4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity

Meyer, Nino; Haemers, Achiel; Mishra, Lallan; Pandey, Hrishi Kesh; Pieters, Luc; Berghe, D. A. Vandern; Vlietinck, A. J.

doi:10.1021/jm00106a039

Cited by 138 publications

(72 citation statements)

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“…Isokaempferide (or IKPF), the main flavonoid of the trunk bark of A. cearensis, also isolated from other plant species (Saeidnia et al, 2005), presented antibacterial activity for C. cucumerinum and B. cerus in earlier study (Wang et al, 1989), as well as antiviral activity against type 1 poliovirus and type 15 rinovirus (De Meyer et al , 1991). These studies corroborate, at least in part, the traditional use of A. cearensis in infectious respiratory diseases.…”

Section: Amburana Cearensis (Allemao) Ac Sm Fabaceae (Umburana-desupporting

confidence: 63%

Bioactivity and potential therapeutic benefits of some medicinal plants from the Caatinga (semi-arid) vegetation of Northeast Brazil: a review of the literature

Silva¹,

Melo²,

Vasconcelos³

et al. 2012

Rev. bras. farmacogn.

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Abstract:Medicinal plants have been used in traditional medicine for several thousand years all over the world. In this sense, information from Brazilian ethnic groups on folk medicine have contributed to the discovery of pharmacological activities from various plant-derived agents potentially leading to the innovative drugs. The Caatinga (semi-arid) vegetation is a highly threatened biome, covering a vast area in northeastern Brazil and has suffered from strong human influence for many decades. Many plants species found in the Caatinga have been widely used in folk medicine and for commercial manufacturing of phytotherapeutic products. Thus, the present review aims to disseminate to the scientific community some known species of medicinal plants found in the Caatinga that have been studied and analyzed in pharmacological scientific assays. Among the species that stood out for their local importance and multiplicity of uses were: Amburana cearensisand Zingiber officinalis L. (gengibre). The present study shows that several herbal constituents from Caatinga plants, whose pharmacological actions have been well characterized, may be relevant candidates for future and innovative therapeutic development.

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Section: Amburana Cearensis (Allemao) Ac Sm Fabaceae (Umburana-desupporting

confidence: 63%

Bioactivity and potential therapeutic benefits of some medicinal plants from the Caatinga (semi-arid) vegetation of Northeast Brazil: a review of the literature

Silva¹,

Melo²,

Vasconcelos³

et al. 2012

Rev. bras. farmacogn.

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“…Anti-rhinovirus type-l B and anti-poliovirus type-2 activities of chalcones (1, 2), f1avanones (3,4,7,16,17) the most active compounds were 3.82 and 4.47IJ.M for 23 and 27, respectively. A positive correlation between the anti-picornavirus activity and the presence of the 3-methoxy group has already been reported for natural and synthetic flavones (Van Hoof et al, 1984;Tsuchiya et al, 1985;De Meyer et al, 1991). The replacement of the 3-methoxy function with different substituents resulted in compounds having lower activity and higher cytotoxicity (De Meyer et el., 1991).…”

Section: Discussionmentioning

confidence: 77%

In vitro Evaluation of the Anti-Picornavirus Activities of New Synthetic Flavonoids

Desideri

Conti

Sestili

et al. 1995

Antivir Chem Chemother

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SummarySubstituted oxazolinylflavons and oxazolinylflavanones were synthesized in order to compare their anti-picornavirus activities with those of related natural and synthetic compounds. The antiviral potencies of the new compounds were evaluated against rhinovirus type 1B and poliovirus type 2 by a plaque reduction assay in HeLa cell cultures. Among the substituted flavanones only 6-chloro-4'-oxazolinylflavanone showed activity against both viruses. A comparison of the effects of 3-substituted f1avones indicated that the presence of a 3-methoxy group enhances the activity against rhinovirus, while the presence of a 3-hydroxy group enhances the activity against poliovirus.

