Licochalcones suppress degranulation by decreasing the intracellular Ca2+ level and tyrosine phosphorylation of ERK in RBL-2H3 cells

Tanifuji, Shota; Aizu-Yokota, Eriko; Funakoshi‐Tago, Megumi; Sonoda, Yoshiko; Inoue, Hideo; Kimura, Tadashi

doi:10.1016/j.intimp.2010.04.007

Cited by 41 publications

(31 citation statements)

References 43 publications

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“…1 They have various biological activities including anti-cancer, 4,5 anti-parasitic, 6 anti-bacterial, 7 superoxidescavenging 7 and anti-oxidant activities. 8 Among the reported retrochalcones, licochalcone B and D (Fig.…”

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confidence: 99%

“…1) strongly inhibited superoxide anion production in the xanthine/ xanthine oxidase system, and displayed potent scavenging activity on 2,2-diphenyl-1-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl radicals. 7,8 Licochalcone B and D have also been linked with potent anti-inflammatory activity involving the inhibition of lipopolysaccharide-induced phosphorylation at serine 276 and transcriptional activation of nuclear factor-kappa B.…”

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confidence: 99%

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Short and Efficient Synthesis of Licochalcone B and D Through Acid-Mediated Claisen-Schmidt Condensation

Wang¹,

Liu²,

Cao³

et al. 2013

Bulletin of the Korean Chemical Society

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Licochalcones A-E and echinatin were isolated and characterized from the roots of licorice (Glycyrrhiza inflata). 1-3These retrochalcones are an unusual phenolic compound family and are distinguished from ordinary chalcones by the absence of an oxygen functionality at the C-2' and C-6' positions.1 They have various biological activities including anti-cancer, 4,5 anti-parasitic, 6 anti-bacterial, 7 superoxidescavenging 7 and anti-oxidant activities. 8 Among the reported retrochalcones, licochalcone B and D (Fig. 1) strongly inhibited superoxide anion production in the xanthine/ xanthine oxidase system, and displayed potent scavenging activity on 2,2-diphenyl-1-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl radicals.7,8 Licochalcone B and D have also been linked with potent anti-inflammatory activity involving the inhibition of lipopolysaccharide-induced phosphorylation at serine 276 and transcriptional activation of nuclear factor-kappa B.6 A recent study reported that licochalcone D inhibits mast cell degranulation by inhibiting extracellular Ca 2+ influx and activation of the MEK-ERK pathway. 7Chemical synthesis of licochalcone B and D was initiated due to low isolation yield from natural sources and high demand for diverse pharmacological activity studies.2 Though the first total synthesis of licochalcone D has been published recently, this synthetic method suffers from limitations including the need for multiple steps, high temperature, and requirement for a special bomb reactor device.9 Herein, we report a short, efficient and practical synthesis of licochalcone B and D with excellent overall yields.The synthesis of licochalcone B and D was accomplished by the procedures shown in Scheme 1. As detailed in earlier studies, 3-and 4-hydroxyl groups in 2,3,4-trihydroxybenzaldehyde (3) was selectively protected as methoxymethyl (MOM) ether to give compound 4 in 71% yield.10 Due to the intramolecular hydrogen bond between the 2-hydroxyl group and the neighboring aldehyde group and/or steric hindrance of 2-hydroxyl group, 3-OH and 4-OH in compound 3 are selectively protected. Subsequent methylation on 2-hydroxyl group in 4 was carried out using methyl iodide and NaH in N,N-dimethylforamide (DMF) to give compound 5 in 95% yield. With the key intermediate 5 in hand, we turned our attention to the preparation of 6b from 6a to complete the synthesis of licochalcone B and D.As shown in Scheme 2, attempts to prepare 6b from 6a by Friedel-Crafts reaction in the presence of BaO-Al 2 O 3 in dichloromethane did not give a satisfactory result (Method

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Short and Efficient Synthesis of Licochalcone B and D Through Acid-Mediated Claisen-Schmidt Condensation

