Strychnogucines A and B, Two New Antiplasmodial Bisindole Alkaloids from Strychnos icaja

• Published in: Journal of natural products (Washington, D.C.) Vol. 64; no. 1; pp. 12 - 16
• Main Authors: Frédérich, Michel, De Pauw, Marie-Claire, Prosperi, Christelle, Tits, Monique, Brandt, Viviane, Penelle, Jacques, Hayette, Marie-Pierre, DeMol, Patrick, Angenot, Luc
• Format: Journal Article Web Resource
• Language: English
• Published: Washington, DC American Chemical Society 01-01-2001; Glendale, AZ American Society of Pharmacognosy
• Subjects: Alkaloids - isolation & purification; Alkaloids - pharmacology; Animals; Antimalarials - isolation & purification; Antimalarials - pharmacology; Biological and medical sciences; Biologie végétale (sciences végétales, sylviculture, mycologie...); General pharmacology; HeLa Cells; Human health sciences; Humans; Immunologie & maladie infectieuse; Immunology & infectious disease; Life sciences; Magnetic Resonance Spectroscopy; Mass Spectrometry; Medical sciences; Pharmacie, pharmacologie & toxicologie; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Pharmacy, pharmacology & toxicology; Phytobiology (plant sciences, forestry, mycology...); Plasmodium falciparum; Plasmodium falciparum - drug effects; Sciences de la santé humaine; Sciences du vivant; Spectrophotometry, Infrared; Spectrophotometry, Ultraviolet; Strychnine - analogs & derivatives; strychnogucine A; strychnogucine B; Congo(Democratic republic); Africa; Antineoplastic agent; Antimalarial; Angular nitrogen heterocycle; Lactam; Cytotoxicity; Medicinal plant; Plasmodium falciparum; Alkaloid; Dicotyledones; Angiospermae; Parasiticid; Loganiaceae; Aromatic compound; Tumor cell; Human; Protozoa; Apicomplexa; Root; Pharmacognosy; Polycyclic compound; In vitro; Biological activity; Cell line; Plant origin; Isolation; Spermatophyta; Structural analysis
• ISSN: 0163-3864; 1520-6025; 1520-6025
• DOI: 10.1021/np000285t

A reinvestigation of Strychnos icaja roots has resulted in the isolation of two tertiary quasi-symmetric bisindole alkaloids named strychnogucines A (1) and B (2). Their structures were identified by means of spectroscopic data interpretation. Compound 2 was highly active in vitro and compound 1 moderately active against four strains of Plasmodium falciparum. Strychnogucine B (2) was more active against a chloroquine-resistant strain than against a chloroquine-sensitive one (best CI50, 80 nM against the W2 strain). In addition, this compound showed a selective antiplasmodial activity with 25−180 times greater toxicity toward P. falciparum, relative to cultured human cancer cells (KB) or human fibroblasts (WI38).