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).
Phenyl glycosides from the leaves of Flacourtia indica (Burm. f.) Merr (Salicaceae)
Lavaud, Catherine,Massiot, Georges,Nguyen, Phuc-Dam,Sayagh, Charlotte
, (2021/08/06)
Thirteen phenolic glycosides, together with fourteen various known compounds, were isolated from the methanolic extract of leaves of Flacourtia indica. Twelve of these were composed of gentisyl or salicyl alcohols, glycosylated on the phenol and acylated on the primary alcohol with various more or less oxidized forms of pyrocatechuic acid. A number of positions on the glucose or on the acid were further acylated by benzoic or cinnamic acid. In addition to these, a glucoside of a phenyl propanoid was also isolated. The gross structures were elucidated by spectroscopic means including 1D and 2D NMR experiments and HR-ESI-MS analyses. Several of these structures, for example, xylosmin, were previously described but it proved extremely difficult to conclude on their exact identity with the absence of clear data on absolute configuration in the literature.
Selective ether bond breaking method of aryl alkyl ether
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Paragraph 0081-0091, (2020/09/16)
The invention discloses a selective aryl alkyl ether cracking method, which comprises that aryl alkyl ether, aluminum iodide and an additive are subjected to a selective ether bond cleavage reaction in an organic solvent at a temperature of -20 DEG C to a reflux temperature to generate phenol and derivatives thereof. The method is mild in condition and simple and convenient to operate, is suitablefor cracking aryl alkyl ether containing o-hydroxyl and o-carbonyl and acetal ether, and can also be used for removing tertiary carbon hydroxyl protecting groups with higher steric hindrance, such astriphenylmethyl, tertiary butyl and the like.