Structure and antibacterial activity of plantamajoside, a caffeic acid sugar ester from Plantago major subs major

1988 ◽  
Vol 27 (11) ◽  
pp. 3433-3437 ◽  
Author(s):  
Helle Ravn ◽  
Leon Brimer
Holzforschung ◽  
2006 ◽  
Vol 60 (5) ◽  
pp. 492-497 ◽  
Author(s):  
Toshinari Kawada ◽  
Yuko Yoneda ◽  
Ryuji Asano ◽  
Ippei Kan-no ◽  
Walther Schmid

Abstract The first total synthesis of plantamajoside (1), 2-(3′,4′-dihydroxylphenyl)ethyl-4-O-caffeoyl-3-O-(β-D-glucopyranosyl)-β-D-glucopyranoside, which is one of the dihydroxyphenylethyl glycosides (caffeic acid sugar esters), is described. Key intermediate 2, 2-[3′,4′-bis(O-benzyl)phenyl]ethyl 2,6-di-O-acetyl-4-O-[3′,4′-bis(O-benzyl)caffeoyl]-β-D-glucopyranoside was glycosylated with trichloroacetoimidoyl 2,3,4,6-tetra-O-acetyl-α-D-glycopyranoside (3) to afford plantamajoside derivative 4a, 2-[3′,4′-bis(O-benzyl)phenyl]ethyl 2,6-di-O-acetyl-4-O-[3′,4′-bis(O-benzyl)caffeoyl]-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside, in 39% yield. Plantamajoside derivative 4a was successfully converted into the target compound, plantamajoside (1), through a series of de-protective procedures. 1H- and 13C nuclear magnetic resonance (NMR) spectral data of the synthesized plantamajoside (1) were identical to those of the natural compound.


2015 ◽  
Vol 32 (8) ◽  
pp. 804-810 ◽  
Author(s):  
Eva Pinho ◽  
Graça Soares ◽  
Mariana Henriques

Author(s):  
Min-Young Park ◽  
Dong-Hyun Kang

The aim of this study was to evaluate the antibacterial activity of caffeic acid (CA) which is a natural polyphenol, combined with Ultraviolet-A (UV-A) light against the representative foodborne bacteria, Escherichia coli O157:H7, Salmonella Typhimurium and Listeria monocytogenes. The inactivation results were obtained depending on the CA concentration, light wavelength and light dose.E. coli O157:H7 and S. Typhimurium were reduced to the detection limit when treated with 3 mM CA and UV-A for 3 J/cm2 and 4 J/cm2 respectively, and 5 J/cm2 treatment induced 3.10 log reduction in L. monocytogenes. To investigate the inactivation mechanism, measurement of polyphenol uptake, membrane damage assessment, enzymatic activity assay, and transmission electron microscopy (TEM) were conducted against S. Typhimurium and L. monocytogenes. It was revealed that CA was significantly (P < 0.05) absorbed by bacterial cells, and UV-A light allowed a higher uptake of CA for both pathogens. Additionally, CA + UV-A treatment induced significant (P < 0.05) cell membrane damage. In the enzymatic activity assay, both pathogens showed a reduction in their activity by CA and a higher reduction occurred by CA + UV-A. Moreover, TEM images indicated that CA + UV-A treatment notably destroyed the intercellular structure. In addition, antibacterial activity was also observed in commercial apple juice, which showed similar results to those obtained from PBS, resulting in a significant (P < 0.05) reduction for all three pathogens without any changes in color parameters (L*, a*, and b*), total phenolic compounds and DPPH (2,2-diphenyl-1-picrylhydrazyl) free radical scavenging activity. IMPORTANCE Photodynamic inactivation (PDI), which involves photoactivation of a photosensitizer (PS), is an emerging field of study as it effectively reduces various kinds of microorganisms. Although there are several PSs that have been used for PDI, there is a need to find naturally occurring PSs for safer application in food industry. Caffeic acid, a natural polyphenol found in most of fruits and vegetables, has recently been studied for its potential to act as a novel photosensitizer. However, no studies have been conducted regarding its antibacterial activity depending on treatment conditions and its antibacterial mechanism. In this study we closely examined the effectiveness of caffeic acid in combination with UV-A light for inactivating representative foodborne bacteria in liquid medium. Therefore, the results of this research are expected to be utilized as basic data for future application of caffeic acid in PDI, especially when controlling pathogens in liquid food processing.


Author(s):  
Ji-Hoon Kim ◽  
Daeung Yu ◽  
Sung-Hwan Eom ◽  
Song-Hee Kim ◽  
Junghwan Oh ◽  
...  

The object of this study was to discover an alternative therapeutic agent with fewer side effects against acne vulgaris, which is one of the most common skin diseases. Acne vulgaris often associates with acne-related bacteria such as &lt;i&gt;Propionibacterium acnes&lt;/i&gt;, &lt;i&gt;Staphylococcus epidermidis&lt;/i&gt;, &lt;i&gt;Staphylococcus aureus&lt;/i&gt; and &lt;i&gt;Pseudomonas aeruginosa&lt;/i&gt;, some of which exhibit a resistant against commercial antibiotics used in the treatment of acne vulgaris (tetracycline, erythromycin, and lincomycin). In the current study, we evaluated &lt;i&gt;in vitro&lt;/i&gt; antibacterial activity of chitosan-phytochemical conjugates against acne-related bacteria. Three of chitosan-phytochemical conjugates used in this study showed stronger antibacterial activity than that of chitosan (unmodified control). Chitosan-caffeic acid conjugate (CCA) exhibited the highest antibacterial activity against acne-related bacteria with minimum inhibitory concentration values of 8 &mu;g/mL to 256 &mu;g/mL. In addition, the MICs of antibiotics against antibiotic resistant &lt;i&gt;P. acnes&lt;/i&gt; and &lt;i&gt;P. aeruginosa&lt;/i&gt; strains were dramatically reduced in the combination with CCA, suggesting that CCA would restore the antibacterial activity of the antibiotics. The analysis of fractional inhibitory concentration indices clearly revealed a synergistic antibacterial effect between CCA and the antibiotics. Thus, the median &sum;FIC values against the antibiotic resistant bacterial strains were ranged from 0.375 to 0.533 in the combination mode of CCA and antibiotics.


Author(s):  
Vimalasruthi Narayanan ◽  
Manawwer Alam ◽  
Naushad Ahmad ◽  
Suganya Bharathi Balakrishnan ◽  
Vigneshkumar Ganesan ◽  
...  

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