Antiplasmodial activity of sesquilignans and sesquineolignans from Bonamia spectabilis

• Published in: Phytochemistry (Oxford) 2002-05, Vol.60 (2), p.167-173
• Main Authors: Kraft, Carola, Jenett-Siems, Kristina, Köhler, Inga, Tofern-Reblin, Britta, Siems, Karsten, Bienzle, Ulrich, Eich, Eckart
• Format: Article
• Language: English
• Subjects: Animals; Antimalarials - chemistry; Antimalarials - pharmacology; Antiplasmodial activity; Biological and medical sciences; Bonamia spectabilis; Bonaspectin C 4″- O-glucoside; Chemical constitution; Chloroquine - pharmacology; Convolvulaceae; Convolvulaceae - chemistry; Drug Resistance; Fundamental and applied biological sciences. Psychology; General pharmacology; Inhibitory Concentration 50; Lignans; Lignans - chemistry; Lignans - pharmacology; Magnetic Resonance Spectroscopy; Medical sciences; Molecular Structure; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plant physiology and development; Plasmodium falciparum; Plasmodium falciparum - drug effects; Sesquilignans; Sesquineolignans
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/S0031-9422(02)00101-2

Phytochemical re-investigation of the aerial parts of Bonamia spectabilis (Convolvulaceae) led to the isolation of four minor tetrahydrofuran-type sesquilignans (bonaspectins E–H) together with the known neolignan virolongin A and the known lignan rel-(7 S,8 R,7′ R,8′ R)-3,3′,4,4′,5,5′-hexamethoxylignan. Their structures were established on the basis of spectral data. These six compounds as well as further seven lignanoids from B. spectabilis, characterised previously, were tested for their antiplasmodial activity against a chloroquine-sensitive strain (PoW) and a chloroquine-resistant clone (Dd2) of Plasmodium falciparum. Bonaspectin C 4″- O-glucoside, its aglycone, and bonaspectin D 4″- O-glucoside revealed the highest antiplasmodial activities (IC 50 values: 1.3, 2.0, 6.5 μM [PoW]; 1.7, 4.6, 3.7 μM [Dd2], respectively). Four minor tetrahydrofuran-type sesquilignans (bonaspectins E–H) together with virolongin A and rel-(7 S,8 R,7′ R,8′ R)-3,3′,4,4′,5,5′-hexamethoxylignan have been isolated from the aerial parts of Bonamia spectabilis (Convolvulaceae). These compounds as well as further lignanoids of this plant species were tested for their antiplasmodial activity in vitro.