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1998 Fiscal Year Final Research Report Summary

Bioorganically Chemical Studies on Antitumor Substances contained in Trees

Research Project

Project/Area Number 08456056
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionTohoku University

Principal Investigator

ORITANI Takayuki  Faculty of Agriculture, Department of Applied Biological Chemistry, Professor, 農学部, 教授 (20005630)

Co-Investigator(Kenkyū-buntansha) TANAKA Akira  Toyama Prefecutual University, Junior College Professor, 農学部, 助教授 (70005651)
SUGIYAMA Takeyoshi  Faculty of Agriculture, Department of Biological Chemistry, Associate Professor, 農学部, 助教授 (10125586)
Project Period (FY) 1996 – 1998
KeywordsAnnonaceous acetogenin / Squamostanal-A / Corossoline / 4-deoxygigantecin / Zeylenol analogs / taxanediterpenoid / taxinine / 9,10-deacetyltaxinine
Research Abstract

1. Bioorganically chemical research on Annonaceous acetogenins : Squamostanal-A, epoxyrollin A and diepomuricanin, which were proposed as biosynthetic intermediates for Annonaceous acetogenins, were synthesized by using stereoselective reactions. The spectral analysis of the synthesized epoxyrollin A showed that the structure proposed for natural epoxyrollin A is mistaken. Furthermore, (8^2R) and (8^2S)-corossoline and (+)-4-deoxygigantecin, Annonaceous acetogenins, were synthesized by the stereoselective methods using chiral bulding blocks. Separation and structural elucidation of biologically active components from Uvaria purpurea, a Chinese plant of Annonaceae species, was tried to separate new derivatives belong to zeylenol.
2. Studies on the chemical transformation of taxanediterpenoids.
1) Stereoselective deacetylation of taxinine, a major component of Japanese yew, using chemical (Mg(OCH_3)_2 )and enzymatic methods (pancreatine) gave 9,10-deacetyl taxinine.
2) Treatment of 2,5,7,9,10,13,20-heptaacetyl 3,8-secotaxa-3,8,11-triene with Pd(Ph_3P)_4 in acetic acid gave 2,5,10, 13,20-pentaacetyl-3,8-secotaxa-3,7-die-9-one. Which was identical with a new minor compound separated from Chinese yew, Taxus mairel.
3) Side chain elongation of 5-decinnamoyl taxinine with vinylethylether in the presence of Hg(OAc)_2 gave a new analog of taxanditerpenenoid with 20-formylmethyl group.

  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] H.Makabe: "Total Synthesis of(+)-4-Deoxygigantecin" Tetrahedron. 54. 6329-6340 (1998)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 折谷 隆之: "タキサンジテルペノイド類の化学的および酵素的脱アセチル化" 日本農芸化学会誌、大会講演要旨集. 72. 272- (1998)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 史 清文: "中国産イチイTaxus maireiの針葉に含まれる二環性タキサン類" 香料、テルペンおよび精油に関する討論会講演旨集. 42. 284-286 (1998)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 竹内 嘉房: "中国山椒子に含まれる生理活性物質の単離と構造決定" 日本農芸化学会誌、大会講演要旨集. 72. 63- (1998)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hiroyuki Konno: "Synthesis of Squamostanal-A" Biosci.Biotech.Biochem.60. 526-527 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hiroyuki Konno: "Synthesis of Two possible Diastereoisomers of the Epoxy Lactone Proposed for an Annonaceous Acetogenin, Epoxyrollin A" Tetrahedron. 52. 9399-9408 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hiroyuki Konno: "Total Synthesis of (15S,16R,19S,20R,34S) -Diepomuricanin" Tetrahedron Letters. 37 (30). 5393-5396 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hidefumi Makabe: "Total Synthesis of (8'R) -and (8'S) -. Corossoline" Heterocycles. 43 (10). 2229-2248 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hidefumi Makabei: "Total Synthesis of (+) -4-Deoxygigantecin" Tetrahedron Letters. 38 (24). 4247-4250 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Akira Tanaka: "Synthetic studies of Annonaceous acetogenin" J.Synthetic Organic Chemistry Japan. 55 (10). 877-885 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hidefumi Makabei: "Total Synthesis of (+) -4-Deoxygigantecin" Tetrahedron. 54. 6329-6340 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Qig-Wen Shi: "Novel bicyclic taxoids from the needles of Taxas maire" 42th Symposium Papers on Perfumes・Terpenes and Essentail Oil Chemistry. 284-28* (1998)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1999-12-08  

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