Dimeric Anthracenones from<i>Karwinskia</i>Species

Rivas, Gustavo Villacís; Torres, S. R.; Waksman, Noemí

doi:10.1055/s-2006-961151

Cited by 14 publications

(5 citation statements)

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“…The anthracenone compound known as T‐514 or peroxisomicine A1 (PA1), T544, T‐496, and T‐516 in the buckthorn fruit are responsible for its toxicity ( Dreyer et al, 1975; Rivas et al, 1990; Waksman and Ramirez, 1992 ) . Buckthorn fruit produces a distal, ascending, symmetrical, and progressive flaccid paralysis of the limbs in humans and animals 3 or 4 week after ingestion.…”

Section: Introductionmentioning

confidence: 99%

An experimental model of peripheral neuropathy induced in rats by Karwinskia humboldtiana (buckthorn) fruit

Salazar-Leal¹,

Flores²,

Sepúlveda-Saavedra³

et al. 2006

J Peripheral Nervous Sys

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Intoxication by Karwinskia humboldtiana (buckthorn) fruit presents a neurological picture similar to that of Guillain-Barré syndrome. In this report, we describe an experimental animal model of peripheral neuropathy induced by buckthorn fruit. Four groups of Wistar rats received one oral dose of 1.5 g/kg followed by oral doses of 0.5 g/kg at days 3, 7, 10, and 14 of dried and ground buckthorn fruit in aqueous suspension. Rats were sacrificed at 24, 48, 58, and 112 days after initial dose. Treated animals developed progressive paralysis through 58 days, then completely recovered by 112 days. Sciatic nerves showed segmental demyelination and cellular infiltrates until 58 days after exposure and then remyelinating changes at 112 days. This experimental model for peripheral neuropathy is reproducible and easy to handle. Its manipulation is relatively innocuous and allows us to study reversible peripheral nerve damage. This model can be developed in other animal species and may be useful to test new therapies for peripheral neuropathy.

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Section: Introductionmentioning

confidence: 99%

An experimental model of peripheral neuropathy induced in rats by Karwinskia humboldtiana (buckthorn) fruit

Salazar-Leal¹,

Flores²,

Sepúlveda-Saavedra³

et al. 2006

J Peripheral Nervous Sys

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“…Although their absolute stereochemistry remains undefined, according to NMR spectra one should be the 3R,3′R isomer and the other the 3S,3′S isomer [6,20]. Isolation of isoperoxisomicine A1 from fruits of K. humboldtiana has also been reported [21]. Garza-Ocañas compared the hepatotoxicity of PA1 (T514) and PA2 in primary liver cell cultures.…”

Section: Compounds Isolated From the Karwinskia Genusmentioning

confidence: 98%

“…Researchers were not able to find even traces of T510 after analyzing 50 samples of K. humboldtiana collected in different locations, which suggest that the isolation of T510 can be used to distinguish between the tehuacana and the humboldtiana species. T510 showed similar toxicity than T514 in preliminary studies [21]. Garza-Ocañas compared the hepatotoxicity of PA1 (T514) and PA2 in primary liver cell cultures.…”

Section: Compounds Isolated From the Karwinskia Genusmentioning

confidence: 99%

“…Rivas et al [21] isolated from the fruit of K. tehuacana T496, T514, and T544, but also a fourth compound characterized by chromatography and spectra data as anhydroperoxisomicine-quinone-A1 or T510 ( Figure 4). Researchers were not able to find even traces of T510 after analyzing 50 samples of K. humboldtiana collected in different locations, which suggest that the isolation of T510 can be used to distinguish between the tehuacana and the humboldtiana species.…”

Section: Compounds Isolated From the Karwinskia Genusmentioning

confidence: 99%

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Toxicity and Anticancer Potential of Karwinskia: A Review

et al. 2020

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Karwinskia genus consists of shrubs and small trees. Four toxic compounds have been isolated from Karwinskia plants, which were typified as dimeric anthracenones and named T496, T514, T516, and T544. Moreover, several related compounds have been isolated and characterized. Here we review the toxicity of the fruit of Karwinskia plants when ingested (accidentally or experimentally), as well as the toxicity of its isolated compounds. Additionally, we analyze the probable antineoplastic effect of T514. Toxins cause damage mainly to nervous system, liver, lung, and kidney. The pathophysiological mechanism has not been fully understood but includes metabolic and structural alterations that can lead cells to apoptosis or necrosis. T514 has shown selective toxicity in vitro against human cancer cells. T514 causes selective and irreversible damage to peroxisomes; for this reason, it was renamed peroxisomicine A1 (PA1). Since a significant number of malignant cell types contain fewer peroxisomes than normal cells, tumor cells would be more easily destroyed by PA1 than healthy cells. Inhibition of topoisomerase II has also been suggested to play a role in the effect of PA1 on malignant cells. More research is needed, but the evidence obtained so far indicates that PA1 could be an effective anticancer agent.

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“…It is distributed throughout the Mexican Republic, South America, Central America and Northern of Colombia (Fernández, 1992). Dreyer et al (1975) isolated from the endocarp of Kh four dimeric anthracenonic compounds named as T-496, T-514, T-516 and T 544, according to their molecular weights, which have been demonstrated to be responsible for the toxicity of this plant (Dreyer et al, 1975;Waksman et al, 1989, Rivas et al, 1990Bermúdez et al, 1992, Waksman andRamirez, 1992).…”

Section: Introductionmentioning

confidence: 99%

Liver damage in an experimental model of peripheral neuropathy induced by Karwinskia humboldtiana (Buckthorn) fruit: Histopathological evidence

García-Garza¹,

Salazar-Leal²,

Romero-DÃaz³

et al. 2016

J. Med. Plants Res.

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Karwinskia humboldtiana (Kh) is a poisonous shrub that causes acute or chronic intoxication in animals and humans. In chronic intoxication, the main sign is the presence of paralysis. Previously we reported a model of intoxication with Kh fruit that reproduces paralysis and clinical phases in humans when they do not die; however, there are no studies that describe damage to liver in this model. The objective was to evaluate histopathological alterations in liver during chronic intoxication. Wistar rats (n=25) were divided into five groups (n= 5). Four groups were intoxicated with Kh and one received only water as a control group. Animals were euthanized at different times during paralysis evolution. Samples of liver were obtained, and processed either for light or electron microscopy evaluation. Histological, histochemistry and immunohistochemistry analyses were performed, including a morphometric analysis. Results demonstrated necrotic areas, vascular congestion and vacuoles in the cytoplasm of hepatic cells that increased during intoxication and decreased in the recovery stage. These findings were confirmed at electron microscopy level. Morphometric analysis demonstrated statistically significant difference in occurrence of necrotic cells and PCNA positive cells between control and intoxicated groups. This was not observed with TUNEL staining. These findings demonstrate that during Kh intoxication there is a severe damage in liver that is reversible. Thus, it could be suggested that Kh causes a systemic intoxication not only damage to peripheral nervous system.

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Dimeric Anthracenones fromKarwinskiaSpecies

Cited by 14 publications

References 0 publications

An experimental model of peripheral neuropathy induced in rats by Karwinskia humboldtiana (buckthorn) fruit

An experimental model of peripheral neuropathy induced in rats by Karwinskia humboldtiana (buckthorn) fruit

Toxicity and Anticancer Potential of Karwinskia: A Review

Liver damage in an experimental model of peripheral neuropathy induced by Karwinskia humboldtiana (Buckthorn) fruit: Histopathological evidence

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