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Study on the Alkaloid Production of Two Gelsemium Plants by Using their Callus Cultures and Chemical and Pharmacological Investigation of Gelsemium Alkaloids.

Research Project

Project/Area Number 14571996
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionCHIBA UNIVERSITY

Principal Investigator

KITAJIMA Mariko  Chiba University, Graduate School of Pharmceutical Sci., Research Associate, 大学院・薬学研究院, 助手 (60195261)

Co-Investigator(Kenkyū-buntansha) YAMAZAKI Mami  Chiba University, Graduate School of Pharmaceutical Sciences, Associate Professor, 大学院・薬学研究院, 助教授 (70222370)
TAKAYAMA Hiromitsu  Chiba University, Graduate School of Pharmaceutical Sciences, Associate Professor, 大学院・薬学研究院, 助教授 (90171561)
AIMI Norio  Chiba University, Graduate School of Pharmaceutical Sciences, Professor, 大学院・薬学研究院, 教授 (30009170)
YANO Shingo  Chiba University, Graduate School of Pharmaceutical Sciences, Professor, 大学院・薬学研究院, 教授 (90009655)
Project Period (FY) 2002 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2003: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 2002: ¥2,400,000 (Direct Cost: ¥2,400,000)
KeywordsLoganiaceae / Gelsemium elegans / Gelsemium sempervirens / alkaloid / callus / phylogenelic analyses of DNA / toxicity / antitumor activity / Gelsemium sempervirens / イリドイド / テルペン / 急性毒性 / 毛状根 / アゼチジン環 / 系統解析
Research Abstract

Gelsemium elegant and G.sempervirens belonging to Loganiaceae are known to be toxic and rich sources of indole alkaloids.
Callus cultures of Gelsemium plants were successfully obtained from the leaf segments of G.elegans and G.sempervirens, respectively. By the chemical investigation of G.sempervirens callus, it became clear that the callus did not produce alkaloidal constituents.
Phylogenetic comparison of DNA among G.elegans, G.sempervirens, Strychnos nux-vomica and Gardneria nutans were investigated. The analysis revealed that the two.Gelsemium plants formed a cluster but they were not closely related.
By exhaustive investigation of the, constituents in Gelsemium plants, fourteen alkaloids including four new compounds (14,15-dihydroxygelsenicine, GE-2, GE-3, GE-4) were isolated from the leaves of G.elegans. 14,15-Dihydroxygelsenicine is the first Gelsemium oxindole alkaloid having a vicinal diol. The stricture of the known alkaloid, gelsemoxonine, was revised to be a novel oxindole possessing an azetidine unit. This is the first example of the monoterpenoid indole alkaloid having an azetidine unit in the molecule. From the stems of G.sempervirens, fourteen compounds including three new oxindole alkaloids (GS-1, GS-2, GS-3) and one new iridoid (GSIR-1) were isolated. Among them, six compounds were also isolated from the leaves.
Lethal effect of the representative Gelsemium alkaloids on rat hepatocytes (H4-II-E-C3 cell) was evaluated. It was found that koumine and humantenine were quite effective than antitumor reagent, cisplatin.

Report

(3 results)
  • 2003 Annual Research Report   Final Research Report Summary
  • 2002 Annual Research Report
  • Research Products

    (20 results)

All Other

All Publications (20 results)

