Antioxidant activity of coumarins and flavonols from the resinous exudate of Haplopappus multifolius

Torres, René; Faini, Francesca; Modak, Brenda; Urbina, Francisco Zúñiga; Labbé, Cecilia; Guerrero, Juan

doi:10.1016/j.phytochem.2006.03.016

Cited by 80 publications

(46 citation statements)

References 10 publications

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“…The structures of all the natural coumarins isolated from Haplopappus multifolius 14,15 , and the derivative 8, were characterized by spectroscopic methods and comparison with known compounds. The structures of the compounds are shown in Figure 1: 1 7-O-prenyl-coumarin; 2 6-hydroxy-7-[(E,E)-3',7'-dimethyl-7'-hydroxy-2',5'-octodienyloxy] coumarin; 3 6-hydroxy-7-[(E,E)-3',7'-dimethyl-5'-hydroxy-2',6'-octodienyloxy] coumarin; 4 6-hydroxy-7-prenyl coumarin (prenyletin); 5 6,7-dihydroxy (esculetin); 6 7-hydroxy coumarin (umbelliferone; 7 6[β-D-glucopyrasyl]-7-hydroxy coumarin (esculin); 8 6,7 diacetyl-esculetin.…”

Section: Resultsmentioning

confidence: 99%

“…Coumarins 1-7 were isolated from leaves of Haplopappus multifolius and their structures had been reported previously 14,15 . Compound 8 was prepared from 5, by an acetylation in the common way.…”

Section: Methodsmentioning

confidence: 99%

“…Searching for new LOX inhibitors, we evaluated in-vitro seven coumarins previously isolated in our Laboratories from Haplopappus multifolius 14,15 and one diacetyl derivative of esculetin (5), against soybean lipoxygenase (15-sLOX). Some of those compounds presented better inhibitory activity than quercetin, taked as comparison compound.…”

Section: Introductionmentioning

confidence: 99%

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Coumarins of Haplopappus Multifolius and Derivative as Inhibitors of Lox: Evaluation in-Vitro and Docking Studies

Torres

Mascayano

Núñez

et al. 2013

J. Chil. Chem. Soc.

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Several natural compounds containing a coumarin moiety have been reported. They have multiple biological activities, e.g., as scavengers of reactive oxygen species (ROS) and to reduce the inflammatory processes by inhibition of enzymes like COX or LOX.A study was made of the inhibitory capacity of seven natural coumarins and one derivative of esculetin, against soybean 15-lipoxygenase (15-sLOX). The studied coumarins showed interesting degrees of inhibition compared to quercetin, a known LOX inhibitor. Docking studies of some compounds into the binding site of 15-sLOX and 5-hLOX were also made.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Coumarins of Haplopappus Multifolius and Derivative as Inhibitors of Lox: Evaluation in-Vitro and Docking Studies

Torres

Mascayano

Núñez

et al. 2013

J. Chil. Chem. Soc.

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“…Coumarins are a group of natural compounds which are extremely variable in structure (Beillerot et al, 2008), leading to compounds displaying multiple biological properties as in vitro antiproliferative and in vivo antitumor activities (Kostova, 2005); antioxidant activity (Beillerot et al, 2008;Farombi and Nwaokeafor, 2005;Fylaktakidou et al, 2004;Girennavar et al, 2007;Kontogiorgis et al, 2004;Torres et al, 2006;Wua et al, 2007;von Kruedener et al, 1996); inhibitory activity against cytochrome P450 enzyme (Girennavar et al, 2007); neuroprotective, anticancer and antimutagenic activities (Borges et al, 2005;Stanczyk et al, 2005); anti-inflammatory activity (Borges et al, 2005;Khan and Sharma, 1993;Kontogiorgis et al, 2004;Stanczyk et al, 2005); vasorelaxant (Hoult and Paya, 1996) and anticoagulant activities (Khan and Sharma, 1993). Some studies reveal that the multiple pharmacological activities of coumarins may be related to their antioxidant properties (Borges et al, 2005;Stanczyk et al, 2005), as oxidative damage to biomolecules causes accelerated aging and many chronic diseases, including neurodegenerative diseases, cancer, cardiovascular …”

Section: Resultsmentioning

confidence: 99%

In vitro cytotoxic, antioxidant and antiviral effects of Pterocaulon alopecuroides and Bidens segetum extracts

Silveira¹,

Martins²,

Costa³

et al. 2009

Rev. bras. farmacogn.

