• Title/Summary/Keyword: Purpurogallin

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Anti-inflammatory functions of purpurogallin in LPS-activated human endothelial cells

  • Kim, Tae-Hoon;Ku, Sae-Kwang;Lee, In-Chul;Bae, Jong-Sup
    • BMB Reports
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    • v.45 no.3
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    • pp.200-205
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    • 2012
  • Enzymatic oxidation of commercially available pyrogallol was efficiently transformed to an oxidative product, purpurogallin. Purpurogallin plays an important role in inhibiting glutathione S-transferase, xanthine oxidase, catechol O-methyltransferase activities and is effective in the cell protection of several cell types. However, the anti-inflammatory functions of purpurogallin are not well studied. Here, we determined the effects of purpurogallin on lipopolysaccharide (LPS)-mediated proinflammatory responses. The results showed that purpurogallin inhibited LPS-mediated barrier hyper-permeability, monocyte adhesion and migration and such inhibitory effects were significantly correlated with the inhibitory functions of purpurogallin on LPS-mediated cell adhesion molecules (vascular cell adhesion molecules, intracellular cell adhesion molecule, E-selectin). Furthermore, LPS-mediated nuclear factor-${\kappa}B$ (NF-${\kappa}B$) and tumor necrosis factor-${\alpha}$ (TNF-${\alpha}$) releases from HUVECs were inhibited by purpurogallin. Given these results, purpurogallin showed its anti-inflammatory activities and could be a candidate as a therapeutic agent for various systemic inflammatory diseases.

Antimelanogenic Effect of Purpurogallin in Murine Melanoma Cells (마우스 흑색종세포에서 Purpurogallin의 멜라닌 생성 억제 효과)

  • Kim, Han-Hyuk;Kim, Tae Hoon
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.44 no.12
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    • pp.1905-1911
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    • 2015
  • Melanin is one of the most important factors affecting skin color. Melanogenesis is the bioprocess of melanin production by melanocytes in the skin and hair follicles and is mediated by several enzymes, such as tyrosinase, tyrosinase related protein (TRP)-1, and TRP-2. Convenient enzymatic transformation of the simple phenol pyrogallol with polyphenol oxidase originating from pear to an oxidative product, purpurogallin, was efficient. The structure of the pyrogallol oxidation product was identified on the basis of spectroscopic methods. The biotransformation product purpurogallin showed significant inhibitory effects against both melanin synthesis and tyrosinase activity in a dose-dependent manner in B16 melanoma cells. In addition, purpurogallin significantly attenuated melanin production by inhibiting TRP-1, and TRP-2 expression through modulation of their corresponding transcription factors, and microphthalamia- associated transcription factor in B16 cells. Consequently, purpurogallin derived from convenient enzymatic transformation of pyrogallol might be a beneficial material for reducing skin hyperpigmentation.

Purpurogallin Protects Keratinocytes from Damage and Apoptosis Induced by Ultraviolet B Radiation and Particulate Matter 2.5

  • Zhen, Ao Xuan;Piao, Mei Jing;Hyun, Yu Jae;Kang, Kyoung Ah;Ryu, Yea Seong;Cho, Suk Ju;Kang, Hee Kyoung;Koh, Young Sang;Ahn, Mee Jung;Kim, Tae Hoon;Hyun, Jin Won
    • Biomolecules & Therapeutics
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    • v.27 no.4
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    • pp.395-403
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    • 2019
  • Purpurogallin, a natural phenol obtained from oak nutgalls, has been shown to possess antioxidant, anticancer, and anti-inflammatory effects. Recently, in addition to ultraviolet B (UVB) radiation that induces cell apoptosis via oxidative stress, particulate matter 2.5 ($PM_{2.5}$) was shown to trigger excessive production of reactive oxygen species. In this study, we observed that UVB radiation and $PM_{2.5}$ severely damaged human HaCaT keratinocytes, disrupting cellular DNA, lipids, and proteins and causing mitochondrial depolarization. Purpurogallin protected HaCaT cells from apoptosis induced by UVB radiation and/or $PM_{2.5}$. Furthermore, purpurogallin effectively modulates the pro-apoptotic and anti-apoptotic proteins under UVB irradiation via caspase signaling pathways. Additionally, purpurogallin reduced apoptosis via MAPK signaling pathways, as demonstrated using MAPK-p38, ERK, and JNK inhibitors. These results indicate that purpurogallin possesses antioxidant effects and protects cells from damage and apoptosis induced by UVB radiation and $PM_{2.5}$.

