• Title, Summary, Keyword: Amentoflavone

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Cytotoxic Activities of Amentoflavone against Human Breast and Cervical Cancers are Mediated by Increasing of PTEN Expression Levels due to Peroxisome Proliferator-Activated Receptor γ Activation

  • Lee, Eun-Jung;Shin, So-Young;Lee, Jee-Young;Lee, So-Jung;Kim, Jin-Kyoung;Yoon, Do-Young;Woo, Eun-Rhan;Kim, Yang-Mee
    • Bulletin of the Korean Chemical Society
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    • v.33 no.7
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    • pp.2219-2223
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    • 2012
  • Human peroxisome proliferator-activated receptor gamma ($hPPAR{\gamma}$) has been implicated in numerous pathologies, including obesity, diabetes, and cancer. Previously, we verified that amentoflavone is an activator of $hPPAR{\gamma}$ and probed the molecular basis of its action. In this study, we investigated the mechanism of action of amentoflavone in cancer cells and demonstrated that amentoflavone showed strong cytotoxicity against MCF-7 and HeLa cancer cell lines. We showed that $hPPAR{\gamma}$ expression in MCF-7 and HeLa cells is specifically stimulated by amentoflavone, and suggested that amentoflavone-induced cytotoxic activities are mediated by activation of $hPPAR{\gamma}$ in these two cancer cell lines. Moreover, amentoflavone increased PTEN levels in these two cancer cell lines, indicating that the cytotoxic activities of amentoflavone are mediated by increasing of PTEN expression levels due to $hPPAR{\gamma}$ activation.

Anti-inflammatory Effects of Amentoflavone on Modulation of Signal Pathways in LPS-stimulated RAW264.7 Cells

  • Lee, Eun-Jung;Shin, So-Young;Kim, Jin-Kyoung;Woo, Eun-Rhan;Kim, Yang-Mee
    • Bulletin of the Korean Chemical Society
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    • v.33 no.9
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    • pp.2878-2882
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    • 2012
  • Amentoflavone is naturally occurring bioflavonoid that is found in a number of plants. In this paper, the anti-inflammatory activity of amentoflavone in LPS-stimulated macrophages and its mode of action were examined. Using LPS-stimulated RAW264.7 macrophage cells, we found that amentoflavone exerted anti-inflammatory activities through inhibition of nitric oxide (NO) production and tumor necrosis factor (TNF)-${\alpha}$ and macrophage inflammatory protein (MIP)-2 secretion. Amentoflavone (1.0-20 ${\mu}M$) gradually inhibited nitrite production without cytotoxicity. Amentoflavone (1.0 and 10 ${\mu}M$) effectively suppressed both TNF-${\alpha}$ and MIP-2 cytokine release from LPS-stimulated RAW264.7 cells. The expression of mIL-$1{\beta}$ and mMIP-2 cytokine mRNAs was completely inhibited while expression of mMIP-1 was effectively suppressed and mTNF-${\alpha}$ expression was slightly inhibited by 10 ${\mu}M$ amentoflavone. We also demonstrated that the innate immune response to amentoflavone involves the toll-like receptor (TLR) and mitogen-activated protein kinase (MAPK) pathways. LPS-induced upregulation of p38 MAPK phosphorylation was significantly reduced by 10 ${\mu}M$ amentoflavone. These results suggest that amentoflavone exhibits effective anti-inflammatory activities through regulation of TLR4 and phosphorylation of p38 MAPKs.

