Chemistry:Scoulerine
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]
References
- ↑ Hagel, Jillian M; Morris, Jeremy S; Lee, Eun-Jeong; Desgagne-Penx, Isabel; Bross, Crystal D; Chang, Limei; Chen, Xue; Farrow, Scott C et al. (2015). "Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants". BMC Plant Biology 15: 227. doi:10.1186/s12870-015-0596-0. PMID 26384972. PMC 4575454. http://openlib.tugraz.at/download.php?id=564f2fa60a35b&location=browse.
- ↑ 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.
- ↑ 3.0 3.1 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.
- ↑ 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. 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. 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.
- ↑ "The berberine bridge forming enzyme in tetrahydroprotoberberine biosynthesis". Tetrahedron Lett. 25 (9): 951–952. 1984. doi:10.1016/S0040-4039(01)80070-8.
- ↑ "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. 1991. doi:10.1073/pnas.88.22.9969. PMID 1946465. Bibcode: 1991PNAS...88.9969D.
- ↑ "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. 1995. doi:10.1074/jbc.270.41.24475. PMID 7592663.
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