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天然物有機化学の新展開を目標とした総合的研究

Research Project

Project/Area Number 61303004
Research Category

Grant-in-Aid for Co-operative Research (A)

Allocation TypeSingle-year Grants
Research Field 天然物有機化学
Research InstitutionOsaka City University

Principal Investigator

野老山 喬  大阪市立大学, 理学部, 教授 (90046938)

Co-Investigator(Kenkyū-buntansha) 柿沢 寛  筑波大学, 化学系, 教授 (50015492)
後藤 俊夫  名古屋大学, 農学部, 教授 (20023369)
吉越 昭  東北大学, 非水溶液化学研究所, 教授 (20006290)
山口 勝  九州大学, 理学部, 教授 (60037140)
伊藤 椒 (伊東 しょう / 伊東 椒)  徳島文理大学, 薬学部, 教授 (00004242)
芝 哲夫  大阪大学, 理学部, 教授 (30028089)
平田 義正  名城大学, 藥学部, 教授 (10022493)
高橋 武美  東京大学, 理学部, 教授 (90011410)
Project Period (FY) 1986 – 1988
Project Status Completed (Fiscal Year 1988)
Budget Amount *help
¥13,100,000 (Direct Cost: ¥13,100,000)
Fiscal Year 1988: ¥4,000,000 (Direct Cost: ¥4,000,000)
Fiscal Year 1987: ¥2,600,000 (Direct Cost: ¥2,600,000)
Fiscal Year 1986: ¥6,500,000 (Direct Cost: ¥6,500,000)
Keywords不斉合成 / 立体選択的合成 / 培養細胞による変換 / 海産テルペイノド / 海洋無脊椎動物成分 / マイコトキシン / 構造・活性相関 / アントシアニンの構造 / 生物活性天然有機化合物の合成 / 生物活性天然有機化合物の構造 / 海産動植物成分 / 抗腫瘍性天然有機化合物 / 神経活性ペプチド / 土壌菌中の抗植物病菌成分 / 植物培養細胞による物質変換 / アントシアニジンの構造
Research Abstract

1.生物活性物質の合成:海産プロスタノイド、クロロプロン、ラブダン-8α、15-ジオール、3種の大環状ピロリチジンアルカロイド(インテゲリミン、モリクロタリン、ジクロタリン)の光学活性形の全合成が達成された。光学活性ビニルスルホキシドを用いるβ、γ-ブチロラクトンの不斉合成法が開発され、(+)-ポドリゾン、(+)-ケルカスラクトンなどの合成に利用された。アゲラシジン類、マノアリド類、セコトリネルビタン類の合成法の効率化も行われた。マノコトキシン・アステルトキシン、およびベルコシジン、トリテルペン・プスチメリン、含ハロゲン海産天然物・ダクチリン、苔類大環状ビフェニル化合物・プラジオチンDの合成にも大きな進展が見られた。一方0-カルバメートの閉環反応を利用したヒドロキシン-α-アミノ酸の高立体選択的合成法の確立、2-アセトキシメテル-5-エトキシピロリジンの5位のアルキル化の立体選択性の検討、培養細胞による水酸化の立体選択性、酸化還元反応の動力学的研究もなされた。細菌リポ多糖の糖脂質部分の構造・活性相関の研究を目的とした構造類緑体の合成も行われた。
2.生物活性物質の構造研究:土壌菌より植物病菌抑制作用をもつチアゾール誘導体、過酸化脂質生成阻害活性をもつプラストキノン類緑体、シトロビリジン生産菌ハイブリッド菌株よりのクルブラリン形代謝物が單離され構造が確認された。抗カケクシア活性をもつ海綿成分グリコオカダ酸の構造、活性相関が研究され、南西四国沿岸産軟体サンゴより蚕幼虫成長阻害活性をもつ3種のジテルペンおよび2種の分技脂脂酸が單離、構造決定された。ベッコウバチ毒液中の神経作用物質の生理作用の検討も行われた。ツユクサ科観葉植物数種のアントシアニン色素の單離、構造研究が行われ、ヒラキハミゾゴケの含酸系セスキテルペン成分およびコクテンギ果実成分の構造研究も進展した。

Report

(3 results)
  • 1988 Annual Research Report
  • 1987 Annual Research Report
  • 1986 Annual Research Report

Research Products

(105 results)

All Other

All Publications (105 results)

