Alkaloids from Eschscholzia californica and Their Capacity to Inhibit Binding of [3H]8-Hydroxy-2-(di-N-propylamino)tetralin to 5-HT1A Receptors in Vitro

• Published in: Journal of natural products (Washington, D.C.) Vol. 69; no. 3; pp. 432 - 435
• Main Authors: Gafner, S, Dietz, B.M, McPhail, K.L, Scott, I.M, Glinski, J.A, Russell, F.E, McCollom, M.M, Budzinski, J.W, Foster, B.C, Bergeron, C
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.03.2006; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: 8-hydroxy-2-(di-N-propylamino)tetralin; 8-Hydroxy-2-(di-n-propylamino)tetralin - pharmacology; alkaloids; Alkaloids - chemistry; Alkaloids - isolation & purification; Alkaloids - pharmacology; Benzylisoquinolines - chemistry; Benzylisoquinolines - isolation & purification; Benzylisoquinolines - pharmacology; Biological and medical sciences; californidine; caryachine; chemical structure; Chemistry, Medicinal; cultured cells; Dioxoles - chemistry; Dioxoles - isolation & purification; Dioxoles - pharmacology; escholtzine; Eschscholzia - chemistry; Eschscholzia californica; General pharmacology; hamsters; human health; Humans; Life Sciences & Biomedicine; Medical sciences; methylcaryachine; methyllaurotetanine; Molecular Structure; naphthalene; Papaveraceae; pavine alkaloids; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; plant extracts; Plant Sciences; Receptor, Serotonin, 5-HT1A - drug effects; receptors; Science & Technology; serotonin; Serotonin Receptor Agonists - pharmacology; Serotonin receptors; spectral analysis; stereochemistry; SEROTONIN RECEPTOR; GLYCOSIDES; CLONING; PHARMACOLOGY; ARGEMONINE; CCKB; ABSOLUTE CONFIGURATION; EXTRACTS; EXPRESSION; DERIVATIVES; Organic cation; Ligand; Pharmacognosy; 5-HT7 serotonin receptor; In vitro; Naphthalene derivatives; Papaveraceae; Biological activity; Circular dichroism; Medicinal plant; Quaternary ammonium compound; Alkaloid; 5-HT1A Serotonine receptor; Dicotyledones; Angiospermae; Absolute configuration; Plant origin; Isolation; Above ground plant part; Spermatophyta; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np058114h

A 70% ethanol extract of California poppy (Eschscholzia californica) was able to bind to 5-HT1A and 5-HT7 receptors at 100 mu g/mL. The subsequent isolation procedure yielded the known alkaloids californidine (1), escholtzine (2), N-methyllaurotetanine (3), caryachine (4), and O-methylcaryachine (5), along with a new pavine alkaloid, 6S,12S-neocaryachine-7-O-methyl ether N-metho salt (7). The structure of 7 was determined by spectroscopic data interpretation, while the absolute stereochemistry was determined by means of circular dichroism. From the results obtained from the radioligand-binding assay of the pure compounds, including the commercially available protopine (6), it was evident that the activity on the 5-HT,A receptor was at least partly due to the presence of the aporphine alkaloid 3, which showed the highest inhibition of [H-3]8-hydroxy-2-(di-N-propylamino)tetralin ([H-3]8-OH-DPAT) binding with an EC50 value of 155 nM and a Ki of 85 nM.