From Wikipedia, the free encyclopedia
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
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
Y Key: KNWVMRVOBAFFMH-HNNXBMFYSA-N
Y
Oc1c4c(ccc1OC)C[C@H]3c2c(cc(OC)c(O)c2)CCN3C4
Properties
C 19 H 21 N O 4
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).
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 .
[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
^ 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 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 .
^ 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 .