6137-86-6Relevant academic research and scientific papers
Understanding the regioselectivity in the oxidative condensation of catechins using pyrogallol-type model compounds
Yanase, Emiko,Ochiai, Yuto,Hirose, Sayumi
, p. 12359 - 12366 (2020/11/10)
Catechins are found in many foods, including tea. These compounds are bioactive. Previous studies have shown that catechins form dimers on oxidation, and there seem to be distinct regioselective effects. However, the dimerization mechanism and regioselectivity are not well understood. Therefore, we investigated the oxidation of four pyrogallol-type model compounds of epigallocatechin (EGC) having various substituents with 1 equiv of copper chloride and 30% dioxane in water. Compounds having 2C-2C or 2C-4C bonds in the B-ring were obtained in different product ratios. Comparison of the oxidation rates of each compound revealed that the model compounds having an oxygen atom corresponding to the 1-position of the C-ring of EGC underwent slow oxidation. In addition, using density functional theory calculations, we found that the highest occupied molecular orbital energies of these compounds were higher than those of the others. Further, the 2C-2C-bonded oxidation product having an A-ring and an oxygen atom at the C-ring 1-position was confirmed to have the highest thermodynamic stability. From these results, it is suggested that the regioselective condensation reaction of the catechin B-ring is related to interactions between the A-rings, as indicated by earlier studies, and the presence of oxygen at the 1-position of the C-ring in EGC.
Compound for treating or preventing hepatopathy (by machine translation)
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Paragraph 0178-0179; 0182; 0191-0192; 0195, (2019/10/01)
The invention discloses a compound, an optical isomer or a pharmaceutically acceptable salt, an optical isomer or a pharmaceutically acceptable salt thereof for treating or preventing hepatopathy, and the compound, optical isomer or pharmaceutically acceptable salt thereof can be applied to the preparation of a medicine for treating or preventing liver diseases. (by machine translation)
ANTHOCYANIN SYNTHESIS PROMOTER AND CHLOROPHYLL DEGRADATION PROMOTER
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Paragraph 0073; 0075, (2017/06/24)
PROBLEM TO BE SOLVED: To provide an anthocyanin synthesis promoter and a chlorophyll degradation promoter that are safe and practicable. SOLUTION: The present invention provides an anthocyanin synthesis promoter and a chlorophyll degradation promoter comprising extract of plant belonging to Hydrocharitaceae Egeria or Elodea. The extract preferably comprises at least one of a compound of formula (I) and a compound of formula (II) as an active compound. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
Antioxidant and antimicrobial activity evaluation of polyhydroxycinnamic acid ester derivatives
Venkateswarlu, Somepalli,Ramachandra, Mareullapudi S.,Krishnaraju, Alluri V.,Trimurtulu, Golakoti,Subbaraju, Gottumukkala V.
, p. 252 - 257 (2007/10/03)
Polyhydroxycinnamic acid esters 5a-p have been synthesized starting from the appropriately substituted benzaldehydes. The antioxidant activity of these esters has been determined by superoxide free radical scavenging activity and DPPH free radical scavenging activity. The SAR studies reveal that pyrogallol, catechol moieties are essential for good antioxidant activity and an increase in the length of alkyl chain of the ester decreases the activity. Butyl hydroxycinnamates exhibit higher antibacterial activity among the synthesized hydroxycinnamates 5a-p, but, none of these show significant antifungal activity.
Synthesis and retrostructural analysis of libraries of AB3 and constitutional isomeric AB2 phenylpropyl ether-based supramolecular dendrimers
Percec, Virgil,Peterca, Mihai,Sienkowska, Monika J.,Ilies, Marc A.,Aqad, Emad,Smidrkal, Jan,Heiney, Paul A.
