Scoulerine

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title: "Scoulerine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["isoquinolinoisoquinolines", "natural-opium-alkaloids", "hydroxyarenes", "catechol-ethers", "methoxy-compounds"] topic_path: "general/isoquinolinoisoquinolines" source: "https://en.wikipedia.org/wiki/Scoulerine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| 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 = | ChemSpiderID = 388725 | ChEMBL_Ref = | ChEMBL = 1235966 | PubChem = 439654 | StdInChI_Ref = | 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 = | StdInChIKey = KNWVMRVOBAFFMH-HNNXBMFYSA-N | CASNo_Ref = | CASNo = 6451-73-6 | ChEBI_Ref = | ChEBI = 17129 | KEGG_Ref = | 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. 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

References

  1. (2015). "Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants". BMC Plant Biology.
  2. (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.]].
  3. (2003). "Alkaloids from ''Croton flavens L.'' and their affinities to GABA-receptors". [[Nat Prod Res]].
  4. Ito K. (1999). "Studies on the alkaloids of ''Erythrina'' plants". Yakugaku Zasshi.
  5. (1993). "Pharmacological activity of (−)-discretamine, a novel vascular α-adrenoceptor and 5-hydroxytryptamine receptor antagonist, isolated from ''Fissistigma glaucescens''". [[Br J Pharmacol]].
  6. (1994). "(−)-Discretamine, a selective α1D-adrenoceptor antagonist, isolated from ''Fissistigma glaucescens''". [[Br J Pharmacol]].
  7. (2003). "Positive cooperation of protoberberine type 2 alkaloids from ''Corydalis cava'' on the GABA(A) binding site". [[Planta Med.]].

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isoquinolinoisoquinolinesnatural-opium-alkaloidshydroxyarenescatechol-ethersmethoxy-compounds