3843-74-1Relevant articles and documents
CESTRIC ACID, A CAFFEIC ACID ESTER FROM CESTRUM EUANTHES
Nagels, Luc,Dongen, Walter van,Parmentier, Frits
, p. 743 - 746 (1982)
Cestric acid, a new phenolic ester was isolated from leaves of Cestrum euanthes.By means of GC, HPLC, mass spectroscopy, GC/MS, and 13C NMR, it was shown to be an ester of caffeic acid with glucaric acid.The ester occurs as an equilibrium mixture of four isomers.Key Word Index - Cestrum euanthes; Solanaceae; caffeic acid; glucaric acid; phenolic esters; isomers.
β-Lactoglobulin Peptide Fragments Conjugated with Caffeic Acid Displaying Dual Activities for Tyrosinase Inhibition and Antioxidant Effect
Yang, Jin-Kyoung,Lee, Eunjin,Hwang, In-Jun,Yim, Dabin,Han, Juhee,Lee, Yoon-Sik,Kim, Jong-Ho
, p. 1000 - 1005 (2018)
The regulation of tyrosinase activity and reactive oxygen species is of great importance for the prevention of dermatological disorders in the fields of medicine and cosmetics. Herein, we report a strategy based on solid-phase peptide chemistry for the sy
Mushroom Tyrosinase-Based Enzyme Inhibition Assays Are Not Suitable for Bioactivity-Guided Fractionation of Extracts
Mayr, Fabian,Sturm, Sonja,Ganzera, Markus,Waltenberger, Birgit,Martens, Stefan,Schwaiger, Stefan,Schuster, Daniela,Stuppner, Hermann
, p. 136 - 147 (2019)
Tyrosinase (Tyr) catalyzes the rate-limiting step of melanogenesis in human skin and is thus the main target for treating pigmentation disorders today. This has led to an increased research interest in Tyr inhibitors during the last decades, with a frequent focus on polyphenols. In the early stages of drug discovery, it is typical to avoid the high costs of human Tyr by using the more economic mushroom tyrosinase (mh-Tyr). Since some polyphenols are accepted as substrates by mh-Tyr, the present study aimed to more generally investigate this enzyme's specificity toward polyphenols and to discuss its significance in the context of bioactivity-guided fractionation. Mh-Tyr substrates can change the sample color during an inhibition assay, leading to unreliable inhibition constants or to the discontinuation of a bioactivity-guided fractionation campaign. A data set of 56 natural products was investigated and classified into assay interferers (AIs) and noninterferers, using a spectrophotometric and an LC-ESIHRMS assay. Based on these experimental findings, structure-activity relationships defining AIs were deduced and implemented into an in silico tool that will allow for rapid prescreening in the future. We anticipate that these results will aid in the search for new Tyr inhibitors and contribute to the understanding of this enzyme, as well as its optimal use in pharmacological research.
Development of a clickable designer monolignol for interrogation of lignification in plant cell walls
Bukowski, Natalie,Pandey, Jyotsna L.,Doyle, Lucas,Richard, Tom L.,Anderson, Charles T.,Zhu, Yimin
, p. 2189 - 2196 (2014)
Lignin is an abundant and essential polymer in land plants. It is a prime factor in the recalcitrance of lignocellulosic biomass to agricultural and industrial end-uses such as forage, pulp and papermaking, and biofuels. To better understand lignifi catio
PHENYLPROPANOID GLYCOSIDES OF PRUNUS SSIORI
Abdallah, O. M.,Kamel, M. S.,Mohamed, M. H.
, p. 1689 - 1692 (1994)
Two new bitter phenylpropanoid glucosides, 2-(3,4-methyllenedioxyphenyl)-ethyl-(6-O-caffeoyl)-β-D-glucopyranoside and 3-O-caffeoyl-β-D-fructofuranosyl, 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside, have been isolated together with the know compounds, 6-O-caffeoyl-D-glucopyranoside and 2-(3,4-dihydroxyphenyl)-ethyl-(6-O-caffeoyl)-β-D-glucopyranoside, from the bark of Prunus ssiori.The structures of the isolated compounds have been established by extensive spectroscopic studies. - Key words: Prunus ssiori; Rosaceae; bark; phenylpropanoid glucosides; caffeic acid esters.
