202650-88-2Relevant academic research and scientific papers
Cloning and functional characterization of a p-coumaroyl quinate/shikimate 3′-hydroxylase from potato (Solanum tuberosum)
Knollenberg, Benjamin J.,Liu, Jingjing,Yu, Shu,Lin, Hong,Tian, Li
, p. 462 - 467 (2018)
Chlorogenic acid (CGA) plays an important role in protecting plants against pathogens and promoting human health. Although CGA accumulates to high levels in potato tubers, the key enzyme p-coumaroyl quinate/shikimate 3′-hydroxylase (C3′H) for CGA biosynthesis has not been isolated and functionally characterized in potato. In this work, we cloned StC3′H from potato and showed that it catalyzed the formation of caffeoylshikimate and CGA (caffeoylquinate) from p-coumaroyl shikimate and p-coumaroyl quinate, respectively, but was inactive towards p-coumaric acid in in vitro enzyme assays. When the expression of StC3′H proteins was blocked through antisense (AS) inhibition under the control of a tuber-specific patatin promoter, moderate changes in tuber yield as well as phenolic metabolites in the core tuber tissue were observed for several AS lines. On the other hand, the AS and control potato lines exhibited similar responses to a bacterial pathogen Pectobacterium carotovorum. These results suggest that StC3′H is implicated in phenolic metabolism in potato. They also suggest that CGA accumulation in the core tissue of potato tubers is an intricately controlled process and that additional C3′H activity may also be involved in CGA biosynthesis in potato.
Thermal stability of 5-o-caffeoylquinic acid in aqueous solutions at different heating conditions
Dawidowicz, Andrzej L.,Typek, Rafal
experimental part, p. 12578 - 12584 (2011/10/30)
Chlorogenic acid is a naturally occurring phenolic compound found in all higher plants. This component, being the ester of caffeic acid with quinic acid, is an important biosynthetic intermediate and plays an important role in the plant's response to stress. Potential uses of chlorogenic acid are suggested in pharmaceuticals, foodstuffs, feed additives, and cosmetics due to its recently discovered biomedical activity. This finding caused new interest in chlorogenic acid properties, its isomers, and its natural occurrence. It has been found that as many as nine compounds (chlorogenic acid derivatives and its reaction product with water) can be formed from 5-o-caffeoylquinic acid during the heating of its water solution. Three of them, two hydroxylated 5-o-caffeoylquinic acid derivatives and 4,5-dicaffeoylquinic acid, have been not reported, yet. The amount of each formed component depends on the heating time and temperature. The presented results are important for researchers investigating plant metabolism and looking for new plant components. The transformation product can be mistakenly treated as a new component, not found before in the examined plant, or can be a cause of erroneous quantitative estimations of plant composition.
First efficient synthesis of chlorogenic acid
Sefkow, Michael
, p. 1137 - 1141 (2007/10/03)
The first efficient synthesis of chlorogenic acid (1) was achieved in four steps (three purifications) from quinic acid (2). The overall yield was 65%, The key intermediate was quinic acid bisacetonide (6), selectively prepared by a modified kinetic aceta
