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Scoulerine

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Scoulerine
Scoulerine
Names
IUPAC name 3,10-Dimethoxyberbine-2,9-diol
Systematic IUPAC name (13aS)-3,10-Dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolinoisoquinoline-2,9-diol
Other names (S)-Scoulerin; Discretamine; Aequaline
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
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/s1Key: KNWVMRVOBAFFMH-HNNXBMFYSA-N
SMILES
  • Oc1c4c(ccc1OC)C3c2c(cc(OC)c(O)c2)CCN3C4
Properties
Chemical formula C19H21NO4
Molar mass 327.380 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. It is found in many plants, including opium poppy, Croton flavens, and certain plants in the genus Erythrina.

Studies show that scoulerine is an antagonist in vitro at the α2-adrenoceptor, α1D-adrenoceptor and 5-HT receptor. It has also been found to be a GABAA receptor agonist in vitro.

References

  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.
  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.
  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.
  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.
  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.
  6. Ko FN; Guh JH; Yu SM; Hou YS; Wu YC; Teng CM (1994). "(−)-Discretamine, a selective α1D-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.
  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.
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