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Biosynthesis of Benzo[c]phenanthridine Alkaloids Sanguinarine, Chelirubine and Macarpine
✍ Scribed by Narao Takao; Miyoko Kamigauchi; Momoyo Okada
- Publisher
- John Wiley and Sons
- Year
- 1983
- Tongue
- German
- Weight
- 797 KB
- Volume
- 66
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
The biosynthesis of the benzo[c]phenanthridine alkaloids was investigated in a cell suspension culture of Macleaya cordata (papaveraceae). Feeding experiments define the biosynthetic pathway (–)‐7,8,13,13a‐tetrahydrocoptisine →(–)‐cis‐N‐methyl‐7,8,13,13a‐tetrahydrocoptisinium salt 15→ protopine (5)→ sanguinarine (1)→ chelirubine (3)→ macarpine (4).
📜 SIMILAR VOLUMES
C and in some cases also 15 N chemical shifts of quaternary benzo[c]phenanthridine alkaloids (fagaronine, chelerythrine, chelilutine, chelirubine, nitidine, sanguilutine, sanguinarine, and sanguirubine) were systematically studied by NMR spectroscopy and ab initio calculations. The assignment of sig