Oxidation of Ferulic Acid by Momordica charantia Peroxidase and Related Anti-inflammation Activity Changes

Ou, Li; Kong, Ling‐Yi; Zhang, Xianming; Niwa, Masayuki

doi:10.1248/bpb.26.1511

Cited by 84 publications

(63 citation statements)

References 26 publications

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“…FA is a phenolic compound with three distinctive structural motifs that can possibly contribute to its free radical scavenging capability (Srinivasan et al, 2007). It has been reported that FA decreases the levels of inflammatory mediators (prostaglandin E2 and TNF-α; Ou et al, 2003), and nitric oxide synthase (iNOS) expression and function (Tetsuka et al, 1996). In addition, hydrophobic ester derivatives of FA seem to have enhanced inhibitory activity on iNOS protein expression in LPS/interferon-γ (IFN-γ) activated RAW264.7 cells (Murakami et al, 2002).…”

Section: Examples Of Hormetic Dietary Phytochemicalsmentioning

confidence: 99%

Hormetic Dietary Phytochemicals

2008

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Compelling evidence from epidemiological studies suggest beneficial roles of dietary phytochemicals in protecting against chronic disorders such as cancer, and inflammatory and cardiovascular diseases. Emerging findings suggest that several dietary phytochemicals also benefit the nervous system and, when consumed regularly, may reduce the risk of disorders such as Alzheimer's and Parkinson's diseases. The evidence supporting health benefits of vegetables and fruits provide a rationale for identification of the specific phytochemicals responsible, and for investigation of their molecular and cellular mechanisms of action. One general mechanism of action of phytochemicals that is emerging from recent studies is that they activate adaptive cellular stress response pathways. From an evolutionary perspective, the noxious properties of such phytochemicals play an important role in dissuading insects and other pests from eating the plants. However at the relatively small doses ingested by humans that consume the plants, the phytochemicals are not toxic and instead induce mild cellular stress responses. This phenomenon has been widely observed in biology and medicine, and has been described as 'preconditioning' or 'hormesis'. Hormetic pathways activated by phytochemicals may involve kinases and transcription factors that induce the expression of genes that encode antioxidant enzymes, protein chaperones, phase-2 enzymes, neurotrophic factors and other cytoprotective proteins. Specific examples of such pathways include the sirtuin -FOXO pathway, the NF-κB pathway and the Nrf-2 -ARE pathway. In this article we describe the hormesis hypothesis of phytochemical actions with a focus on the Nrf2/ARE signaling pathway as a prototypical example of a neuroprotective mechanism of action of specific dietary phytochemicals.

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Section: Examples Of Hormetic Dietary Phytochemicalsmentioning

confidence: 99%

Hormetic Dietary Phytochemicals

2008

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“…The two sets of CH groups of the saturated part were connected each other though CH group (8a) and CH group (8b), because the correlations of H-8b to C-7a, H-8a to (1) C-7b, H-7b to C-8a, H-7a to C-8b, H-8a to C-9b and H-8b to C-5c were detected. According to above analysis, the planar structure of triFA1 with a 3a,9b-dihydro-1H-furo [3,4-c] [1]benzopyran-3(4H)-one ring system was concluded.…”

Section: Resultsmentioning

confidence: 92%

mentioning

confidence: 82%

“…1) We found that although MCP shared spectral and kinetic features with other peroxidases, the enzyme had several unique characteristics, including enzyme pH stability (pH 3.8-8.0) and thermostability (20-45°C) wider than those of other peroxidases such as horseradish peroxidase. 2) So MCP can be expected to oxidize a wider range of substrates, especially cinnamic acid derivatives, when considering the potential applications of MCP for useful biotransformation.…”

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confidence: 82%

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Biotransformation of Ferulic Acid into Two New Dihydrotrimers by Momordica charantia Peroxidase

