37-Dihydroxy-8-methoxyflavone from Zuccagnia punctata

doi:10.1016/S0031-9422(00)80459-8

Phytochemistry

Volume 23, Issue 6, 14 May 1984, Pages 1340-1341

https://doi.org/10.1016/S0031-9422(00)80459-8 Get rights and content

Abstract

A phytochemical examination of the leaves of Zuccagnia punctata resulted in the isolation and identification of 3,7-dihydroxyflavone and 3,7-dihydroxy-8-methoxyflavone. The latter is a new natural product.

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Cited by (19)

Histochemical localization and characterization of chalcones on the foliar surface of Zuccagnia punctata Cav. Insights into their physiological role
2015, Phytochemistry Letters
Citation Excerpt :
Z. punctata aerial parts have been extensively used as a traditional medicine for the treatment of bacterial and fungal infections, asthma, arthritis and rheumatism (Ratera and Ratera, 1980; Toursarkissian, 1980). The constituents of Z. punctata aerial parts include phytochemicals such as flavonoids (flavanones, flavones and mainly chalcones), oxygenated monoterpene-rich essential oils (Álvarez et al., 2012) and caffeoyl esters (Agüero et al., 2010; Pederiva et al., 1975; Pederiva and Giordano, 1984; Svetaz et al., 2004). Z. punctata extracts and chalcones were reported to have antioxidant (Morán Vieyra et al., 2009), antibacterial (Zampini et al., 2005, 2012), antifungal (Agüero et al., 2010; Nuño et al., 2014; Quiroga et al., 2001; Svetaz et al., 2004, 2007), antiulcerous (De la Rocha et al., 2003) and antigenotoxic (Zampini et al., 2008) properties.
Dihydroxychalcones as well as other metabolites synthesized via the phenylpropanoid pathway have a wide range of biological activities. Although this class of phenolic compounds is found in very large amounts in some tissues, their physiological significance remains unclear.
This approach focused on the chemical analysis of Zuccagnia punctata leaf rinse extract in which dihydroxychalcones (99.25 μg 2′,4′-dihydroxychalcone/cm² and 73.38 μg 2′,4′-dihydroxy-3′-methoxychalcone/cm²) are the main constituents. Histochemical analysis (fluorescence microscope and emission scanning electron microscope coupled with an energy dispersive X-ray spectrometer) revealed a high flavonoid concentration on the foliar surface. The high accumulation of phenolic compounds, flavonoids or chalcones in the cuticle of Z. punctata leaves would act as defense mechanisms against UV radiation for the protection of photosynthetic tissues against oxidative stress.
Effects of Zuccagnia punctata extracts and their flavonoids on the function and expression of ABCB1/P-glycoprotein multidrug transporter
2012, Journal of Ethnopharmacology
Citation Excerpt :
Zuccagnia punctata extracts have been reported to show antioxidant (Morán Vieyra et al., 2009), antifungal (Quiroga et al., 2001; Svetaz et al., 2004, 2007; Agüero et al., 2010), antiulcer (De la Rocha et al., 2003), antigenotoxic (Zampini et al., 2008) properties and antibacterial activity, using in vitro and in vivo models, against antibiotic resistant Gram-negative (Zampini et al., 2005) and Gram-positive (Zampini et al., 2012) bacteria. The bioactive constituents of Zuccagnia punctata include polyphenolic compounds such as flavanones, flavones, chalcones and caffeoyl esters (Pederiva et al., 1975; Pederiva and Giordano, 1984; Svetaz et al., 2004; Zampini et al., 2005; Agüero et al., 2010). Previous papers have demonstrated the antibacterial (Zampini et al., 2005, 2012), antioxidant (Morán Vieyra et al., 2009), antigenotoxic (Zampini et al., 2008) and anti-inflammatory (Alberto et al., 2007) activities of flavonoids isolated from Zuccagnia punctata.
Zuccagnia punctata extracts (ZpE) are used in ethnomedicine as antimicrobial and anti-inflammatory drugs. The pharmacological properties of ZpE and their polyphenolic components suggest that they may be used as potential modulators on the P-glycoprotein (P-gp) multidrug transporter. P-gp is well known for its role in the acquired drug resistance by tumors following chemotherapy, causing a low drug bioavailability by extruding them out of the cells.
To evaluate the effects of ZpE and three of their phenolic components: 7-hydroxyflavanone (HF), 3,7-dihydroxyflavone (DHF) and 2′,4′-dihydroxychalcone (DHC) on P-gp activity and expression.
The effects of natural products on ABCB1/P-gp function and expression were evaluated by R-123 accumulation assay and western blot analysis using HK-2 cells as experimental model. The ABCB1 mRNA content was determined by SQRT-PCR.