A new Potential Anti-inflammatory Agent

  • Kim, Hee-Kee;Son, Kun-Ho;Chang, Hyeun-Wook;Kang, Sam-Sik;Kim, Hyun-Pyo
    • Archives of Pharmacal Research
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    • v.21 no.4
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    • pp.406-410
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    • 1998
  • Biflavonoid is one of unique classes of naturally-occurring bioflavonoids. Certain biflavonoids including amentoflavone were previously reported to have inhibitory effect on the group 11 phospholipase $A_2$ activity. Amentoflavone was also found to inhibit cyclooxygenase from guinea-pig epidermis without affecting lipoxygenase. In this study, anti-inflammatory and analgesic activities of amentoflavone were evaluated. When amentoflavone was administered intraperitoneally, it showed a potent anti-inflammatory activity as determined by amelioration of croton-oil induced mouse ear edema. It also showed a potent anti-inflammatory activity in the rat carrageenan paw edema model ($ED_{50}$=42 mg/kg) compared to the activity of prednisolone (35 mg/kg) and indomethacin (10 mg/kg). However, amentoflavone did not show a significant inhibitory activity against rat adjuvant-induced arthritis, a chronic inflammatory model. In addition, amentoflavone was found to possess a potent analgesic activity in the acetic acid writhing test ($ED_{50}$=9.6 mg/kg) compared to the activity of indomethacin (3.8 mg/kg). These results suggest that amentoflavone may be a potential lead for a new type of anti-inflammatory agents having dual inhibitory activity of group 11 phospholipase $A_2$ and cyclooxygenase.

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Antifungal Effect of Amentoflavone derived from Selaginella tamariscina

  • Jung, Hyun-Jun;Sung, Woo-Sang;Yeo, Soo-Hwan;Kim, Hyun-Soo;Lee, In-Seon;Woo, Eun-Rhan;Lee, Dong-Gun
    • Archives of Pharmacal Research
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    • v.29 no.9
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    • pp.746-751
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    • 2006
  • Amentoflavone is a plant biflavonoid that was isolated from an ethyl acetate extract of the whole plant of Selaginella tamariscina (Beauv.) spring. 1D and 2D NMR spectroscopy including DEPT, HMQC, and HMBC were used to determine its structure. Amentoflavone exhibited potent antifungal activity against several pathogenic fungal strains but had a very low hemolytic effect on human erythrocytes. In particular, amentoflavone induced the accumulation of intracellular trehalose on C. albicans as a stress response to the drug, and disrupted the dimorphic transition that forms pseudo-hyphae during pathogenesis. In conclusion, amentoflavone has great potential to be a lead compound for the development of antifungal agents.

Antibacterial Effect of Amentoflavone and Its Synergistic Effect with Antibiotics

  • Hwang, Ji Hong;Choi, Hyemin;Woo, Eun-Rhan;Lee, Dong Gun
    • Journal of Microbiology and Biotechnology
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    • v.23 no.7
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    • pp.953-958
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    • 2013
  • Selaginella tamariscina is a traditional herb used in medicine. Phytochemical amentoflavone, a biflavonoid class of flavonoids, was isolated from the plant of Selaginella tamariscina. In this study, the antibacterial effects and combination effects of amentoflavone and conventional antibiotics such as ampicillin, cefotaxime, and chloramphenicol were investigated. These results showed that amentoflavone had a considerable antibacterial effect and synergistic interaction with antibiotics against various bacterial strains (fractional inhibitory concentration index ${\leq}$ 0.5), except for Streptococcus mutans. To study the mechanism(s) involved in the synergistic activities between amentoflavone and antibiotics, we detected hydroxyl radical formation using 3'-(p-hydroxyphenyl) fluorescein and measured the $NAD^+/NADH$ ratio by $NAD^+$ cycling assay. The results indicated that the formation of hydroxyl radical would be a cause of the synergistic effect and that this oxidative stress originated from a transient NADH depletion. This study suggests that amentoflavone synergizes with antibiotics and has potential as a therapeutic agent for antimicrobial chemotherapy.

Amentoflavone Acts as a Radioprotector for Irradiated v79 Cells by Regulating Reactive Oxygen Species (ROS), Cell Cycle and Mitochondrial Mass

  • Xu, Ping;Jiang, En-Jin;Wen, Si-Yuan;Lu, Dan-Dan
    • Asian Pacific Journal of Cancer Prevention
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    • v.15 no.18
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    • pp.7521-7526
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    • 2014
  • Radioprotective effects of amentoflavone were investigated by examining cell viability, apoptosis, cell cycling concentrations of intracellular ROS (reactive oxygen species), and relative mitochondrial mass by flow cytometry after $^{60}Co$ irradiation. Pretreatment with amentoflavone 24 hours prior to 8 Gy $^{60}Co$ ${\gamma}$-ray irradiation significantly inhibited apoptosis, promoted the G2 phase, decreased the concentration of ROS and mitochondrial mass. These results collectively indicate that amentoflavone is an effective radioprotective agent.

