Antioxidant and Antimicrobial Activity Evaluation of Polyhydroxycinnamic Acid Ester Derivatives.

Venkateswarlu, S.; Ramachandra, Marellapudi S.; Krishnaraju, Alluri V.; Golakoti, Trimurtulu; Subbaraju, Gottumukkala V.

doi:10.1002/chin.200618070

Cited by 16 publications

(27 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…This type of study was only conducted for identification purposes of the corresponding natural cinnamyl esters. However the synthetic procedures reported so far involve protection and deprotection steps, operations that conduct in general to low to moderate yields [8,9]. So, herein a novel synthetic strategy is presented in which the synthesis of long chain alkyl cinnamates 8e21 was performed by using monomalonates 5e7 and substituted benzaldehyde derivatives as starting material and applying the Verley-Doebner modification of Knoevenagel condensation reaction [11,12] (Scheme 1).…”

Section: Chemistrymentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and antioxidant activity of long chain alkyl hydroxycinnamates

Menezes

Kamat

Cavaleiro

et al. 2011

European Journal of Medicinal Chemistry

102

View full text Add to dashboard Cite

Long chain alkyl hydroxycinnamates (8-21) were synthesized from the corresponding half esters of malonic acid (5-7) and benzaldehyde derivatives by Knoevenagel condensation. The total antioxidant capacity of these hydroxycinnamyl esters was evaluated using DPPH and ABTS assays. The observed antioxidant activity was highest for esters of caffeic acid followed by sinapic esters and ferulic esters. The parameters for drug-likeness of these hydroxycinnamyl esters were also evaluated according to the Lipinski's 'rule-of-five'. All the ester derivatives were found to violate one of the Lipinski's parameters (cLogP>5), even though they have been found to be soluble in protic solvents. The predictive topological polar surface area (TPSA) data allow concluding that they could have a good capacity for penetrating cell membranes. Therefore, one can propose these novel lipophilic compounds as potential antioxidants for tackling oxidative processes.

show abstract

Section: Chemistrymentioning

confidence: 99%

“…Long chain alkyl cinnamates have been previously prepared by using the appropriate cinnamic acid [8,9] or acid chloride [10] and the suitable long chain alkanol. This type of study was only conducted for identification purposes of the corresponding natural cinnamyl esters.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and antioxidant activity of long chain alkyl hydroxycinnamates

Menezes

Kamat

Cavaleiro

et al. 2011

European Journal of Medicinal Chemistry

102

View full text Add to dashboard Cite

show abstract

“…HCAs and their derivatives have a broad spectrum of biological activities including antitumoral [42][43][44][45], antimicrobial [46], antioxidant [47][48][49][50][51][52] and neuroprotective effects [53][54][55].…”

Section: Coo Hmentioning

confidence: 99%

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

Razzaghi‐Asl¹,

Garrido²,

Khazraei³

et al. 2013

CMC

172

View full text Add to dashboard Cite

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...

show abstract

“…4-hydroxy-transcinnamate ester 8,13 , β-sitosterol 4,14 , quercetin and quercitrin 11,15 ). Preliminary phytochemical analysis of C. dichotoma bark indicated the presence of allantoin, β-sitosterol and 3', 5-dihydroxy-4'-methoxy flavanone-7-O-alpha-L-rhamnopyranoside 4,16 .…”

Section: Botanical Descriptionmentioning

confidence: 99%

Exploring Phytochemicals and Pharmacological Uses of Cordia Dichotoma (Indian Cherry): A Review

Prajapati

Kar

Maurya

et al. 2017

J. Drug Delivery Ther.

View full text Add to dashboard Cite

The use of phytoconstituents single or combined with standard medicines has been utilized in cure of different diseases. Many plants of genus Cordia comprise of trees and shrubs are widely distributed in warmer regions and have been utilized in management of various diseases. Various phytoconstituents like flavonoids, alkaloids, terpenes, tannins, and glyceridess having different activities were screened and isolated from different parts of C. dichotoma. Various important Pharmacological properties including Antiulcer, Contraceptives, anti-inflammatory, anthelmintic, analgesic, anticancer, Antioxidant, antimicrobial, hepatoprotective, antidiabetic and others have been well documented for this plant. Therefore, we have briefly reviewed the various bioactivities of C. dichotoma to improve our knowledge on plant phytochemicals as therapeutic entities. The present review describes the various phytoconstituents and therapeutic potential of C. dichotoma that can be followed for future research on this plant for human health benefits.

show abstract

Antioxidant and Antimicrobial Activity Evaluation of Polyhydroxycinnamic Acid Ester Derivatives.

Cited by 16 publications

References 0 publications

Synthesis and antioxidant activity of long chain alkyl hydroxycinnamates

Synthesis and antioxidant activity of long chain alkyl hydroxycinnamates

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

Exploring Phytochemicals and Pharmacological Uses of Cordia Dichotoma (Indian Cherry): A Review

Contact Info

Product

Resources

About