The accumulation of R-123 in HK-2 cells was significantly increased by ZpE and DHF, and to a lesser extent by DHC, indicating their roles on the efflux transporter activity. However, HF did not show any effect. HK-2 cells maintained in the presence of ZpE or DHF for 72 h, showed an increase in P-gp expression whereas activity was unchanged or decreased. No changes were observed in ABCB1 mRNA content. Furthermore, in these assay conditions, more sensibility of HK-2 cells to the cytotoxic action of cyclosporine A (P-gp substrate) was observed.
These results may suggest an impact of Zuccagnia punctata and some of its components on the pharmacokinetics of drugs that are P-gp substrates, as well as a potential role on multidrug resistance modulation.
Potentiality of standardized extract and isolated flavonoids from Zuccagnia punctata for the treatment of respiratory infections by Streptococcus pneumoniae: In vitro and in vivo studies
2012, Journal of Ethnopharmacology
Citation Excerpt :
In addition, Zuccagnia punctata is reported to have antioxidant (Morán Vieyra et al., 2009), antibacterial (Zampini et al., 2005), antifungal (Quiroga et al., 2001; Svetaz et al., 2004, 2007; Agüero et al., 2010), antiulcer (De la Rocha et al., 2003), and antigenotoxic (Zampini et al., 2008) properties. The constituents of Zuccagnia punctata include phytochemicals such as flavonoids (flavanones, flavones, chalcones) and caffeoyl esters (Pederiva et al., 1975; Pederiva and Giordano, 1984; Svetaz et al., 2004; Agüero et al., 2010). In addition, it was reported that the standardized extracts of Zuccagnia punctata and chalcone isolated from this plant possesses antibacterial activity against Gram-negative bacteria (Zampini et al., 2005) including several multiple drug-resistant clinical strains such as Escherichia coli, Enterococcus faecalis, Klebsiella pneumonia, Pseudomonas aeruginosa and others.
Zuccagnia punctata Cav. (Fabaceae) is a monotypic species distributed in western Argentina and is traditionally used for the treatment of bacterial and fungal infections. The aim of this study was to demonstrated the antibacterial activity of the Zuccagnia punctata standardized extract and the structurally related non-methoxylated flavonoids with similar pattern of substitution and differences in ring C present in this plant species: 7-hydroxyflavanone (HF), 2′,4′-dihydroxychalcone (DHC) and 3,7-dihydroxyflavone (DHF), against Streptococcus pneumoniae clinical isolates using in vitro and in vivo models.
MIC values of natural products were determined by agar macrodilution method. In vivo activities were investigated in a Streptococcus pneumoniae infection model in mice. Lung and blood samples were obtained for bacterial cell counts. The serum was used by biochemical analysis (alanine transaminase, aspartate transaminase, urea and creatinine) in order to evaluate the toxicity of natural products.
All samples showed antimicrobial activity in vitro with MIC values between 50 and 500 μg/ml. Zuccagnia punctata extract (1 mg/mice) and HF (1 mg/mice) significantly reduced the number of viable Streptococcus pneumoniae in lung (p < 0.01) while lower quantities has not effect. Therefore, the present study has shown that intake once or twice a day of 1 mg of Zuccagnia punctata extract or HF for seven days did not result in toxicity.
Our results showed that Zuccagnia punctata extract as well as one of its isolated flavonoids, 7-hydroxyflavanone, could be useful for the development of a novel respiratory infections treatment.
(-)-5,6-Dehydrocamphor from the antifungal essential oil of Zuccagnia punctata
2012, Phytochemistry Letters
Citation Excerpt :
Previous studies have shown antifungal activity in the dichloromethane, chloroform and methanol extracts of its aerial parts. The bioassay-guided fractionation of the antifungal extracts led to the isolation of chalcones, flavonols, flavanones and caffeic esters (Pederiva and Giordano, 1984; Svetaz et al., 2004, 2007) some of which displayed interesting antifungal activities. Earlier studies on secretory structures in Caesalpinieae tribe showed that abundant small capitate glands are embedded in both leaf surfaces of Z. punctata (Lersten and Curtis, 1996).
The essential oils from aerial parts of nine populations of Zuccagnia punctata Cav. (Fabaceae) were obtained by hydrodistillation and analyzed by GC–FID, GC–MS and ¹³C NMR. A total of 80 constituents, mainly oxygenated monoterpenes, were identified representing from 79.0 to 95.2% of the total oils which showed different composition patterns. The unusual compound (−)-5,6-dehydrocamphor, the major constituent in six of the samples investigated with percentages ranging from 12.3% to 56.5%, was isolated for the first time from nature and its structure was completely defined from NMR spectrometric data. Microscope studies of leaves indicated that not only capitate glands but also non-glandular trichomes, not previously described in this species, were present on the leaf surfaces.
