- Synthesis and biological evaluation of caffeic acid derivatives as potent inhibitors of α-MSH-stimulated melanogenesis
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We have disclosed our effort to develop caffeic acid derivatives as potent and non-toxic inhibitors of α-MSH-stimulated melanogenesis to treat pigmentation disorders and skin medication including a cosmetic skin-whitening agent. The SAR studies revealed t
- Jo, Hyeju,Choi, Minho,Sim, Jaeuk,Viji, Mayavan,Li, Siyuan,Lee, Young Hee,Kim, Youngsoo,Seo, Seung-Yong,Zhou, Yuanyuan,Lee, Kiho,Kim, Wun-Jae,Hong, Jin Tae,Lee, Heesoon,Jung, Jae-Kyung
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supporting information
p. 3374 - 3377
(2017/07/07)
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- Novel Chlorogenic Acid Derivatives and Composition for Treating Inflammatory Disease Comprising the Same
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The present invention relates to a novel chlorogenic acid derivative compound having anti-inflammatory activities and an anti-inflammatory composition comprising the same as an active ingredient. The chlorogenic acid derivative compound of the present invention inhibits overproduction of nitrogen oxide (NO) induced by treating LPS in macrophage. The chlorogenic acid derivative compound of the present invention suppresses activation of NF-κB which is a signal transmission-mediated transcription factor significant in an oxidative stress and inflammation-promoting path. The chlorogenic acid derivative compound of the present invention can be developed as medicine for various inflammatory diseases by inhibiting overproduction of nitrogen oxide and activation of NF-κB.
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Paragraph 0179; 0180; 0181; 0182
(2017/08/02)
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- Synthesis of 1-O-methylchlorogenic acid: Reassignment of structure for MCGA3 isolated from bamboo (Phyllostachys edulis) leaves
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The first synthesis of 1-O-methylchlorogenic acid is described. The short and efficient synthesis of this compound provides laboratory-scale quantities of the material to investigate its biological properties. The synthesis involves C-1 alkylation of the
- Zeller, Wayne E.
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p. 1860 - 1865
(2014/03/21)
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- In vitro evaluation of caffeoyl and cinnamoyl derivatives as potential prolyl oligopeptidase inhibitors
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A screening of the natural product chlorogenic acid, isolated from the Brazilian medicinal plant Hypericum brasiliense, caffeic acid, cinnamic acid, and p-methoxycinnamic acid, and derivatives of caffeoylquinic, caffeoyl, and cinnamoyl against the enzymes prolyl oligopeptidase and dipeptidyl peptidase IV was carried out. Caffeoylquinic, caffeoyl, and cinnamoyl derivatives were prepared using simple derivatization procedures and through coupling reactions with the amino acid proline. The dipeptidyl peptidase IV assay showed inhibitory activity of the tested compounds at a high concentration (500 μM) in the range of 81.5-7.2%. In contrast, the derivatives methyl ester and 1,7-acetonide obtained from chlorogenic acid, and caffeic acid and its methyl ester derivative showed selectivity and activity as prolyl oligopeptidase inhibitors, with IC50 values of 3 to 14 mM.
- Adolpho, Luciana O.,Marin, Daniele,Puigpinos, Albert,Mendieta, Laura,Tarrago, Teresa,Morel, Ademir F.,Giralt, Ernest,Dalcol, Ionara I.
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p. 1531 - 1535
(2013/12/04)
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- Synthesis of designed acylquinic acid derivatives involved in blue color development of hydrangea and their co-pigmentation effect
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The blue sepal color of hydrangea may be developed by an unstable stipramolecular metal-complex pigment composed of delphinidin 3-glucoside (1), 5-O-caffeoylquinic acid (2) and 5-O-p-coumaroylquinic acid (3) as co-pigments and Al3+ in aqueous s
- Toyama-Kato, Yuki,Kondo, Tadao,Yoshida, Kumi
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p. 239 - 254
(2008/03/12)
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- Essential structure of co-pigment for blue sepal-color development of hydrangea
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Blue sepal-color of Hydrangea macrophylla might be due to a supramolecular metal-complex pigment consisting of delphinidin 3-glucoside (1), co-pigments (5-O-caffeoylquinic acid (2), and/or 5-O-p-coumaroylquinic acid (3)) and Al 3+ in an aqueous
- Kondo, Tadao,Toyama-Kato, Yuki,Yoshida, Kumi
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p. 6645 - 6649
(2007/10/03)
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- Chlorogenic acid and synthetic chlorogenic acid derivatives: Novel inhibitors of hepatic glucose-6-phosphate translocase
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The enzyme system glucose-6-phosphatase (EC 3.1.3.9) plays a major role in the homeostatic regulation of blood glucose. It is responsible for the formation of endogenous glucose originating from gluconeogenesis and glycogenolysis. Recently, chlorogenic acid was identified as a specific inhibitor of the glucose-6-phosphate translocase component (Gl-6-P translocase) of this enzyme system in microsomes of rat liver. Glucose 6- phosphate hydrolysis was determined in the presence of chlorogenic acid or of new synthesized derivatives in intact rat liver microsomes in order to assess the inhibitory potency of the compounds on the translocase component. Variation in the 3-position of chlorogenic acid had only poor effects on inhibitory potency. Introduction of lipohilic side chain in the 1-position led to 100-fold more potent inhibitors. Functional assays on isolated perfused rat liver with compound 29i, a representative of the more potent derivatives, showed a dose-dependent inhibition of gluconeogenesis and glycogenolyosis, suggesting glucose-6-phosphatase as the locus of interference of the compound for inhibition of hepatic glucose production also in the isolated organ model. Gl-6-P translocase inhibitors may be useful for the reduction of inappropriately high rates of hepatic glucose output often found in non-insulin-dependent diabetes.
- Hemmerle, Horst,Burger, Hans-Joerg,Below, Peter,Schubert, Gerrit,Rippel, Robert,Schindler, Peter W.,Paulus, Erich,Herling, Andreas W.
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p. 137 - 145
(2007/10/03)
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