article] Degraded and Oxetane-bearing Limonoids from Melia azedarach2006

    • Author(s)
      Y. Fukuyama, M. Nakaoka, T. Yamamoto, H. Takahashi, H. Minami
    • Journal Title

      Chem. Pharm. Bull. 54

      Pages: 1219-1222

    • Peer Reviewed
  • [Journal Article] A Norbergenin Derivatives Inhibits Neuronal Cell Damage Induced by Tunicamycin2006

    • Author(s)
      S. Suzuki, Y. Okuse, M. Kawase, M. Takiguchi, Y. Fukuyama, H. Takahashi, M. Sato
    • Journal Title

      Biol. Pharm. Bull. 29

      Pages: 1335-1338

    • Peer Reviewed
  • [Journal Article] First Enantioselective Synthesis of (-)-Talaumidin, a Neutrotrophic Diaryltetrahydrofuran-type Lignan2006

    • Author(s)
      T. Esumi, D. Houjyou, H. Zhai, Y. Fukuyama
    • Journal Title

      Tetrahedron Lett. 47

      Pages: 3979-3983

    • Peer Reviewed
  • [Presentation] Cavicularin の合成研究2009

    • Author(s)
      島尚喜、原田研一、久保美和、日置英彰、福山愛保
    • Organizer
      日本薬学会第129 年会
    • Place of Presentation
      京都
    • Year and Date
      20090300
  • [Presentation] 核内受容体 LXRαアゴニスト Riccardin C とその誘導体の合成研究2008

    • Author(s)
      島尚喜、川口幸太、原田研一、久保美和、日置英彰、福山愛保
    • Organizer
      第34 回反応と合成の進歩シンポジウム
    • Place of Presentation
      京都
    • Year and Date
      20081100
  • [Presentation] 核内受容体 LXRαアゴニスト Riccardin C の合成研究2008

    • Author(s)
      島尚喜、川口幸太、原田研一、久保美和、日置英彰、福山愛保
    • Organizer
      日本薬学会第128 年会
    • Place of Presentation
      横浜
    • Year and Date
      20080300
  • [Book] 神経毒と神経突起、栄養因子活性物質. 天然物化学-植物編-(山村庄亮、長谷川宏司 編)2007

    • Author(s)
      福山愛保
    • Publisher
      アイピーシー
  • [Patent(Industrial Property Rights)] 神経細胞賦活剤2008

    • Inventor(s)
      橋本麻美子、井ノ瀬利明、木村隆、橋本敏弘、吉川和子、福山愛保
    • Industrial Property Rights Holder
      ユニチカ(株)
    • Industrial Property Number
      公開特許、JP2008-292309
    • Filing Date
      2008-10-30
  • [Patent(Industrial Property Rights)] 神経細胞突起伸展作用を有する置換シクロヘキセンを有効成分として含有する植物を利用することを特徴とする健康組成物2008

    • Inventor(s)
      福山愛保、日置英彰、堂上美和、原田研一、加藤榮信
    • Industrial Property Rights Holder
      細田真也
    • Industrial Property Number
      公開特許、JP2008-260691
    • Filing Date
      2008-10-07
  • [Patent(Industrial Property Rights)] ビステトラヒドロフラン化合物、その製造方法及び該化合物の用途2007

    • Inventor(s)
      西沢麦夫、福山愛保、今川洋
    • Industrial Property Rights Holder
      大塚化学(株)
    • Industrial Property Number
      公開特許、JP2007-51664
    • Filing Date
      2007-03-01

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Published: 2010-06-10   Modified: 2016-04-21  

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