The essential oil showed antifungal activity against the dermatophytes Microsporum gypseum, Tricophyton rubrum and T. mentagrophytes with MIC values between 15.6 and 125 μg ml⁻¹, being T. rubrum the most susceptible species.
Evaluation of genotoxic and antigenotoxic effects of hydroalcoholic extracts of Zuccagnia punctata Cav.
2008, Journal of Ethnopharmacology
Zuccagnia punctata Cav. (Fabaceae), a widely used plant species in Argentine folk medicine, has been shown to have a broad spectrum of antibacterial, antifungal, antioxidant and cytoprotective activities. In this study, the hydroalcoholic extract of Zuccagnia punctata and 2′,4′-dihydroxychalcone isolated from it were investigated for genotoxicity/antigenotoxicity in the in vitro comet assay test on human hepatoma HepG2 cells. No acute toxicity of the extract could be determined. HepG2 cells were treated with three different concentrations (2.5, 5.0 and 10.0 μg/mL) or 2′,4′-dihydroxychalcone (0.01, 0.10 and 1.00 μg/mL). To explore the potential mechanisms of action, two approaches were followed: co-treatment with 4-nitroquinoline-N-oxyde (4-NQO), a direct genotoxic compound, and a pre-treatment protocol with benzo[a]pyrene (B[a]P), an indirect genotoxic compound. The natural products neither affected cell viability nor induced DNA damage in the concentration range tested. Zuccagnia punctata tinctures were able to diminish the DNA damage induced in HepG2 cells by 4-NQO and B[a]P in 31% and 10%, respectively at 10 μg/mL. Pre-treatment of HepG2 cells with 2′,4′-dihydroxychalcone was highly effective in decreasing B[a]P-induced DNA damage at a statistically significant level, with an almost clear dose–response relationship. The inhibition values were 28.2–43.9% for the tested concentrations of 0.01–1 μg/mL, respectively. The results clearly indicate that the phytoextract from Zuccagnia punctata, under the experimental conditions tested, is not genotoxic and that 2′,4′-dihydroxychalcone contributes to a high degree to the antigenotoxic effects of Zuccagnia punctata tincture.
Antibacterial activity of Zuccagnia punctata Cav. ethanolic extracts
2005, Journal of Ethnopharmacology
The present study was conducted to investigate antibacterial activity of Zuccagnia punctata ethanolic extract against 47 strains of antibiotic-resistant Gram-negative bacteria and to identify bioactive compounds. Inhibition of bacterial growth was investigated using agar diffusion, agar macrodilution, broth microdilution and bioautographic methods. Zuccagnia punctata extract was active against all assayed bacteria (Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Enterobacter cloacae, Serratia marcescens, Morganella morganii, Acinetobacter baumannii, Pseudomonas aeruginosa, Stenotrophomonas maltophilia) with minimal inhibitory concentration (MIC) values ranging from 25 to 200 μg/mL. Minimal bactericidal concentration (MBC) values were identical or two-fold higher than the corresponding MIC values. Contact bioautography, indicated that Zuccagnia punctata extracts possess one major antibacterial component against Pseudomonas aeruginosa and at least three components against. Klebsiella pneumoniae and Escherichia coli. Activity-guided fractionation of 1he ethanol extract on a silica gel column yielded a compound (2′,4′-dihydroxychalcone), which exhibited strong antibacterial activity with MIC values between 0.10 and 1.00 μg/mL for Proteus mirabilis, Enterobacter cloacae, Serratia marcescens, Morganella morganii, Acinetobacter baumannii, Pseudomonas aeruginosa, Stenotrophomonas maltophilia. These values are lower than imipenem (0.25–16 μg/mL). Zuccagnia punctata might provide promising therapeutic agents against infections with multi-resistant Gram-negative bacteria.

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Phytochemistry

Short Report37-Dihydroxy-8-methoxyflavone from Zuccagnia punctata

Abstract

Phytochemistry

Phytochemistry

An. Asoc. Quím. Argentina

An. Asoc. Quím. Argentina

Histochemical localization and characterization of chalcones on the foliar surface of Zuccagnia punctata Cav. Insights into their physiological role

Effects of Zuccagnia punctata extracts and their flavonoids on the function and expression of ABCB1/P-glycoprotein multidrug transporter

Potentiality of standardized extract and isolated flavonoids from Zuccagnia punctata for the treatment of respiratory infections by Streptococcus pneumoniae: In vitro and in vivo studies

(-)-5,6-Dehydrocamphor from the antifungal essential oil of Zuccagnia punctata

Evaluation of genotoxic and antigenotoxic effects of hydroalcoholic extracts of Zuccagnia punctata Cav.

Antibacterial activity of Zuccagnia punctata Cav. ethanolic extracts

Short Report
37-Dihydroxy-8-methoxyflavone from Zuccagnia punctata