Abstract:. do Café, s/n, 14040-903 Ribeirão Preto -SP, BrasilRecebido em 18/5/07; aceito em 14/11/07; publicado na web em 19/3/08 NEW PYRANOFLAVONES AND TRYPANOCIDAL ACTIVITY OF COMPOUNDS ISOLATED FROM Conchocarpus heterophyllus. The phytochemical investigation of trypanocidal extracts from leaves and stems of Conchocarpus heterophyllus (A. St.-Hil.) Kallunki & Pirani (Rutaceae) afforded new pyranoflavones along with the known compounds flavone, 7-methoxyflavone, 5-hydroxyflavone, haplotusine, 1-methyl-2-phenyl-4-quino… Show more
“…Similar studies involving the trypanocidal activity of Meliaceae and Rutaceae species have been reported by our group (Mafezoli et al, 2000;Vieira et al, 2001;Ambrozin et al, 2004Ambrozin et al, , 2005aAmbrozin et al, , 2008 showing that these plants can be considered a promising source of active compounds against trypomastigote forms of T. cruzi. Thus, the significant results obtained from the extracts of C. fruticosa are consistent with those previously reported for this family.…”
Section: Resultssupporting
confidence: 87%
“…The bioassays were carried out according to the procedures described by Ambrozin et al (2008). The activity of crude extracts was evaluated in triplicate at 4 mg/mL and pure substances at 250, 100, and 50 µg/ mL.…”
RESUMO: "Atividade tripanocida de flavonoides e limonoides isolados de extratos ativos de plantas de Myrsinaceae e Meliaceae". A atividade de extratos brutos de três espécies de Rapanea (Myrsinaceae) e de Cipadessa fruticosa (Meliaceae) foi avaliada in vitro contra formas tripomastigotas de Trypanosoma cruzi. Foram obtidos 33 extratos de diferentes órgãos das espécies estudadas, sendo que onze deles apresentaram atividades significantes (% de lise > 50) nos ensaios realizados. O fracionamento de um extrato ativo dos galhos de R. lancifolia (99,5%) resultou no isolamento de dois flavonoides (quercetina e taxifolina), que apresentaram baixa atividade tripanocida. De um extrato ativo dos frutos de C. fruticosa (97,7%) foram isolados os limonoides mexicanolídeos cipadesina, mexicanolídeo, febrifugina e cipadesina A, que foram moderadamente ativos sobre T. cruzi. Além disso, outros dois flavonoides (flavona e 7-metoxiflavona), previamente ensaiados contra T. cruzi, foram isolados do extrato hexânico dos galhos de C. fruticosa (100%). Os resultados obtidos aqui sugerem que as plantas avaliadas podem constituir fontes de novas substâncias ativas sobre o T. cruzi.Unitermos: Myrsinaceae, Meliaceae, atividade tripanocida, flavonoides, limonoides.
ABSTRACT:The activity of crude extracts of three Rapanea species (Myrsinaceae) and Cipadessa fruticosa (Meliaceae) was evaluated in vitro against the trypomastigote forms of Trypanosoma cruzi. Thirty-three extracts from different organs of these species were assayed and eleven of them showed significant activity (lysis % >50). The fractionation of an active extract from branches of R. lancifolia (99.5%) led to the isolation of two flavonoids: quercetin and taxifolin, which have weak trypanocidal activity. Additionally, one active extract from fruits of C. fruticosa (97.7%) afforded mexicanolide limonoids: cipadesin, mexicanolide, febrifugin and cipadesin A, that were slightly active on T. cruzi. Moreover, other two flavonoids (flavone and 7-methoxyflavone), previously assayed against T. cruzi, were isolated from the hexane extract from branches of C. fruticosa (100%). The results presented here suggest that the plants evaluated could be a source of new active compounds against T. cruzi.
