Scoulerine

Last updated
Scoulerine
Scoulerine Scoulerine-S.png
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
PubChem CID
  • 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 Yes check.svgY
    Key: KNWVMRVOBAFFMH-HNNXBMFYSA-N Yes check.svgY
  • 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).

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]

Biosynthesis

Scoulerine is produced by action of the enzyme reticuline oxidase, which uses oxygen to convert the N-methyl group of (S)-reticuline into a so-called "berberine bridge". [8] [9] [10]

(S)-reticuline.svg
(S)-reticuline
 
O2
2 H2O
Scoulerine
 
 
 
Scoulerine-S.png
scoulerine

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. 1 2 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.
  8. ↑ Steffens P, Nagakura N, Zenk MH (1984). "The berberine bridge forming enzyme in tetrahydroprotoberberine biosynthesis". Tetrahedron Lett. 25 (9): 951–952. doi:10.1016/S0040-4039(01)80070-8.
  9. ↑ Dittrich H, Kutchan TM (1991). "Molecular cloning, expression, and induction of berberine bridge enzyme, an enzyme essential to the formation of benzophenanthridine alkaloids in the response of plants to pathogenic attack". Proc. Natl. Acad. Sci. U.S.A. 88 (22): 9969–73. Bibcode:1991PNAS...88.9969D. doi: 10.1073/pnas.88.22.9969 . PMC   52848 . PMID   1946465.
  10. ↑ Kutchan TM, Dittrich H (1995). "Characterization and mechanism of the berberine bridge enzyme, a covalently flavinylated oxidase of benzophenanthridine alkaloid biosynthesis in plants". J. Biol. Chem. 270 (41): 24475–81. doi: 10.1074/jbc.270.41.24475 . PMID   7592663.
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