Electron-Transfer Reaction of Cinnamic Acids and Their Methyl Esters with the DPPH. Radical in Alcoholic Solutions
Foti, Mario C.,Daquino, Carmelo,Geraci, Corrada
, p. 2309 - 2314 (2004)
The kinetic behavior of cinnamic acids, their methyl esters, and two catechols 1-10 (ArOH) in the reaction with DPPH. in methanol and ethanol is not compatible with a reaction mechanism that involves hydrogen atom abstraction from the hydroxyl
Quinic acid derivatives from Pimpinella brachycarpa exert anti-neuroinflammatory activity in lipopolysaccharide-induced microglia
Lee, Seung Young,Moon, Eunjung,Kim, Sun Yeou,Lee, Kang Ro
, p. 2140 - 2144 (2013)
Five new quinic acid derivatives (1-5), together with 10 known quinic acid derivatives (6-15), were isolated from the MeOH extract of Pimpinella brachycarpa (Umbelliferae). Their structures were established on the basis of spectroscopic analyses including extensive 2D NMR studies (COSY, HMQC and HMBC). Isolated compounds 1-15 were evaluated for their inhibitory activities on nitric oxide (NO) production in an activated murine microglial cell line. Compounds 2, 3, 8 and 11 significantly inhibited NO production without high cell toxicity in lipopolysaccharide (LPS)-activated BV-2 cells, a microglia cell line (IC50 = 4.66, 12.52, 9.04 and 12.11 μM, respectively).
Prenylated trans-cinnamic esters and ethers against clinical fusarium spp.: Repositioning of natural compounds in antimicrobial discovery
Balmas, Virgilio,Carta, Paola,Casalini, Stefano,Chtioui, Wiem,Delogu, Giovanna,Dettori, Maria A.,Fabbri, Davide,Migheli, Quirico,Oufensou, Safa
, (2021/06/14)
Onychomycosis is a common nail infection mainly caused by species belonging to the F. oxysporum, F. solani, and F. fujikuroi species complexes. The aim of this study was to evaluate the in vitro susceptibility of six representative strains of clinically relevant Fusarium spp. toward a set of natural-occurring hydroxycinnamic acids and their derivatives with the purpose to develop naturally occurring products in order to cope with emerging resistance phenomena. By introducing a prenylated chain at one of the hydroxy groups of trans-cinnamic acids 1–3, ten prenylated derivatives (coded 4–13) were preliminarily investigated in solid Fusarium minimal medium (FMM). Minimal inhibitory concentration (MIC) and lethal dose 50 (LD50) values were then determined in liquid FMM for the most active selected antifungal p-coumaric acid 3,3′-dimethyl allyl ester 13, in comparison with the conventional fungicides terbinafine (TRB) and amphotericin B (AmB), through the quantification of the fungal growth. Significant growth inhibition was observed for prenylated derivatives 4–13, evidencing ester 13 as the most active. This compound presented MIC and LD50 values (62–250 μM and 7.8–125 μM, respectively) comparable to those determined for TRB and AmB in the majority of the tested pathogenic strains. The position and size of the prenylated chain and the presence of a free phenol OH group appear crucial for the antifungal activity. This work represents the first report on the activity of prenylated cinnamic esters and ethers against clinical Fusarium spp. and opens new avenues in the development of alternative antifungal compounds based on a drug repositioning strategy.
Structure?Activity Relationships of Cinnamate Ester Analogues as Potent Antiprotozoal Agents
Bernal, Freddy A.,Kaiser, Marcel,Wünsch, Bernhard,Schmidt, Thomas J.
, p. 68 - 78 (2019/11/22)
Protozoal infections are still a global health problem, threatening the lives of millions of people around the world, mainly in impoverished tropical and sub-tropical regions. Thus, in view of the lack of efficient therapies and increasing resistances against existing drugs, this study describes the antiprotozoal potential of synthetic cinnamate ester analogues and their structure-activity relationships. In general, Leishmania donovani and Trypanosoma brucei were quite susceptible to the compounds in a structure-dependent manner. Detailed analysis revealed a key role of the substitution pattern on the aromatic ring and a marked effect of the side chain on the activity against these two parasites. The high antileishmanial potency and remarkable selectivity of the nitro-aromatic derivatives suggested them as promising candidates for further studies. On the other hand, the high in vitro potency of catechol-type compounds against T. brucei could not be extrapolated to an in vivo mouse model.