“…Similar studies involving the trypanocidal activity of Meliaceae and Rutaceae species have been reported by our group (Mafezoli et al, 2000;Vieira et al, 2001;Ambrozin et al, 2004Ambrozin et al, , 2005aAmbrozin et al, , 2008 showing that these plants can be considered a promising source of active compounds against trypomastigote forms of T. cruzi. Thus, the significant results obtained from the extracts of C. fruticosa are consistent with those previously reported for this family.…”
Section: Resultssupporting
confidence: 87%
“…The bioassays were carried out according to the procedures described by Ambrozin et al (2008). The activity of crude extracts was evaluated in triplicate at 4 mg/mL and pure substances at 250, 100, and 50 µg/ mL.…”
RESUMO: "Atividade tripanocida de flavonoides e limonoides isolados de extratos ativos de plantas de Myrsinaceae e Meliaceae". A atividade de extratos brutos de três espécies de Rapanea (Myrsinaceae) e de Cipadessa fruticosa (Meliaceae) foi avaliada in vitro contra formas tripomastigotas de Trypanosoma cruzi. Foram obtidos 33 extratos de diferentes órgãos das espécies estudadas, sendo que onze deles apresentaram atividades significantes (% de lise > 50) nos ensaios realizados. O fracionamento de um extrato ativo dos galhos de R. lancifolia (99,5%) resultou no isolamento de dois flavonoides (quercetina e taxifolina), que apresentaram baixa atividade tripanocida. De um extrato ativo dos frutos de C. fruticosa (97,7%) foram isolados os limonoides mexicanolídeos cipadesina, mexicanolídeo, febrifugina e cipadesina A, que foram moderadamente ativos sobre T. cruzi. Além disso, outros dois flavonoides (flavona e 7-metoxiflavona), previamente ensaiados contra T. cruzi, foram isolados do extrato hexânico dos galhos de C. fruticosa (100%). Os resultados obtidos aqui sugerem que as plantas avaliadas podem constituir fontes de novas substâncias ativas sobre o T. cruzi.Unitermos: Myrsinaceae, Meliaceae, atividade tripanocida, flavonoides, limonoides.
ABSTRACT:The activity of crude extracts of three Rapanea species (Myrsinaceae) and Cipadessa fruticosa (Meliaceae) was evaluated in vitro against the trypomastigote forms of Trypanosoma cruzi. Thirty-three extracts from different organs of these species were assayed and eleven of them showed significant activity (lysis % >50). The fractionation of an active extract from branches of R. lancifolia (99.5%) led to the isolation of two flavonoids: quercetin and taxifolin, which have weak trypanocidal activity. Additionally, one active extract from fruits of C. fruticosa (97.7%) afforded mexicanolide limonoids: cipadesin, mexicanolide, febrifugin and cipadesin A, that were slightly active on T. cruzi. Moreover, other two flavonoids (flavone and 7-methoxyflavone), previously assayed against T. cruzi, were isolated from the hexane extract from branches of C. fruticosa (100%). The results presented here suggest that the plants evaluated could be a source of new active compounds against T. cruzi.
