Synthesis of chlorogenic acid derivatives with promising antifungal activity

Ma, Cui; Kully, Maureen; Khan, Jehangir K.; Hattori, Masao; Daneshtalab, Mohsen

doi:10.1016/j.bmc.2007.07.038

Cited by 57 publications

(30 citation statements)

References 12 publications

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“…Although attempts to biochemically characterize QDH3 proved unsuccessful, its predominant expression in leaves and its induction in response to wounding and fungal infection suggest a defensive role in leaves through production of quinate and its derivatives such as chlorogenic acid (74). Chlorogenic acid has both anti-herbivore and antimicrobial activities (75)(76)(77), and quinate might also act as an astringent herbivore deterrent in the above-mentioned organs (78). The possible role of QDH3 in defense is further highlighted by its increased expression in poplar plant overexpressing WRKY23, as transcription factors involved in the regulation of plant defense against pathogens and abiotic stresses (79).…”

Section: Discussionmentioning

confidence: 99%

Molecular Characterization of Quinate and Shikimate Metabolism in Populus trichocarpa

Guo

Carrington

Alber

et al. 2014

Journal of Biological Chemistry

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Background: Shikimate is essential for protein biosynthesis. Quinate and its derivatives are protective secondary metabolites. Results: Members of the same gene family encode enzymes with either shikimate or quinate dehydrogenase activity. Conclusion:The molecular genetic basis of plant quinate metabolism has been unraveled in vitro. Significance: Identifying quinate metabolic enzymes will allow testing its ecological function and may enable biotechnological applications.

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Section: Discussionmentioning

confidence: 99%

Molecular Characterization of Quinate and Shikimate Metabolism in Populus trichocarpa

Guo

Carrington

Alber

et al. 2014

Journal of Biological Chemistry

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“…Coffee beans are one of the best dietary sources of CGA [59]. Moreover, CGAs possess a variety of biological activi-ties ranging from antifungal [63,64], antiviral [65,66] and neuroprotective [67] to antidiabetic [68,69] and cholesterol lowering [70] effects.…”

Section: Antioxidant Activity Of Hydroxycin-namic Acidsmentioning

confidence: 99%

Antioxidant Properties of Hydroxycinnamic Acids: A Review of Structure- Activity Relationships

Razzaghi‐Asl¹,

Garrido²,

Khazraei³

et al. 2013

CMC

172

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Hydroxycinnamic acids (HCAs) are important phytochemicals possessing significant biological properties. Several investigators have studied in vitro antioxidant activity of HCAs in detail. In this review, we have gathered the studies focused on the structure-activity relationships (SARs) of these compounds that have used medicinal chemistry to generate more potent antioxidant molecules. Most of the reports indicated that the presence of an unsaturated bond on the side chain of HCAs is vital to their activity. The structural features that were reported to be of importance to the antioxi-dant activity were categorized as follows: modifications of the aromatic ring, which include alterations in the number and position of hydroxy groups and insertion of electron donating or withdrawing moieties as well as modifications of the car-boxylic function that include esterification and amidation process. Furthermore, reports that have addressed the influence of physicochemical properties including redox potential, lipid solubility and dissociation constant on the antioxidant activ-ity were also summarized. Finally, the pro-oxidant effect of HCAs in some test systems was addressed. Most of the investigations concluded that the presence of ortho-dihydroxy phenyl group (catechol moiety) is of significant importance to the antioxidant activity, while, the presence of three hydroxy groups does not necessarily improve the activity. Optimiza-tion of the structure of molecular leads is an important task of modern medicinal chemistry and its accomplishment relies on the careful assessment of SARs. SAR studies on HCAs can identify the most successful antioxidants that could be use-ful for management of oxidative stress-related diseases.Keywords: Antioxidant, hydroxycinnamic acids, in vitro, ROS, structure-activity relationships. OXIDATIVE STRESS AND ANTIOXIDANTSReactive oxygen species (ROS) are oxygen derived molecules that readily react with other compounds and macromolecules and oxidize them. Some representative exam-ples of these species include superoxide (O2•-), hydroxy (HO • ) and peroxy (ROO • ) radicals, hydrogen peroxide (H2O2) and singletROS are involved in important physiological processes such as immune response, gene expression, signal transduc-tion and growth regulation [5,6]; however if they are not kept under tight control by physiological antioxidant systems they will be able to oxidize and damage various biological molecules leading to a condition called oxidative stress [1,7,8]. In this regard, oxidative stress has been reported to be in-volved in the pathogenesis of diseases such as cancer [9], neurodegenerative diseases [10], stroke [11], and others [12,13].Since an important source of ROS comes from environment [14], with the industrial development and the change in life style, oxidative stress related diseases need a special attention [15].Antioxidants operate by preventing or slowing the progression of oxidative damage reactions [16,17]. An antioxidant has been defined as "any substance that delays, p...

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“…In fact, other researchers have reported that CRA has antiinflammatory [30,31] and antifungal [10] effects. Since the antiinflammatory effect report was based on carrageenan-induced inflammation, we were curious whether CRA could be effective against inflammation caused by an infectious pathogen.…”

Section: Discussionmentioning

confidence: 99%

“…Recent reports [7,9] indicate that the compound is shown to be an antioxidant and anticarcinogenic. More recent reports show that CRA also has analgesic, antipyretic activities and of more importance, anti-inflammatory [8], and antifungal effect as well [10]. Especially, regarding this anti-inflammatory activity, the researchers [8] determined such activity in an experimental model of carrageenaninduced inflammation in rats.…”

Section: Introductionmentioning

confidence: 98%

Chlorogenic acid, a polyphenolic compound, treats mice with septic arthritis caused by Candida albicans

Lee

Park

Kim

et al. 2008

International Immunopharmacology

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Synthesis of chlorogenic acid derivatives with promising antifungal activity

Cited by 57 publications

References 12 publications

Molecular Characterization of Quinate and Shikimate Metabolism in Populus trichocarpa

Molecular Characterization of Quinate and Shikimate Metabolism in Populus trichocarpa

Antioxidant Properties of Hydroxycinnamic Acids: A Review of Structure- Activity Relationships

Chlorogenic acid, a polyphenolic compound, treats mice with septic arthritis caused by Candida albicans

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