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“…Experimental Chemistry 1 H-(300 MHz) and 13 C-NMR (75 MHz) spectra were obtained with a Varian Gemini-2000 spectometer. Chemical shifts (d) are reported in ppm relative to tetramethylenesilane as internal standard.…”

Section: Synthesis and Ppar-g G Ligand-binding Activity Of The New Sementioning

confidence: 99%

“…5Ј-Chloro-2Ј-hydroxy-4-methoxychalcone (7) In Vitro Biological Activity The PPAR-g ligand-binding activity of the chalcones (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) and chalconylidene-TZD (18)(19)(20) was determined using transient transfection assays.…”

Section: Synthesis and Ppar-g G Ligand-binding Activity Of The New Sementioning

confidence: 99%

Synthesis and PPAR-.GAMMA. Ligand-Binding Activity of the New Series of 2'-Hydroxychalcone and Thiazolidinedione Derivatives

Jung

Park²,

Pak³

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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Peroxisome proliferator-activated receptor (PPAR)-g is a member of the PPAR family and has been the subject of extensive research due to its mechanistic importance in glucose and lipid homeostasis.1) It is the predominant molecular target for the insulin-sensitizing thiazolidinedione (TZD) drugs such as troglitazone, pioglitazone, and rosiglitazone. 2,3) Those TZD derivatives can activate PPAR-g and improve insulin resistance by increasing the number of small adipocytes resulting in normal function as differentiated from preadipocytes and inducing apoptosis in large adipocytes, which produce and secrete adipocytokines such as leptin, tumor necrosis factor (TNF)-a, and free fatty acid.4) Recently, it has been reported that novel sulfonylurea or TZD derivatives containing a flavonoid ring system have antidiabetic activity. 5,6) Chalcones, originally isolated from natural plant sources, have been reported to have a variety of biological properties including antioxidant, antiinflammatory, and anticancer activities 7) and several synthetic chalcone derivatives are known to have inhibitory activity against diabetic complications. 8,9)It was envisaged that compounds containing these moieties in the same molecule may show enhanced biological activity. It was therefore of interest to synthesize some TZDs with a chalcone moiety (chalconylidene-TZDs) as a substituent at the C-5 position.In this study, we selected a group of 2Ј-hydroxychalcones (3-17) and chalconyl-TZDs (18-20) and tested them for PPAR-g ligand-binding activity in the transient reporter assay. ChemistryAs depicted in Chart 1, the chalcones (c) were synthesized by Winget's condensation of an aromatic acetophenone (a) with the appropriate aromatic aldehyde (b).10) The olefin parts of these chalcones were confirmed to have trans geometry based on the 1 H-NMR spectrum, in which the coupling constant between the two vinylic protons appearing at 6.9-7.2 and 7.8-8.3 ppm is approximately 15 Hz. A comparison of the physical and spectroscopic data of the synthesized compounds with the reported values showed good agreement.The chalconylidene-TZDs (18-20) were synthesized as shown in Chart 2. First, dicarboxybenzaldehyde (d) was condensed with TZD with anhydrous sodium acetate in acetic acid to form p-carboxybenzylidene-TZD (e, mp 155-157°C) (i.e., by Knoevenagel reaction). The Winget condensation gave products that were insoluble yellowish polymers made from d. On the other hand, the reaction of appropriate (a) compared with aldehyde (e) using Winget's condensation gave chalconylidene-TZDs (f). In the literature, it was reported that unsubstituted imidazolidinediones and benzaldehydes in acetic medium gave mainly the Z isomer. 11)In this study, only one isomer was obtained. However, due to the low solubility of the compounds and the difficulties of obtaining suitable crystals for X-ray analysis, the isomer could not be analyzed structurally in detail. Results and DiscussionThe results of the PPAR-g ligand-binding activity of 2Ј-hydroxychalcone and chalconylidene-TZD d...

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4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity

Cited by 138 publications

References 0 publications

Bioactivity and potential therapeutic benefits of some medicinal plants from the Caatinga (semi-arid) vegetation of Northeast Brazil: a review of the literature

Bioactivity and potential therapeutic benefits of some medicinal plants from the Caatinga (semi-arid) vegetation of Northeast Brazil: a review of the literature

In vitro Evaluation of the Anti-Picornavirus Activities of New Synthetic Flavonoids

Synthesis and PPAR-.GAMMA. Ligand-Binding Activity of the New Series of 2'-Hydroxychalcone and Thiazolidinedione Derivatives

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