, p. 3324 - 3334 (2007/10/03)
We report the synthesis of methyl esters of 3-(4-hydroxyphenyl)propionic, 3-(3,4-dihydroxyphenyl)propionic, 3-(3,5-dihydroxyphenyl)propionic, and 3-(3,4,5-trihydroxyphenyl)propionic acids and their use in a convergent iterative strategy to prepare up to four generations of three libraries, one of 3,4,5- and two of constitutional isomeric 3,4- and 3,5-substituted 3-phenylpropyl dendrons. Each library contains 3-[3,4,5-tris(dodecyl-1-oxy) phenyl]propyl-, 3-[3,4-bis(dodecyl-1-oxy)phenyl]propyl-, 3-{3,4-bis[3-(4- dodecyl-1-oxyphenyl)propyl-1-oxy]phenyl}propyl-, and 3-{3,4,5-tris[3-(4-dodecyl- 1-oxyphenyl)propyl-1-oxy]phenyl}propyl ether first-generation dendrons on their periphery and -CO2CH3, -COOH, and -CH2OH groups at their apex. Regardless of their generation number and their periphery, internal, and apex structures, these dendrons self-assemble into supramolecular dendrimers that self-organize into all periodic and quasi-periodic assemblies encountered previously and in several unencountered with architecturally related benzyl ether-based supramolecular dendrimers. A variety of porous columnar lattices that were previously obtained only from dendritic dipeptides and hollow supramolecular spheres were also discovered from these building blocks. The more flexible and less compact 3-phenylpropyl ether repeat units are stable under acidic conditions, facilitate a simpler synthetic strategy, provide faster dynamics of self-assembly into higher-order supramolecular structures of larger dimensions, exhibit lower transition temperatures than the corresponding benzyl ether homologues, and demonstrate the generality of the self-assembly concept based on amphiphilic dendrons.
Novel flavanoids as chemotherapeutic, chemopreventive, and antiangiogenic agents
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, (2008/06/13)
Novel compounds are useful as chemotherapeutic, chemopreventative, and antiangiogenic agents are provided. The compounds are flavanoids, including flavanones, flavanols, and chalcones. The compounds have the structure of formula (I) 1wherein R1 through R3 and R5 through R11 are defined herein, and α, β, and γ are optional bonds, providing that when α is absent, β is present, and when β is absent, α is present. When α is present, preferred R4 moieties are selected from O, S, NH and CH2, and when α is absent, preferred R4 groups are selected from OH, SH, NH2 and CH3. When γ is present, the preferred R5 substituent is O, while when γ is absent, the preferred R5 substituent is OH. Pharmaceutical compositions are provided as well, as are methods of synthesis and use.
Analogs of green tea polyphenols as chemotherapeutic and chemopreventive agents
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, (2008/06/13)
Novel compounds useful as chemotherapeutic and chemopreventive agents are provided. The compounds are analogs of polyphenol catechins that occur in green tea, such as epigallocatichin-3-gallate (EGCG), and have the structure of formula (I) wherein R1 through R11 are defined herein. Preferred R4 moieties are selected from O, S, NH and CH2, and in exemplary compounds, R4 is O and R5 is a tri-substituted aroyloxy substituent, such as a 3,4,5-substituted benzoyloxy group. Pharmaceutical compositions are provided as well, as are methods of chemotherapy and chemoprevention.
Dendronized protein polymers: Synthesis and self-assembly of monodisperse cylindrical macromolecules
Zhuravel, Michael A.,Davis, Nicolynn E.,Nguyen, SonBinh T.,Koltover, Ilya
, p. 9882 - 9883 (2007/10/03)
Monodisperse dendronized protein polymers (DPPs), cylindrical dendrimers containing protein core, can be efficiently produced through a combined modular biosynthetic strategy. These DPP materials possess predictable size, shape, and solubility. In organic
A new convergent approach to dendritic macromolecules
Cao, Xiaoping,Wang, Feng,Guo, Shu
, p. 3149 - 3158 (2007/10/03)
The novel convergent growth approach to dendritic macromolecules is described. Polyether dendritic sectors [G-na]-OH from the first to the fourth generations, respectively, were prepared by this approach from readily available starting material.
Synthesis of a 3,4,5-trimethoxybenzoyl ester analogue of epigallocatechin-3-gallate (EGCG): A potential route to the natural product green tea catechin, EGCG
Zaveri, Nurulain T.
, p. 843 - 845 (2007/10/03)
matrix presented The synthesis of a trimethoxybenzoyl ester (D-ring) analogue of epigallocatechin-3-gallate (EGCG) is described. The versatile synthesis route can be used to synthesize A, B, and D ring analogues of EGCG and involves a key cyclization of t