Inhibitory Activity of Amentoflavone on Arachidonic Acid Releasing Enzyme, Phopholipase $A_2$ and Inhibition of Histamine Release from Mast Cells (Amentoflavone의 아라키돈산 유리효소인 phopholipase $A_2$에 대한 저해활성 및 비만세포에서 histamine 유리 억제효과)

  • Moon, Tae-Chul;Lee, Eun-Kyung;Lee, Sung-Ho;Son, Kun-Ho;Kim, Hyun-Pyo;Kang, Sam-Sik;Chang, Hyeun-Wook
    • Korean Journal of Pharmacognosy
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    • v.33 no.1
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    • pp.49-52
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    • 2002
  • Amentoflavone, naturally occurring biflavonoid, isolated from the leaves of Ginko biloba, selectively inhibited human seceretory phospholipase $A_2$. This compound potently and irreversibly inhibited human group IIA in a dose dependent manner with an $IC_50$ about $3\;{\mu}M$. Amentoflavone inhibited phospholipase $A_2$ by a noncompetitive manner with the apparent Ki value of $1{\times}10^{-5}M$. In addition, the inhibitory activity of amentoflavone is rather specific against group IIA phospholipase $A_2$ than group IB phospholipase $A_2$. Furthermore, this compound strong inhibit histamine release from $A_{23187}$ treated rat peritoneal mast cells. These results indicate naturally occurring biflavonoid represents a novel anti-inflammatory agent.

Binding Model of Amentoflavone to Peroxisome Proliferator-Activated Receptor γ

  • Lee, Jee-Young;Kim, Jin-Kyoung;Lee, So-Jung;Lee, Eun-Jung;Shin, So-Young;Jin, Qinglong;Yoon, Do-Young;Woo, Eun-Rhan;Kim, Yang-Mee
    • Bulletin of the Korean Chemical Society
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    • v.33 no.5
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    • pp.1475-1479
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    • 2012
  • Human peroxisome proliferator-activated receptor gamma ($hPPAR{\gamma}$) has been implicated in numerous pathologies, including obesity, diabetes, and cancer. In this study, we verified that amentoflavone is an agonist of $hPPAR{\gamma}$ and probed the molecular basis of its action. It was demonstrated that amentoflavone bound $hPPAR{\gamma}$ with high (picomolar) affinity and increased the binding between $hPPAR{\gamma}$ and steroid receptor coactivator-1 (SRC-1) by approximately 4-fold. Based on a docking study, for the first time, we propose a model of amentoflavone and $hPPAR{\gamma}$ binding in which amentoflavone forms three hydrogen bonds with the side chains of His323, Tyr327, and Arg280 in $hPPAR{\gamma}$ and participates in two hydrophobic interactions.

Biflavonoids from the Leaves of Cephalotaxus koreana Nakai

  • Yook, Chang-Soo;Jung, Jin-Hwan;Jeong, Jin-Hyun;Nohara, Toshihiro;Chang, Seung-Yeup
    • Natural Product Sciences
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    • v.6 no.1
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    • pp.1-4
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    • 2000
  • Four biflavonoids were isolated from the leaves of Cephalotaxus koreana. Based on spectroscopic data, the compounds were identified as amentoflavone-7',7",4',4"'-tetramethyl ether, sciadopitysin, ginkgetin and bilobetin, respectively.

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Flavonoid Constituents of Selaginella tamariscina (권백의 Flavonoid 성분)

  • Shin, Dong-In;Kim, Jin-Woong
    • Korean Journal of Pharmacognosy
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    • v.22 no.4
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    • pp.207-210
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    • 1991
  • From the chloroform and n-butanol extracts of Selaginella tamariscina, three biflavonoids were isolated by chromatographic separation. Structures of these compounds were determined as cryptomerin B, amentoflavone and isocryptomerin by spectroscopic analysis, and amentoflavone was further identified by comparison with the authentic sample. This is the first report of isolation of cryptomerin B from Selaginellaceae.

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