The synthesis of caffeic acid esters, a new group of naturally occurring contact allergens

1989 ◽  
Vol 76 (9) ◽  
pp. 426-427 ◽  
Author(s):  
H. -T. Stüwe ◽  
G. Bruhn ◽  
W. A. König ◽  
B. M. Hausen
Keyword(s):  
Caffeic Acid ◽  
Contact Allergens ◽  
Naturally Occurring ◽  
Caffeic Acid Esters ◽  
Acid Esters

scholarly journals Chemo and regioselective serendipitous electrochemically initiated spirocyclization of caffeic acid esters with barbituric acid derivatives

2015 ◽  
Vol 178 ◽  
pp. 533-540 ◽  
Author(s):  
Abdolhamid Alizadeh ◽  
Mohammad Mehdi Khodaei ◽  
Mitra Fakhari ◽  
Gisya Abdi ◽  
Sohrab Ghouzivand
Keyword(s):  
Caffeic Acid ◽  
Barbituric Acid ◽  
Caffeic Acid Esters ◽  
Barbituric Acid Derivatives ◽  
Acid Esters

Structure of Green Pigment Formed by the Reaction of Caffeic Acid Esters (or Chlorogenic acid) with a Primary Amino Compound

2001 ◽  
Vol 65 (10) ◽  
pp. 2121-2130 ◽  
Author(s):  
Goro YABUTA ◽  
Yukimichi KOIZUMI ◽  
Kazuko NAMIKI ◽  
Mitsuhiko HIDA ◽  
Mitsuo NAMIKI
Keyword(s):  
Chlorogenic Acid ◽  
Caffeic Acid ◽  
Amino Compound ◽  
Green Pigment ◽  
Primary Amino ◽  
Caffeic Acid Esters ◽  
Acid Esters

scholarly journals Caffeic Acid Esters Are Effective Bactericidal Compounds Against Paenibacillus larvae by Altering Intracellular Oxidant and Antioxidant Levels

Biomolecules ◽  
2019 ◽  
Vol 9 (8) ◽  
pp. 312 ◽  
Author(s):  
William Collins ◽  
Noah Lowen ◽  
David J. Blake
Keyword(s):  
Caffeic Acid ◽  
Bacterial Growth ◽  
Bactericidal Effect ◽  
Caffeic Acid Phenethyl Ester ◽  
Benzyl Ester ◽  
Paenibacillus Larvae ◽  
Bacterial Disease ◽  
Bee Foraging ◽  
Caffeic Acid Esters ◽  
Acid Esters

American Foulbrood (AFB) is a deadly bacterial disease affecting pupal and larval honey bees. AFB is caused by the endospore-forming bacterium Paenibacillus larvae (PL). Propolis, which contains a variety of organic compounds, is a product of bee foraging and is a resinous substance derived from botanical substances found primarily in trees. Several compounds from the class of caffeic acid esters, which are commonly found in propolis, have been shown to have antibacterial activity against PL. In this study, six different caffeic acid esters were synthesized, purified, spectroscopically analyzed, and tested for their activity against PL to determine the minimum inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs). Caffeic acid isopropenyl ester (CAIE), caffeic acid benzyl ester (CABE), and caffeic acid phenethyl ester (CAPE) were the most effective in inhibiting PL growth and killing PL cell with MICs and MBCs of 125 µg/mL when used individually, and a MIC and MBC of 31.25 µg/mL for each compound alone when CAIE, CABE, and CAPE are used in combination against PL. These compounds inhibited bacterial growth through a bactericidal effect, which revealed cell killing but no lysis of PL cells after 18 h. Incubation with CAIE, CABE, and CAPE at their MICs significantly increased reactive oxygen species levels and significantly changed glutathione levels within PL cells. Caffeic acid esters are potent bactericidal compounds against PL and eliminate bacterial growth through an oxidative stress mechanism.

scholarly journals Feature-Based Molecular Networking to Target the Isolation of New Caffeic Acid Esters from Yacon (Smallanthus sonchifolius, Asteraceae)