Anti-inflammatory Effects of Purpurogallin Carboxylic Acid, An Oxidation Product of Gallic Acid in Fermented Tea (발효차중의 미량 성분인 gallic acid 산화물 purpurogallin carboxylic acid의 항염증 효과)

  • Jhoo, Jin-Woo
    • Korean Journal of Food Science and Technology
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    • v.40 no.6
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    • pp.707-711
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    • 2008
  • The principal objective of the current study was to isolate a purpurogallin derivative as an oxidation product from gallic acid, in an effort to assess the anti-inflammatory effects of this compound. Purpurogallin derivative is known to be the one of the oxidation products of gallic acid. This compound has been identified as a minor chemical component in fermented tea products. It has been previously demonstrated that theaflavins, the oxidation products of catechins found in fermented tea products, exert profound antioxidant and anti-inflammatory effects. However, the biological activities of a minor chemical component in fermented teas have yet to be evaluated. Purpurogallin carboxylic acid (PCA) was identified as a major oxidation product of gallic acid from a peroxidase/hydrogen peroxide oxidation model system. The identity of the PCA was verified by $^{1}H$ NMR, $^{13}C$ NMR and MS techniques. PCA treatment significantly suppressed the generation of pro-inflammatory mediators including nitric oxide and IL-6 in lipopolysaccharide (LPS)-stimulated RAW264.7 murine macrophages. According to the nitrite assay, PCA 100, 75, and $50{\mu}g/mL$ treatment dose-dependently inhibited NO production by 57.6, 41.5, and 21.8%, respectively, in LPS-stimulated RAW264.7 murine macrophage cells. Moreover, IL-6 production was inhibited to a significant degree with PCA treatment of 100 and $75{\mu}g/mL$ at 43.1 and 23.9%, respectively. PCA treatment also significantly suppressed $PGE_2$ production at levels of 100 and $75{\mu}g/mL$. These results showed that PCA exerts inhibitory effects on the production of inflammatory mediators.

Antiplatelet and antithrombotic activities of purpurogallin in vitro and in vivo

  • Ku, Sae-Kwang;Bae, Jong-Sup
    • BMB Reports
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    • v.47 no.7
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    • pp.376-381
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    • 2014
  • Enzymatic oxidation of pyrogallol was efficiently transformed to an oxidative product, purpurogallin (PPG). Here, the anticoagulant activities of PPG were examined by monitoring activated partial thromboplastin time (aPTT), prothrombin time (PT), and the activities of thrombin and activated factor X (FXa). And, the effects of PPG on expression of plasminogen activator inhibitor type 1 (PAI-1) and tissue-type plasminogen activator (t-PA) were evaluated in tumor necrosis factor (TNF)-${\alpha}$ activated human umbilical vein endothelial cells (HUVECs). Treatment with PPG resulted in prolonged aPTT and PT and inhibition of the activities of thrombin and FXa, as well as inhibited production of thrombin and FXa in HUVECs. In addition, PPG inhibited thrombin-catalyzed fibrin polymerization and platelet aggregation. PPG also elicited anticoagulant effects in mice. In addition, treatment with PPG resulted in significant reduction of the PAI-1 to t-PA ratio. Collectively, PPG possesses antithrombotic activities and offers a basis for development of a novel anticoagulant.

Antioxidant Effect of some Phenolics on Soybean Oil (식용대두유에 대한 Phenolics의 항산화 효과)

  • Cho, Mi-Za;Kwon, Tae-Bong;Oh, Sung-Ki
    • Applied Biological Chemistry
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    • v.32 no.1
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    • pp.37-43
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    • 1989
  • Some phenolics were examined as an antioxidant for the autoxidation of soybean oil. Soybean oil was autoxidized under a mild condition (the flow rate of 67ml $O_{2}/min$ and $50^{\circ}C$). The antioxidant effect was estimated by active oxygen method. Phenolics show distinctive antioxidant effect, and the effect is prominent when cupper or iron was added. Phenolics showed a tendency to increase antioxidant effect with an increase of the number of hydroxyl group, and the increasing order was ferulic acid, quinalizarin, sesamol, alizarin, fisetin and purpurogallin. However, the effect was remarkably low in ferulic acid, alizarin and quinalizarin. It was found that the antioxidant effect was dependent on the functional group and geometric molecular structure of phenolics.

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