Biological activity of metabolites of the incubated alkaloids by cultured cells of several species of Papaveraceae
| Project/Area Number |
59570911
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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 | Kobe Women's College of Pharmacy |
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Principal Investigator |
TAKAO Narao Kobe Women's College of Pharmacy ; Professor, 薬学部, 教授 (60068319)
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| Co-Investigator(Kenkyū-buntansha) |
SUGIURA Makiko Kobe Women's College of Pharmacy ; Lecturer, 薬学部, 講師 (00098500)
YAMAGAMI Chisako Kobe Women's College of Pharmacy ; Associate Professor, 薬学部, 助教授 (20140410)
KAMIGAUCHI Miyako Kobe Women's College of Pharmacy ; Lecturer, 薬学部, 講師 (60098499)
IWASA Kinuko Kobe Women's College of Pharmacy ; Lecturer, 薬学部, 講師 (30068340)
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| Project Period (FY) |
1984 – 1986
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| Project Status |
Completed (Fiscal Year 1986)
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| Budget Amount *help |
¥1,600,000 (Direct Cost: ¥1,600,000)
Fiscal Year 1986: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1985: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1984: ¥900,000 (Direct Cost: ¥900,000)
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| Keywords | Callus / Biotransformation / Conformation / Antibacterial test / アルカロイド |
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| Research Abstract |
1. It has been found that the protoberberine <alpha> -N-methyl salts were transformed in some Papaverous plants and the callus cultures via the protopines into benzo[c]phenanthridines. At present bioconversions in callus cultures of Corydalis species of both trans- and cis-13-methylprotoberberine N-quaternary salts into a corycavine analogue as well as of both trans- and cis-13-hydroxyprotoberberine N-quaternary salts into 13-oxoprotopine-type, which is biotransformed into spirobenzylisoquinoline and benzindenoazepine, are demonstrated. Of <alpha> - and <beta> -N-quaternary salts, <alpha> -N-methyl salt bearing a cis quinolizidine ring was biotransformed. It was also demonstrated that the aliphatic O-methyl group of the spirobenzylisoquinoline arises from the N-methyl group of the protopine skeleton, ie. migration of the methyl group from N to O occurs during the ring rearrangement. (-)-Trans-13-hydroxyprotoberberine having the methoxyl group at C-1 was also bioconverted to 13-oxoprotopine- and benzindenoazepine-type alkaloids. Phthalideisoquinoline alkaloids were metabolized the simple tetrahydroisoquinoline and meconin by cell cultures.
2. A number of the precursors have demonstrated biological and pharmacological activities. In order to obtain the relationships between stereostructure and physiological activity and to clarify the mechanism for stereoselective bioconversion, conformational analyses of protoberberine-, protopine-benzo[c]phenanthridine-, and phthalideisoquinoline-type alkaloids were carried out. Some new informations for conformation of these alkaloids were obtained.
3. The derivatives of protoberberine-, protopine-, and benzo[c]phenanthridine-type alkaloids were submited to antileukemic screening and antibacterial tests. A number of new informations were obtained on antibacterial action. Many compounds can be considered inactive for leukemia p388 in mice. The results on some alkaloids were limited because of toxicity.
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Report
(1 results)
Research Products
(14 results)
