Pronuciferine N-Oxide, a Proaporphine N-Oxide Alkaloid from Berberis coletioides

Abstract

Pronuciferine N-oxide (1), a proaporphine N-methyl-N-oxide alkaloid, along with the parent alkaloid pronuciferine (2) were isolated from Berberis coletioides. The structure of the new compound was determined by spectroscopic evidence. Compound 1 is the first naturally occurring proaporphinoid alkaloid with an N-oxide functionality.

Proaporphine and aporphine alkaloids with acetylcholinesterase inhibitory activity from Stephania epigaea

“…Compound 1 was obtained as a white amorphous powder and its molecular formula was deduced to be C 21 [6] which was also isolated from S. epigaea in this study, strongly suggested a proaporphine alkaloid for 1. The main difference between them was that compound 1 possesses no N-methyl group which exists To clarify the absolute configuration of C-6a and C-2′ in 1, the ECD data of four possible structures were calculated and compared with experimental spectrum.…”

“…An unusual proaporphine alkaloid bearing an isopropanenitrile group at isoquinoline nitrogen, named epigasine A (1) and a new aporphine alkaloid, epigasine B (2), together with eight known proaporphine/aporphine alkaloids, pronuciferine (3) [6], dehydrodicentrine (4) [7], romerine (5) [8], romeline (6) [9], Nmethylcalycinine (7) [10], phanostenine (8) [11,12], dicentrine (9) [13], and N-methyllaurotetanine (10) [14] (Fig. 1) were isolated from the roots of S. epigaea.…”

A review on biological and chemical diversity in Berberis (Berberidaceae)

“…B. tabiensis: Quevedo et al, 2008[ 101 ]. B. coletioides: Fajardo et al, 2009[ 34 ]. B. waziristanica: Hussain, 1992[ 52 ]).…”

New alkaloids sinomacutines A–E, and cephalonine-2-O-β-d-glucopyranoside from rhizomes of Sinomenium acutum

“…The additional ROESY correlation of H-6 0 a/H-12 0 indicated that H-6 0 a and H-12 0 were a syn-periplanar relationship and H-6 0 a was the b-orientation. 12 Furthermore, the electronic circular dichroism (ECD) spectra ( Fig. 3) of 1 showed negative trough (Dε, À1.61) and positive crest (Dε, þ4.75) at 273 and 232 nm, respectively, similar to those of sinomenine, suggesting that the absolute configuration of subunit 'a' was the same as that of sinomenine.…”