1991 Fiscal Year Final Research Report Summary
Chemical Study on Camptothecinoid Glycosidic Alkaloids of Ophiorrhiza pumila
| Project/Area Number |
02670942
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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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, Faculty of Pharmaceutical Sciences, Associate Professor, 薬学部, 助教授 (30009170)
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| Co-Investigator(Kenkyū-buntansha) |
KITAJIMA Mariko Chiba University, Faculty of Pharamaceutical Sciences, Research Associate, 薬学部, 教務職員 (60195261)
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| Project Period (FY) |
1990 – 1991
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| Keywords | Ophiorrhiza pumila / chaboside / Rubiaceae / alkaloid / camptothecins / glycoside / total synthesis / structure determination |
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| Research Abstract |
A Rubiaceous plant, ophiorrhiza pumila distributes in the Amami and Ryukyu islands, a southern region of Japan under subtropical climate. The foregoing studies revealed that this species has special potency as a resource plant of important lead compounds towards developing clinical drugs. Until 1990 we succeeded in isolating pumiloside and deoxypumiloside, new type of camptothecinoid glucosides. They were f ound to be the longsought biosynthetic intermediates of camptothecin group of quinoline alkaloids. Further study allowed us to isolate another member of glucocamptothecinoid, a compound named chaboside. The present project deals with the structure elucidation' and total synthesis of this compound.
Chaboside, C_<28>H_<32>O_<10>, was shown to be the first natural glucosidic campto hecin. The A ring was foun carry one methoxyl and one glucosyl oxy groups. ^1H-and ^<13>C-NMR spectra indicated the positions of the substituents ; C-9 for methoxyland C-10 for glucosyloxy groups.
Then synthetic study on chaboside and related alkaloids were undertaken. A general synthetic strategy developed by Shanghai group was employed. The Aring segment with glucoside moiety at the proper position was prepared from o-vanillin. This compound was condensed with chiral CDE ring moiety prepared by the method of the research group of Daiichi Pharmaceutical Co. The synthesized material was shown to be completely identical with the natural chaboside. Here the structure of chaboside including the absolute configuration at C-20 was proved. Similarly chaboside aglycone, i. g. 9-methoxy-10-hydroxycamptothecin, and a new natural product, 10-hydroxy-20-deoxycamptothecin, were synthesized.
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Research Products
(2 results)
