Two New Dihydrochalcones from Lindera erythrocarpa

Ichino, Kunio; Tanaka, Hitoshi; Itô, Kazuo; Tanaka, Toshihiro; Mizuno, Mizuo

doi:10.1021/np50059a016

Cited by 27 publications

(14 citation statements)

References 6 publications

(15 reference statements)

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“…The separation in the IP values for the different structures is also smaller in solution than in vacuo, indicating that, in solution, most compounds have nearly similar tendency to react through ET mechanism. The ET mechanism may offer an explanation for the observation that LD, LR and mLR have the ability to scavenge free radical species, as reported by some experimental researchers [2][3][4][5][6][7][8][9][10]. In all the media, the tendency to scavenge free radicals increases with the increase in the number of OCH 3 groups as substituents on the main moiety, in this way, mLR and LD have the highest and the lowest tendency, respectively, to scavenge free radical species.…”

Section: H-bond Parameters a Bcp Parametersmentioning

confidence: 72%

“…Lucidone (LD), linderone (LR) and methyllinderone (mLR) are acylcyclopentene-1,3-dione derivatives isolated from Lindera erythrocarpa Makino plant, which belongs to the large Lauraceae family and consists mostly of trees or shrubs [1][2][3][4][5][6]. In most part of the world where this plant is found, it is utilised as a traditional medicine for the treatment of several illnesses including analgesic, digestive, diuretic and headache problems [1].…”

Section: Introductionmentioning

confidence: 99%

“…In most part of the world where this plant is found, it is utilised as a traditional medicine for the treatment of several illnesses including analgesic, digestive, diuretic and headache problems [1]. The isolated compounds exhibit several biological activities including antitumor, antiviral, antioxidant, antibacterial, antifungal and antiinflammatory activities, [1][2][3][4][5][6][7][8][9][10][11][12][13]. Therefore, LD, LR and mLR are attractive for utilisation in the therapeutical treatment of degenerative diseases because they are isolated from natural sources and therefore have potential to reduce the risk of drug toxicity [11,12].…”

Section: Introductionmentioning

confidence: 99%

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Conformational, electronic and antioxidant properties of lucidone, linderone and methyllinderone: DFT, QTAIM and NBO studies

et al. 2014

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Theoretical studies on lucidone, linderone and methyllinderone were performed to investigate factors that contribute to structural stability and to elucidate the antioxidant properties and mechanisms. The study was performed in different media utilising the density functional theory with different functionals and the 6-311 + G(d,p) basis set. The antioxidant activity has been considered through the electron transfer and metal chelation mechanisms. The results show that the stability of the tautomers and conformers is due to the presence of several intramolecular hydrogen bonds. The ionisation potential values suggest that the antiradical activity increases with the increase in the number of OCH 3 groups substituted on the cyclopentene-1,3-dione ring. In vacuo, the spin density of the Fe(II) cation upon ligand coordination decreases to 3.0−3.5, whereas the ligand spin density approaches 1, indicating that it is oxidised to a radical cation. The metal ion affinity (MIA) is influenced by the position and number of OCH 3 substituted on the acylcyclopentene-1,3-dione ring. A very favourable MIA, in vacuo, is obtained when Fe(II) is chelated between the sp 2 O and sp 3 O atoms. An estimation of MIA in an aqueous solution shows a remarkable decrease with respect to the results in vacuo.

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Section: H-bond Parameters a Bcp Parametersmentioning

confidence: 72%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Conformational, electronic and antioxidant properties of lucidone, linderone and methyllinderone: DFT, QTAIM and NBO studies

et al. 2014

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“…Lindera erythrocarpa Makino is one of the Lauraceae woody plants, which are distributed widely in Asia, including Taiwan, Japan, Korea and China. The fruit of L. erythrocarpa is used as a folk medicine as for its analgesic, digestive, diuretic, antidote and antibacterial properties (Liu et al, 1973;Ichino et al, 1988). However, little scientific study has been reported on the bioactivities of L. erythrocarpa.…”

Section: Introductionmentioning

confidence: 99%

Antiinflammatory activity of Lindera erythrocarpa fruits

Wang

Lan

Xiao

et al. 2007

Phytotherapy Research

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In this study, in vitro and in vivo antiinflammatory activities of fruits from Lindera erythrocarpa Makino were evaluated. The ethyl acetate soluble fraction derived from the ethanol extract of L. erythrocarpa fruits inhibited significantly nitric oxide (NO) production in lipopolysaccharide (LPS) induced NO in the murine macrophage cell line (RAW264.7) assay, the EC(50) being 16.35 microg/mL. Four compounds, including lucidone (1), cis/trans-methylludicone (2), methyl linderone (3) and linderone (4) were identified from the active fraction based on the bioactivity-guided fractionation procedure. Of these lucidone possessed the strongest NO inhibitory activity with an EC(50) value of 4.22 microg/mL. Furthermore, results from the protein expression assay demonstrated that lucidone suppressed iNOS and COX-2 protein expression in a dose-dependent manner. Lucidone also provided antiinflammatory activity in the croton oil-induced ear edema assay. When it was applied topically at a dosage of 0.5 and 1 mg per ear, the percent edema reduction in treated mice was 44% and 25%, respectively. The results obtained in this study indicated that lucidone has a good potential to be developed as an antiinflammation agent.