Liu

Kong

Takaya

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Previously, we reported the physical and chemical characterization of Momordica charantia peroxidase (MCP), a novel plant peroxidase with high acidic amino acid purified from the fruits of Momordica charantia and applied the purified MCP to transform ferulic acid (FA) into FA-2, a FA dehydrodimer, which had more powerful anti-inflammation than FA. 1) We found that although MCP shared spectral and kinetic features with other peroxidases, the enzyme had several unique characteristics, including enzyme pH stability (pH 3.8-8.0) and thermostability (20-45°C) wider than those of other peroxidases such as horseradish peroxidase. 2)So MCP can be expected to oxidize a wider range of substrates, especially cinnamic acid derivatives, when considering the potential applications of MCP for useful biotransformation.FA, which is an extremely abundant and widespread cinnamic acid derivative, was a good substrate for most plant peroxidases such as lignin peroxidase, wheat germ peroxidase and horseradish peroxidase.3,4) FA dehydrodimers produced both in vitro and in vivo by plant peroxidases have been extensively characterizied.5-11) They result from oxidative coupling of ferulate esters and represent mainly products of 8-5, 8-O-4, 4-O-5 and 5-5 radical couplings. Recently, it was reported that in incubation with lignin peroxidase and ectomycorrhizal fungi, dihydrotrimers of FA were formed.12,13) However, only two structures of FA dehydrotrimers were elucidated by NMR spectrum, although higher oligomers of FA on a template of a tyrosine-containing tripeptide have recently been yielded enzymically in vitro. 14) In order to further study the biotransformation of FA by purified MCP and analyze FA dehydrotrimers, we have investigated the oxidative coupling of FA with H 2 O 2 /MCP at pH 5.0 in the presence of acetone. Two new FA dehydrotrimers, triFA1 (1) and triFA2 (2), have been identified. TriFA1 (1) is a unique FA dehydrotrimer possessing a 3a,9b-dihydro-1H-furo [3,4-c][1]benzopyran-3(4H)-one ring system.In the present paper, we report on the biotransformation of FA by MCP and the isolation and the structural characterization of the two new FA dehydrotrimers, as well as the possible formation mechanism for triFA1 (1). Results and DiscussionTriFA1 (1) As a result of a continuing investigation of the biotransformation of ferulic acid with H 2 O 2 /Momordica charantia peroxidase at pH 5.0 in the presence of acetone, triFA1 (1) and triFA2 (2), two new FA dehydrotrimers, have been isolated. The structures were elucidated from the spectroscopic data including 2D-NMR such as HSQC, HMBC and NOESY data. TriFA1 (1) is a unique FA dehydrotrimer possessing a 3a,9b-dihydro-1H-furo[3,4-c][1]benzopyran-3(4H)-one ring system. The possible mechanism for the formation of triFA1 was also discussed.

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“…Likewise, drugs that lower PDE4B expression and stimulate the cyclic AMP (cAMP)/cAMP response element binding protein (CREB) pathway may enhance anti-inflammatory activity. A number of antioxidants including ferulic acid (FA) and related ester derivatives decrease the levels of some inflammatory mediators, such as TNF-α and IL-1β, as well as limit their associated functions [21][22][23] . FA is a plant component that is a free radical scavenger, and it exhibits strong anti-oxidant and anti-inflammatory capacity [24] .…”

Section: Original Articlementioning

confidence: 99%

Ferulic acid prevents LPS-induced up-regulation of PDE4B and stimulates the cAMP/CREB signaling pathway in PC12 cells

Huang

Qian²,

et al. 2016

Acta Pharmacol Sin

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Aim: Phosphodiesterase 4 (PDE4) isozymes are involved in different functions, depending on their patterns of distribution in the brain. The PDE4 subtypes are distributed in different inflammatory cells, and appear to be important regulators of inflammatory processes. In this study we examined the effects of ferulic acid (FA), a plant component with strong anti-oxidant and anti-inflammatory activities, on lipopolysaccharide (LPS)-induced up-regulation of phosphodiesterase 4B (PDE4B) in PC12 cells, which in turn regulated cellular cAMP levels and the cAMP/cAMP response element binding protein (CREB) pathway in the cells. Methods: PC12 cells were treated with LPS (1 μg/mL) for 8 h, and the changes of F-actin were detected using laser scanning confocal microscopy. The levels of pro-inflammatory cytokines were measured suing ELISA kits, and PDE4B-specific enzymatic activity was assessed with a PDE4B assay kit. The mRNA levels of PDE4B were analyzed with Q-PCR, and the protein levels of CREB and phosphorylated CREB (pCREB) were determined using immunoblotting. Furthermore, molecular docking was used to identify the interaction between PDE4B2 and FA. Results: Treatment of PC12 cells with LPS induced thick bundles of actin filaments appearing in the F-actin cytoskeleton, which were ameliorated by pretreatment with FA (10-40 μmol/L) or with a PDE4B inhibitor rolipram (30 μmol/L). Pretreatment with FA dose-dependently inhibited the LPS-induced production of TNF-α and IL-1β in PC12 cells. Furthermore, pretreatment with FA dosedependently attenuated the LPS-induced up-regulation of PDE4 activity in PC12 cells. Moreover, pretreatment with FA decreased LPS-induced up-regulation of the PDE4B mRNA, and reversed LPS-induced down-regulation of CREB and pCREB in PC12 cells. The molecular docking results revealed electrostatic and hydrophobic interactions between FA and PDE4B2. Conclusion: The beneficial effects of FA in PC12 cells might be conferred through inhibition of LPS-induced up-regulation of PDE4B and stimulation of cAMP/CREB signaling pathway. Therefore, FA may be a potential therapeutic intervention for the treatment of neuroinflammatory diseases such as AD.

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Oxidation of Ferulic Acid by Momordica charantia Peroxidase and Related Anti-inflammation Activity Changes

Cited by 84 publications

References 26 publications

Hormetic Dietary Phytochemicals

Hormetic Dietary Phytochemicals

Biotransformation of Ferulic Acid into Two New Dihydrotrimers by Momordica charantia Peroxidase

Ferulic acid prevents LPS-induced up-regulation of PDE4B and stimulates the cAMP/CREB signaling pathway in PC12 cells

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