  • [Publications] A.Murai.: Chemistry Letters. 357-358 (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] Y.Homma.: Soil.Biol.Biochem.(1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] F.Hirayama.: Phytochemistry. (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] T.Hayashi.: Phytochemistry. (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] H.Hagiwara.: J.Org.Chem.53. 2308-2311 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] H.Hagiwara.: J.Chem.Soc.,Chem.Commun.815-817 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] H.Hagiwara.: Chemistry Letters. 1793-1796 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] N.Harada.: J.Am.Chem.Soc.110. 8483-8487 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] H.Hagiwara.: Bull.Chem.Soc.Jpn.62. (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] H.Kosugi.: J.Chem.Soc.,Perkin Trans.1. (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] G.C.Zheng.: Heterocycles. 27. 1341-1344 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] G.C.Zheng.: Bull.Chem.Soc.Jon.62. No.2 (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] H.Hirota.: Bull.Chem.Soc.Jpn.61. 4023-4028 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Y.Shizuri.: Chemistry Letters. 1419-1422 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] S.Nishiyama.: Tetrahedron. 44. 6315-6324 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] S.Lei.: Tetrahedron Letters. 30. inpress (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] I.Muramatsu.: Br.J.Pharmacol.93. 811-816 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] H.Niwa.: Bull.Chem.Soc.Jon.61. 3017-3019 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] H.Niwa.: Tetrahedron Letters. 29. 5139-5142 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] S.Arata.: FEMS Microbiology Letters. 49. 479-482 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] H.Takada.: Eur.J.Biochem.175. 573-580 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] T.Nakamura.: Eur.J.Biochem.176. 89-94 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] S.Kusumoto.: Pure Appl.Chem.61. 461-464 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] S.Katsumura.: Tetrahedron Letters. 29. 1173-1176 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] S.Isoe.: Tetrahedron Letters. 28. 5865-5868 (1987)

    • Related Report
      1988 Annual Research Report
  • [Publications] S.Isoe.: Tetrahedron Letters. 29. 4591-4594 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] T.Suga.: Phytochemistry. 27. 1041-1044 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] S.Izumi.: Bull.Chem.Soc.Jpn.61. 1715-1720 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] 菅隆辛: 組織培養(特集:植物培養細胞による生合成と変換). 14. 400-406 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] T.Hirata.: Phytochemistry. 28. (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] M.Hirama.: J.Chem.Soc.,Chem.Commun.(1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] M.Hirama.: J.Chem.Soc.,Chem.Commun.3125-3128 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] M.Hirama.: Heterocycles. inpress (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] M.Kodama.: J.Org.Chem.53. 72-77 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] M.Kodama.: J.Org.Chem.53. 1437-1441 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] M.Kodama.: Tetrahedron. 44. 7055-7062 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] M.Ochi.: Chemistry Letters. 1661-1662 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] M.Ochi.: Heterocycles. 29. 39-41 (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] D.Uemura.;Y.Hrata.: "Antitumor Polyethers from Marine Animals, Studies in Natural Products Chemistry, Vol.2" Elsevier, (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] A.Kondo: Chemistry Letters. 1491-1494 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] M.Hirama: Journal of Organic Chemistry. 52. 3342-3346 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] M.Hirama: Journal of Chemical Society,Chemical Communication. 1523-1524 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] T.Kato: Journal of Chemical Society,Chemical Communication. 977-978 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] H.Kosugi: Journal of Organic Chemistry. 52. 1078-1082 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] H.Hagiwara: Journal of Chemical Society,Chemical Communications. 1333-1335 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] H.Hagiwara: Journal of Chemical Society,Chemical Communications. 1351-1353 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] H.Hagiwara: Journal of Organic Chemistry. 53. in press (1988)

    • Related Report
      1987 Annual Research Report
  • [Publications] S.Nishiyama: Chemistry Letters. 515-518 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Y.Shizuri: Chemistry Letters. 1381-1384 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] I.Muramatsu: Br.J.Parmacol.(1988)

    • Related Report
      1987 Annual Research Report
  • [Publications] H.Niwa: Journal of Organic Chemistry. 52. 2941-2943 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] M.Niwa: Chemical and Pharmaceutical Bulletin. 36. in press (1988)

