Purpurasolol, a highly oxygenated coumarin from Pterocaulon purpurascens

Debenedetti, Sílvia; Nadinic, Elena L.; Gómez, María Celeste; Coussio, J.; Kimpe, Norbert De; Boeykens, Marc

doi:10.1016/0031-9422(95)00974-4

Cited by 19 publications

(11 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…As shown in Table 2, no synergism was detected for this mixture. It is noteworthy that, although the scavenging activity of the tested coumarins was high, their reducing power, measured with the FeCl 3 /K 3 Fe(CN) 6 system, was weak (around 10%).…”

Section: Figurementioning

confidence: 95%

Antioxidant and XOD Inhibitory Coumarins from Pterocaulon polystachyum DC

Vera

Zampini

Isla

et al. 2007

Natural Product Communications

View full text Add to dashboard Cite

The antioxidant capacity of prenyletin (6-hydroxy-7-isoprenyloxycoumarin (1), prenyletin-6-methylether (6-methoxy-7isoprenyloxycoumarin (2), and ayapin (6,7-methylenedioxycoumarin (3), isolated from an Argentine collection of Pterocaulon polystachyum, was investigated. Compound 1 displayed a higher scavenging activity on DPPH (72%) and ABTS (89%), at 100 µg/mL, than 2 and 3. In the non-enzymatic system of O 2•generation, compound 1 scavenged (46%) superoxide radicals at a scavenging concentration (SC 50 ) of 100 µg/mL. In addition, 1 inhibited 82% uric acid formation at 100 µg/mL, while allopurinol, employed as positive control, displayed 93% inhibition at the same concentration. The antioxidant ability of 1 is dose-dependant and apparently its OH group on C-6 is a structural requirement for the observed activity. A synergistic scavenging action of a ternary mixture (ratio 1:8:1) of 1, 2 and 3 was also observed.

show abstract

Section: Figurementioning

confidence: 95%

Antioxidant and XOD Inhibitory Coumarins from Pterocaulon polystachyum DC

Vera

Zampini

Isla

et al. 2007

Natural Product Communications

View full text Add to dashboard Cite

show abstract

“…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].…”

Section: And G Von Posermentioning

confidence: 99%

Distribution of coumarins in the tribe Plucheeae, genus Pterocaulon

et al. 2007

View full text Add to dashboard Cite

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].

show abstract

“…Isolou-se uma cumarina 5,6,7,8-tetraoxigenada, {2,3-dihidro-6-hidroxi-2-(1-hidroxi-1-metiletil)-5-metoxi-9H-pirano[2,3-f]-1,4-benzodioxina-9-ona} denominada purpurasolol de Pterocaulon purpurascens (DEBENEDETTI, 1996).…”

Section: Gênero Pterocaulonunclassified