Three New Monoterpenoid Indole Alkaloids from Ervatamia pandacaqui

Abstract

Three new monoterpenoid indole alkaloids, ervapandine A (1), (3R)-hydroxyibogaine (3), 12-hydroxyakuammicine N(4)-oxide (6), along with four known ones, were isolated from the twigs and leaves of Ervatamia pandacaqui. The structures of the new alkaloids were elucidated by spectroscopic methods and sugar hydrolysis experiment. All of the compounds were evaluated for their cytotoxicity against three human cell lines. Compound 7 showed moderate cytotoxic activity.

Chemical Diversity and Bioactivities of Monoterpene Indole Alkaloids (MIAs) from Six Apocynaceae Genera

“…Ervapandine A ( 354 ) [ 182 ], 3 R -hydroxyibogaine ( 355 ) [ 182 ], and 12-hydroxyakuammicine N 4 -oxide ( 356 ) [ 182 ], along with four known ones, 313 , 305 , 19- epi -voacristine ( 357 ) [ 183 ] , taberdivarine I ( 358 ) [ 184 ] and 12-hydroxyakuamicine ( 359 ) [ 185 ], ( Figure 28 ) were identified from the leaves and twigs of Chinese E. pandacaqui [ 182 ].…”

“…Liu et al (2018) [ 186 ] studied the roots of E. divaricate and identified two unprecedented trimeric MIAs, Ervadivamines A ( 360 ) and B ( 361 ), together with the dimeric compound, 19,20-dihydroervahanine A ( 362 ), ( Figure 29 ) and two monomeric ones, ibogaine ( 305 ) and Ibogamine (363 ) [ 187 ] . Compound 359 displayed a moderate cytotoxic effect against MCF-7, with an IC 50 value = 33.61 μM [ 182 ]. Compound 360 showed a significant positive cytotoxicity against MCF-7, A-549, HT-29 and HepG2/ADM and showed potent effect against HepG2/ADM, with an IC 50 value = 12.55 ± 0.54 μM (Adriamycin, IC 50 = 45.70 ± 2.15 μM) [ 186 ].…”

“…Ervapandine A (354) [182], 3R-hydroxyibogaine (355) [182], and 12-hydroxyakuammicine N 4 -oxide (356) [182], along with four known ones, 313, 305, 19-epi-voacristine (357) [183], taberdivarine I (358) [184] and 12-hydroxyakuamicine (359) [185], (Figure 28) were identified from the leaves and twigs of Chinese E. pandacaqui [182]. Liu et al (2018) [186] studied the roots of E. divaricate and identified two unprecedented trimeric MIAs, Ervadivamines A (360) and B (361), together with the dimeric compound, 19,20-dihydroervahanine A (362), (Figure 29) and two monomeric ones, ibogaine (305) and Ibogamine (363) [187].…”