Three New Indole Alkaloids from the Leaves of Alstonia scholaris

Abstract

Three new akuamillan-type indole alkaloids, i.e., 5-methoxystrictamine ( methyl (5b,16R,19E)-5methoxyakuammilan-17-oate; 1), methyl (16R,19E)-1,2-dihydro-16-(hydroxymethyl)-5-oxoakuammilan-17oate (2), and methyl (2b,16R,19E)-4,5-didehydro-1,2-dihydro-2-hydroxy-16-(hydroxymethyl)akuammilan-4ium-17-oate chloride (3), have been isolated from the leaves of Alstonia scholaris, together with ten known compounds. Their structures were determined by spectroscopic means. None of the constituents showed significant cytotoxic activity towards WT cells.

Effects of indole alkaloids from leaf of Alstonia scholaris on post-infectious cough in mice

“…Its leaves have long been used in "dai" ethno-pharmacy for the treatment of whooping cough (post infectious cough), chronic bronchitis, asthma, and other respiratory tract infections in Yunnan Province, PR China (Compiling Group of Yunnan Traditional Chinese Medicine, 1977). Phytochemical constituents of different parts of the plant were investigated intensively by our group (Cai et al, 2010(Cai et al, , 2008a(Cai et al, , 2008b(Cai et al, , 2007Chen et al, 2016;Du et al, 2007aDu et al, , 2007bFeng et al, 2009Feng et al, , 2008Liu et al, 2015;Pan et al, 2016;Qin et al, 2015aQin et al, , 2015bXu et al, 2009;Yang et al, 2015aYang et al, , 2015bYang et al, , 2014aYang et al, , 2014bZhang et al, 2014;Zhou et al, 2005). Meanwhile, the chemical profiling and metabolites of alkaloidal extract of A. scholaris were reported (Cao et al, 2015), in which scholaricine, 19-epischolaricine, vallesamine, and picrinine were the major indole alkaloids of its leaf ( Fig.…”

Alstonic acids A and B, unusual 2,3-secofernane triterpenoids from Alstonia scholaris

“…It should be mentioned that the configuration of 5-OCH 3 in 5 was wrongly assigned in the original literature (Zhou et al, 2005) and should be revised to be in an a orientation. This discrepancy was observed by comparing the NMR spectroscopic data, especially the characteristic coupling constants, with those of analogues (Abe et al, 1994(Abe et al, , 1998.…”

“…have been extensively investigated; nearly 400 compounds have been isolated and characterized (Cai et al, 2008). Most of the compounds identified so far are indole and quinoline alkaloids (Abe et al, 1989;Atta-ur-Rahman et al, 1985, 1987Cai et al, 2007Cai et al, , 2008Macabeo et al, 2005;Salim et al, 2004;Yamauchi et al, 1990;Zhou et al, 2005). Alstonia scholaris (Linn.)…”

“…As part of our effort to discover structurally diverse and biologically active secondary metabolites from local medicinal plants, the phytochemical investigation of the leaves of A. scholaris has led to the isolation of alstonic acids A and B (1-2), new 2,3-secofernanetype triterpenoids, as well as a new monoterpene indole alkaloid, N 1 -methoxymethyl picrinine (3), together with six known alkaloids, picrinine (4) (Abe et al, 1989), 5a-methoxystrictamine (5) (Zhou et al, 2005), picralinal (6) (Abe et al, 1989), 19,20-(E)-vallesamine (7) (Atta-ur-Rahman et al, 1987), leuconolam (8) (Goh et al, 1984), and scholaricine (9) (Atta-ur-Rahman et al, 1985). To the best of our knowledge, this report is the first to document naturally occurring 2,3-secofernanes.…”

Alstonia scholaris: It′s Phytochemistry and pharmacology

“…5-methoxystrictamine (=methyl (5β,16R,19E)-5methoxyakuaramilan-17-oate, methyl (16R,19E)-1,2-dihydro-16-(hydroxymethyl)-5-oxoakuammilan-17-oate, and methyl (2β,16R,19E)-4,5-didehydro-1,2-dihydro-2-hydroxy-16-(hydroxymethyl) akuammilan-4-ium-17-oate chloride [39] Methanolic extract The first seco-uleine alkaloids, manilamine (18-hydroxy-19,20-dehydro-7,21-seco-uleine) and N4methyl angustilobine B, together with the known indole alkaloids, (E)-vallesamine, angustilobine B N4 oxide, (S)-tubotaiwine, and 6,7-seco-angustilobine B [40] Leaves extract Three new indole alkaloids, nareline ethyl ether, 5-epi-nareline ethyl ether and scholarine-N(4)oxide, in addition to nareline methyl ether, picrinine and scholaricine [41] Leaves extract Picrinine and akuammidine [42] Alcoholic extract Picralinal [43] Alcoholic extract A new indole alkaloid, alstonamine, and a sitsirikine type indole alkaloid, rhazimanine [44] Methanol extract A new alkaloid, 19,20-Z-vallesamine, along with 19,20-E-vallesamine [45] Leaves extract 19,20-Dihydrocondylocarpine [46] Ethanolic extract A new alkaloid, scholaricine, has been isolated. It was elucidated as 2 (demethylscholarine) [47] Ethanolic percolate A new alkaloid designated scholaricine.…”