scoulerine

{{chembox

| Verifiedfields = changed

| verifiedrevid = 464388032

| Name = Scoulerine

| ImageFile = Scoulerine-S.png

| ImageName = Scoulerine

| IUPACName = 3,10-Dimethoxyberbine-2,9-diol

| SystematicName = (13aS)-3,10-Dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-2,9-diol

| OtherNames = (S)-Scoulerin; Discretamine; Aequaline

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 388725

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1235966

| PubChem = 439654

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C19H21NO4/c1-23-17-4-3-11-7-15-13-9-16(21)18(24-2)8-12(13)5-6-20(15)10-14(11)19(17)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3/t15-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = KNWVMRVOBAFFMH-HNNXBMFYSA-N

| CASNo_Ref = {{cascite|changed|CAS}}

| CASNo = 6451-73-6

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 17129

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C02106

| SMILES = Oc1c4c(ccc1OC)C[C@H]3c2c(cc(OC)c(O)c2)CCN3C4

}}

|Section2={{Chembox Properties

| C=19 | H=21 | N=1 | O=4

}}

}}

Scoulerine, also known as discretamine and aequaline, is a benzylisoquinoline alkaloid (BIA) that is derived directly from (S)-reticuline through the action of berberine bridge enzyme. It is a precursor of other BIAs, notably berberine, noscapine, (S)-tetrahydropalmatine, and (S)-stylopine, as well as the alkaloids protopine, and sanguinarine.{{Cite journal|last1=Hagel|first1=Jillian M|last2=Morris|first2=Jeremy S|last3=Lee|first3=Eun-Jeong|last4=Desgagne-Penx|first4=Isabel|last5=Bross|first5=Crystal D|last6=Chang|first6=Limei|last7=Chen|first7=Xue|last8=Farrow|first8=Scott C|last9=Zhang|first9=Ye|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|pages=227|doi=10.1186/s12870-015-0596-0|pmid=26384972|pmc=4575454|doi-access=free}} It is found in many plants, including opium poppy,{{cite journal |author1=Frick S |author2=Chitty JA |author3=Kramell R |author4=Schmidt J |author5=Allen RS |author6=Larkin PJ |author7=Kutchan TM | title=Transformation of opium poppy (Papaver somniferum L.) with antisense berberine bridge enzyme gene (anti-bbe) via somatic embryogenesis results in an altered ratio of alkaloids in latex but not in roots | journal=Transgenic Res. | year=2004 | pages=607–613 | volume=13 | issue=6 | pmid=15672841 | doi=10.1007/s11248-004-2892-6|s2cid=38780571 }} Croton flavens,{{cite journal |author1=Eisenreich WJ |author2=Hofner G |author3=Bracher F | title=Alkaloids from Croton flavens L. and their affinities to GABA-receptors | journal=Nat Prod Res | year=2003 | pages=437–440 | volume=17 | issue=6 | pmid=14577695 | doi=10.1080/1478641031000111516|s2cid=13192928 }} and certain plants in the genus Erythrina.{{cite journal | author=Ito K | title=Studies on the alkaloids of Erythrina plants | journal= Yakugaku Zasshi | year=1999 | pages=340–356 | volume=119 | issue=5 | doi=10.1248/yakushi1947.119.5_340 | pmid=10375996| doi-access=free }}

Studies show that scoulerine is an antagonist in vitro at the α₂-adrenoceptor, α_1D-adrenoceptor and 5-HT receptor.{{cite journal |author1=Ko FN |author2=Yu SM |author3=Su MJ |author4=Wu YC |author5=Teng CM | title=Pharmacological activity of (−)-discretamine, a novel vascular α-adrenoceptor and 5-hydroxytryptamine receptor antagonist, isolated from Fissistigma glaucescens | journal=Br J Pharmacol | year=1993 | pages=882–888 | volume=110 | issue=2 | pmid=7902181 | pmc=2175899 | doi=10.1111/j.1476-5381.1993.tb13895.x}}{{cite journal |author1=Ko FN |author2=Guh JH |author3=Yu SM |author4=Hou YS |author5=Wu YC |author6=Teng CM | title=(−)-Discretamine, a selective α_1D-adrenoceptor antagonist, isolated from Fissistigma glaucescens | journal=Br J Pharmacol | year=1994 | pages=1174–1180 | volume=112 | issue=4 | pmid=7952879 | pmc=1910235 | doi=10.1111/j.1476-5381.1994.tb13207.x}} It has also been found to be a GABA_A receptor agonist in vitro.{{cite journal |author1=Halbsguth C |author2=Meissner O |author3=Haberlein H | title=Positive cooperation of protoberberine type 2 alkaloids from Corydalis cava on the GABA(A) binding site | journal=Planta Med. | year=2003 | pages=305–309 | volume=69 | issue=4 | pmid=12709895 | doi=10.1055/s-2003-38869|s2cid=260282359 }}