Inhibition of Activator Protein-1, NF-κB, and MAPKs and Induction of Phase 2 Detoxifying Enzyme Activity by Chlorogenic Acid

Feng, Rentian; Lu, Yongju; Bowman, Linda; Qian, Yong; Castranova, Vincent; Ding, Min

doi:10.1074/jbc.m503347200

Cited by 359 publications

(265 citation statements)

References 45 publications

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“…Chlorogenic acid, abundant in plum and cherry, increased the activity of the phase II detoxifying enzymes GST and NADPH quinone oxidoreductase (NQO) in mouse epidermal cells [58]. Similarly, drinks rich in phenolic compounds, tea and mate increased QR activity in the Hepa1c1c7 cells [57] and in general, phenolic compounds, such as quercetin, hesperidin, disomin, chlorogenic acid, etc., prevented GSH depletion and ROS formation after an oxidative injury caused by different prooxidants [45,59].…”

Section: Effects On Phase-i and -Ii Enzymesmentioning

confidence: 99%

Cancer chemoprevention and chemotherapy: Dietary polyphenols and signalling pathways

Ramos¹

2008

Molecular Nutrition Food Res

627

499

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Prevention of cancer through dietary intervention recently has received an increasing interest, and dietary polyphenols have become not only important potential chemopreventive, but also therapeutic, natural agents. Polyphenols have been reported to interfere at the initiation, promotion and progression of cancer. They might lead to the modulation of proteins in diverse pathways and require the integration of different signals for the final chemopreventive or therapeutic effect. Polyphenols have been demonstrated to act on multiple key elements in signal transduction pathways related to cellular proliferation, differentiation, apoptosis, inflammation, angiogenesis and metastasis; however, these molecular mechanisms of action are not completely characterized and many features remain to be elucidated. The aim of this review is to provide insights into the molecular basis of potential chemopreventive and therapeutic activities of dietary polyphenols with emphasis in their ability to control intracellular signalling cascades considered as relevant targets in a cancer preventive approach.

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Section: Effects On Phase-i and -Ii Enzymesmentioning

confidence: 99%

Cancer chemoprevention and chemotherapy: Dietary polyphenols and signalling pathways

Ramos¹

2008

Molecular Nutrition Food Res

627

499

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“…Nuclear extracts from JB6 cells were prepared as described previously (22). For the immunocytochemical analysis of Nrf2, cells were plated on the chamber slide and treated with zerumbone.…”

Section: Preparation Of Nuclear Proteins and Immunocytochemical Analysismentioning

confidence: 99%

Zerumbone Induces Heme Oxygenase-1 Expression in Mouse Skin and Cultured Murine Epidermal Cells through Activation of Nrf2

Shin

Ohnishi

Murakami

et al. 2011

Cancer Prevention Research

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Zerumbone, a sesquiterpene derived from tropical ginger, contains an electrophilic a,b-unsaturated carbonyl moiety and was found to suppress chemically induced papilloma formation in mouse skin. Here, we report that topical application of zerumbone onto dorsal skin of hairless mice induces activation of NF-E2-related factor 2 (Nrf2) and expression of heme oxygenase-1 (HO-1). We compared the levels of HO-1 protein in the skin of zerumbone-treated Nrf2 wild-type and Nrf2 knockout mice, and nrf2-deficient mice expressed HO-1 protein to a much lesser extent than the wild-type animals following topical application of zerumbone. Treatment of mouse epidermal JB6 cells with zerumbone caused a marked increase of Nrf2 nuclear translocation followed by the promoter activity of HO-1, and also enhanced direct binding of Nrf2 to the antioxidant response element. Moreover, knockdown of Nrf2 in JB6 cells diminished the zerumbone-induced upregulation of HO-1. Notably, a-humulene and 8-hydroxy-a-humulene, the structural analogues of zerumbone that lack the a,b-unsaturated carbonyl group, failed to activate Nrf2 and were unable to increase HO-1 expression. Unlike zerumbone, these nonelectrophilic analogues could not suppress the 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced JB6 cell transformation and the intracellular accumulation of reactive oxygen species (ROS). Interestingly, when JB6 cells were treated with carbon monoxide-releasing molecule that mimics the HO-1 activity, the TPA-induced ROS production was markedly reduced. Taken together, these findings suggest that upregulation of HO-1 expression by zerumbone is mediated through activation of Nrf2 signaling, which provides a mechanistic basis for the chemopreventive effects of this sesquiterpene on mouse skin carcinogenesis. Cancer Prev Res; 4(6); 860-70. Ó2011 AACR.

