56254-05-8Relevant academic research and scientific papers
Structural Fine-Tuning of Desmuramylpeptide NOD2 Agonists Defines Their in Vivo Adjuvant Activity
Guzelj, Samo,Nabergoj, Sanja,Gobec, Martina,Pajk, Stane,Klan?i?, Veronika,Slütter, Bram,Frkanec, Ru?a,?timac, Adela,?ket, Primo?,Plavec, Janez,Mlinari?-Ra??an, Irena,Jakopin, ?iga
supporting information, p. 7809 - 7838 (2021/06/28)
We report on the design, synthesis, and biological evaluation of a series of nucleotide-binding oligomerization-domain-containing protein 2 (NOD2) desmuramylpeptide agonists with improved in vitro and in vivo adjuvant properties. We identified two promising compounds: 68, a potent nanomolar in vitro NOD2 agonist, and the more lipophilic 75, which shows superior adjuvant activity in vivo. Both compounds had immunostimulatory effects on peripheral blood mononuclear cells at the protein and transcriptional levels, and augmented dendritic-cell-mediated activation of T cells, while 75 additionally enhanced the cytotoxic activity of peripheral blood mononuclear cells against malignant cells. The C18 lipophilic tail of 75 is identified as a pivotal structural element that confers in vivo adjuvant activity in conjunction with a liposomal delivery system. Accordingly, liposome-encapsulated 75 showed promising adjuvant activity in mice, surpassing that of muramyl dipeptide, while achieving a more balanced Th1/Th2 immune response, thus highlighting its potential as a vaccine adjuvant.
Biophysical properties and cytotoxicity of feruloylated helix lucorum hemocyanin
Guncheva, Maya,Idakieva, Krassimira,Stoyanova, Elena,Todinova, Svetla,Yancheva, Denitsa
, p. 253 - 259 (2020/03/30)
For the first time Helix lucorum hemocyanin (HlH) has been feruloylated. Two HlH conjugates with 40- and 120- ferulic acid residues were prepared, denoted as FA-HlH-1 and FA-HlH-2. Expectedly, the feruloylation of HlH induced a rearrangement of the protei
Multifunctional diamine AGE/ALE inhibitors with potential therapeutical properties against Alzheimer's disease
Lohou, Elodie,Sasaki, N. André,Boullier, Agnès,Sonnet, Pascal
, p. 702 - 722 (2016/07/26)
An important part of pathogenesis of Alzheimer's disease (AD) is attributed to the contribution of AGE (Advanced Glycation Endproducts) and ALE (Advanced Lipid peroxidation Endproducts). In order to attenuate the progression of AD, we designed a new type of molecules that consist of two trapping parts for reactive carbonyl species (RCS) and reactive oxygen species (ROS), precursors of AGE and ALE, respectively. These molecules also chelate transition metals, the promoters of ROS formation. In this paper, synthesis of the new AGE/ALE inhibitors and evaluation of their physicochemical and biological properties (carbonyl trapping capacity, antioxidant activity, Cu2+-chelating capacity, cytotoxicity and protective effect against in?vitro MGO-induced apoptosis in the model AD cell-line PC12) are described. It is found that compounds 40b and 51e possess promising therapeutic potentials for treating AD.
A Maillard approach to 2-formylpyrroles: Synthesis of magnolamide, lobechine and funebral
Yuen, Tsz-Ying,Eaton, Samantha E.,Woods, Tom M.,Furkert, Daniel P.,Choi, Ka Wai,Brimble, Margaret A.
, p. 1431 - 1437 (2014/03/21)
A convenient synthesis of the traditional medicine constituents magnolamide, lobechine and funebral is described. Construction of the 2-formylpyrrole core of these natural products was achieved by means of a Maillard reaction, involving condensation of the sugar surrogate, dihydropyranone 9, with the requisite primary amines. This approach offers a very direct and general route to the 2-formylpyrrole ring system. The synthesis of the 2-formylpyrrole core found in the traditional medicine constituents, magnolamide, lobechine and funebral, was constructed by a Maillard reaction, involving condensation of the sugar surrogate, dihydropyranone 9, with the requisite primary amines. This approach offers a very direct and general route to the 2-formylpyrrole ring system. Copyright
New series of avenanthramides in oat seed
Ishihara, Atsushi,Kojima, Kana,Fujita, Takeshi,Yamamoto, Yuya,Nakajima, Hiromitsu
, p. 1975 - 1983 (2015/03/18)
Avenanthramides are characteristic constituents of oat seeds. We analyzed the methanol extract of oat seeds by HPLC and detected three compounds 1, 2, and 3 eluted at retention times similar to avenanthramides. The three compounds were purified by column
A Maillard Approach to 2-Formylpyrroles: Synthesis of Magnolamide, Lobechine and Funebral
Yuen, Tsz-Ying,Eaton, Samantha E.,Woods, Tom M.,Furkert, Daniel P.,Choi, Ka Wai,Brimble, Margaret A.
