1997 Fiscal Year Final Research Report Summary
Chemical and Biological Studies on Production of Camptothecin-related Molecules by Use of the Domestic Medicinal Resource Plant
| Project/Area Number |
08457578
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Chiba University |
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Principal Investigator |
AIMI Norio Chiba University, Fac.Pharm.Sciences, Professor, 薬学部, 教授 (30009170)
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| Co-Investigator(Kenkyū-buntansha) |
SAITO Kazuki Chiba University, Fac.Pharm.Sciences, Professor, 薬学部, 教授 (00146705)
KITAJIMA Mariko Chiba University, Fac.Pharm.Sciences, Research Associate, 薬学部, 助手 (60195261)
TAKAYAMA Hiromitsu Chiba University, Fac.Pharm.Sciences, Associate Professor, 薬学部, 助教授 (90171561)
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| Project Period (FY) |
1996 – 1997
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| Keywords | Rubiaceae / Ophiorrhiza pumila / regenerated plants / hairy roots / camptothecin / deoxypumiloside / alkaloid / chiral synthesis |
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| Research Abstract |
[l] Secondary metabolites isolated from regenerated plants and hairy roots of Ophiorrhiza pumila (Rubiaceae)
(1) Constituents of regenerated plants of O.pumila : Regenerated plants, which were formed from callus cultures through differentiation, produced camptothecin, five camptothecin-related alkaloids and other nine known compounds. A new gluco camptothecin, 9-beta-D-glucosyloxy-camptothecin, was also isolated.
(2) Constituents of hairy roots of O.pumila : Hairy roots of O.pumila were obtained by the inoculation of Agrobacterium rhizogenes (pRi15834 ; pGSGlucl) to regenerated plants. From hairy roots cultivated on the solid medium, four camptothecin-related alkaloids including 3(S)- and 3(R)-deoxypumiloside and three anthraquinones were isolated. The existence of camptothecin could not be detected. From hairy roots cultivated in the liquid medium, four camptothecin-related alkaloids including camptothecin and six anthraquinones were isolated. It was found that both regenerated plants and hairy roots of O.pumila produce camptothecin. The finding that both the 3(S)- and 3(R)-deoxypumiloside are present in hairy roots as in the wild plants is quite important in clarification of the camptothecin biosynthesis.
[2] Synthetic studies of camptothecin-related compounds
According to the plausible biogenetic pathway, both the 3(S)- and 3(R)-deoxypumiloside were converted from 3(S)- and 3(R)-pumiloside through a reductive deoxygenation at C-7 position in pumiloside.
9-beta-D-Glucosyloxycamptothecin, a new alkaloid isolated from regenerated plants of O.pumila, was synthesized and its structure and the absolute configuration were established.
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