“…It is caused by parasitic protozoan Trypanosoma cruzi and represents one of the most serious endemics diseases in Brazil. Of particular public health concern, it affects 16-18 million individuals in the Americas, with 100 million under risk of contamination (Ambrozin et al 2008). The parasite can be transmitted to humans through the faces and urine of vectors (triatomines), infection with T. cruzi through the transfusion of blood products and organ transplants from the infected donors.…”
Context Melissa officinalis subsp. inodora Bornm. (Lamiaceae) has been used since ancient times in folk medicine against various diseases, but it has not been investigated against protozoa. Objective To evaluate the activities of M. officinalis against Leishmania braziliensis, Leishmania infantum and Trypanosoma cruzi as well as its cytotoxicity in fibroblast cell line. Materials and methods The fresh leaves were chopped into 1 cm 2 pieces, washed and macerated with 99.9% of ethanol for 72 h at room temperature. Antiparasitic activity of M. officinalis was accessed by direct counting of cells after serial dilution, while the cytotoxicity of M. officinalis was evaluated in fibroblast cell line (NCTC929) by measuring the reduction of resazurin. The test duration was 24 h. High-performance liquid chromatography (HPLC) was used to characterise the extract.Results The extract at concentrations of 250 and 125 mg/mL inhibited 80.39 and 54.27% of promastigote (LC 50 value ¼ 105.78 mg/mL) form of L. infantum, 80.59 and 68.61% of L. brasiliensis (LC 50 value ¼ 110.69 mg/mL) and against epimastigote (LC 50 value ¼ 245.23 mg/mL) forms of T. cruzi with an inhibition of 54.45 and 22.26%, respectively, was observed. The maximum toxicity was noted at 500 mg/mL with 95.41% (LC 50 value ¼ 141.01 mg/mL). The HPLC analysis identified caffeic acid and rutin as the major compounds. Discussion The inhibition of the parasites is considered clinically relevant (5500 mg/mL). Rutin and caffeic acids may be responsible for the antiprotozoal effect of the extract. Conclusion The ethanol extract of M. officinalis can be considered a potential alternative source of natural products with antileishmania and antitrypanosoma activities.
ARTICLE HISTORY
“…[3][4][5] Literature reports of phytochemical studies with Conchocarpus species have shown the presence of alkaloids, flavonoids and coumarins in addition to anti-Trypanosome cruzy activity. [6][7][8][9] In the present paper, we used stems from Conchocarpus cyrtanthus commonly known as "Orelha de cabra" to describe the isolation and characterization of two new diterpenes 16-hydroxylarixol (1), 16-hydroxy-7-labden-6-one (2) besides twelve known compounds: three coumarins seselin (3), xantoxiletin (4) in de Oliveira, L. S. S. et al Rev. Virtual Quim.…”
Section: Introductionmentioning
confidence: 99%
“…|Vol 8| |No. 1| |87-96| 89 mixture, luvangetin (5), the alkaloid dictamin (6), six steroids -sitosterol (7), stigmasterol (8), campesterol (9) in mixture, 7-hydroxy--sitosterol (10), 7-hydroxy-stigmasterol (11) 7-hydroxy-campesterol (12) in mixture, three diterpenes manool (13), 16-hydroxymanoiloxide (14) 16-hydroxy-13-epimanoyloxide (15), and the lignan siringaresinol (16).…”
Resumo: Dois novos diterpenos do tipo labdano denominados 16-hidroxilarixol (1) e 16-hidroxi-7-labden-6-ona (2) foram isolados de Conchocarpus cyrtanthus, juntamente com mais três cumarinas: seselina (3), xantoxiletina (4), luvangetina (5); o alcaloide dictamina (6); seis esteroides: -sitosterol (7), estigmasterol (8), campesterol (9), 7-hidroxi--sitosterol (10), 7-hidroxiestigmasterol (11) e 7-hidroxicampesterol (12); três diterpenos: manool (13), 16-hidroximanoiloxido (14) e 16-hidroxi-13-epi-manoiloxido (15)
AbstractTwo new labdane-type diterpenes called 16-hydroxylarixol (1) and 16-hydroxy-7-labden-6-one (2) were isolated from Conchocarpus cyrtanthus, along with three coumarins, seselin (3), xantoxiletin (4), luvangetin (5); the alkaloid dictamin (6); six steroids, -sitosterol (7), stigmasterol (8), campesterol (9), 7-hydroxy--sitosterol (10), 7-hydroxy-stigmasterol (11) and 7-hydroxy-campesterol (12); three diterpenes, manool (13), 16-hydroxymanoiloxide (14), and 16-hydroxy-13-epi-manoyloxide (15) and the lignan siringaresinol (16). These compounds were characterized based on analysis of data provided by one-and two-dimensional Nuclear Magnetic Resonance (NMR of 1 H and 13 C), High-resolution Mass Spectrometry, besides comparison with data reported in the literature.
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