Quantitative determination by HPLC of ent-kaurenoic and grandiflorenic acids in aerial parts of Wedelia paludosa D.C.

Batista, Ronan; Braga, Fernão Castro; Oliveira, Alaı́de Braga de

doi:10.1590/s0102-695x2005000200009

Cited by 20 publications

(29 citation statements)

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“…In addition, a general survey and some taxonomic implications of the occurrence of kaurane and other classes of diterpenes in the Asteraceae family are discussed by Alvarenga and collaborators [39]. Kaurenoic acid (1), an ent-kaurane diterpene that possesses a wide spectrum of bioactivities such as antiinflammatory, antibacterial, antifungal and moluscical properties, among others [6], is not commercially available, but it is relatively abundant in some species belonging to the Wedelia [40], Mikania [41], Annona [42] and Xylopia [43] genera, which has motivated its quantification in these plant species [42][43][44][45][46][47], enabling the use of all of them as natural sources of this diterpene. Figure 3.…”

Section: Taxanes Tiglianesmentioning

confidence: 99%

“…[47], in addition to the lack of a general method for the synthesis of alkyl kaurenoates through the esterification of 1, motivated Boeck and collaborators [86] to carry out the chemical modification of this diterpene in order to synthesize new kaurane derivatives and to evaluate their respective potential pharmacological activities. As a result, a simple method was developed for preparing kauranic esters through the alkylation of the acids with alkyl halides, in a KOH-acetone system, avoiding the use of anhydrous conditions and establishing a reproducible method for the reaction.…”

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Occurrence, Biological Activities and Synthesis of Kaurane Diterpenes and their Glycosides

2007

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This paper presents a review on kaurane diterpenes and their glycoside derivatives, covering aspects of their occurrence, biological activities and the synthesis of these natural products and their analogues. First, it shows and classifies diterpenes, in accordance with the already established structural criteria in the literature. Then, kaurane diterpenes are presented, focusing on their chemical structures, occurrence in the plant kingdom and their main, recently described, biological activities. Moreover, the most significant works, published between 1964 and November 2006, which describe the total synthesis or structural transformations of some kaurane diterpenes, including either semisynthetic and/or microbiological methodologies, are consisely reviewed. At this point, some general considerations on glycosides are introduced, and kaurane glycosides are presented and discussed on the basis of their toxic importance and occurrence in the plant kingdom, having focused on related aspects of their biological activities and the relationships between these activities and the structural factors of their molecules. Finally, the principal methods of glycosidation by enzymatic and chemical processes are both presented, and a few papers on the synthesis of kaurane glycosides are succinctly discussed. Molecules 2007, 12 456

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Section: Taxanes Tiglianesmentioning

confidence: 99%

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confidence: 99%

Occurrence, Biological Activities and Synthesis of Kaurane Diterpenes and their Glycosides

2007

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“…Thus, we were motivated to quantify both kaurenoic (1) and grandiflorenic (2) acids in dry dichloromethane fraction (DF) of W. paludosa, employing the RP-HPLC quantitation method which was previously developed and validated for these diterpenes in the aerial parts of W. paludosa D.C. (Batista et al, 2005).…”

Section: Resultsmentioning

confidence: 99%

“…Several biological effects have been described for the ethanol extract of W. paludosa D.C. aerial parts including antinociceptive (Block et al, 1998a), trypanosomicidal (Chiari et al, 1996), hypoglycemic (Block et al, 1998b) and antifungal (Sartori et al, 2003) activities, among others. Previous phytochemical studies on this plant afforded the kaurane diterpenes ent-kaur- 16-en-19-oic acid (1, kaurenoic acid) and ent-kaur-9(11),16-dien-19oic acid (2, grandiflorenic acid) as major compounds, besides other related diterpenes, triterpenes and eudesmanolide lactones as minor constituents (Roque et al, 1987;Ferreira et al, 1994;Block et al, 1998a;Block et al, 1998b;Batista et al, 1999;Carvalho et al, 2001;Batista et al, 2005).…”

Section: Introductionmentioning

confidence: 99%

Cytotoxicity of Wedelia paludosa D.C. extracts and constituents

Batista¹,

Brandão²,

Braga³

et al. 2009

Rev. bras. farmacogn.