, p. 1431 - 1437 (2015/10/05)
A convenient synthesis of the traditional medicine constituents magnolamide, lobechine and funebral is described. Construction of the 2-formylpyrrole core of these natural products was achieved by means of a Maillard reaction, involving condensation of the sugar surrogate, dihydropyranone 9, with the requisite primary amines. This approach offers a very direct and general route to the 2-formylpyrrole ring system. The synthesis of the 2-formylpyrrole core found in the traditional medicine constituents, magnolamide, lobechine and funebral, was constructed by a Maillard reaction, involving condensation of the sugar surrogate, dihydropyranone 9, with the requisite primary amines. This approach offers a very direct and general route to the 2-formylpyrrole ring system.
Vir-gene-inducing activities of hydroxycinnamic acid amides in Agrobacterium tumefaciens
Berthelot, Karine,Buret, David,Guerin, Brigitte,Delay, Didier,Negrel, Jonathan,Delmotte, Francis M.
, p. 1537 - 1548 (2007/10/03)
Expression of Agrobacterium tumefaciens virulence genes and transformation of dicots by this organism are dependent upon host plant phenolic compounds. Several alkylsyringamides have recently been shown to be powerful inducers of these vir-genes. These synthetic amides, and especially ethylsyringamide, are much stronger inducers than syringic acid. In this work, four alkylamides derived from ferulic or sinapic acids were synthesized by a dicyclohexylcarbodiimide method and tested for their potential to induce vir-gene expression on A. tumefaciens strains harbouring virB::lacZ or virE::lacZ fusion plasmids. Their effectiveness was compared to that of ethylsyringamide and tyraminylferulamide, a naturally occurring amide in plants. Whatever the amine moiety of the amide (ethylamine, propylamine, tyramine or β-alanine ethyl ester) conjugation of the acid functional group clearly diminished the toxicity to the bacteria of the respective acid at high concentration and thereby increased the vir-inducing potential. However, none of the inducers tested exhibited higher activity than acetosyringone, the reference compound for vir-gene induction, with the exception of ethylsyringamide at concentrations above 1 mM. When tested on Agrobacterium tumefaciens strain A348(pSM243cd), ethylferulamide and ethylsinapamide were more efficient than the corresponding phenolic acids but only above 100 μM.
QUINOLIZIDINE ALKALOIDS AND THE ENZYMATIC SYNTHESIS OF THEIR CINNAMIC AND HYDROXYCINNAMIC ACID ESTERS IN LUPINUS ANGUSTIFOLIUS AND L. LUTEUS
Strack, Dieter,Becher, Andrea,Brall, Sabine,Witte, Ludger
, p. 1493 - 1498 (2007/10/02)
The accumulation pattern of quinolizidine alkaloids during development of seedings and young plants of Lupinus angustifolius and L. luteus are described.The enzymes catalysing the syntheses of the cinnamic acid O-ester of 13-hydroxylupanine and hydroxycinnamic acid O-esters of lupinine (4-coumaroyl- and feruloyllupinine) are characterized and classified as cinnamoyl-CoA:13-hydroxylupanine O-cinnamoyltransferase (EC 2.3.1.-) and hydroxy cinnamoyl-CoA:lupinine O-hydroxycinnamoyltransferase (EC 2.3.1.-). Key Word Index - Lupinus angustifolius; L. luteus; Fabaceae; quinolizidine alkaloids; hydroxycinnamic acid esters; acyltransferase; hydroxycinnamoyl-coenzyme A; biosynthesis.
THE PHOSPHOHYDROLYSIS OF HYDROXYCINNAMOYL-COENZIME A THIOESTERS IN PLANT EXTRACTS
Negrel, Jonathan,Smith, Terence A.
, p. 31 - 34 (2007/10/02)
In barley seedling extracts, p-coumaroyl-CoA is rapidly hydrolysed to p-coumaroyl-dephospho-CoA, p-coumaroyl-4'-phosphopantetheine and p-coumaroyl-pantetheine. p-Coumaroyl-4'-phosphopantetheine is active as a substrate of agmatine coumaroyl transferase in the formation of p-coumaroyl agmatine, but p-coumaroyl-pantetheine is inactive.The phosphohydrolysis can be partly inhibited by inorganic pyrophosphate, sodium fluoride and purine nucleotides.A simplified method for the synthesis of N-hydroxysuccinimide esters of hydroxycinnamic acids, used in the synthesis of CoA thioesters, is also described.Key Word Index -- Hordeum vulgare; Gramineae; barley seedlings; plant extracts; phosphohydrolysis; hydroxycinnamoyl-CoA; p-coumaroylagmatine.
