Cheilanthifoline

Cheilanthifoline
Names
	Preferred IUPAC name (6aS)-9-Methoxy-6,6a,11,14-tetrahydro-2H,12H-[1,3]dioxolo[4,5-h]isoquinolino[2,1-b]isoquinolin-8-ol
	Other names (S)-Cheilanthifoline
Identifiers
CAS Number	(S)-: 483-44-3;
3D model (JSmol)	rac: Interactive image; (S)-: Interactive image;
ChEBI	rac: CHEBI:140670; (S)-: CHEBI:16233;
ChemSpider	rac: 513559;
KEGG	(S)-: C05174;
PubChem CID	rac: 590762; (S)-: 440582;
CompTox Dashboard (EPA)	rac: DTXSID70964044 ;
	show InChI
	show SMILES
Properties
Chemical formula	C19H19NO4
Molar mass	325.364 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

(S)-Cheilanthifoline is a benzylisoquinoline alkaloid (BIA) which has been isolated from ^[1] and Argemone mexicana.^{[citation needed]} (S)-Cheilanthifoline is metabolically derived from (S)-reticuline, 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 and sanguinarine.^[2]

References[]

^ Wangchuk, P; Keller, PA; Pyne, SG; Willis, AC; Kamchonwongpaisan, S (2012). "Antimalarial alkaloids from a Bhutanese traditional medicinal plant Corydalis dubia". Journal of Ethnopharmacology. 143 (1): 310–3. doi:10.1016/j.jep.2012.06.037. PMID 22796506.
^ Hagel, Jillian; Morris, Jeremy S; Lee, Eun-Jeong; Desgagne-Penix, Isabel; Bross, Crystal D; Chang, Limei; Chen, Xue; Farrow, Scott C; Zhang, Te (2015). "Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants". BMC Plant Biology. 15: 227. doi:10.1186/s12870-015-0596-0. PMC 4575454. PMID 26384972.

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[1] Wangchuk, P; Keller, PA; Pyne, SG; Willis, AC; Kamchonwongpaisan, S (2012). "Antimalarial alkaloids from a Bhutanese traditional medicinal plant Corydalis dubia". Journal of Ethnopharmacology. 143 (1): 310–3. doi:10.1016/j.jep.2012.06.037. PMID 22796506.

[2] Hagel, Jillian; Morris, Jeremy S; Lee, Eun-Jeong; Desgagne-Penix, Isabel; Bross, Crystal D; Chang, Limei; Chen, Xue; Farrow, Scott C; Zhang, Te (2015). "Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants". BMC Plant Biology. 15: 227. doi:10.1186/s12870-015-0596-0. PMC 4575454. PMID 26384972.

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