Scoulerine

Scoulerine
Names
	IUPAC name 3,10-Dimethoxyberbine-2,9-diol
	Systematic IUPAC name (13aS)-3,10-Dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-2,9-diol
	Other names (S)-Scoulerin; Discretamine; Aequaline
Identifiers
CAS Number	6451-73-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17129 ;
ChEMBL	ChEMBL1235966 ;
ChemSpider	388725 ;
KEGG	C02106 ;
PubChem CID	439654;
	InChI InChI=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 Key: KNWVMRVOBAFFMH-HNNXBMFYSA-N ;
	SMILES Oc1c4c(ccc1OC)C[C@H]3c2c(cc(OC)c(O)c2)CCN3C4;
Properties
Chemical formula	C19H21NO4
Molar mass	327.380 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.^[1] It is found in many plants, including opium poppy,^[2] Croton flavens,^[3] and certain plants in the genus Erythrina.^[4]

Studies show that scoulerine is an antagonist in vitro at the α₂-adrenoceptor, α_1D-adrenoceptor and 5-HT receptor.^[5]^[6] It has also been found to be a GABA_A receptor agonist in vitro.^[3]^[7]

References

^ Hagel, Jillian M; Morris, Jeremy S; Lee, Eun-Jeong; Desgagne-Penx, Isabel; Bross, Crystal D; Chang, Limei; Chen, Xue; Farrow, Scott C; Zhang, Ye (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.
^ Frick S; Chitty JA; Kramell R; Schmidt J; Allen RS; Larkin PJ; Kutchan TM (2004). "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". Transgenic Res. 13 (6): 607–613. doi:10.1007/s11248-004-2892-6. PMID 15672841. S2CID 38780571.
^ ^a ^b Eisenreich WJ; Hofner G; Bracher F (2003). "Alkaloids from Croton flavens L. and their affinities to GABA-receptors". Nat Prod Res. 17 (6): 437–440. doi:10.1080/1478641031000111516. PMID 14577695. S2CID 13192928.
^ Ito K (1999). "Studies on the alkaloids of Erythrina plants". Yakugaku Zasshi. 119 (5): 340–356. doi:10.1248/yakushi1947.119.5_340. PMID 10375996.
^ Ko FN; Yu SM; Su MJ; Wu YC; Teng CM (1993). "Pharmacological activity of (−)-discretamine, a novel vascular α-adrenoceptor and 5-hydroxytryptamine receptor antagonist, isolated from Fissistigma glaucescens". Br J Pharmacol. 110 (2): 882–888. doi:10.1111/j.1476-5381.1993.tb13895.x. PMC 2175899. PMID 7902181.
^ Ko FN; Guh JH; Yu SM; Hou YS; Wu YC; Teng CM (1994). "(−)-Discretamine, a selective α_1D-adrenoceptor antagonist, isolated from Fissistigma glaucescens". Br J Pharmacol. 112 (4): 1174–1180. doi:10.1111/j.1476-5381.1994.tb13207.x. PMC 1910235. PMID 7952879.
^ Halbsguth C; Meissner O; Haberlein H (2003). "Positive cooperation of protoberberine type 2 alkaloids from Corydalis cava on the GABA(A) binding site". Planta Med. 69 (4): 305–309. doi:10.1055/s-2003-38869. PMID 12709895. S2CID 260282359.

[1] Hagel, Jillian M; Morris, Jeremy S; Lee, Eun-Jeong; Desgagne-Penx, Isabel; Bross, Crystal D; Chang, Limei; Chen, Xue; Farrow, Scott C; Zhang, Ye (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.

[transformation-Frick-2] Frick S; Chitty JA; Kramell R; Schmidt J; Allen RS; Larkin PJ; Kutchan TM (2004). "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". Transgenic Res. 13 (6): 607–613. doi:10.1007/s11248-004-2892-6. PMID 15672841. S2CID 38780571.

[alkaloids-from-croton-Eisenreich-3] Eisenreich WJ; Hofner G; Bracher F (2003). "Alkaloids from Croton flavens L. and their affinities to GABA-receptors". Nat Prod Res. 17 (6): 437–440. doi:10.1080/1478641031000111516. PMID 14577695. S2CID 13192928.

[studies-on-the-alkaloids-Ito-4] Ito K (1999). "Studies on the alkaloids of Erythrina plants". Yakugaku Zasshi. 119 (5): 340–356. doi:10.1248/yakushi1947.119.5_340. PMID 10375996.

[pharmacological-activity-Ko-5] Ko FN; Yu SM; Su MJ; Wu YC; Teng CM (1993). "Pharmacological activity of (−)-discretamine, a novel vascular α-adrenoceptor and 5-hydroxytryptamine receptor antagonist, isolated from Fissistigma glaucescens". Br J Pharmacol. 110 (2): 882–888. doi:10.1111/j.1476-5381.1993.tb13895.x. PMC 2175899. PMID 7902181.

[discretamine-Ko-6] Ko FN; Guh JH; Yu SM; Hou YS; Wu YC; Teng CM (1994). "(−)-Discretamine, a selective α_1D-adrenoceptor antagonist, isolated from Fissistigma glaucescens". Br J Pharmacol. 112 (4): 1174–1180. doi:10.1111/j.1476-5381.1994.tb13207.x. PMC 1910235. PMID 7952879.

[positive-Halbsguth-7] Halbsguth C; Meissner O; Haberlein H (2003). "Positive cooperation of protoberberine type 2 alkaloids from Corydalis cava on the GABA(A) binding site". Planta Med. 69 (4): 305–309. doi:10.1055/s-2003-38869. PMID 12709895. S2CID 260282359.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

Scoulerine

References

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