Scoulerine

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
  • 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 checkY
    Key: KNWVMRVOBAFFMH-HNNXBMFYSA-N checkY
  • Oc1c4c(ccc1OC)C[C@H]3c2c(cc(OC)c(O)c2)CCN3C4
Properties
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).
☒N verify (what is checkY☒N ?)

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, α1D-adrenoceptor and 5-HT receptor.[5][6] It has also been found to be a GABAA receptor agonist in vitro.[3][7]

References

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  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. ^ 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.
  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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