(S)-Magnoflorine is a quaternary benzylisoquinoline alkaloid (BIA) of the aporphine structural subgroup which has been isolated from various species of the family Menispermaceae, such as Pachygone ovata,[1] Sinomenium acutum,[2] and Cissampelos pareira.[3]
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| Names | |
|---|---|
| IUPAC name 1,11-Dihydroxy-2,10-dimethoxy-6-methylaporphin-6-ium | |
| Systematic IUPAC name (6aS)-1,11-Dihydroxy-2,10-dimethoxy-6,6-dimethyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-6-ium | |
| Other names Magnoflorine; Thalictrin; Escholin; Escholine; Thalictrine | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.208.671 |
| KEGG | |
PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
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| Properties | |
| C20H24NO4+ | |
| Molar mass | 342.41 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
It was identified among the verified anti-inflammatory components in an extract of Sinomenii caulis[4] and has been proposed to have other potential physiological effects, such as sedative and anxiolytic,[2] reduction of erythrocyte hemolysis,[5] antifungal activity,[6] improvement of LPS-induced acute lung injury,[7] and protection against muscle atrophy.[8] Furthermore, magnoflorine has been identified to be an inhibitor of NF-κB activation and to be an agonist at the β2 -adrenergic receptor.[9]
(S)-Magnoflorine is metabolically derived from (S)-reticuline, a pivotal intermediate in the biosynthesis of numerous BIA structural subgroups, through two enzymatic steps: first, (S)-corytuberine synthase/CYP80G2 to (S)-corytuberine, and secondly, (S)-corytuberine-N-methyltransferase to (S)-magnoflorine.[10][11]