Effect of tingenone, a quinonoid triterpene, on growth and macromolecule biosynthesis inTrypanosoma cruzi

Goijman, Silvia G.; Turrens, Julio F.; Marini-Bettòlo, G. B.; Stoppani, A. O. M.

doi:10.1007/bf02007701

Cited by 26 publications

(14 citation statements)

References 20 publications

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“…Quantitative data are not available for miconidin, but espintanol exhibited an IC 90 in the 25-100 µg/mL range against twenty different T. cruzi strains [45], and a prenylated phloroglucinol derivative ( 12), inhibited P. falciparum growth in vitro with an EC 50 of 0.88 µg/mL [46]. The mode of action of these semiquinones is unclear.…”

Section: Simple Phenols Phenolic Acids and Coumarinsmentioning

confidence: 99%

Natural products as potential antiparasitic drugs

Kayser

Kiderlen

Croft

2002

Studies in Natural Products Chemistry

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Pharmaceutical research in natural products represents a major strategy for discovering and developing new drugs. The use of medicinal plants for the treatment of parasitic diseases is well known and documented since ancient times e.g. by the use of Cinchona succiruba (Rubiaceae) as an antimalarial. This chapter provides a comprehensive review of the latest results in the field of antiparasitic drug development from biologic sources (plants, bacteria, fungi and marine organisms) focussing on the treatment of protozoal infections (Plasmodium, Leishmania, Trypanosoma spp.). The status of validated in vitro and in vivo assays is reviewed, discussing their different features, problems and limitations. Because of the high number of natural products tested against the aforesaid protozoa in the last years, we limit the discussion to lignans, phenolics, terpenoids, and alkaloids as defined natural product classes. The review also covers essential research topics of recent publications on specific natural products (e.g. licochalcone A, benzyl-and naphthylisoquinoline alkaloids, and artemisinin) and gives an outlook to semisynthetic approaches of drugs already introduced in clinics or in clinical trial studies.

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Section: Simple Phenols Phenolic Acids and Coumarinsmentioning

confidence: 99%

Natural products as potential antiparasitic drugs

Kayser

Kiderlen

Croft

2002

Studies in Natural Products Chemistry

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“…The results evidenced a significative increase of the IC50 values for both substances in both cell lines, and thus a decrease in the cytotoxicity of these triterpenes (Table 2). The interaction between tingenone and DNA was appointed as one likely mechanism for its cytotoxicity (Godjiman et al, 1985) and antineoplastic activities (Campanelli et al, 1980). This interaction was noticed by spectral methods, but no evidence could be concerning about a relationship between the binding mode and the base composition.…”

Section: Resultsmentioning

confidence: 99%

Antitumoral, mutagenic and (anti)estrogenic activities of tingenone and pristimerin

Gomes¹,

Cardoso²,

Varanda³

et al. 2011

Rev. bras. farmacogn.

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Cancer constitutes the second main mortality cause in the world, after cardiovascular diseases. In spite of the progresses in the chemotherapeutics treatments, many patients fail chemotherapy, mainly because of side effects or multidrugs resistance, proving the need and importance of the research for new molecules with anticancer activity, more effective and with smaller adverse effects. Various compounds derived from plant secondary metabolites are commonly used in the chemotherapy against cancer and the natural products play an important role in the research for new molecules. Among several molecules of natural origin evaluated by MTT assay in murine tumor cell lines [breast (LM3) and lung (LP07)] the quinonamethide triterpenes tingenone and pristimerin showed marked cytotoxic activity presenting IC50 around 2 and 5 µM respectively. The structure-activity relationship suggests that rings A and B containing an α, ß-unsaturated carbonyl group are essential for the observed cytotoxic activity. The interaction between these positions and acetylcisteyne residues suggests a probable mechanism of action. The in vitro mutagenic activity was also evaluated by the Salmonella microsome assay (Ames test) for pristimerin and tingenone with and without metabolic activation (S9) in the strains TA98, TA97a, TA100 and TA102, none of which showed mutagenic potential in any strains. Estrogenic and anti-estrogenic activities were also studied by the e-screen assay in MCF-7 cells with negative results. The present data point to the importance of pristimerin and tingenone as representative of an emerging class of potential anticancer chemicals.

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“…Tingenone (Maitenine) other natural quinonoid 5 , that differs from 20a-hydroxy-tingenone only by the presence of a methyl instead of the hydroxyl group at 20-position, inhibited T. (S.) cruzi growth mainly by DNA double-strand intercalation mechanism 17 . Otherwise, the presence of a carboxylic group at the 20-position, such as in epikatonic acid, populnilic acid or populninic acid rises loss of activity, possible by difficulties in cross cell cytoplasmatic membrane.…”

Section: T (S) Cruzi Growth Inhibition Experiments Were Carried Out mentioning

confidence: 99%

Anti-trypanosomal activity of pentacyclic triterpenes isolated from Austroplenckia populnea (Celastraceae)

Duarte¹,

Filho²,

Silva³

et al. 2002

Rev. Inst. Med. trop. S. Paulo

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SUMMARYFour pentacyclic triterpenes isolated from Austroplenckia populnea and four compounds of known anti T. cruzi or anti-malarial activity were tested. Of those triterpenes tested 20a-hydroxy-tingenone showed high activity, epikatonic acid was less active, while populnilic and populninic acids were inactive against the trypanosome of the subgenus Schizotrypanum tested. Benzonidazole, nifurtimox, ketoconazole and primaquine presented a remarkable dose-dependent inhibitory effect reaching practically to a total growth inhibition of the parasite at the end of incubation time. The trypanosome tested appear to be a suitable model for preliminary screen for anti T. (S.) cruzi compounds.

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Effect of tingenone, a quinonoid triterpene, on growth and macromolecule biosynthesis inTrypanosoma cruzi

Cited by 26 publications

References 20 publications

Natural products as potential antiparasitic drugs

Natural products as potential antiparasitic drugs

Antitumoral, mutagenic and (anti)estrogenic activities of tingenone and pristimerin

Anti-trypanosomal activity of pentacyclic triterpenes isolated from Austroplenckia populnea (Celastraceae)

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