Studies on the Alkaloids of Berberidaceous Plant. XXXIII

Abstract

A small amount of the tertiary phenolic base, m.p. 128°, isolated from Nandina domestica f. shinananten HORT. (Japanese name " Shina-nanten "), which was reported previously, has been identified as isoboldine (I).

Online Structural Elucidation of Alkaloids and Other Constituents in Crude Extracts and Cultured Cells of Nandina domestica by Combination of LC-MS/MS, LC-NMR, and LC-CD Analyses

“…The compound corresponding to peak d 1 was identified as nantenine by comparison of its LC-NMR spectrum (Figure , D) with that of domesticine (Figure , C). Isoboldine, sinoacutine, domesticine, and nantenine have been isolated previously from N. domestica . − ,− …”

“…Isoboldine, sinoacutine, domesticine, and nantenine have been isolated previously from N. domestica. [4][5][6][7][8][10][11][12][13][14][15][16][17][18] The absolute configuration at C-6a of the isolated aporphine alkaloids (isoboldine, domesticine, and nantenine) were determined from LC-CD analysis. Initially, CD spectra of commercially available (S)-boldine and (S)-isocorydine in the stopped-flow mode were recorded at 220-420 nm to find a suitable wavelength for the measurement of LC-CD spectra.…”

“…Shoji et al reported that the alkaloid nantenine is a serotonergic receptor antagonist. The fruits, seeds, roots, and stem bark contain aporphine-, promorphine-, protoberberine-, and protopine-type alkaloids. − Twelve protoberberines and magnoflorine have been identified from tissue cultures of N. domestica . − …”

“…The fruits, seeds, roots, and stem bark contain aporphine-, promorphine-, protoberberine-, and protopine-type alkaloids. [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] Twelve protoberberines and magnoflorine have been identified from tissue cultures of N. domestica. [19][20][21][22] Application of LC-NMR combined with LC-MS to drug metabolism, identification of natural products in crude plant extracts and the characterization of isomeric mixtures prepared by chemical reactions have been summarized.…”

The Aporphine Alkaloids

“…new aporphine alkaloid, has been obtained from the trunk bark of Nandina domestica(20,123).Hofmann degradation of isoboldine diethyl ether yielded 3,6-dimethoxy-4,7-diethoxy-l-vinylphenanthrene. Subsequent oxidation and decarboxylation gave 2,5-diethoxy-3,6-dimethoxyphenanthrene.…”