Scoulerine

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Scoulerine
Scoulerine
Names
IUPAC name
(13aS)-3,10-dimethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline-2,9-diol
Other names
Discretamine, Aequaline, Scoulerin.
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
Properties
C19H21NO4
Molar mass 327.37 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Scoulerine, also known as discretamine and aequaline, is a benzylisoquinoline alkaloid that derives from reticuline and is a precursor of berberine. It is found in many plants, including Opium poppy,[1] Croton flavens,[2] and certain plants in the Erythrina genus.[3]

Studies show that scoulerine is an antagonist in vitro at the α2-adrenoceptor, α1D-adrenoceptor and 5-HT receptor.[4][5] It has also been found to be a GABAA receptor agonist in vitro.[2][6]

References[edit]

  1. ^ 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. 
  2. ^ 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. 
  3. ^ Ito K (1999). "Studies on the alkaloids of Erythrina plants". Yakugaku Zasshi. 119 (5): 340–356. PMID 10375996. 
  4. ^ 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 2175899Freely accessible. PMID 7902181. 
  5. ^ 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 1910235Freely accessible. PMID 7952879. 
  6. ^ 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.