Coumarins from Pterocaulon balansae and P. lanatum

Magalhães, Aderbal F.; Magalhães, Eva G.; Filho, H F Leitao; Frighetto, R. T. S.; Barros, S. M.

doi:10.1016/0031-9422(81)80042-8

Cited by 24 publications

(11 citation statements)

References 7 publications

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“…The Et 2 O residue (2.0 g) of the ethanolic extract from P. alopecuroides, afforded, after different chromatographic procedures, 11.8 mg of 7-(2,3-dihydroxy-3-methylbutoxy)-6-methoxycoumarin (1) 6 , 10.8 mg of 5,6-methylenedioxy-7-(2,3-dihydroxy-3-methylbutoxy)coumarin (2) 7…”

Section: Resultsmentioning

confidence: 99%

Secondary Metabolites from Pterocaulon alopecuroides and their Antiproliferative Activities

Castillo¹,

Padrón²,

Emiliano³

2019

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Objective: To isolate secondary metabolites from the aerial parts of Pterocaulon alopecuroides, elucidate their structures and evaluate their antiproliferative activities on selected human cancer cell lines. Materials and Methods: The ethanolic extract of P. alopecuroides afforded five compounds, which were characterized using spectroscopic techniques and by comparison with data from the literature. Antiproliferative activities of all isolates were evaluated. Results: The compounds 7-(2,3-dihydroxy-3-methylbutoxy)-6-methoxycoumarin (1), 5,6-methylenedioxy-7-(2,3-dihydroxy-3-methylbutoxy) coumarin (2), Dihydrokaempferol (3), 5,7,4´-trihydroxy-6-(α,α-dimethylallyl)dihydroflavonol (4) and 5,4´-dihydroxy-7-(γ,γ-dimethylallyloxy)dihydroflavonol (5) were isolated. The antiproliferative activity of all compounds was evaluated in a panel of six human solid tumor cell lines showing GI 50 values for the most active compounds in the low micromolar range. Conclusion: Compound 2 is reported for first time from P. alopecuroides. Isolated coumarins show no antiproliferative activity, whilst among flavonoids compound 5 showed the best antiproliferative activity.

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Section: Resultsmentioning

confidence: 99%

Secondary Metabolites from Pterocaulon alopecuroides and their Antiproliferative Activities

Castillo¹,

Padrón²,

Emiliano³

2019

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“…C. Stein, 1 D. Fritz, 1 L. F. Paiva Lima, 2 N. I. Matzenbacher, 2 UDC 547.972 J. Schripsema, 3 V. Pires, 4 P. Sonnet, 4 …”

Section: Distribution Of Coumarins In the Tribe Plucheeae Genus Ptermentioning

confidence: 99%

“…About half of the Pterocaulon species have been analyzed previously and many compounds have been isolated: caffeoylquinic acids from P. virgatum [2]; thiophene acetylenes and flavanols from P. virgatum [3]; polyacetylenes from P. alopecuroides, P. balansae, P. lanatum, and P. rugosum [4]; hydroxy-α-caryophyllene from P. serrulatum [5]; flavonoids from P. sphacelatum [6], P. purpurascens [7], and P. alopecuroides [8]; and coumarins from P. balansae, P. lanatum [4], P. purpurascens [9][10][11], P. redolens [12], P. virgatum [13][14][15][16], P. polystachyum [17], and P. alopecuroides [8]. Several species of the genus are used in folk medicine as insecticides and agents against snake bites [15].…”

