Pyrano chalcones and a flavone from Neoraputia magnifica and their Trypanosoma cruzi glycosomal glyceraldehyde-3-phosphate dehydrogenase-inhibitory activities

Tomazela, Daniela M.; Pupo, Mônica Tallarico; Passador, Edna A. P.; Silva, Maria Fátima das Graças Fernandes da; Vieira, Paulo C.; Fernandes, João B.; Fo, Edson Rodrigues; Oliva, Glaucius; Pirani, José Rubens

doi:10.1016/s0031-9422(00)00248-x

Cited by 71 publications

(56 citation statements)

References 10 publications

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“…The structure of GAPDH from glycosomes was reported and comparison with that of the mammalian counterpart led to the group of Oliva to consider the possibility of development of specific inhibitors of the parasite enzyme (Souza et al 1998). In a subsequent work the isolation of flavonoids from the fruits of Neoraptua magnifica led to the compound 3',4',5',5,7-pentamethoxyflavone that showed the highest activity over flavones and pyrano chalcones against the GAPDH of the parasite (Tomazela et al 2000). Crystal structure of trypanosomatids and human GAPDHs provided details about the interaction of adenosyl moiety of NAD + with proteins.…”

Section: Glyceraldehyde-3-phosphate Dehydrogenasementioning

confidence: 99%

A Critical Review on Chagas Disease Chemotherapy

Coura¹,

Castro

2002

Mem. Inst. Oswaldo Cruz

845

444

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Section: Glyceraldehyde-3-phosphate Dehydrogenasementioning

confidence: 99%

A Critical Review on Chagas Disease Chemotherapy

Coura¹,

Castro

2002

Mem. Inst. Oswaldo Cruz

845

444

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“…Other promising compounds are the 2-aryl and 2-alkylquinoline alkaloids isolated from the extracts of the stem bark, root bark and leaves of Galipea longiflora (Rutaceae) (Fournet et al 1994) and lignans from Zanthoxylum naranjillo (Rutaceae) (Bastos et al 1999). In addition, we have been studying species of the order Rutales (Rutaceae, Meliaceae, Simaroubaceae, Burseraceae, and Cneoraceae) and several active substances have been isolated, mainly trypanocidal compounds (Mafezoli et al 2000, Tomazela et al 2000, Vieira et al 2001.In this paper, we present the results of the trypanocidal activity of some extracts and fractions of Almeidea coerulea, Almeidea rubra, Conchocarpus heterophyllus, and Galipea carinata (from Rutaceae family), as well as Trichilia ramalhoi (from the family Meliaceae). Also, the results of the in vitro trypomastigote bioassay with flavone (1) and 7-methoxyflavone (2), the major compounds of one active fraction, are described.…”

mentioning

confidence: 99%

mentioning

confidence: 99%

Trypanocidal activity of Meliaceae and Rutaceae plant extracts

Ambrozin

Vieira

Fernandes

et al. 2004

Mem. Inst. Oswaldo Cruz

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(WHO 1997). Its treatment is still a challenge, since the only drug commercially available (benznidazole) possesses severe side effects and its activity is limited to the acute phase of the disease (De Castro 1993, Fairlamb 1999. Coura and De Castro (2002) mention that an effective chemotherapy is needed for the people who are already infected. The demonstration of parasites in chronic patients reinforces the need of finding more efficient and less toxic drugs.In the context of efforts to improve the therapy of Chagas disease, higher plants are a potential source of new drugs, with high activity and low toxicity (Phillipson & Wright 1991). Sepúlveda-Boza and Cassels (1996) mentioned a broad spectrum of chemical classes of substances showing activity against the parasite. Other promising compounds are the 2-aryl and 2-alkylquinoline alkaloids isolated from the extracts of the stem bark, root bark and leaves of Galipea longiflora (Rutaceae) (Fournet et al. 1994) and lignans from Zanthoxylum naranjillo (Rutaceae) (Bastos et al. 1999). In addition, we have been studying species of the order Rutales (Rutaceae, Meliaceae, Simaroubaceae, Burseraceae, and Cneoraceae) and several active substances have been isolated, mainly trypanocidal compounds (Mafezoli et al. 2000, Tomazela et al. 2000, Vieira et al. 2001.In this paper, we present the results of the trypanocidal activity of some extracts and fractions of Almeidea coerulea, Almeidea rubra, Conchocarpus heterophyllus, and Galipea carinata (from Rutaceae family), as well as Trichilia ramalhoi (from the family Meliaceae). Also, the results of the in vitro trypomastigote bioassay with flavone (1) and 7-methoxyflavone (2), the major compounds of one active fraction, are described. MATERIALS AND METHODSPlant material -All screened plants were collected in Southeastern Brazil, and identified by Dr José R Pirani from the Department of Botany, University of São Paulo, Brazil. The voucher herbarium specimens were deposited at the Herbarium of that Department (Table I).Preparation of crude extracts -Selected parts of the plants (leaves, stems, and/or branches) were dried carefully by forced air at 40°C and reduced to powder, followed by extraction three times with hexane by maceration at room temperature for 72 h. After the evaporation of the solvent under reduced pressure, crude hexane extracts were obtained. This process was repeated with methanol. The hexane and methanol extracts so obtained were assayed against T. cruzi.Fractionation of crude extracts -Methanol extracts of T. ramalhoi were fractionated through liquid-liquid partition with hexane-methanol-water, dichloromethanemethanol-water, ethyl acetate-methanol-water, and butanol-methanol-water. The crude extracts of A. coerulea, A. rubra, C. heterophyllus, G. carinata, and the hexane extract of the leaves of T. ramalhoi were submitted to vacuum liquid chromatography over silica gel using a gradient hexane, dichloromethane, ethyl acetate, and methanol, to yield the corresponding fractions, which were subsequently tested ...

