(''S'')-Cheilanthifoline is a
benzylisoquinoline alkaloid
Substitution of the heterocycle isoquinoline at the C1 position by a benzyl group provides 1‑benzylisoquinoline, the most widely examined of the numerous benzylisoquinoline structural isomers. The 1-benzylisoquinoline moiety can be identified ...
(BIA) which has been isolated from ''
Corydalis dubia
''Corydalis'' (from Greek ''korydalÃs'' " crested lark") is a genus of about 470 species of annual and perennial herbaceous plants in the family Papaveraceae, native to the temperate Northern Hemisphere and the high mountains of tropical ...
'' and ''
Argemone mexicana
''Argemone mexicana'' (Mexican poppy, Mexican prickly poppy, flowering thistle, cardo or cardosanto) is a species of poppy found in Mexico and now widely naturalized in many parts of the world. An extremely hardy pioneer plant, it is tolerant ...
''. (''S'')-Cheilanthifoline is metabolically derived from (''S'')-
reticuline
Reticuline is a chemical compound found in a variety of plants including '' Lindera aggregata'', ''Annona squamosa'', and ''Ocotea fasciculata'' (also known as ''Ocotea duckei''). It is based on the benzylisoquinoline structure.
Reticuline is o ...
, a pivotal intermediate in the biosynthesis of numerous BIAs. (''S'')-Cheilanthifoline is the immediate precursor of the BIA
(''S'')-stylopine (
(''S'')-stylopine synthase/CYP719A20), which is the precursor for the alkaloids
protopine
Protopine is an alkaloid occurring in opium poppy, ''Corydalis'' tubers and other plants of the family papaveraceae, like ''Fumaria officinalis''. Protopine is metabolically derived from the benzylisoquinoline alkaloid ''(S)''-Reticuline through a ...
and
sanguinarine
Sanguinarine is a polycyclic quaternary alkaloid. It is extracted from some plants, including the bloodroot plant, from whose taxonomic name, ''Sanguinaria canadensis,'' its name is drawn; the Mexican prickly poppy (''Argemone mexicana''); '' Che ...
.
References
Benzodioxoles
Quinolizidines
Heterocyclic compounds with 5 rings
Methoxy compounds
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