:Cheilanthifoline

{{Chembox

| ImageFile = (-)-(S)-Cheilanthifoline.svg

| IUPACName = 2-Methoxy-2′H-[1,3]dioxolo[4′,5′:9,10]berbin-3-ol

| SystematicName = (6aS)-9-Methoxy-6,6a,11,14-tetrahydro-2H,12H-[1,3]dioxolo[4,5-h]isoquinolino[2,1-b]isoquinolin-8-ol

| OtherNames = (S)-Cheilanthifoline

|Section1={{Chembox Identifiers

| CASNo1 = 483-44-3

| ChEBI = 140670

| ChEBI1 = 16233

| KEGG1 = C05174

| PubChem1 = 101277425

| SMILES1 = COC1=C(C=C2[C@@H]3CC4=C(CN3CCC2=C1)C5=C(C=C4)OCO5)O

| index1_label = (S)-

| PubChem = 590762

| index_label = rac

| ChemSpiderID = 513559

| ChemSpiderID1 = 62987502

| SMILES = COc1cc2c(cc1O)CCN3C2Cc4ccc5c(c4C3)OCO5

| 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

| InChIKey = MKRKFSHHTKVRAR-UHFFFAOYSA-N

| InChI1 = 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/t15-/m0/s1

| InChIKey1 = MKRKFSHHTKVRAR-HNNXBMFYSA-N

}}

|Section2={{Chembox Properties

| C=19 | H=19 | N=1 | O=4

| Appearance =

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|Section3={{Chembox Hazards

| MainHazards =

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(S)-Cheilanthifoline is a benzylisoquinoline alkaloid (BIA) which has been isolated from Corydalis dubia{{cite journal |pmid=22796506|year=2012|last1=Wangchuk|first1=P|last2=Keller|first2=PA|last3=Pyne|first3=SG|last4=Willis|first4=AC|last5=Kamchonwongpaisan|first5=S|title=Antimalarial alkaloids from a Bhutanese traditional medicinal plant Corydalis dubia |volume=143|issue=1|pages=310–3|doi=10.1016/j.jep.2012.06.037|journal=Journal of Ethnopharmacology|url=https://ro.uow.edu.au/cgi/viewcontent.cgi?article=7675&context=scipapers}} and Argemone mexicana.{{cn|date=March 2021}} (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.{{Cite journal|last1=Hagel |first1=Jillian |last2=Morris|first2=Jeremy S|last3=Lee|first3=Eun-Jeong|last4=Desgagne-Penix|first4=Isabel|last5=Bross|first5=Crystal D|last6=Chang|first6=Limei|last7=Chen|first7=Xue|last8=Farrow|first8=Scott C|last9=Zhang|first9=Te|date=2015|title=Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants|url=http://openlib.tugraz.at/download.php?id=564f2fa60a35b&location=browse|journal=BMC Plant Biology|volume=15|issue=1 |pages=227|doi=10.1186/s12870-015-0596-0|pmid=26384972|pmc=4575454 |doi-access=free |bibcode=2015BMCPB..15..227H }}