N1,N2,N3-Trisisopentenyl Guanidine and N1,N2-Diisopentenyl Guanidine, Two Cytotoxic Alkaloids from Alchornea Cordifolia (Schumach. & Thonn.) Müll. Arg. (Euphorbiaceae) Root Barks

Abstract

This paper describes the purification of two guanidine alkaloids: N1, N2-diisopentenyl guanidine (DIPG) 1 and N1,N2,N3-triisopentenyl guanidine (TIPG) 2 from Alchornea cordifolia root bark and reports their cytotoxic properties on cancer (HeLa, Mel-5, J774) and non cancer (WI 38) cells. TIPG showed the highest cytotoxicity with IC50 values from 0.7 to 14.3 μg/mL (2.6 to 54.3 μM) on the four cell lines while DIPG was much less active: IC50 45.8 and 97.6 μg/mL (234.8 and 500.5 μM) on Mel-5 and HeLa and > 512.8 μM on J774 and WI 38. The results indicate that the cytotoxicity notably decreased with the loss of one isopentenyl substituent.

Anti-inflammatory compounds from leaves and root bark of Alchornea cordifolia (Schumach. & Thonn.) Müll. Arg.

“…As the alkaloid rich fraction was also previously shown to have AIA (Mavar-Manga et al, 2004), we also tested the two alkaloids, diisopentenyl guanidine (5) and triisopentenyl guanidine (6), recently isolated from the plant (Mavar-Manga et al, 2006). They exhibited a higher AIA than indomethacin, with the better activity for 6 (135% and 119% respectively of the activity of indomethacin) (Table 1).…”

“…They exhibited a higher AIA than indomethacin, with the better activity for 6 (135% and 119% respectively of the activity of indomethacin) (Table 1). 6, in contrast to 5, was cytotoxic on several cell lines (Mavar-Manga et al, 2006), so the possibility that the toxicity is related to the anti-inflammatory effect is reduced because 5 shows little cytotoxcity and may be a promising lead compound. This paper reports for the first time the presence of ␤-sitosterol (1), daucosterol (2), di(2-ethylhexyl) phthalate (3) in A. cordifolia leaves and their topical AIA.…”

“…Unfortunately, the yield of this extract was very low, so it was decided to isolate them from other A. cordifolia extracts from leaves and root bark, which contained the same compounds as could be seen from their chromatographic profiles. The alkaloids recently isolated from the root barks were also tested since, in our previous work, the alkaloid rich fraction also gave interesting anti-inflammatory activity (Mavar-Manga et al, 2004, 2006 (Fig. 1).…”

“…AR-H fraction also gave 2 (6.7 mg; 1920-1968 ml) and 4 (46.1 mg; 160-220 ml). 5 and 6, as well as compound 3, were isolated from AL-M fraction as previously described (Mavar-Manga et al, 2006).…”

Recent trends in phytochemistry, ethnobotany and pharmacological significance of Alchornea cordifolia (Schumach. & Thonn.) Muell. Arg.

“…More recently, paracetamol induced hepatotoxicity was used as a model to investigate the hepatoprotective effect of A. cordifolia leaves in combination with Costus afer. The mixture of both plants could lower the level of liver enzymes including AST, ALT and ALP (Arhoghro et al, 2015)(Table 5) Mavar-Manga et al (2006). conducted a study in order to provide the therapeutic potential of A. cordifolia in the treatment of cancer.…”