Wang¹,

Liu²,

Cao³

et al. 2013

Bulletin of the Korean Chemical Society

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“…The calcium ionophore A23187 induces the release of intracellular free Ca 2+ , which regulates granule-plasma membrane fusion and eicosanoid synthesis. PMA activates PKC, thereby inducing pro-inflammatory cytokine production (Tanifuji et al, 2010;Westcott et al, 1996;Jung et al, 2009). In this study, it has been demonstrated that OA inhibits PMA plus A23187-mediated secretion of TNF-α, IL-6 and IL-8 in HMC-1 cells.…”

Section: Discussionmentioning

confidence: 63%

Anti-inflammatory effect of oleanoic acid 28-O--D-glycopyranosyl ester isolated from Aralia cordata in activated HMC-1 cells

Kang¹

2012

Afr. J. Pharm. Pharmacol.

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Aralia cordata is known in traditional Korean medicine as a remedy for arthritis. As a part of our program to screen medicinal plants for potential anti-inflammatory compounds, oleanoic acid 28-O-β-Dglycopyranosyl ester (OA) was isolated from the roots of Aralia cordata. So, the immune modulation molecular mechanism of OA isolated from A. cordata was studied. One of the possible mechanisms for its protective activities is by down regulation of the inflammatory responses. Therefore, cells from the human mast cell line (HMC-1) were used to investigate this effect. OA significantly inhibits the way in which phorbol 12-myristate 13-acetate (PMA) plus A23187 induces the production of inflammatory cytokines such as tumor necrosis factor (TNF)-α, interleukin (IL)-6, IL-8 and intracellular Ca 2+ levels. In activated HMC-1 cells, phosphorylation of extra-signal response kinase (ERK) 1/2, degradation of IκB, and activation of NF-κB decreased after treatment with OA. OA suppressed the expression of TNF-α, IL-6 and IL-8 through a decrease in the intracellular levels of Ca2+ and ERK 1/2, as well as activation of NF-κB. These results indicated that OA exerted a regulatory effect on inflammatory reactions mediated by mast cells.

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“…1), and Lico D significantly inhibited the mast cell degranulation, play a key role in allergic inflammation, in RBL (rat basophilic leukemia)-2H3 cells with low cytotoxicity compare with the other licochalcones. 12 The 50% inhibitory concentration (IC 50 ) against degranulation and 30% cytotoxicity (CC 30 ), respectively, of each chalcones are as follows; Lico A: 17 & 24 μM, Lico C: 24 & >30 μM, Lico D: 21 & >30 μM. On the other hand, Lico B, echinatin and isoliquiritigenin showed no significant inhibitory effects.…”

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confidence: 98%

First Total Synthesis of Highly Anti-Inflammatory Active Licochalcone D Through Water-Accelerated [3,3]-Sigmatropic Rearrangement

Kim

Jun²

2013

Bulletin of the Korean Chemical Society

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Licochalcones, derived from the dried roots of Glycyrrhiza inflata, have been reported to show various biological activities including antitumor, antiparasitic, antileishmanial, antioxidative, superoxide scavenging, antibacterial, and PTP1B activity. Licochalcone D has an allyl group on ring A instead of ring B, however, most other natural licochalcones possess the group on ring B. Total synthesis of licochalcone D has not been reported even possessing the strongest anti-inflammatory activity. Therefore, the first total synthesis of licochalcone D has been developed by using water-accelerated [3,3]-sigmatropic rearrangement method.

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Licochalcones suppress degranulation by decreasing the intracellular Ca2+ level and tyrosine phosphorylation of ERK in RBL-2H3 cells

Cited by 41 publications

References 43 publications

Short and Efficient Synthesis of Licochalcone B and D Through Acid-Mediated Claisen-Schmidt Condensation

Short and Efficient Synthesis of Licochalcone B and D Through Acid-Mediated Claisen-Schmidt Condensation

Anti-inflammatory effect of oleanoic acid 28-O--D-glycopyranosyl ester isolated from Aralia cordata in activated HMC-1 cells

First Total Synthesis of Highly Anti-Inflammatory Active Licochalcone D Through Water-Accelerated [3,3]-Sigmatropic Rearrangement

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