2′,4-Dihydroxy-3′,4′,6′-trimethoxychalcone from <i>Chromolaena odorata</i> possesses anti-inflammatory effects via inhibition of NF-κB and p38 MAPK in lipopolysaccharide-activated RAW 264.7 macrophages

Dhar, Rana; Kimseng, Rungruedee; Chokchaisiri, Ratchanaporn; Hiransai, Poonsit; Utaipan, Tanyarath; Suksamrarn, Apichart; Chunglok, Warangkana

doi:10.1080/08923973.2017.1405437

Cited by 28 publications

(19 citation statements)

References 37 publications

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“…As macrophage polarization is a complex field that intersects with most physiological and pathological scenarios, M1 macrophages are typically activated by IFN-γ or LPS to produce pro-inflammatory cytokines, phagocytize microbes, and eventually initiate an immune response (Cavender et al, 1991). Activation of macrophages by LPS enhances the production of proinflammatory mediators and cytokines such as TNF-α and the IL-family (Dhar et al, 2018). Analogs of diacyl glycerol (DAG) such as PMA are known to induce protein kinase C (PKC).…”

Section: Discussionmentioning

confidence: 99%

In vitro Antimycobacterial, Apoptosis-Inducing Potential, and Immunomodulatory Activity of Some Rubiaceae Species

et al. 2019

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Tuberculosis (TB), a disease caused by microorganisms of the Mycobacterium tuberculosis complex, infects almost one-third of the world’s population. The TB epidemic has been further exacerbated by the emergence of multi, extensively, and totally-drug-resistant (MDR, XDR, and TDRTB) strains. An effective immune response plays a crucial role in determining the establishment of TB infection. Therefore, the modulation of the immune system has been considered as a vital approach for the treatment or control of various immune-related diseases such as TB. In this study, the antimycobacterial, immunomodulatory, and apoptosis-inducing effects of six Rubiaceae species were evaluated. A twofold serial dilution method was used to determine the minimum inhibitory concentration values of the plant extracts. The effect of the extracts on the activity of 15-lipoxygenase was investigated. The levels of six different cytokines, IL-2, IL-4, IL-5, IL-10, IFN-γ, and TNF-α, were measured in LPS-activated U937 cell line while the apoptosis-inducing effect of the extracts was evaluated using an annexin V/PI assay using a flow cytometer. The results obtained revealed that all the six extracts tested had antimycobacterial activity against M. tuberculosis H37Rv, M. tuberculosis ATCC 25177, and Mycobacterium bovis ATCC 27299 strains, with MIC values ranging from 39 to 312 μg/mL. The extracts of Cremaspora triflora and Cephalanthus natalensis were the most active against M. tuberculosis (MIC = 39 μg/mL), followed by Pavetta lanceolata and Psychotria zombamontana against M. bovis (MIC = 78 μg/mL). The extracts of P. zombamontana and Psychotria capensis had remarkable IC50 values of 4.32 and 5.8 μg/mL, respectively, better than that of quercetin. The selected extracts promoted Th1/Th2 balances in an in vitro model at the tested concentration which may suggest the therapeutic value of the plant in diseases where inflammation is a significant factor such as TB. The addition of the crude extracts of C. triflora, P. capensis, and P. zombamontana at the tested concentrations to the cell culture medium induced apoptosis in a time- and dose-dependent manner. This interesting preliminary result generated from this study encourages further investigations of these extracts owing to the LOX-inhibitory effect, immunomodulatory, and apoptotic-inducing properties in addition to their antimycobacterial properties.

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Section: Discussionmentioning

confidence: 99%

In vitro Antimycobacterial, Apoptosis-Inducing Potential, and Immunomodulatory Activity of Some Rubiaceae Species

et al. 2019

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“…Chalcones have been utilized as a precursor for the synthesis of compounds which possess pharmacological importance (Straub, 1995). The chalcones' chemistry remains a major interest for scientists in the 21st century, producing a diversity of promising pharmacological activities like anti-inflammatory (Dhar et al, 2018;Fu et al, 2019;Gan et al, 2018;Li et al, 2017;Mahapatra et al, 2017;Md Idris et al, 2018;Sayed et al, 2018), analgesic (Fu et al, 2019), antigout as xanthine oxidase inhibitors (Hofmann et al, 2016), antihistaminic (Padaratz et al, 2009Rossi and Avellino, 1957), anticancer (Gan et al, 2018;Hsieh et al, 2019;Khanapure et al, 2018;Özdemir et al, 2017;Pingaew et al, 2014;Sashidhara et al, 2010), antileishmanial (Insuasty et al, 2015, antimalarial (Pingaew et al, 2014), antiviral (Wan et al, 2015), antiulcer , antimicrobial (Benouda et al, 2019;Lal et al, 2018;Monga et al, 2014;Özdemir et al, 2017;Sayed et al, 2018), antioxidant (Bandgar et al, 2010), antidiabetic (Balu et al, 2019Emayavaramban et al, 2013;Gaur et al, 2014;Hsieh et al, 2012;Rammohan et al, 2020;Shukla et al, 2017), etc. Metochalcones increase bile secretion by stimulating the liver (Sahu et al, 2012) and sofalcone as an antiulcer agent, which increases the concentration of Prostaglandins from the mucosa causing a gastroprotection from Helicobacter pylori-induced ulcers (Higuchi et al, 2010).…”

