138769-50-3Relevant academic research and scientific papers
7-O-Esters of taxifolin with pronounced and overadditive effects in neuroprotection, anti-neuroinflammation, and amelioration of short-term memory impairment in vivo
Decker, Michael,Fischer, Wolfgang,Gunesch, Sandra,Hoffmann, Matthias,Kiermeier, Carolina,Maher, Pamela,Maurice, Tangui,Pinto, Antonio F. M.
, (2020)
Alzheimer's disease (AD) is a multifactorial disease and the most common form of dementia. There are no treatments to cure, prevent or slow down the progression of the disease. Natural products hold considerable interest for the development of preventive neuroprotectants to treat neurodegenerative disorders like AD, due to their low toxicity and general beneficial effects on human health with their anti-inflammatory and antioxidant features. In this work we describe regioselective synthesis of 7-O-ester hybrids of the flavonoid taxifolin with the phenolic acids cinnamic and ferulic acid, namely 7-O-cinnamoyltaxifolin and 7-O-feruloyltaxifolin. The compounds show pronounced overadditive neuroprotective effects against oxytosis, ferroptosis and ATP depletion in the murine hippocampal neuron HT22 cell model. Furthermore, 7-O-cinnamoyltaxifolin and 7-O-feruloyltaxifolin reduced LPS-induced neuroinflammation in BV-2 microglia cells as assessed by effects on the levels of NO, IL6 and TNFα. In all in vitro assays the 7-O-esters of taxifolin and ferulic or cinnamic acid showed strong overadditive activity, significantly exceeding the effects of the individual components and the equimolar mixtures thereof, which were almost inactive in all of the assays at the tested concentrations. In vivo studies confirmed this overadditive effect. Treatment of an AD mouse model based on the injection of oligomerized Aβ25-35 peptide into the brain to cause neurotoxicity and subsequently memory deficits with 7-O-cinnamoyltaxifolin or 7-O-feruloyltaxifolin resulted in improved performance in an assay for short-term memory as compared to vehicle and mice treated with the respective equimolar mixtures. These results highlight the benefits of natural product hybrids as a novel compound class with potential use for drug discovery in neurodegenerative diseases due to their pharmacological profile that is distinct from the individual natural components.
Hybrids of aurantiamide acetate and isopropylated genipin as potential anti-inflammatory agents: The design, synthesis, and biological evaluation
Wang, Hongwei,Gao, Sufan,Li, Jiaming,Ma, Xiaodong,Liu, Wandong,Qian, Shihu
, p. 797 - 808 (2020/12/03)
A novel series of hybrids designed on the basis of aurantiamide acetate and isopropylated genipin were synthesized and biologically evaluated as anti-inflammatory agents. Among them, compound 7o exhibited the best inhibitory activity against TNF-α secretion (IC50?=?16.90?μM) and was selected for further in vitro and in vivo functional study. The results demonstrated that 7o was capable of suppressing the expression of LPS-induced iNOS and COX-2, as well as reducing the production of NO at the concentration of 5?μM, which may be resulted from its regulation of NF-κB signaling and MAPK signaling. Moreover, compound 7o exhibited favorable in vivo anti-inflammatory activity with an inhibition rate of 53.32% against xylene-induced ear swelling in mice at the dose of 5?mg/kg.
Coumarin derivative as well as preparation method and application thereof
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Paragraph 0075-0077, (2020/05/05)
The invention discloses a coumarin derivative as well as a preparation method and application thereof. The chemical structural formula of the coumarin derivative is represented by a formula (I) or a formula (II), wherein in the formula, R1 is H, CH3, OCH3
Synthetic Guaiacol Derivatives as Promising Myeloperoxidase Inhibitors Targeting Atherosclerotic Cardiovascular Disease
Premkumar, Jayaraj,Sampath, Parthasarathy,Sanjay, Rajagopalan,Chandrakala, Aluganti,Rajagopal, Desikan
supporting information, p. 1187 - 1199 (2020/05/25)
Myeloperoxidase (MPO) is known to cause oxidative stress and inflammation leading to cardiovascular disease (CVD) complications. MPO-mediated oxidation of lipoproteins leads to dysfunctional entities altering the landscape of lipoprotein functionality. The specificity of guaiacol derivatives toward preventing MPO-mediated oxidation to limit MPO's harmful effects is unknown. Diligent in silico studies were accomplished for a portfolio of compounds with guaiacol as a building block. The compounds’ activity toward MPO inhibition was also validated. The role of these chemical entities in controlling MPO-mediated oxidation of lipoproteins (LDL and HDL) was shown to agree with our approach of developing powerful MPO inhibitors. The mechanism of MPO inhibition was demonstrated to be reversible in nature. This study reveals that there is great potential for guaiacol derivatives as therapeutics for CVD by modulating lipid profiles, reducing atherosclerotic plaque burden, and subsequently optimizing cardiovascular functions.