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RESUMO: "Efeitos citotóxico, antioxidante e antiviral in vitro de extratos de Pterocaulon alopecuroides e Bidens segetum". Pterocaulon alopecuroides (Lamark) De Candolle e Bidens segetum Mart. ex Colla são duas espécies pertencentes à família Asteraceae. Os extratos dessas duas espécies foram avaliados quanto às suas atividades citotóxica, antioxidante e antiviral. Todos os extratos analisados apresentaram citotoxidade muito alta contra linhagens de células RBL-2H3. O ensaio de atividade antioxidante demonstrou uma alta atividade das frações em acetato de etila de B. segetum e P. alopecuroides. Isso pode ser parcialmente explicado pelo alto conteúdo de cumarinas, ao menos para P. alopecuroides. Nenhum dos extratos etanólicos totais de B. segetum mostraram atividade significativa contra o vírus Herpes simplex (Tipos 1 e 2 resistentes ao aciclovir). O extrato etanólico de P. alopecuroides também foi inativo contra o vírus Herpes simplex tipo 1 resistente ao aciclovir. Entretanto, este extrato apresentou atividade inibitória contra o vírus Herpes simplex tipo 2 resistente ao aciclovir. Do extrato etanólico bruto de P. alopecuroides foi possível isolar a 7-(2',3'-dihidroxi-3'-metilbutiloxi)-6-metoxicumarina, a qual foi testada nas mesmas condições, demonstrando um índice de inibição viral quase duas vezes maior do que o da amostra de P. alopecuroides para HSV-2-ACVr. A cumarina tabém foi ativa contra HSV-1-ACVr. Esses resultados evidenciam a importância de Pterocaulon alopecuroides e Bidens segetum como plantas medicinais.Unitermos: Pterocaulon alopecuroides, Bidens segetum, atividade antiviral, atividade citotóxica, atividade antioxidante, 7-(2',3'-dihidroxi-3'-metilbutiloxi)-6-metoxicumarina. ABSTRACT:Pterocaulon alopecuroides (Lamark) De Candolle and Bidens segetum Mart. ex Colla are two species belonging to the Asteraceae family. Extracts from those two species were evaluated to their cytotoxic, antioxidant and antiviral activities. All the extracts assayed have shown a very high cytotoxity against RBL-2H3 cell line. The antioxidant assay pointed out a really high activity of the ethyl acetate extracts for B. segetum and P. alopecuroides. This can be partially explained due to the high content of coumarins, at least for P. alopecuroides. None of the total ethanol extracts from B. segetum showed significant activity against the two strains of Herpes simplex virus (Types 1 and 2 resistant to acyclovir). P. alopecuroides ethanol extract was also inactive against the Herpes simplex virus type 1 resistant to acyclovir. However, this extract presented inhibitory activity against the Herpes simplex virus type 2 resistant to acyclovir. From the ethanol crude extract of P. alopecuroides, it was possible to isolate 7-(2',3'-dihidroxy-3'-methylbutyloxy)-6-methoxycoumarin, which was tested in the same conditions, showing a viral inhibitory rate almost twice bigger than the P. alopecuroides sample for HSV-2-ACVr. The coumarin was also active against HSV-1-ACVr. Those results provide further evidence of the importance of Pter...

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“…namely kynurenic acid (1), alaschanioside C (2), umbelliferone (3), bergaptol-O-␤-d-glucopyranoside (4), nodakenin (5), oxypeucedanin (6), bergapten (7), diosmetin (8), oxypeucedanin hydrate (9), O-prenyl-umbelliferone (10), phellopterin (11) and isoimperatorin (12) were isolated in our laboratory from the seeds of N. incisum and N. franchetii and their structures ( Fig. 1) were elucidated by comparison of UV, MS, 1 H NMR and 13 C NMR spectral data with the literature values [4,5,[23][24][25][26][27][28][29]. The purity of each compound was determined to be higher than 98% by HPLC-UV analysis.…”

Section: Chemicals and Materialsmentioning

confidence: 99%

Discrimination of the seeds of Notopterygium incisum and Notopterygium franchetii by validated HPLC-DAD–ESI-MS method and principal component analysis

Kong

Jiang

Zhou

et al. 2011

Journal of Pharmaceutical and Biomedical Analysis

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Antioxidant activity of coumarins and flavonols from the resinous exudate of Haplopappus multifolius

Cited by 80 publications

References 10 publications

Coumarins of Haplopappus Multifolius and Derivative as Inhibitors of Lox: Evaluation in-Vitro and Docking Studies

Coumarins of Haplopappus Multifolius and Derivative as Inhibitors of Lox: Evaluation in-Vitro and Docking Studies

In vitro cytotoxic, antioxidant and antiviral effects of Pterocaulon alopecuroides and Bidens segetum extracts

Discrimination of the seeds of Notopterygium incisum and Notopterygium franchetii by validated HPLC-DAD–ESI-MS method and principal component analysis

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