Alkaloids from the roots of Stemona javanica (Kunth) Engl. (Stemonaceae) and their anti-malarial, acetylcholinesterase inhibitory and cytotoxic activities

Abstract

. Alkaloids from the roots of Stemona javanica (Kunth) Engl. (Stemonaceae) and their anti-malarial, acetylcholinesterase inhibitory and cytotoxic activities. Phytochemistry Letters, Alkaloids from the roots of Stemona javanica (Kunth) Engl. (Stemonaceae) and their anti-malarial, acetylcholinesterase inhibitory and cytotoxic activities AbstractTwo new protostemonine-type alkaloids, javastemonine A and B (3 and 4) have been isolated from the root extracts of Stemona javanica together with four known Stemona alkaloids, 13-demethoxy-11(S*),12(R*)-dihydroprotostemonine (1), isoprotostemonine (2), protostemonine and isomaistemonine. The structures and relative configurations of the new alkaloids were determined by spectroscopic analysis. The alkaloids 1 and 2 and protostemonine showed moderated antiplasmodial activities against the Plasmodium falciparum strains, TM4 (IC50 values of 17.7 ± 3.7, 16.8 ± 5.4, 16.0 ± 4.2 μg/mL, respectively) and K1 (IC50 values of 16.8 ± 3.1, 14.1 ± 3.7, 11.9 ± 3.3 μg/mL, respectively). These compounds showed no significant cytotoxicities against KB or Vero cells or acetylcholinesterase inhibitory activities. Disciplines Medicine and Health Sciences | Social and Behavioral Sciences Publication DetailsRamli, R., Pudjiastuti, P., Tjahjandaric, T. S., Lie, W., Rattanajak, R., Kamchonwongapaisan, S. & Pyne, S. G. values of 17.7 ± 3.7, 16.8 ± 5.4, 16.0 ± 4.2 µg/mL, respectively) and K1 (IC 50 values of 16.8 ± 3.1, 14.1 ± 3.7, 11.9 ± 3.3 µg/mL, respectively). These compounds showed no significant cytotoxicities against KB or Vero cells or acetylcholinesterase inhibitory activities.2

Inhibitory Activity and Docking Analysis of Antimalarial Agents from Stemona sp. toward Ferredoxin-NADP+ Reductase from Malaria Parasites

“…The IC 50 of croomine to the DHFR was 5.29 μ M, while tuberostemonine was not active to the enzyme [ 17 ]. Ramli et al (2015) reported that isoprotostemonine and javastemonine A have low to in active against multidrug resistant K1CB1 and wild type and antifolate strains of P. falciparum parasites in vitro [ 20 ]. On the other hand, isoprotostemonine and javastemonine A showed negative inhibition and they accelerated FNR reaction.…”

“…On the other hand, isoprotostemonine and javastemonine A showed negative inhibition and they accelerated FNR reaction. The javastemonine A exhibited moderate activities against P. falciparum TM4 and KI strains with IC 50 of 17.7 and 16.8 ppm, respectively [ 20 ].…”

“…Previous study exhibited that tuberostemonine, croomine, and epi -croomine were treated to antifolate target of DHFR enzymes. Isoprotostemonine and javastemonine A from S. javanica were carried out against P. falciparum multidrug resistant and wild type parasites at Medical Molecular Research Unit, Thailand Science Park, Pathumthani, Thailand [ 20 ]. The structures of alkaloids were shown in Figure 1 .…”

Isolation and Bioactivities of Stemona Alkaloid: A Review

“…(11Z )-1 ′ ,2 ′ didehydrostemofoline displayed the strongest larvicidal activity with a LC50 value of 2.44 mM. In a study reported by Ramli et al, 61 3 alkaloids including 13-demethoxy-11(S*), 12(R*)-dihydroprotostemonine, isoprotostemonine, and protostemonine exhibited moderate antiplasmodial activities against the Plasmodium falciparum strains, TM4 (IC 50 values of 17.7 3.7, 16.8 5.4, and 16.0 4.2 mg/mL, respectively) and K1 (IC 50 values of 16.8 3.1, 14.1 3.7, and 11.9 3.3 mg/mL, respectively).…”

“…Isoneostemocochinine- N -oxide ( 96 ) and neostemocochinine- N -oxide ( 97 ), 2 alkaloids with an N-oxide group, were achieved from the roots of Stemona cochinchinensis (Figure 4). 60 Ramli et al 61 separated and identified javastemonines A ( 98 ) and B ( 99 ) from the root extracts of Stemona javanica (Figure 4). These compounds have a lactone ring attached to C11.…”