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RESUMO: "Citotoxidade de extratos e constituintes de Wedelia paludosa D.C." Wedelia paludosa D.C. (Asteraceae) é uma planta ornamental facilmente encontrada em várias regiões do Brasil, principalmente nos estados de Santa Catarina, São Paulo, Minas Gerais, Bahia e Pernambuco. Objetivando descobrir novas substâncias citotóxicas a partir desta espécie, o extrato hidrometanólico de W. paludosa (HME) e as frações diclorometânica (FD) e aquosa (FA) resultantes de sua partição em CH 2 Cl 2 -H 2 O foram avaliados utilizando-se o bioensaio em Artemia salina. A fração diclorometânica (FD) apresentou a maior atividade citotóxica (CL 50 = 140,6 mg/mL), e sua análise por cromatografia líquida de alta eficiência empregando-se fase reversa (FR-CLAE) revelou os ácidos caurenóico (1, 6,22 ± 0,23%) e grandiflorênico (2, 3,22 ± 0,31%) como constituintes majoritários. As amostras HME (CL 50 = 980 mg/mL), FD (CLC 50 = 140,6 mg/mL), 1 (CL 50 = 15,9 mg/mL) e 2 (CL 50 = 29,8 mg/mL) foram citotóxicas contra A. salina, enquanto que a fração aquosa (FA, CL 50 >> 1000 mg/mL) mostrou-se inativa. Conclui-se que a citotoxidade observada para HME e FD pode ser atribuída à presença dos ácidos caurenóico (1) e grandiflorênico (2) nestes extratos.Unitermos: Wedelia paludosa, Asteraceae, atividade citotóxica, toxidade em Artemia salina, ácido caurenóico, ácido grandiflorênico, CLAE.ABSTRACT: Wedelia paludosa D.C. (Asteraceae) is an ornamental species occurring in many regions of Brazil. Aiming to find new cytotoxic compounds, the hydromethanol extract of W. paludosa (HME), as well as the dichloromethane (DF) and water (WF) fractions resulting from its partition, were submitted to the brine shrimp lethality bioassay (BSLB) in order to evaluate their cytotoxicity. Dichloromethane fraction (DF) was shown to be the most cytotoxic fraction (LC 50 = 140.6 mg/mL), and its analysis by reversed phase high performance liquid chromatography (RP-HPLC) revealed ent-kaurenoic (1, 6.22 ± 0.23%) and grandiflorenic (2, 3.22 ± 0.31%) acids as important constituents. HME (LC 50 = 980 mg/mL), DF (LC 50 = 140.6 mg/mL), 1 (LC 50 = 15.9 mg/ mL) and 2 (LC 50 = 29.8 mg/mL) were found to be cytotoxic, while the water fraction (WF, LC 50 >> 1000 mg/mL) was inactive. As conclusion, the cytotoxicity observed for HME and DF is mainly due to the presence of 1 and 2 in their constitution.

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“…Diversos constituintes químicos podem ser encontrados nas plantas da família Asteraceae: poliacetilenos, lactonas sesquiterpênicas, alcalóides (Cronquist, 1981), óleos essenciais (Agostini et al, 2005), antocianinas (Takeda;Harborne;Self, 1986), fl avonóides (Markham, 1982), diterpenos (Batista et al, 2005) entre outros.…”

Section: Introductionunclassified

Atividade antibacteriana e antifúngica de extratos etanólicos de Aster lanceolatus Willd., Asteraceae

Dias¹,

Virtuoso²,

Davet³

et al. 2006

Rev. bras. farmacogn.

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RESUMO:Conhecida popularmente como áster-arbustiva, margarida-de-são-miguel e montecassino, Aster lanceolatus é uma planta ornamental de corte. Sabendo-se que não existem estudos que atestem a atividade biológica desta espécie, procurou-se neste trabalho atividades antibacteriana e antifúngica. Para tanto se utilizaram extratos brutos etanólicos de duas porções distintas, das fl ores e dos caules com folhas. Para a atividade antibacteriana, oito bactérias patogênicas foram submetidas a ensaio de difusão em gel e concentração inibitória mínima. Demonstrou-se atividade do extrato bruto etanólico de fl ores contra Streptococcus pyogenes, em difusão em gel e atividade de extrato bruto etanólico de caules e folhas contra Salmonella typhimurium e Streptococcus pyogenes em concentração inibitória mínima. Para a atividade antifúngica, utilizaram-se três fungos patogênicos em ensaios de crescimento micelial em placas e bioautografi a direta. No ensaio de crescimento micelial em placas verifi cou-se a inibição de Fusarium oxysporum e na bioautografi a direta, inibição do Cylindrocladium spathulatum. Os resultados delinearam uma nova fonte de pesquisa, as plantas ornamentais. Estas podem ser fonte de constituintes químicos capazes de servirem como protótipos para novos agentes terapêuticos e para tratamento sanitário de plantas medicinais. Unitermos:Aster lanceolatus, atividade antibacteriana, atividade antifúngica, difusão em gel, concentração inibitória mínima.ABSTRACT: "Antibacterial and antifungal activity of ethanolics extracts from Aster lanceolatus Willd., Asteraceae". Popularly known as aster-arbustiva, margarida-de-são-miguel and monte-cassino, Aster lanceolatus is an ornamental plant. Having the knowledge that there is no studies on the biological activity of this species, this work aimed to check the antibacterial and antifungal activities. The ethanol extracts of the fl owers and of the stems with leaves were used. For the antibacterial activity eight pathogenic bacteria were submitted to the diffusion test in gel and minimal inhibitory concentration. The activity of the ethanolic extract of the fl owers has been demonstrated against Streptococcus pyogenes in diffusion in gel and the activity of the ethanol extract of the stems and leaves against Salmonella typhimurium and Streptococcus pyogenes in minimal inhibitory concentration. For the antifungal activity, three pathogenic yeasts have been used in the micelial growth tests in plates and direct bioautography. In the micelial growth tests in plates the inhibition of Fusarium oxysporum has been verifi ed and in the direct bioautography, inhibition of the Cylindrocladium spathulatum. The results indicated a new research source, the ornamental plants. These can be the source of chemicals capable of serving as prototypes for new therapeutic agents and for sanitary treatment of medicinal plants.

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Quantitative determination by HPLC of ent-kaurenoic and grandiflorenic acids in aerial parts of Wedelia paludosa D.C.

Cited by 20 publications

References 24 publications

Occurrence, Biological Activities and Synthesis of Kaurane Diterpenes and their Glycosides

Occurrence, Biological Activities and Synthesis of Kaurane Diterpenes and their Glycosides

Cytotoxicity of Wedelia paludosa D.C. extracts and constituents

Atividade antibacteriana e antifúngica de extratos etanólicos de Aster lanceolatus Willd., Asteraceae

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