Benzophenanthridine and Benzylisoquinoline Alkaloids from Argemone
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Cytotoxic benzophenanthridine and benzylisoquinoline alkaloids from Argemone mexicana.
Fractionation of the chloroform extract from the aerial part of Argemone mexicana led to the isolation of two benzophenanthridine-type alkaloids, N-demethyloxysanguinarine and pancorine; three benzylisoquinoline-type alkaloids, (+)-1,2,3,4-tetrahydro-1-(2-hydroxymethyl-3,4-dimethoxyphenylmethyl)-6,7-methylenedioxyisoquinoline, (+)-higenamine and (+)-reticuline. Among them, N-demethyloxysanguina...
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Alkaloid contents in Argemone mexicana cell line AMMiF were analyzed during a 36-day culture cycle. The benzophenanthridine sanguinarine (SA) represented the main alkaloid. Dihydrosanguinarine (DHSA), a SA biosynthetic precursor and a less toxic benzophenanthridine, was also identified, based on chromatographic properties and further confirmed by gas chromatography coupled to mass spectrometry....
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BACKGROUND Benzylisoquinoline is the structural backbone of many alkaloids with a wide variety of structures including papaverine, noscapine, codeine, morphine, apomorphine, berberine, protopine and tubocurarine. Many benzylisoquinoline alkaloids have been reported to show therapeutic properties and to act as novel medicines. Thus it is important to collect and compile benzylisoquinoline alkalo...
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S-Adenosyl-l-methionine:tetrahydroprotoberberine cis-N-methyltransferase (EC 2.1.1.122) catalyzes the conversion of (S)-stylopine to the quaternary ammonium alkaloid, (S)-cis-N-methylstylopine, as a key step in the biosynthesis of protopine and benzophenanthridine alkaloids in plants. A full-length cDNA encoding a protein exhibiting 45 and 48% amino acid identity with coclaurine N-methyltransfe...
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