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confidence: 99%

Distribution of coumarins in the tribe Plucheeae, genus Pterocaulon

et al. 2007

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The genus Pterocaulon (Asteraceae) is included in the tribe Plucheeae [1]. About half of the Pterocaulon species have been analyzed previously and many compounds have been isolated: caffeoylquinic acids from P. virgatum [2]; thiophene acetylenes and flavanols from P. virgatum [3]; polyacetylenes from P. alopecuroides, P. balansae, P. lanatum, and P. rugosum [4]; hydroxy-α-caryophyllene from P. serrulatum [5]; flavonoids from P. sphacelatum [6], P. purpurascens [7], and P. alopecuroides [8]; and coumarins from P. balansae, P. lanatum [4], P. purpurascens [9][10][11], P. redolens [12], P. virgatum [13][14][15][16], P. polystachyum [17], and P. alopecuroides [8]. Several species of the genus are used in folk medicine as insecticides and agents against snake bites [15].In this work we investigate the occurrence of coumarins in exudates of the species of Pterocaulon native to Brazil and isolate the most abundant compounds. The taxonomic significance of these compounds is discussed.In Plucheeae the only genus that contains coumarins is Pterocaulon in which 40 different coumarins were previously found in ten species. In this work we analyzed five other species native to South Brazil, and coumarins were found in all of them. These data indicate that these compounds could be considered chemotaxonomic markers for the genus Pterocaulon.Although the species of Pterocaulon exhibit other classes of compounds, coumarins are characteristic of the genus. In Pterocaulon, coumarins can be di-, tri-, or tetraoxygenated, and all of them are 6,7 oxygenated.Pterocaulon alopecuroides and P. polystachyum were studied previously, but in this work we investigated the exudate instead of the extract of the powdered plant. The exudate of P. alopecuroides afforded 5-methoxy-6,7-methylenedioxycoumarin (1) and 7-(2,3-epoxy-3-methyl-3-butyloxy)-6-methoxycoumarin (2), previously found in P. virgatum [13,18]. To our knowledge this is the first report on the occurrence of coumarins 1 and 2 in Pterocaulon alopecuroides. From this plant, the compounds 7-(2,3-dihydroxy-3-methylbutyloxy)-6-methoxycoumarin and 7-(2,3-dihydroxy-3-methylbutyloxy)-5-hydroxy-6-coumarin were previously obtained [8]. This difference could be due to the extraction method employed and to the fact that the plants were collected in different places. Nevertheless, it is worthwhile to state that the plant exudate contained several coumarins of which only the most abundant were isolated.The exudate of P. polystachyum, besides 5-methoxy-6,7-methylenedioxycoumarin (1), afforded three other coumarins, namely ayapin (3), prenyletin (4), and prenyletin methyl-ether (5). These compounds were previously isolated from the chloroform extract of the powdered plant material [17,19].

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“…The chemistry of several of them has been studied; their common metabolites include flavonoids and coumarins [2], [3], [4], [5], [6], [7], [8], [9]. Plants from the genus Pterocaulon are used in traditional medicine in different zones of the world and antibiotic [9], antiviral [10], cytotoxic [11] and antifungal [12], [13] activities have been reported for them.…”

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confidence: 99%

Flavonoids fromPterocaulon alopecuroideswith Antibacterial Activity

Alarcón

Flores²,

Ocampos³

et al. 2008

Planta Med

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Three flavonoids, (2 R,3 R)-5,4'-dihydroxy-3'- O-methyl-7-(gamma,gamma-dimethylallyloxy)dihydroflavonol 1, (2 R,3 R)-5,7,4'-trihydroxy-3'- O-methyl-6-(alpha,alpha-dimethylallyl)dihydroflavonol 2, and (2 R,3 R)-5,7,4'-trihydroxy-6-(alpha,alpha-dimethylallyl)dihydroflavonol 3, together with three known flavonoids ( 4 - 6), were isolated from the aerial parts of PTEROCAULON ALOPECUROIDES. The structures of the compounds were determined by mass and by 1 D and 2 D NMR spectroscopy. Screening of the antibacterial activity of all six compounds was conducted by a disc diffusion test against BACILLUS CEREUS, BACILLUS SUBTILIS, SALMONELLA TYPHIMURIUM and PROTEUS MIRABILIS. The minimum inhibitory concentration (MIC) of the active compounds ( 2, 3, 4, 6) was determined by a microdilution assay. These compounds were active only against both Gram+ bacteria with MIC values < or = 200 microg/mL.

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Coumarins from Pterocaulon balansae and P. lanatum

Cited by 24 publications

References 7 publications

Secondary Metabolites from Pterocaulon alopecuroides and their Antiproliferative Activities

Secondary Metabolites from Pterocaulon alopecuroides and their Antiproliferative Activities

Distribution of coumarins in the tribe Plucheeae, genus Pterocaulon

Flavonoids fromPterocaulon alopecuroideswith Antibacterial Activity

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