Macroline–sarpagine and macroline–pleiocarpamine bisindole alkaloids from Alstonia angustifolia

Bioactive indole alkaloids isolated from Alstonia angustifolia

“…According to previous phytochemical investigations on Alstonia species, the effects described in traditional medicinal usage are probably due to the presence of indole alkaloids, which have been reported to be the major secondary metabolites of these plants (Hamaker and Cook, 1994; Osorio et al, 2008). Thus far, more than 60 indole alkaloids, with the majority being macroline-type derivatives, have been isolated and identified from A. angustifolia species (Ghedira et al, 1988; Hu, et al, 1989; Kam and Choo, 2004; Tan, et al, 2011; Tan, et al, 2013), and some of these compounds have been reported to possess antiprotozoal properties (Wright et al, 1992) and activities against multidrug-resistant in KB cells (Tan et al, 2011). …”

“…The present investigation led to the isolation and identification of a new sarpagine-type indole alkaloid ( 1 ), together with nine known alkaloids (Fig. 1), including four macroline derived alkaloids, 21-deoxy- N (4)-methyl-21-oxo- N (4),21-secotalpinine [ N (4)-methyl- N (4),21-secotalpinine, 2 ) (Kam et al, 2004)], alstonerinal ( 3 ) (Kam et al, 1999), alstonerine ( 4 ) (Bi et al, 1994), macrocarpine B ( 5 ) (Kam et al, 2004), a sarpagine-type alkaloid affinisine ( 6 ) (Zocoler et al, 2005), as well as four macroline-pleiocarpamine bisindole alkaloids, villalstonine ( 7 ) (Ghedira et al, 1988), villalstonine N (4)-oxide ( 8 ) (Ghedira et al, 1988), villalstonidine D ( 9 ) (Tan et al, 2013) and villalstonidine E ( 10 ) (Tan et al, 2013). …”

Bioactive indole alkaloids isolated from Alstonia angustifolia

“…According to previous phytochemical investigations on Alstonia species, the effects described in traditional medicinal usage are probably due to the presence of indole alkaloids, which have been reported to be the major secondary metabolites of these plants (Hamaker and Cook, 1994;Osorio et al, 2008). Thus far, more than 60 indole alkaloids, with the majority being macroline-type derivatives, have been isolated and identified from A. angustifolia species (Ghedira et al, 1988;Hu, et al, 1989;Kam and Choo, 2004;Tan, et al, 2011;Tan, et al, 2013), and some of these compounds have been reported to possess antiprotozoal properties (Wright et al, 1992) and activities against multidrug-resistant in KB cells (Tan et al, 2011).…”

“…The present investigation led to the isolation and identification of a new sarpagine-type indole alkaloid (1), together with nine known alkaloids ( Fig. 1), including four macroline derived alkaloids, 21-deoxy-N(4)-methyl-21oxo-N(4),21-secotalpinine [N(4)-methyl-N(4),21-secotalpinine, 2) (Kam et al, 2004)], alstonerinal (3) (Kam et al, 1999), alstonerine (4) (Bi et al, 1994), macrocarpine B (5) (Kam et al, 2004), a sarpagine-type alkaloid affinisine (6) (Zocoler et al, 2005), as well as four macroline-pleiocarpamine bisindole alkaloids, villalstonine (7) (Ghedira et al, 1988), villalstonine N(4)-oxide (8) (Ghedira et al, 1988), villalstonidine D (9) (Tan et al, 2013) and villalstonidine E (10) (Tan et al, 2013).…”

Stereospecific Approach to the Synthesis of Ring-A Oxygenated Sarpagine Indole Alkaloids. Total Synthesis of the Dimeric Indole Alkaloid P-(+)-Dispegatrine and Six Other Monomeric Indole Alkaloids

“…24 Additionally, 6 is known to exhibit promising vasorelaxant actvity. 25 Most recently, 6 and 7 were found to be present in some of the new macroline-sarpagine bisindoles (13–15, Figure 2) isolated from Alstonia angustifolia by Kam et al 26 The promising bioactivity of some of the members of these ring-A oxygenated group of indole alkaloids combined with their complex architecture made them very attractive targets.…”