    • Related Report
      1987 Annual Research Report
  • [Publications] T.Wakamiya: Tetrahedron Letters. 28. 5887-5888 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] T.Teshima: Peptide Chemistry 1986. 169-174 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] M.Nishizawa: Phytochemistry. 27. 237-239 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] S.Isoe: Tetrahedron Letters. 28. 5865-5868 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] S.Katsumura: Tetrahedron Letters. 29. 1173-1176 (1988)

    • Related Report
      1987 Annual Research Report
  • [Publications] T.Hirata: Bulletin of Chemical Society of Japan. 60. 289-293 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] T.Suga: Chemistry Letters. 425-428 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] T.Suga: Chemistry Letters. 471-474 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] F.Sakamura: Journal of Science,Hiroshima University,Ser.A. 51. 61-67 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] T.Suga: Chemistry Letters. 903-906 (1988)

    • Related Report
      1987 Annual Research Report
  • [Publications] T.Suga: Phytochemistry. 27. (1988)

    • Related Report
      1987 Annual Research Report
  • [Publications] M.Ochi: Chemistry Letters. 2207-2210 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] M.Kodama: Chemical and Pharmaceutical Bulletin. 35. 4039-4042 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] M.Kodama: Journal of Organic Chemistry. 53. 72-77 (1988)

    • Related Report
      1987 Annual Research Report
  • [Publications] M.Kodama: Journal of Organic Chemistry. 53. (1988)

    • Related Report
      1987 Annual Research Report
  • [Publications] M.Matsukawa: Tetrhedron Letters. 28. 5877-5878 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] K.Ueda: Bull.Coll.Sci.Univ.Ryukyus No.43. 61-69 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] M.Morita: Tetrhedron Letters. 28. 1425-1426 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Akihiro Kondo: Chemistry Lett.(1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] Masahiro Hirama: J.Chem.Soc,Chem.Commun.

    • Related Report
      1986 Annual Research Report
  • [Publications] Masahiro Hirama: Tetrahedron Lett.27. 5281-5284 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Masahiro Hirama: J.Org.Chem.52. (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] Tadahiro Kato: Tetrahedron Lett.28. (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] Hisahiro Hagiwara: J Chem.Soc.,Chem.Commun.860-861 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Hiroshi Kosugi: J Chem.Soc.,Chem.Commun.1268-1270 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Hiroshi Kakisawa: Bull.Chem.Soc.Jpn. 60. (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] Takeyoshi Takahashi: Bull.Chem.Soc.Jpn. 60. (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] Yoshikazu Sizuri: Chemistry Lett.1129-1132 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Sigeru Nishiyama: Chemistry Lett.1973-1976 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Sigeru Nishiyama: Tetrahedron Lett.27. 723-726 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Yoshimasa Hirata: Pure Appl.Chem.58. 701-710 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Haruki Niwa: Tetrahedron Lett.27. 4601-4604 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Haruki Niwa: Tetrahedron Lett.27. 4605-4608 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Haruki Niwa: Tetrahedron Lett.27. 4609-4610 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] H.Tamura: Tetrahedron Lett.27. 1801-1804 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] E.Ikeda: Chemistry Lett.145-148 (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] Masatake Niwa: Chem.Pharm.Bull.34. 3249-3251 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Masatake Niwa: Chem.Pharm.Bull.34. 3631-3634 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Masatake Niwa: Chem.Pharm.Bull.35. 108-111 (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] Tateaki Wakamiya: Tetrahedron Lett.27. 2143-2144 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Hidejiro Matsutani: Bull.Japan Soc.Sci.Fish. 53. 467 (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] Mugio Nishizawa: J.Org.Chem.51. 806-813 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Migio Nishizawa: Tetrahedron Lett.27. 187-190 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Sigeru Katsumura: Tetrahedron Lett.28. (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] Takayuki Suga: Bull.Chem.Soc.Jpn. 59. 2865-2867 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Takayuki Suga: Chemistry Lett.(1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] Takayuki Suga: Chemistry Lett.(1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] Akihiko Matsuo: Chemistry Lett.369-372 (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] Mitsuaki Kodama: Tetrahedron Lett.27. 2157-2160 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] S.Ikegami: Chemistry Lett.83-86 (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] K.Ueda: Bull.of the College of Science,Univ.of the Ryukyus. (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] M.Morotake: Tetrahedron Lett.28. (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] 芝哲夫: "海洋天然物化学-新しい生理活性物質をもとめて" 化学同人, (1987)

    • Related Report
      1986 Annual Research Report

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Published: 1987-03-30   Modified: 2016-04-21  

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