Rotenoids, Flavonoids, and Chalcones from the Root Bark of Millettia usaramensis

Abstract

Five new compounds, 4-O-geranylisoliquiritigenin (1), 12-dihydrousararotenoid B (2), 12-dihydrousararotenoid C (3), 4'-O-geranyl-7-hydroxyflavanone (4), and 4'-O-geranyl-7-hydroxydihydroflavanol (5), along with 12 known natural products (6-17) were isolated from the CH2Cl2/MeOH (1:1) extract of the root bark of Millettia usaramensis ssp. usaramensis by chromatographic separation. The purified metabolites were identified by NMR spectroscopic and mass spectrometric analyses, whereas their absolute configurations were established on the basis of chiroptical data and in some cases also by X-ray crystallography. The crude extract was moderately active (IC50 = 11.63 μg/mL) against the ER-negative MDB-MB-231 human breast cancer cell line, and accordingly compounds 6, 8, 9, 10, 12, and 16 also showed moderate to low cytotoxic activities (IC50 25.7-207.2 μM). The new natural product 1 exhibited antiplasmodial activity with IC50 values of 3.7 and 5.3 μM against the chloroquine-sensitive 3D7 and the chloroquine-resistant Dd2 Plasmodium falciparum strains, respectively, and was also cytotoxic to the HEK293 cell line.

Isoflavones Isolated from the Seeds of Millettia ferruginea Induced Apoptotic Cell Death in Human Ovarian Cancer Cells

“…Phytochemical studies with Millettia species revealed that these species have a rich source of flavonoids, including isoflavonoids, rotenoids, chalcones, and pterocarpans [11,12]. M. ferruginea (Hochst) Baker, is an endemic of Ethiopia and has two representative species; ssp.…”

Enantiomeric high-performance liquid chromatography resolution and absolute configuration of 6β-benzoyloxy-3α-tropanol

“…Alternatively, compounds previously isolated using chromatographic instrumentation can be studied offline using suitable methodologies. Among these are the conventional usage of ECD and polarimetric measurements , chemical correlation , diasteromeric NMR analysis , X‐ray diffraction analysis , when one is lucky and obtains crystalline samples, and VCD []. The later technique has shown many advantages for the stereochemical analysis of natural substances since it can be applied in the solution state with the use of rather inexpensive computational calculations.…”

Antimicrobial activity and DNA-fragmentation effect of isoflavonoids isolated from seeds of Millettia ferruginea, an endemic legume tree in Ethiopia

“…Traditionally, the indigenous people use aerial parts of Millettia plants as fishing poison and protecting stored food-grains from insects, which appear to be compatible with the typical presence of rotenoid compounds found in M. ferruginea and other species [3]. Most of the published literature on Millettia involved phytochemical analysis of the plant samples and this genus was found to contain a rich variety of structurally distinct isoflavonoids [5,15,23,24]. Unfortunately, these compounds have not been studied adequately regarding their prospective pharmacological properties.…”

“…contains various phenolic compounds belonging to the groups of flavonoids, alkaloids, rotenoids, diterpenes and pterocarpans [5,15,23,24]. Initially, the isoflavonoid durmillone was isolated from the seeds of Millettia dura and M. ferruginea [4,27].…”