Cycloartane Triterpenoid and Alkaloids from Ameidea SPP

Santos, Celcione S.; Januário, Ana Helena; Vieira, Paulo; Fernandes, João B.; Silva, M. Fátima G.F. da; Pirani, José Rubens

doi:10.1590/s0103-50531998000100007

Cited by 12 publications

(11 citation statements)

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“…C-glucosyl flavones (Jay et al 1979, Wirasutisna et al 1986), 2-quinolone and other alkaloids (Moulis et al 1983), cycloartane triterpenoids and further alkaloids (Santos et al 1998) have already been isolated from Almeidea. Galipea has afforded a hydroxychalcone (López et al 1998), a chromone (López et al 1997), a coumarin (Wirasutisna et al 1987), O-and Cglycosylflavones (Bakhtiar et al 1990(Bakhtiar et al , 1994, and several 2-quinoline alkaloids (Fournet et al 1989, Vieira & Kubo 1990, Rakotoson et al 1998, Jacquemond-Collet et al 1999.…”

Section: Resultsmentioning

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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Section: Resultsmentioning

confidence: 99%

Trypanocidal activity of Meliaceae and Rutaceae plant extracts

Ambrozin

Vieira

Fernandes

et al. 2004

Mem. Inst. Oswaldo Cruz

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“…2,11 In order to improve the therapy of Chagas disease, we have been studying species of the order Rutales (Rutaceae, Meliaceae, Simaroubaceae, Burseraceae, and Cneoraceae) aiming to isolate hit compounds that could be used in the development of new antichagasic drugs.…”

Section: A Rel-(7r8r)-8-[(e)-3-hydroxy-3-methyl-1-butenyl]-mentioning

confidence: 99%

“…From Almeidea guyanensis was isolated C-arabinosyl flavones, 2-and 4-quinolones, and flavone C-glycosides. 1 We have previously reported the isolation of triterpenoids, acridone, 2-quinolone, and furoquinoline alkaloids, and a new tetrahydrofuroquinoline alkaloid from A. coeruela and A. rubra 2 besides steroids, one sesquiterpene, one cromone, and one flavone. 3 Chagas' disease (American Trypanosomiasis) is caused by the flagellate protozoan Trypanosoma cruzi, affecting more than 18 million people in Latin America.…”

Section: Introductionmentioning

confidence: 99%

New pyrone and quinoline alkaloid from Almeidea rubra and their trypanocidal activity

Ambrozin¹,

Mafezoli²,

Vieira³

et al. 2005

J. Braz. Chem. Soc.

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O estudo da fração acetato de etila do extrato metanólico das folhas de Almeidea rubra A. St.-Hil. (Rutaceae) permitiu o isolamento de duas substâncias inéditas: 4-metoxi-6-[2-(metilamino)fenil]-2H-piran-2-ona e acetato de rel-(7R,8R)-8-[(E)-3-hidroxi-3-metil-1-butenil]-4,8-dimetoxi-5,6,7,8-tetraidrofuro[2,3-b]quinolin-7-ila; e dos alcalóides arborinina, N-metil-1-hidroxi-3-metoxiacridona, esquimianina, cocusagina, isodutaduprina, isoesquimianina e isococusagina. Através da análise dos dados espectroscópicos foram estabelecidas as estruturas químicas das substâncias isoladas sendo que para os alcalóides inéditos tais dados são descritos pela primeira vez. Além disso, os ensaios bilógicos sobre as formas tripomastigotas do Trypanosoma cruzi das substâncias isoladas mostraram que elas possuem atividade tripanocida moderada.The investigation of the ethyl acetate fraction of methanol extract from leaves of Almeidea rubra A. St.-Hil. (Rutaceae) afforded two new compounds 4-methoxy-6-[2-(methylamino)phenyl]-2H-pyran-2-one and rel-(7R,8R)-8- [(E)-3-hydroxy-3-methyl-1-butenyl]-4,8-dimethoxy-5,6,7,8-tetrahydrofuro[2,3-b]quinoline-7-yl acetate, along with the known compounds arborinine, N-methyl-1-hydroxy-3-methoxyacridone, skimmianine, kokusagine, isodutaduprine, isoskimmianine, and isokokusagine. Their structures were established based on their spectral data, and for the new compounds these data are described herein. Additionally, these compounds were assayed on the tripomastigote forms of Trypanosoma cruzi showing moderate trypanocidal activity.

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“…O gênero Almeidea é encontrado nos Estados de São Paulo, Rio de Janeiro e Espírito Santo. Santos et al (1998) identifi caram, nas folhas de Almeidea coerulea, a presença de cinco alcalóides como o 7-Oacetilhaplofi lidina, dutadrupina, isodutadrupina, 7-metoxi-8-(3,3-dimetilalil)-dictamina e arborina, e nas folhas de Almeidea rubra, alcalóides dos tipos furoquinílinico, 2quinolona e acridônico, além de cumarinas. Claude et al (1983) também isolaram alcalóides do tipo 2-quinolona do caule e raízes de Almeidea guyanensis.…”

Section: Introducãounclassified

Constituintes químicos de Almeidea coerulea (Nees & Mart.) A. St.-Hil. Rutaceae

Cortez¹,

Cortez²,

Ferreira³

et al. 2006

Rev. bras. farmacogn.

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RESUMO: Do extrato diclorometano do caule de Almeidea coerulea (Nees & Mart.) A. St.-Hil. foi isolado um triterpeno o 20-hidroxi-diidrolupeol (1), e do extrato metanólico foram isolados os alcalóides dictamina (2) e eskimianina (3), além de uma mistura dos esteróides sitosterol (4) e estigmasterol (5). A identifi cção substâncias foi realizada pela análise dos espectros de Massas, RMN 1 H, RMN 13 C, HSQC, HMBC, e por comparação com dados da literatura.

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Cycloartane Triterpenoid and Alkaloids from Ameidea SPP

Cited by 12 publications

References 0 publications

Trypanocidal activity of Meliaceae and Rutaceae plant extracts

Trypanocidal activity of Meliaceae and Rutaceae plant extracts

New pyrone and quinoline alkaloid from Almeidea rubra and their trypanocidal activity

Constituintes químicos de Almeidea coerulea (Nees & Mart.) A. St.-Hil. Rutaceae

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