Contortisiliosides A‐G: Isolation of Seven New Triterpene Bisdesmosides from Enterolobium contortisiliquum and Their Cytotoxic Activity.

Abstract

Seven new bisdesmosidic triterpene saponins, with up to eight monosaccharides, which were given the trivial names contortisiliosides A ± G (1 ± 7), were isolated from Enterolobium contortisiliquum. The structures of the new saponins were determined on the basis of extensive spectroscopic and chromatographic analyses of both intact and acid-hydrolyzed compounds. The isolated saponins were evaluated for their cytotoxic activities against BAC1.2F 5 mouse macrophages, EL-4 mouse lymphoma cells, and L-929 mouse fibroblasts. Whereas contortisiliosides A (1) and C (3) were moderately cytotoxic to both BAC1.2F 5 macrophages and EL-4 cells, and contortisiliosides D ± G (4 ± 7) did not show any apparent cytotoxic activities against the three cell lines, contortisilioside B (2) exhibited selective cytotoxic activity against BAC1.2F 5 mouse macrophages, with an IC 50 value of 3.4 mm. The macrophage death caused by 2 was shown to be neither necrotic nor apoptosis-inducing based on the unique morphological change of the killed cells, whose cytosols were transformed into large vacuoles, and according to the TUNEL assay.

Experimental poisoning by Enterolobium contortisiliquum in sheep

“…Overall, the present results suggest that liver damage in cases of spontaneous intoxication occurs when animals do not experience acidosis (because of diet type and amount of pods consumed per day), but they ingest sufficiently high doses to cause liver damage. The hepatotoxicity of E. contortisiliquum is associated with the presence of triterpene bisdesmoside saponins (enterolosaponins A, B, and C and contortisilioside B), which are toxic to macrophages and/or murine lymphoma cells (Mimaki et al 2003(Mimaki et al , 2004.…”

“…Spontaneous intoxication was reported in cattle (Grecco et al 2002, Mendonça et al 2009), sheep (Bezerra et al 2012) and goats (Benicio et al 2007). The toxic active compound, appa- rently, consists of saponins, which are toxic to macrophages and lymphocytes (Mimaki et al 2003(Mimaki et al , 2004. Only mild photodermatitis was already reproduced experimentally (Grecco et al 2002), despite the epidemiological evidence that implicates this plant specie in hepatogenous photosensitization and abortion (Tokarnia et al 1999).…”

Natural and Experimental Poisoning of Cattle by Enterolobium contortisiliquum Pods (Fabaceae Mimosoideae) in Central-Western Brazil

“…In such cases photosensitization is unusual, because a sufficient number of hepatocytes commonly escape such damage, removing the phylloerythrin of circulation (Yager and Scott 1993). However, further experiments with the pods of E. contortisiliquum should be carried out on cattle so that the plant's importance as a photosensitizer can be proved, because it is known that the contortisiliosides found in the plant's pods, display moderate cytotoxic activity in vitro (Mimaki et al 2004). …”

“…in vitro cytotoxic activity (Mimaki et al 2004). It was also shown that the pods contain enterolobin, a haemolytic protein that induces a potent pleural exudation, cellular infiltration and paw oedema in rats (Castro-Faria-Neto et al 1991).…”

Intoxicação aguda e abortos em cobaias pelas favas de Enterolobium contortisiliquum (Leg. Mimosoideae)

“…Saponinas triterpénicas bismedesidicas denomindas de enterolosaponinas A e B (Mimaki et al 2003) e contortosiliosides A, B, C, D, E e G (Mimaki et al 2004) foram isoladas de E. contortisiliquum. Enterolosaponina A e contortisilioside B resultaram tóxicos para macrófagos de rato e contortisilioside A e C resultaram tóxicas para macrófagos de rato e células de linfoma murino (Minaki et al 2003(Minaki et al , 2004.…”