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“…1A), isolated from the fruit of Lindera erythrocarpa that specifically inhibited HCV RNA replication. L. erythrocarpa Makino, belonging to the family Lauraceae, is widely cultured in Asian countries such as Taiwan, Japan, Korea, and China, and its fruits are traditionally used in folk medicine because of their extensive pharmacological properties, such as analgesic, digestive, diuretic, antidotal, and antibacterial properties (15). The lucidone derivatives, such as methyllinderone and methyllucidone, also exhibited anti-inflammation activity and anti-farnesyl protein transferase (16,17).…”

mentioning

confidence: 99%

Lucidone Suppresses Hepatitis C Virus Replication by Nrf2-Mediated Heme Oxygenase-1 Induction

Chen

Wang

Chiu

et al. 2013

Antimicrob Agents Chemother

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dUpon screening of plant-derived natural products against hepatitis C virus (HCV) in the replicon system, we demonstrate that lucidone, a phytocompound, isolated from the fruits of Lindera erythrocarpa Makino, significantly suppressed HCV RNA levels with 50% effective concentrations of 15 ؎ 0.5 M and 20 ؎ 1.1 M in HCV replicon and JFH-1 infectious assays, respectively. There was no significant cytotoxicity observed at high concentrations, with a 50% cytotoxic concentration of 620 ؎ 5 M. In addition, lucidone significantly induced heme oxygenase-1 (HO-1) production and led to the increase of its product biliverdin for inducing antiviral interferon response and inhibiting HCV NS3/4A protease activity. Conversely, the anti-HCV activity of lucidone was abrogated by blocking HO-1 activity or silencing gene expression of HO-1 or NF-E2-related factor 2 (Nrf2) in the presence of lucidone, indicating that the anti-HCV action of lucidone was due to the stimulation of Nrf-2-mediated HO-1 expression. Moreover, the combination of lucidone and alpha interferon, the protease inhibitor telaprevir, the NS5A inhibitor BMS-790052, or the NS5B polymerase inhibitor PSI-7977, synergistically suppressed HCV RNA replication. These findings suggest that lucidone could be a potential lead or supplement for the development of new anti-HCV agent in the future.A pproximately 170 million people across the world are infected with hepatitis C virus (HCV). The virus causes chronic inflammation of the liver that ultimately leads to severe consequences such as cirrhosis and hepatocellular carcinoma (1). The HCV genome is a 9.6-kb positive single-strand RNA molecule encoding a single polyprotein of 3,000 amino acids that is processed by viral and cellular proteases to produce structural (C, E1, and E2) and nonstructural (NS2, NS3, NS4A, NS4B, NS5A, and NS5B) proteins (2). Pegylated alpha interferon (PEG-IFN-␣) combined with ribavirin is the only recommended standard therapy for hepatitis C patients at present. However, the current therapeutic regimens only achieve a 40 to 50% cure rate in genotype 1 HCV-infected patients (3). In addition, the severe side effects of the current treatments, including depression, fatigue, flu-like symptoms, and hemolytic anemia, often lead to treatment discontinuation (4). Despite recent advancement of therapeutics with the approval of NS3/4A protease inhibitors, telaprevir and boceprevir, in combination with PEG-IFN-␣ and ribavirin, viral resistance and side effect to both inhibitors was still observed in clinical studies (5-7). Therefore, it is essential to develop new anti-HCV agents for therapeutic purposes.Heme oxygenase-1 (HO-1), the rate-limiting enzyme in the oxidative degradation of heme, protects against oxidative stress and liver inflammation (8). Its reaction products including biliverdin, carbon monoxide, and ferrous iron are regarded as potential cytoprotectants (9). Among the various intracellular molecules capable of inducing HO-1, BTB and CNC homolog 1 (Bach1) and nuclear factor erythroid-derived 2 r...

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Two New Dihydrochalcones from Lindera erythrocarpa

Abstract: Two new dihydrochalcones, dihydropashanone [1] and dihydrokanakugiol [2], were isolated from Lindera erythrocarpa. Their structures were elucidated by chemical and spectroscopic means.

Cited by 27 publications

References 6 publications

Conformational, electronic and antioxidant properties of lucidone, linderone and methyllinderone: DFT, QTAIM and NBO studies

Conformational, electronic and antioxidant properties of lucidone, linderone and methyllinderone: DFT, QTAIM and NBO studies

Antiinflammatory activity of Lindera erythrocarpa fruits

Lucidone Suppresses Hepatitis C Virus Replication by Nrf2-Mediated Heme Oxygenase-1 Induction

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