  • [Publications] M.Kitajima et al.: "Camptothecin-related Alkaloids from Hairy Roots of Ophiorrhiza pumila."Tetrahedron. 58. 9169-9178 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kitajima et al.: "Camptothecin-related Akaloids from Culture Medium of Hairy Roots of Ophiorrhiza pumila"Natural Medicines. 56. 275 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kitajima et al.: "Synthesis and Absolute Configuration of a New 3,4-Dihydro-b-carboline-Type Alkaloid, 3,4-Dehydro-5(S)-5-carboxystrictosidine Isolated from Peruvian Una de Gato (Uncaria tomentosa)."Chem.Pharm.Bull.. 50. 1376-1378 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kitajima et al.: "Structure Reinvestigation of Gelsemoxonine, a Constituent of Gelsemium elegans, Reveals a Novel, Azetidine-Containing Indole Alkaloid."Org.Lett.. 5. 2075-2078 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kitajima et al.: "New Oxindole Alkaloids and Indoid from Carolina jasmine (Gelsemium sempervirens Ait.f.)."Chem.Pharm.Bull.. 51. 1211-1214 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Takayama et al.: "Gluco-indole Alkaloids from Nauclea cadamba in Thailand and Transformation of 3α-Dihydrocadambine into the Indolopyridine Alkaloid, 16-Carbomethoxynaufoline."Chem.Pharm.Bull.. 51. 232-233 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kitajima et al.: "Camptothecin-related Alkaloids from Hairy Roots of Ophiorrhiza pumila."Tetrahedron. 58(45). 9169-9178 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kitajima et al.: "Camptothecin-related Alkaloids from Culture Medium of Hairy Roots of Ophiprrhiza pumila."Natural Medicines. 56(6). 275 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kitajima et al.: "Synthesis and Absolute Configuration of a New 3,4-Dihydro-β-carboline-Type Alkaloid,3,4-Dehydro-5(S)-5-carboxystrictosidine, Isolated from Peruvian Uta de Gato (Uncaria tomentosa)."Chem.Pharm.Bull.. 50(10). 1376-1378 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kitajima et al.: "Structure Reinvestigation of Gelsemoxonine, a Constituent of Gelsemium elegans, Reveals a Novel, Azctidine-Containing Indole Alkaloid."Organic Lett.. 5(12). 2075-2078 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kitajima et al.: "New Oxindole Alkaloids and Iridoid from Carolina jasmine (Gelsemium sempervirens Ait.F.)."Chem.Pharm.Bull.. 51(10). 1211-1214 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Takayama et al.: "Gluco-indole Alkaloids from Nauclea cadamba in Thailand and Transformation of 3α-Dihydrocadambine into the Indolopyiidine Alkaloid, 16-Carbomehoxynaufoline."Chem.Pharm.Bull.. 51(2). 232-233 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kitajima et al.: "Structure Reinvestigation of Gelsemoxonine, a Constituent of Gelsemium elegans, Reveals a Novel, Azetidine-Containing Indole Alkaloid."Org.Lett.. 5・12. 2075-2078 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Kitajiina et al.: "New Oxindole Alkaloids and Iridoid from Carolina jasmine (Gelsemium sempervirens Ait. f.)."Chem.Pharm.Bull.. 51・10. 1211-1214 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] H.Takayama et al.: "Gluco-indole Alkaloids from Nauclea cadamba in Thailand and Transformation of 3α-Dihydrocadambine into the Indolopyridine Alkaloid, 16-Carbomethoxynaufoline."Chem.Pharm.Bull.. 51・2. 232-233 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Y.Yamazaki et al.: "Metabolite Profiling of Alkaloids and Strictosidine Synthase Activity in Camptothecin Producing Plants."Phytochem.. 62・3. 461-470 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Kitajima, et al.: "Camptothecin-related Alkaloids from Hairy Roots of Ophiorrhiza pumila"Tetrahedron. 58・45. 9169-9178 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Kitajima, et al.: "Camptothecin-related Akaloids from Culture Medium of Hairy Roots of Ophiorrhiza pumila"Natural Medicines. 56・12. 275 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Kitajima, et al.: "Synthesis and Absolute Configuration of a New 3,4-Dihydro-β-carboline-Type Alkaloid, 3,4-Dehydro-5(S)-5-carboxystrictosidine, Isolated from Peruvian Una de Gato (Uncaria tomentosa)"Chem. Pharm. Bull.. 50・10. 1376-1378 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] H.Takayama, et al.: "Seven New Lycoposium Alkaloids, Lycoposerramines, from Lycposium serratum Thunb"Tetrahedron Lett.. 43・46. 8307-8311 (2002)

    • Related Report
      2002 Annual Research Report

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Published: 2002-04-01   Modified: 2016-04-21  

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