Metabolites ◽  
2020 ◽  
Vol 10 (10) ◽  
pp. 407
Author(s):  
Guillermo F. Padilla-González ◽  
Nicholas J. Sadgrove ◽  
Gari V. Ccana-Ccapatinta ◽  
Olga Leuner ◽  
Eloy Fernandez-Cusimamani
Keyword(s):  
Mass Spectrometry ◽  
Caffeic Acid ◽  
High Resolution Mass Spectrometry ◽  
Chemical Diversity ◽  
Bioactive Metabolites ◽  
Molecular Networking ◽  
Smallanthus Sonchifolius ◽  
Feature Based ◽  
Caffeic Acid Esters ◽  
Acid Esters

Smallanthus sonchifolius (yacon) is an edible tuberous Andean shrub that has been included in the diet of indigenous people since before recorded history. The nutraceutical and medicinal properties of yacon are widely recognized, especially for the improvement of hyperglycemic disorders. However, the chemical diversity of the main bioactive series of caffeic acid esters has not been explored in detail. In this metabolomics study, we applied the latest tools to facilitate the targeted isolation of new caffeic acid esters. Using liquid chromatography coupled to tandem mass spectrometry (LC-MS/MS), we analyzed extracts from different organs (roots, vascular tissues of the stems, stem epidermis, leaves, bracts, and ray flowers) and followed a feature-based molecular networking approach to characterize the structural diversity of caffeic acid esters and recognize new compounds. The analysis identified three potentially new metabolites, one of them confirmed by isolation and full spectroscopic/spectrometric assignment using nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HRMS), and MS/MS. This metabolite (5-O-caffeoyl-2,7-anhydro-d-glycero-β-d-galacto-oct-2-ulopyranosonic acid), along with eight known caffeic acid esters, was isolated from the roots and stems. Furthermore, based on detailed tandem MS analyses, we suggest that the two isomeric monocaffeoyl-2,7-anhydro-2-octulopyranosonic acids found in yacon can be reliably distinguished based on their characteristic MS2 and MS3 spectra. The outcome of the current study confirms the utility of feature-based molecular networking as a tool for targeted isolation of previously undescribed metabolites and reveals the full diversity of potentially bioactive metabolites from S. sonchifolius.

scholarly journals Plant-derived phenolic compounds prevent the DNA single-strand breakage and cytotoxicity induced by tert-butylhydroperoxide via an iron-chelating mechanism

2002 ◽  
Vol 364 (1) ◽  
pp. 121-128 ◽  
Author(s):  
Piero SESTILI ◽  
Giuseppe DIAMANTINI ◽  
Annalida BEDINI ◽  
Liana CERIONI ◽  
Ilaria TOMMASINI ◽  
...  
Keyword(s):  
Caffeic Acid ◽  
Polyphenolic Compounds ◽  
Iron Chelators ◽  
Protective Effects ◽  
Experimental Conditions ◽  
Direct Function ◽  
Tert Butylhydroperoxide ◽  
Caffeic Acid Esters ◽  
Acid Esters

The protective effects of selected members from a series of caffeic acid esters and flavonoids were tested in various toxicity paradigms using U937 cells, previously shown to be sensitive to either iron chelators or bona fide radical scavengers or to both classes of compounds. It was found that all the protective polyphenols were active at very low concentrations and that their effects were observed only under those conditions in which iron chelators also afforded protection. Consistently, active polyphenolic compounds, unlike the inactive ones, effectively chelated iron in an in vitro system. It follows that, at least under the experimental conditions utilized in the present study, the most prominent activity of these polyphenolic compounds resides in their ability to chelate iron. Further studies revealed that the protective effects afforded by the caffeic acid esters and flavonoids were largely mediated by the catechol moiety and that the relative biological potency of these compounds was a direct function of their lipophilicity.

One-pot preparation of caffeic acid esters from 3, 4-dihydroxybenzaldehyde

2006 ◽  
Vol 2006 (9) ◽  
pp. 586-588 ◽  
Author(s):  
Wei-Xiao Hu ◽  
Chun-Nian Xia ◽  
Guo-Hong Wang ◽  
Wei Zhou
Keyword(s):  
Caffeic Acid ◽  
One Pot ◽  
Caffeic Acid Esters ◽  
Acid Esters
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