Anthraquinones with Antiplasmodial Activity from the Roots of Rennellia elliptica Korth. (Rubiaceae)

Abstract

Dichloromethane root extract of Rennellia elliptica Korth. showed strong inhibition of Plasmodium falciparum growth in vitro with an IC50 value of 4.04 µg/mL. A phytochemical study of the dichloromethane root extract has led to the isolation and characterization of a new anthraquinone, 1,2-dimethoxy-6-methyl-9,10-anthraquinone (1), and ten known anthraquinones: 1-hydroxy-2-methoxy-6-methyl-9,10-anthraquinone (2), nordamnacanthal (3), 2-formyl-3-hydroxy-9,10-anthraquinone (4), damnacanthal (5), lucidin-ω-methyl ether (6), 3-hydroxy-2-methyl-9,10-anthraquinone (7), rubiadin (8), 3-hydroxy-2-methoxy-6-methyl-9,10-anthraquinone (9), rubiadin-1-methyl ether (10) and 3-hydroxy-2-hydroxymethyl-9,10-anthraquinone (11). Structural elucidation of all compounds was accomplished by modern spectroscopic methods, notably 1D and 2D NMR, IR, UV and HREIMS. The new anthraquinone 1, 2-formyl-3-hydroxy-9,10-anthraquinone (4) and 3-hydroxy-2-methyl-9,10-anthraquinone (7) possess strong antiplasmodial activity, with IC50 values of 1.10, 0.63 and 0.34 µM, respectively.

Antiplasmodial potential and quantification of aloin and aloe-emodin in Aloe vera collected from different climatic regions of India

“…Several anthraquinones extracted from different plant parts strongly inhibited in vitro growth of a chloroquine sensitive strain of Plasmodium falciparum (3D7) [57]. Anthraquinones may generate reactive oxygen and thus inactivate malaria parasites ( Plasmodium falciparum, P. vinckei and P. berghei ) [58, 59].…”

Alkaloids and Anthraquinones from Malaysian Flora

“…H. capitellata contains furanoanthraquinones (Ahmad, et al, 2005) and H. dichotoma was reported to contain both 9,10-and 1,4-anthraquinone (Hamzah & Lajis, 1998). Genus Rennellia is closely related to Morinda and anthraquinones reported from R. elliptica are similar to those from genus Morinda (Osman et al, 2010). One particular difference is the occurrence of anthraquinone with methyl substitution at C-6 which is characteristic to this plant.…”

“…Its medicinal uses were documented as treatment of body aches, after-birth tonic and aphrodisiac (Mat Salleh & Latiff, 2002). The root extract of R. elliptica was reported to be antimalarial (Osman, et al, 2010) and antioxidant . Further study is warranted to investigate the antimalarial potential of roots of R. elliptca.…”

“…The plant extracts are used in form of poultice, lotion and decoction from various plant parts. Morinda, Hedyotis, Primatomeris and Rennellia are among anthraquinone containing-genera that are widely used in Malaysian traditional medicine (Ismail, et al, 1997;Jasril, et al, 2003;Ahmad, et al, 2005;Lajis, et al, 2006;Osman, et al, 2010).…”

Antimalarial evaluation of the leaf latex of Aloe citrina and its major constituent

“…[1920] For example, several anthraquinones isolated from the root extract of Rennellia elliptica Korth were found to inhibit strongly in vitro growth of a chloroquine sensitive strain of P. falciparum (3D7). [21] Similarly, aloe saponarin I isolated from A. saponaria has been reported to possess a good antiplasmodial activity against the P. falciparum Dd2. [19] 10-(Chrysophanol-7′-yl)-10-(β)-hydroxychrysophanol-9-anthrone and chryslandicin, isolated from the root of Kinphofia foliosa have also been found to display a strong in vitro antimalarial activity against the chloroquine-sensitive 3D7 strain of P. falciparum .…”