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“…For example, this pathway results in formation of the potent antiviral agent, podophyllotoxin (1), which also serves as a semi-synthetic source of the highly successful cancer chemotherapeutic treatments, teniposide, etoposide, and Etopophos (2)(3)(4). Other examples include: matairesinol and secoisolariciresinol, which are some of the dietary sources of the "mammalian" lignans, enterolactone/enterodiol, these being protective against the onset of various malignancies (5); the nordihydroguaiaretic acid derivatives, which show considerable promise against refractory cancers of the neck and the head (6); the potent antioxidant chlorogenic acid, which has well documented anticancer properties (7,8), as well as reducing the risk of cardiovascular disease (9); and the monomeric allyl/propenyl phenols such as chavicol and eugenol, which have well known antibacterial and analgesic properties (10). Other medicinally important phenylpropanoid (acetate) pathway metabolites include dihydroconiferyl alcohol (1; Fig.…”

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confidence: 99%

Mechanistic and Structural Studies of Apoform, Binary, and Ternary Complexes of the Arabidopsis Alkenal Double Bond Reductase At5g16970

Youn

Kim

Moinuddin

et al. 2006

Journal of Biological Chemistry

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In this study, we determined the crystal structures of the apoform, binary, and ternary complexes of the Arabidopsis alkenal double bond reductase encoded by At5g16970. This protein, one of 11 homologues in Arabidopsis thaliana, is most closely related to the Pinus taeda phenylpropenal double bond reductase, involved in, for example, heartwood formation. Both enzymes also have essential roles in plant defense, and can function by catalyzing the reduction of the 7-8-double bond of phenylpropanal substrates, such as p-coumaryl and coniferyl aldehydes in vitro. At5g16970 is also capable of reducing toxic substrates with the same alkenal functionality, such as 4-hydroxy-(2E)-nonenal. The overall fold of At5g16970 is similar to that of the zinc-independent medium chain dehydrogenase/reductase superfamily, the members of which have two domains and are dimeric in nature, i.e. in contrast to their original classification as being zinc-containing oxidoreductases. As provisionally anticipated from the kinetic data, the shape of the binding pocket can readily accommodate p-coumaryl aldehyde, coniferyl aldehyde, 4-hydroxy-(2E)-nonenal, and 2-alkenals. However, the enzyme kinetic data among these potential substrates differ, favoring p-coumaryl aldehyde. Tyr-260 is provisionally proposed to function as a general acid/base for hydride transfer. A catalytic mechanism for this reduction, and its applicability to related important detoxification mammalian proteins, is also proposed.

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Inhibition of Activator Protein-1, NF-κB, and MAPKs and Induction of Phase 2 Detoxifying Enzyme Activity by Chlorogenic Acid

Cited by 359 publications

References 45 publications

Cancer chemoprevention and chemotherapy: Dietary polyphenols and signalling pathways

Cancer chemoprevention and chemotherapy: Dietary polyphenols and signalling pathways

Zerumbone Induces Heme Oxygenase-1 Expression in Mouse Skin and Cultured Murine Epidermal Cells through Activation of Nrf2

Mechanistic and Structural Studies of Apoform, Binary, and Ternary Complexes of the Arabidopsis Alkenal Double Bond Reductase At5g16970

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