Acyl lupeols from cnidoscolus vitifolius

Brum, Rosenei L.; Honda, Nobuaki; Hess, Sônia Corina; Cavalheiro, Alberto José; Monachè, Franco Delle

doi:10.1016/s0031-9422(98)00069-7

Cited by 20 publications

(9 citation statements)

References 2 publications

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“…In fact, these compounds are frequently obtained as a mixture, due to its structural similarity. This mixture has also been reported in C. vitifolius [26]. Other lupane-type triterpenes were reported in C.…”

Section: Discussionsupporting

confidence: 79%

Antibacterial activity of terpenoids isolated from Cnidoscolus quercifolius Pohl (Euphorbiaceae), a Brazilian medicinal plant from Caatinga biome

Oliveira-Júnior

Ferraz

Pontes

et al. 2018

European Journal of Integrative Medicine

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Introduction: Cnidoscolus quercifolius Pohl (Euphorbiaceae) is a Brazilian medicinal plant, popularly known as "favela", "faveleira" and "urtiga-branca". In folk medicine, its leaves and stem barks are used to treat urinary tract infections. In this study, we report the isolation and characterization of a mixture of two lupane-type triterpenes and one bis-nor-diterpene from the hexane extract of the stem barks. Methods: An aliquot of hexane extract was fractioned by means silica gel chromatography column, yielding a mixture of two compounds (1 and 2). Compound 3 was obtained from the chloroform subfraction through preparative thin layer chromatography (TLC). The compounds were identified by comparison of their spectroscopic data to those reported in the literature. The antibacterial activity of these compounds was evaluated by the microdilution method, through determination of minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC), using gram-positive (E. faecalis and S. aureus) and gram-negative (E. coli, K. pneumoniae and S. marcescens) strains. Results: The chemical constituents were identified as a mixture of lupeol-3β-O-cinnamate (1) and lupeol-3β-O-dihydrocinnamate (2) and, phyllacanthone (3). Compounds 1/2 and 3 showed a bacteriostatic effect ten and twenty times higher (MIC = 0.5 and 0.25 mg.ml-1 , respectively) than the hexane extract, respectively (MIC = 5.0 mg.ml-1). The molecules also showed a relevant bactericidal effect, mainly compound 3 (MBC = 0.25 mg.ml-1). Conclusion: These results suggest that C. quercifolius may be considered a promising source of new antibacterial agents. In addition, this investigation supports the medicinal use of this plant for the treatment of urinary tract infections.

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Section: Discussionsupporting

confidence: 79%

Antibacterial activity of terpenoids isolated from Cnidoscolus quercifolius Pohl (Euphorbiaceae), a Brazilian medicinal plant from Caatinga biome

Oliveira-Júnior

Ferraz

Pontes

et al. 2018

European Journal of Integrative Medicine

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“…The compounds were identified by IR, GC/MS, 1 H and 13 C NMR one and two-dimensional techniques, and their structural propose were confirmed by literature data. From stem bark were isolated two pentacyclic triterpenes acyl lupeols (1 and 2, 25 mg, Brum et al, 1998); two coumarins, coumarin (3, 6.5 mg, Tonin & Tavares, 2002) and scopoletin (4, 4.0 mg, Silva et al, 2002); four flavonoids, naringenin (5, 2.5 mg, Almeida et al, 2005), kaempferol (6, 6 mg, Oliveira et al, 1999), quercetin (7, 4.5 mg, Barberá, 1986;Agrawal & Bansal, 1989) and myricitrin (9, 155.0 mg, Timbola et al, 2002), besides 2-methoxy-4-hydroxy-benzoic acid (11, 12 mg, Scott, 1972). From the leaves were isolated the flavonoid rutin (8, 7 mg, Buszewski et al, 1993;Agrawal & Bansal, 1989) and a pentacyclic triterpene ursolic acid (10, 20 mg, Tkachev et al, 2004).…”

Section: Resultsmentioning

confidence: 99%

Chemotaxonomic significance of flavonoids, coumarins and triterpenes of Augusta longifolia (Spreng.) Rehder, Rubiaceae-Ixoroideae, with new insights about its systematic position within the family

Choze¹,

Delprete²,

Lião³

2010

Rev. bras. farmacogn.

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RESUMO: "Significância quimiotaxômica de flavonoides, cumarinas e triterpenos de Augusta longifolia (Spreng.) Rehder, Rubiaceae-Ixoroideae, com novos entendimentos sobre a posição sistemática dentro da família". Augusta tem sido tradicionalmente colocada na tribo Rondeletieae, Cinchonoideae subfamília. No entanto, recentes filogenias moleculares posicionou-a perto de Wendlandia, porém localizando A. longifolia perto do clado Ixoroidinae II. O estudo de A. longifolia resultou em duas cumarinas, cinco flavonoides, três triterpenoides e um derivado do ácido benzóico. Estes metabolitos reforçam a separação da Augusta como um gênero monoespecífico, e Lindenia como um gênero de três espécies, intimamente relacionada com Wendlandia.Unitermos: Rubiaceae, Augusta, Wendlandia, Lindenia, quimiotaxonomia.ABSTRACT: Augusta has traditionally been placed in the tribe Rondeletieae, subfamily Cinchonoideae. However, recent molecular phylogenies positioned it near to Wendlandia (Ixoroideae), but locate A. longifolia near to the clade Ixoroidinae II. The study of A. longifolia afforded two coumarins, five flavonoids, three triterpenoids and one benzoic acid derivative. These metabolites reinforce the separation of Augusta as a monospecific genus, and Lindenia as a genus of three species, closely related to Wendlandia.

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“…Inhibition (Kuttan et al 2011) or cancer prevention (Shanmugam et al 2013) are some of its properties. Lupeol (3β)-lup-20-(29)-en-3-ol (4) is another triterpene which has gained wide attraction as a therapeutic and chemopreventive agent for treatment of cancer (Saleem 2009), which was also used as template for esters transformations and isolated as an ester derivative as well (Brum et al 1998). Besides these triperpenic structures, some phytosterols were also used as lead compounds in our study.…”

Section: Resultsmentioning

confidence: 99%

Terpene Esters from Natural Products: Synthesis and Evaluation of Cytotoxic Activity

Victor

David

Sakukuma

et al. 2017

An. Acad. Bras. Ciênc.

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Natural steroids and triterpenes such as β-sitosterol, stigmasterol, lupeol, ursolic and betulinic acids were transformed into its hexanoic and oleic esters, to evaluate the influence of chemical modification towards the cytotoxic activities against tumor cells. The derivatives were evaluated against five tumor cell lines [OVCAR-8 (ovarian carcinoma); SF-295 (glioblastoma); HCT-116 (colon adenocarcinoma); HL-60 (leukemia); and PC-3 (prostate carcinoma)] and the results showed only betulinic acid hexyl ester exhibits cytotoxic potential activity.

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Acyl lupeols from cnidoscolus vitifolius

Cited by 20 publications

References 2 publications

Antibacterial activity of terpenoids isolated from Cnidoscolus quercifolius Pohl (Euphorbiaceae), a Brazilian medicinal plant from Caatinga biome

Antibacterial activity of terpenoids isolated from Cnidoscolus quercifolius Pohl (Euphorbiaceae), a Brazilian medicinal plant from Caatinga biome

Chemotaxonomic significance of flavonoids, coumarins and triterpenes of Augusta longifolia (Spreng.) Rehder, Rubiaceae-Ixoroideae, with new insights about its systematic position within the family

Terpene Esters from Natural Products: Synthesis and Evaluation of Cytotoxic Activity

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