Natural and Synthetic Coumarin Derivatives with Anti-Inflammatory / Antioxidant Activities

Fylaktakidou, Konstantina C.; Hadjipavlou‐Litina, Dimitra; Litinas, Κonstantinos E.; Nicolaides, D. N.

doi:10.2174/1381612043382710

Cited by 869 publications

(427 citation statements)

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“…Depending on the position of the initial dimethylallylation, furocoumarin derivatives may be angular (23, 24, 26-29, 31, 33) or linear (25). Coumarins isolated from a number of plant species have been shown to possess anti-inflammatory and chemopreventive properties [14,15]. Indeed, coumarins isolated from ashitaba have demonstrated cytotoxic properties [3,16,17] in addition to antidiabetic [18], antiobesity [12], and blood pressure-reducing effects [19].…”

Section: Coumarinsmentioning

confidence: 99%

A Review of the Medicinal Uses and Pharmacology of Ashitaba

Caesar

Cech

2016

Planta Med

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Medicinal plants are commonly employed for therapeutic purposes throughout the world. A recent National Health Interview Survey estimated that nearly 18 % of adults in the United States regularly took non-vitamin, non-mineral dietary supplements in 2012 [1]. Because of the popularity of herbal medicines, it is important to understand the chemical basis behind the purported activities of botanicals. Angelica, a member of the Apiaceae (Umbelliferae) family, is a large genus comprised of over 60 species. Members of the genus have been utilized as medicines across the world, most notably in Asia, to treat numerous ailments, including influenza, hepatitis, arthritis, indigestion, fever, and microbial infections [2]. An increasing number of studies are being conducted on a medicinally promising member of the genus, Angelica keiskei Koidzumi (Apiaceae), or ashitaba. This large leafy perennial plant native to the Pacific coast of Japan is used throughout Asia for its diuretic, laxative, stimulant, and galactagogue properties [3]. In the past decade, several active constituents representing chalcones, flavanones, and coumarins have been isolated and characterized from ashitaba, and several bioactiv-ities have been described. This review presents the current progress on ashitaba pharmacological studies, with a focus on isolated secondary metabolites, biological activity, toxicological data, and clinical relevance. Bioactive Metabolites Isolated from Ashitaba ! Chalcones Most of the literature on the bioactive metabolites from ashitaba concerns the diverse activity of various chalcones (l " Table 1 and Fig. 1), which are most abundant in the root bark of the plant [4]. Chalcones are formed from phenylpropanoid starter units, extended with three malonyl-CoA molecules. The resulting polyketide is folded by the enzyme chalcone synthase to promote Claisen condensations and subsequent enolizations [5]. Interestingly, the bioactive chalcones found in ashitaba are prenylated at the 5′-position (l " Fig. 1), indicating that these molecules have undergone multiple biosynthetic steps, travelling through the acetate, shikimate, and isoprenoid pathways.

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Section: Coumarinsmentioning

confidence: 99%

A Review of the Medicinal Uses and Pharmacology of Ashitaba

Caesar

Cech

2016

Planta Med

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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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“…Although more than 1300 coumarins have been identified from natural sources [17], and various pharmacological and biochemical actions were identified in the past [18], the coumarin in Melilotus suaveolens Ledeb has not been well investigated. The effect of coumarin in Melilotus suaveolens Ledeb on pro-inflammatory cytokines and mediators, on blocking translocation of NF-kappaB, on anti-inflammatory mediators and on comparison to Dexamethasone are first explored in our research.…”

Section: Discussionmentioning

confidence: 99%

Inner Anti-inflammatory Mechanisms of Petroleum Ether Extract from Melilotus suaveolens Ledeb

et al. 2007

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-Summary. Melilotus suaveolens Ledeb is a species of traditional medical plant for treating inflammationrelated disease. This study is to explore the inner anti-inflammatory mechanism on petroleum ether extract from Melilotus suaveolens Ledeb. Materials and Methods. Inflammatory cellular model was founded by intervention of lipopolysaccharide (LPS) on RAW264.7 cell line. Secretion of TNF-a, IL-1b, IL-6, NO and IL-10 in supernatant, mRNA expression of TNF-a, COX-2, iNOS and HO-1, protein expression of COX-2 and HO-1, activation of NFkB and ingredients in the extract were assayed. Results. The extract could not only reduce production of pro-inflammatory mediators by blocking NF-kB activation but promote release of anti-inflammatory mediator HO-1 significantly. The only active ingredient in the extract was coumarin and the concentration of coumarin in each 1 g extract was 0.27822 mg. Conclusion. Compared to Dexamethasone, the extract not only has similar effects on antagonizing proinflammatory mediators and cytokines but has effects on promoting production of anti-inflammatory mediators.

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Natural and Synthetic Coumarin Derivatives with Anti-Inflammatory / Antioxidant Activities

Cited by 869 publications

References 0 publications

A Review of the Medicinal Uses and Pharmacology of Ashitaba

A Review of the Medicinal Uses and Pharmacology of Ashitaba

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

Inner Anti-inflammatory Mechanisms of Petroleum Ether Extract from Melilotus suaveolens Ledeb

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