Coumarin glycoside compound, its preparation process and pharmaceutical composition and use thereof
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Paragraph 0075; 0076, (2019/01/22)
The invention relates to a novel coumarin glycoside compound derived from esculine or skimmin and a synthesis method thereof, and application of the novel coumarin glycoside compound and 7-O-methylesculine as drugs in diseases related to diabetic angiopat
Phenylacrylate derivative and application thereof as neuroprotective drug
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Paragraph 0042; 0043, (2019/05/02)
The invention discloses a phenylacrylate derivative and application thereof as a neuroprotective drug, the phenylacrylate derivative and a medicinal preparation thereof have a good curative treating effect on cranial nerve injury diseases such as cerebral apoplexy and related diseases, are low in acute toxicity and do not have the potential heart toxicity risk, and have a prominent technical effect and a substantial scientific progress compared with existing medicines. The phenylacrylate derivative is a compound represented by a general formula i or a salt thereof as shown in the specification.
L-type amino acid transporter 1 utilizing prodrugs of ferulic acid revealed structural features supporting the design of prodrugs for brain delivery
Puris, Elena,Gynther, Mikko,Huttunen, Johanna,Auriola, Seppo,Huttunen, Kristiina M.
, p. 99 - 109 (2019/01/11)
Ferulic acid (FA), a natural antioxidant, has displayed some potential benefits against Alzheimer's disease. However, due to its poor blood-brain barrier (BBB) permeation and low bioavailability, the clinical use of FA for the treatment of Alzheimer's dis
Synthesis method of benzyl ferulate
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Paragraph 0011; 0015-0017; 0022; 0027; 0032; 0037, (2019/02/13)
The invention provides a synthesis method of benzyl ferulate. Ferulic acid is adopted as the starting raw material to prepare a benzyl ferulate compound through a series of reactions. The synthesis reaction adopted by the method provided by the invention
Synthetic resveratrol-curcumin hybrid derivative inhibits mitosis progression in estrogen positive MCF-7 breast cancer cells
de Freitas Silva, Matheus,Coelho, Letícia Ferreira,Guirelli, Isadora Mitestainer,Pereira, Rodrigo Machado,Ferreira-Silva, Guilherme álvaro,Graravelli, Graciana Y.,Horvath, Renato de Oliveira,Caixeta, Ester Siqueira,Ionta, Marisa,Viegas, Claudio
, p. 75 - 85 (2018/03/13)
Curcumin (1) and resveratrol (2) are bioactive natural compounds that display wide pharmacological properties, including antitumor activity. However, their clinical application has been limited due to their low solubility and bioavailability. Nevertheless
Design, synthesis and evaluation of novel feruloyl-donepezil hybrids as potential multitarget drugs for the treatment of Alzheimer's disease
Dias, Kris Simone T.,de Paula, Cynthia T.,dos Santos, Thiago,Souza, Isis N.O.,Boni, Marina S.,Guimar?es, Marcos J.R.,da Silva, Fernanda M.R.,Castro, Newton G.,Neves, Gilda A.,Veloso, Clarice C.,Coelho, Márcio M.,de Melo, Ivo Souza F.,Giusti, Fabiana C.V.,Giusti-Paiva, Alexandre,da Silva, Marcelo L.,Dardenne, Laurent E.,Guedes, Isabella A.,Pruccoli, Letizia,Morroni, Fabiana,Tarozzi, Andrea,Viegas, Claudio
, p. 440 - 457 (2017/03/11)
A novel series of feruloyl-donepezil hybrid compounds were designed, synthesized and evaluated as multitarget drug candidates for the treatment of Alzheimer's Disease (AD). In?vitro results revealed potent acetylcholinesterase (AChE) inhibitory activity f
