Cheilanthifoline

Cheilanthifoline
Names
	Other names (S)-Cheilanthifoline
Identifiers
3D model (JSmol)	(S)-: Interactive image; rac: Interactive image;
ChemSpider	513559 rac;
PubChem CID	590762 rac; 440582 (S)-;
CompTox Dashboard (EPA)	DTXSID70964044 ;
	InChI InChI=1S/C19H19NO4/c1-22-18-8-13-12(7-16(18)21)4-5-20-9-14-11(6-15(13)20)2-3-17-19(14)24-10-23-17/h2-3,7-8,15,21H,4-6,9-10H2,1H3 Key: MKRKFSHHTKVRAR-UHFFFAOYSA-N; rac: InChI=1/C19H19NO4/c1-22-18-8-13-12(7-16(18)21)4-5-20-9-14-11(6-15(13)20)2-3-17-19(14)24-10-23-17/h2-3,7-8,15,21H,4-6,9-10H2,1H3 Key: MKRKFSHHTKVRAR-UHFFFAOYAZ;
	SMILES (S)-: COC1=C(C=C2[C@@H]3CC4=C(CN3CCC2=C1)C5=C(C=C4)OCO5)O; rac: COc1cc2c(cc1O)CCN3C2Cc4ccc5c(c4C3)OCO5;
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) isolated from Corydalis dubia, which is used in Bhutanese traditional medicine as a febrifuge as well for other conditions.^[1] (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.{{cite journal}}: CS1 maint: unflagged free DOI (link)

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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.{{cite journal}}: CS1 maint: unflagged free DOI (link)

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See also

References