Section: Introductionmentioning

confidence: 99%

“…Chalcones have been known from earlier times to have an interesting moiety which is associated with a wide range of pharmacological activities. The majority of commonly found food chalcones are phloretin (Gerhauser, 2008;Mariadoss et al, 2019;Min et al, 2015) and its glucoside phloridzin, i.e., phloretin 2′-0β-glucopyranoside which are present in apples, chalconaringenin in tomatoes (Echeverria et al, 2009;Kolot et al, 2019;Slimestad and Verheul, 2011), Arbutin in pears (Reiland and Slavin, 2015;Sasaki et al, 2014), and flavokavains in kava plants (Liu et al, 2018;Pinner et al, 2016). Chalcone possess a very good moiety due to which a variety of novel heterocyclic compounds with better pharmacological properties can be designed.…”

Section: Introductionmentioning

confidence: 99%

Chalcones: A review on synthesis and pharmacological activities

Goyal¹,

Kaur²,

Goyal³

et al. 2021

J Appl Pharm Sci

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Chalcone is a privileged species with medicinal significance as it consists of reactive ketoethylenic moiety-CO-CH=CH-belonging to flavonoids. The presence of a reactive α, β-unsaturated carbonyl function in chalcone and its derivatives is the reason for its pharmacological activities. Chalcones exhibit a wide spectrum of pharmacological effects such as antioxidant, antibacterial, anthelmintic, antiulcer, antiviral, insecticidal, antiprotozoal, anticancer, anti-Suzuki's reaction, etc. The purpose of this review is to focus on the methods of synthesis of chalcones and their versatile pharmacological activities.

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“…A large number of naturally occurring and synthetic chalcones have shown potent anticancer activity through multiple mechanisms of action and their specific features depend on the choice of the aryl moieties linked at the 1- and 3-positions of the 2-propen-1-one framework 3 , 4 . Biological activity of chalcones seemed to be mediated by many mechanisms of action and can be ascribed to the capability of the α,β-unsaturated ketone moiety to act as Michael acceptor with nucleophilic moieties, especially with multiple sulfhydryl residues of biological targets, such as glutathione (GSH) 5 , thioredoxin reductases (TrxRs) 6 , 7 , nuclear factor erythroid 2-related factor 2 (Nrf2) 8 , 9 , nuclear factor κB (NF-κB) 10 and cysteine 239 or glutamyl 198 residue of tubulin-microtubule system 11–13 . Due to their antitumour properties against different human cancer cell lines, including haematological malignancies 14 , 15 , over the last few years, considerable efforts have been dedicated by many research groups to identify new potent chalcone-based drug candidate within the oncology field.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of alpha-bromoacryloylamido indolyl pyridinyl propenones as potent apoptotic inducers in human leukaemia cells

Romagnoli

Prencipe

Cara³

et al. 2018

Journal of Enzyme Inhibition and Medicinal Chemistry

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The combination of two pharmacophores into a single molecule represents one of the methods that can be adopted for the synthesis of new anticancer molecules. To investigate the influence of the position of the pyridine nitrogen on biological activity, two different series of α-bromoacryloylamido indolyl pyridinyl propenones 3a–h and 4a–d were designed and synthesized by a pharmacophore hybridization approach and evaluated for their antiproliferative activity against a panel of six human cancer cell lines. These hybrid molecules were prepared to combine the α-bromoacryloyl moiety with two series of indole-inspired chalcone analogues, possessing an indole derivative and a 3- or 4-pyridine ring, respectively, linked on either side of 2-propen-1-one system. The structure-activity relationship was also investigated by the insertion of alkyl or benzyl moieties at the N-1 position of the indole nucleus. We found that most of the newly synthesized displayed high antiproliferative activity against U-937, MOLT-3, K-562, and NALM-6 leukaemia cell lines, with one-digit to double-digit nanomolar IC50 values. The antiproliferative activities of 3-pyridinyl derivatives 3f–h revealed that N-benzyl indole analogues generally exhibited lower activity compared to N-H or N-alkyl derivatives 3a–b and 3c–e, respectively. Moreover, cellular mechanism studies elucidated that compound 4a induced apoptosis along with a decrease of mitochondrial membrane potential and activated caspase-3 in a concentration-dependent manner.

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2′,4-Dihydroxy-3′,4′,6′-trimethoxychalcone from Chromolaena odorata possesses anti-inflammatory effects via inhibition of NF-κB and p38 MAPK in lipopolysaccharide-activated RAW 264.7 macrophages

Abstract: These findings provide evidence that 2',4-dihydroxy-3',4',6'-trimethoxychalcone (1) possesses anti-inflammatory activity via targeting proinflammatory macrophages. This anti-inflammatory chalcone is a promising compound for reducing inflammation.

Cited by 28 publications

References 37 publications

In vitro Antimycobacterial, Apoptosis-Inducing Potential, and Immunomodulatory Activity of Some Rubiaceae Species

In vitro Antimycobacterial, Apoptosis-Inducing Potential, and Immunomodulatory Activity of Some Rubiaceae Species

Chalcones: A review on synthesis and pharmacological activities

Synthesis and biological evaluation of alpha-bromoacryloylamido indolyl pyridinyl propenones as potent apoptotic inducers in human leukaemia cells

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