Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity

Fujisawa, Seiichiro; Atsumi, Toshiko; Kadoma, Yoshinori; Sakagami, Hiroshi

doi:10.1016/s0300-483x(02)00194-4

Cited by 238 publications

(141 citation statements)

References 46 publications

Supporting

Mentioning

127

Contrasting

Unclassified

Order By: Relevance

“…Various techniques were used: 2,2-diphenyl-1-picryl hydrazyl (DPPH) radical scavenging assay [63,69,70,71,72], β-carotene bleaching test [68,70,72], thiobarbituric acid reactive species (TBARS) assay [67,69,73], ferric ion reducing antioxidant power (FRAP) assay [72], oxygen radical absorbance capacity assay [74] and method measuring the formation of hydroperoxydienes from linoleic acid [67]. With help of electron spin resonance (ESR) spectroscopy Fujisawa et al [75] found that eugenol and eugenol-related synthetic compounds possessed radical scavenging activity comparable with the activity of conventional antioxidants. Jirovetz et al [76] proved the scavenging activity of a commercial rectified clove leaf (Eugenia caryophyllus) EO and its main constituent eugenol against the DPPH radical.…”

Section: Mutagenicity Anti-mutagenicity and Dna-protective Effectsmentioning

confidence: 99%

Cytotoxic, anti-carcinogenic and antioxidant properties of the most frequent plant volatiles

Slameñová¹,

Horváthová²

2013

neo

View full text Add to dashboard Cite

Flowers, berries, leaves, barks and roots of different plants have been used through the ages as a source of flavor in food and perfume preparations. The volatiles responsible for the flavor of botanicals can be extracted from the plant material as "essential oils" (EOs), called also volatile oils or ethereal oils. The term essential is intended to indicate that the oil is the fragrant essence of the plant from which it is extracted. EOs are constituted by hydrocarbons (monoterpenes and sesquiterpenes) and oxygenated compounds (alcohols, esters, ethers, aldehydes, ketones, lactones, phenols and phenol ethers). Of the numerous groups of naturally occurring compounds examined so far terpenes are known as fragrances and flavoring agents. The data reported in this review including the data obtained in our laboratory show that many of EOs exhibit a range of biological activities inclusive of antioxidative, anti-mutagenic and anti-carcinogenic activities. Most of them belong to phytochemicals with chemopreventive potential. On the other hand some herbal products can cause serious adverse effects. A complex research of toxic, genotoxic, anti-mutagenic and anti-carcinogenic effects of EOs is therefore very important.

show abstract

Section: Mutagenicity Anti-mutagenicity and Dna-protective Effectsmentioning

confidence: 99%

Cytotoxic, anti-carcinogenic and antioxidant properties of the most frequent plant volatiles

Slameñová¹,

Horváthová²

2013

neo

View full text Add to dashboard Cite

show abstract

“…31 It is relatively stable at room temperature (RT) and at neutral pH conditions; however, it has a stability issue under UV and high pH conditions. 32 In particular, it exhibited cytotoxicity and prooxidant rather than antioxidant effects when exposed to photooxidation states. 33 In the present study, various properties of ND were evaluated with a view to be exploited for topical drug delivery systems and to propose the capability of ND as a practical drug delivery vehicle.…”

Section: Introductionmentioning

confidence: 99%

Comprehensive evaluation of carboxylated nanodiamond as a topical drug delivery system

Lim¹,

Kim²,

Kang³

et al. 2016

IJN

View full text Add to dashboard Cite

The best strategy in the development of topical drug delivery systems may be to facilitate the permeation of drugs without any harmful effects, while staying on the skin surface and maintaining stability of the system. Nanodiamonds (NDs) play a key role with their excellent physicochemical properties, including high biocompatibility, physical adsorption, reactive oxygen species (ROS) scavenging capability, and photostabilizing activity. Z -average sizes of carboxylated ND (ND–COOH) agglutinate decreased significantly as the pH increased. Fluorescein-conjugated ND was observed only on the stratum corneum, and no sample diffused into the dermal layer even after 48 hours. Moreover, ND–COOH and ND–COOH/eugenol complex did not show significant toxic effects on murine macrophage cells. ND improved in vitro skin permeation >50% acting as a “drug reservoir” to maintain a high drug concentration in the donor chamber, which was supported by quartz crystal microbalance results. Moreover, ND–COOH could adsorb a drug amount equivalent to 80% of its own weight. A photostability study showed that ND–COOH increased the photostability ~47% with regard to rate constant of the eugenol itself. A significant decrease in ROS was observed in the ND–COOH and ND–COOH/eugenol complex compared with the negative control during intracellular ROS assay. Moreover, ROS and cupric reducing antioxidant capacity evaluation showed that ND–COOH had synergistic effects of antioxidation with eugenol. Therefore, ND–COOH could be used as an excellent topical drug delivery system with improved permeability, higher stability, and minimized safety issue.

show abstract

“…Many phenol substances of plant origin or synthetic products and some salicylic acid derivatives as aspirin exhibit certain antioxidant and antiproliferative activities. [3][4][5][6][7][8][9][10][11][12][13][14] Bearing the above in mind, one part of the present research was directed to the microwaveinduced synthesis of some new derivatives of salicylic acid, starting from different amino alcohols, diamines and diols, as well as to the determination of their antioxidant and antiproliferative activities. Microvawe irradiation is an alternative to conventional heating for introducing energy into reactions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of some new 2-oxazoline and salicylic acid derivatives

Djurendić¹,

Vujašković²,

Sakač³

et al. 2010

Arkivoc

View full text Add to dashboard Cite

Starting from methyl salicylate and 2-amino-2-(hydroxymethyl)propane-1,3-diol 1a, or 2-amino-2-methylpropane-1-ol 1b, the 2-oxazoline derivatives 2a, 2b or 3, as well as mono-4a and 4b and bis-5a and 5b derivatives of salicylic acid were synthesized. Reactions were performed by microwave irradiation in the presence of tetrabutylammonium bromide or metallic sodium as catalyst, as well as by conventional heating. Microwave-induced reaction of some diols, diamines and amino alcohols with methyl salicylate gave mono-and/or bis-derivatives of salicylic acid 4c, 5c, 5d, 6c, 8c, 7a, 7b, 8a and 8b. The mono-and bis-salicyloyl derivatives 4c, 5c and 5d were transformed to the corresponding phenyl-azo derivatives 9, 10c and 10d. The structure of compound 3 was proved by the X-ray analysis and the R-configuration on its stereocenter was confirmed. The antioxidant and cytotoxic activities of the synthesized derivatives were evaluated in a series of in vitro tests. Compounds 5d, 8b and 8c exhibited very strong activity against hydroxyl radical. Six 4c, 5d, 8a-c, 10c of 16 tested compounds inhibited growth of MDA-MB-231 cells at a nanomolar concentration. Compounds 8c and 10c showed high cytotoxicity against MCF7 cells, whereas compounds 4c, 5d, 8a-c and 10d showed high activity against K562 cells.

show abstract

Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity

Cited by 238 publications

References 46 publications

Cytotoxic, anti-carcinogenic and antioxidant properties of the most frequent plant volatiles

Cytotoxic, anti-carcinogenic and antioxidant properties of the most frequent plant volatiles

Comprehensive evaluation of carboxylated nanodiamond as a topical drug delivery system

Synthesis and biological evaluation of some new 2-oxazoline and salicylic acid derivatives

Contact Info

Product

Resources

About