Strictamine

Cascade Reactions: A Driving Force in Akuammiline Alkaloid Total Synthesis

“…[2] As a result, scientists have investigated the pharmacological effects of akuammiline alkaloids and discovered their wide range of biological properties, which span from anticancer to analgesic effects. For example, (À)-echitamine (1), which was first isolated in 1875, [3] displays both in vitro and in vivo cytotoxicity, [4] whereas (+)-strictamine (2) [5] inhibits the transcription factor NF-kB ( Figure 2). [6] Additionally, derivatives of (+)-picraline (3) [7] inhibit the renal cortex protein SGLT2, [8] while (À)-aspidophylline A [(À)-4] reverses drug resistance in cancerous cell lines.…”

“…[1] Although detailed biosynthetic studies have not been performed, the proposed biogenesis of various akuammilines sheds light on how nature likely assembles these intricate scaffolds. As shown in Figure 3, the union of tryptamine (5) and the monoterpenoid (À)-secologanin (6) first results in the formation of the natural product (+)-geissoschizine (7). In turn, 7 serves as the progenitor to many different alkaloid frame-works including the strychnos, marvacurine, and akuammiline varieties.…”

Sewarine, a New Phenolic Akuammicine Alkaloid from Rhazya stricta

“…Rhazya stricta (Apocynaceae) is used in the unani system for antitumor treatment; previous investigations showed it to be a rich sourceof indole alkaloids. So far, (-)-quebrachamine( I), akuammidine (rhazine) (2), rhazidine (3)(4)(5), (+)-1,2-dehydroaspidospermidine (6), (k)-and (+)-vincadifformine (6), aspidospermidine (7), eburnamonine (7), eburnamenine (7), and vincamidine (strictamine) (8) and the biogenetically important secamines (9), secodines (lo), and strictosidine (1 1) have been isolated. As part of the continuing investigations of the phenolic alkaloids of this plant, a new alkaloid, sewarine, was obtained (12).…”

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progrès Dans La Chimie Des Substances Organiques Naturelles

“…These processes are, however, of limited value even among closely related substances. In the spectrum of powellane (182) the peak corresponding to M-SS has become very small and it is absent in that of deacetylbowdensine (183) which is quite barren of peaks (except that corresponding to the molecular ion), although it contains two functionalities more than (182). for example, exhibits neither a peak at M-SS nor one at M-70.…”

“…The alkaloids which contain this group of acids are shown in Table I9 (p. 392) and may be classified as esters of heliotridine (181, R' = OH or angelate), esters of trachelanthamidine (182), and esters of lindelofidine (183) wherethegroupR·COOisCHa·CHY ·C(OH) [CX(CH a )2J ·COO. The alkaloid indicine is of interest in that it is the only alkaloid in the Crotalaria spp.…”