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“…15) Thus, clearly the here reported isoflavonoids deserve more attention as micromolar inhibitors of GAPDH, mainly due to the fact that the conditions for the D. odorata callus cultures may be manipulated and once optimized will afford a highly attractive source to various bioactive analogues of the isoflavonoid series.…”

Section: )mentioning

confidence: 89%

Isolation and Structure Determination of Bioactive Isoflavones from Callus Culture of Dipteryx odorata

Januário

Lourenço

Domézio

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Great commercial value has been credited to the seeds of Dipteryx odorata WILLD. (AUBL.) (Leguminoseae) native from Amazon and also known as tonka beans or cumaru, because they are considered rich source of coumarins, used in cosmetics and perfumery.1) The presence of umbelliferone in seeds of tonka beans was described by Sullivan who also reported other natural compounds like isoflavonoids, triterpenoids, fatty acids and cassane diterpenoids on seeds of this species.2) Additionally some micromolecules specific of the heartwood of D. odorata as isoflavones retusin, retusin 8-methyl ether, 3Ј-hydroxyretusin 8-methyl ether, odoratin, dipteryxin, dipteryxine and odoratine; the triterpenes lupeol and betulin; and methyl esters of fatty acids have been isolated. 3,4) Isoflavonoids have gained considerable importance due to the diverse broad of biological activities correlated to them, including antioxidative, oestrogenic, inseticidal, piscicidal, antifungal, antimicrobial and contraceptive properties. 5,6) The pharmacological properties of isoflavonoids and the correlation between the consumption of isoflavonoids and reduction on the level of incidence of cardiovascular disease and cancer have increase the interest in the search for biologically active compounds from plant species of both, leguminous and non-leguminous sources. 7)In this work we report the establishment of D. odorata callus cultures focusing on a comparative study related to the production of tripanossomatidal GAPDH inhibitory isoflavones accumulated in roots of the intact plant and in callus cultures of this species. ExperimentalPlant Material Dipteryx odorata plants were collected in the campus of Universidade do Amazonas in Manaus, Brazil. Voucher specimen is deposited under the number HUAM 7276 in the Herbarium of the Universidade do Amazonas.Seed Disinfestations Seeds of D. odorata were soaked in sterile distilled water and maintained under agitation overnight. Seeds were then immersed in 2% Benomyl solution for 4 h under agitation, washed in 70% hydroalcoholic solution, dipped in 1% CaClO for 40 min, washed for three times with sterile distilled water and inoculated into glass flasks (8.5 cmϫ2.5 cm i.d.) containing 5 ml MS medium 8) added with 30 g/l sucrose and 2.0 g/l Phytagel, pH was adjusted to 6.0 before autoclaving. Flasks were sealed with polypropylene closures (Bellco), autoclaved at 121°C and 105 kPa for 20 min and maintained at 25Ϯ2°C, 55-60% relative humidity under 16 h photoperiod with 40 mmol m Ϫ2 s Ϫ1, 85 W coolwhite GE fluorescent lamps.Callus Induction Leaves, hypocotyl, and roots of D. odorata seedlings produced in vitro were used as explants for callus induction. Explants were inoculated onto semisolid MS medium supplemented with 2.0 mg/l 2,4-D, 0.5 mg/l 6-BAP and 340 mg/l KH 2 PO 4 and 2.0 g/l Phytagel, pH ajusted to 6.0. Callus were harvested and subcultured in 30-d intervals.General Analytical Procedures TLC was carried out on silica gel G pre-coated plates (Sigma-Aldrich) using CHCl 3 -MeOH (9 : 1) as solvent system. Spots...

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Pyrano chalcones and a flavone from Neoraputia magnifica and their Trypanosoma cruzi glycosomal glyceraldehyde-3-phosphate dehydrogenase-inhibitory activities

Cited by 71 publications

References 10 publications

A Critical Review on Chagas Disease Chemotherapy

A Critical Review on Chagas Disease Chemotherapy

Trypanocidal activity of Meliaceae and Rutaceae plant extracts

Isolation and Structure Determination of Bioactive Isoflavones from Callus Culture of Dipteryx odorata

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