New CE–ESI-MS analytical method for the separation, identification and quantification of seven phenolic acids including three isomer compounds in virgin olive oil

Nevado, J. J. Berzas; Castañeda, Gregorio; Robledo, Virginia Rodríguez; Martínez, Gabriela Vargas

doi:10.1016/j.talanta.2009.05.021

Cited by 54 publications

(27 citation statements)

References 34 publications

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“…The anti-inflammatory and antioxidant effects of hydroxylphenyl acetic acid were reported [19,20]. Oxidative stress and inflammatory factors alter the redox state of cell membrane proteins and disturb melanocyte homeostasis, resulting in melanogenesis [3,6].…”

Section: Resultsmentioning

confidence: 99%

Tyrosol and Its Analogues Inhibit Alpha-Melanocyte-Stimulating Hormone Induced Melanogenesis

Wen

Chang

Chien

et al. 2013

IJMS

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Melanin is responsible for skin color and plays a major role in defending against harmful external factors such as ultraviolet (UV) irradiation. Tyrosinase is responsible for the critical steps of melanogenesis, including the rate-limiting step of tyrosine hydroxylation. The mechanisms of action of skin hypopigmenting agents are thought to be based on the ability of a given agent to inhibit the activity of tyrosinase and, hence, down regulate melanin synthesis. Tyrosol and its glycoside, salidroside, are active components of Rhodiola rosea, and in our preliminary study we found that Rhodiola rosea extract inhibited melanogenesis. In this study, we examined the effects of tyrosol and its analogues on melanin synthesis. We found that treatment of B16F0 cells to tyrosol (1), 4-hydroxyphenylacetic acid (5), 3-hydroxyphenylacetic acid (6), 2-hydroxyphenylacetic acid (7), or salidroside (11) resulted in a reduction in melanin content and inhibition of tyrosinase activity as well as its expression. Tyrosol (1), 4-hydroxyphenylacetic acid (5) and 2-hydroxyphenylacetic acid (7) suppressed MC1R expression. Tyrosol (1), 4-hydroxyphenylacetic acid (5), 3-hydroxyphenylacetic acid (6), and 2-hydroxyphenylacetic acid (7) inhibited α-MSH induced TRP-1 expression, but salidroside (11) did not. All the compounds did not affect MITF and TRP-2 expression. Furthermore, we found that the cell viability of tyrosol (1), 4-hydroxyphenylacetic acid (5), 3-hydroxyphenylacetic acid (6), and 2-hydroxyphenylacetic acid (7) at concentrations below 4 mM and salidroside (11) at concentrations below 0.5 mM were higher than 90%. The compounds exhibited metal-coordinating interactions with copper ion in molecular docking with tyrosinase. Our results suggest that tyrosol, 4-hydroxyphenylacetic acid, 3-hydroxyphenylacetic acid, 2-hydroxyphenylacetic acid, and salidroside are potential hypopigmenting agents.

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Section: Resultsmentioning

confidence: 99%

Tyrosol and Its Analogues Inhibit Alpha-Melanocyte-Stimulating Hormone Induced Melanogenesis

Wen

Chang

Chien

et al. 2013

IJMS

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“…A "new" analytical method based on capillary electrophoresis-electrospray interface-MS (CE-ESI-MS) was used to identify and determine seven selected antioxidants (cinnamic and benzoic acids) and three isomeric coumaric acids (99). The presence in substantial amounts of hydroxyphenyl acetic, p-coumaric, ferulic, and vanillic acids was confirmed in Spanish VOO and EVOO samples.…”

Section: Frankelmentioning

confidence: 99%

Chemistry of Extra Virgin Olive Oil: Adulteration, Oxidative Stability, and Antioxidants

Frankel

2010

J. Agric. Food Chem.

161

143

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Much analytical work has been published on the chemistry of extra virgin olive oil (EVOO) as a basis for the detection and quantitative analyses of the type and amount of adulteration with cheaper vegetable oils and deodorized olive oils. The analysis and authentication of EVOO represent very challenging analytical chemical problems. A significant amount of literature on EVOO adulteration has depended on sophisticated statistical approaches that require analyses of large numbers of samples. More effort is needed to exploit reliable chemical and instrumental methods that may not require so much statistical interpretation. Large assortments of methods have been used to determine lipid oxidation and oxidative stability and to evaluate the activity of the complex mixtures of phenolic antioxidants found in EVOO. More reliable chemical methods are required in this field to obviate excessive dependence on rapid antiradical methods that provide no information on the protective properties of antioxidants. The extensive literature on olive oil sensory tests, using many descriptors varying in different countries, should be supplemented by more precise gas chromatographic analyses of volatile compounds influencing the odor and flavors of EVOO.

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“…Considering the promising results obtained for this type of nanostructures, the co-encapsulation of three therapeutic hydrophobic antioxidants (with low molecular weight) that have shown excellent properties as preventive agents against cardiovascular diseases, stroke and cancer (Nevado et al, 2009) as well as neuroprotective properties (Garrido et al, 2012;Joshi et al, 2006) was proposed. The three co-encapsulated antioxidants were gentisic acid (Mw:154 Da; Log P: 1.56), p-hydroxybenzoic acid (Mw:138 Da; Log P: 1.42) and p-coumaric acid (Mw: 164 Da; Log P: 1.88).…”

Section: Encapsulation and Release Of Gentisic P-hydroxy Benzoic P-mentioning

confidence: 99%

Design of the interface of edible nanoemulsions to modulate the bioaccessibility of neuroprotective antioxidants

Plaza-Oliver

Baranda

Robledo

et al. 2015

International Journal of Pharmaceutics

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New CE–ESI-MS analytical method for the separation, identification and quantification of seven phenolic acids including three isomer compounds in virgin olive oil

Cited by 54 publications

References 34 publications

Tyrosol and Its Analogues Inhibit Alpha-Melanocyte-Stimulating Hormone Induced Melanogenesis

Tyrosol and Its Analogues Inhibit Alpha-Melanocyte-Stimulating Hormone Induced Melanogenesis

Chemistry of Extra Virgin Olive Oil: Adulteration, Oxidative Stability, and Antioxidants

Design of the interface of edible nanoemulsions to modulate the bioaccessibility of neuroprotective antioxidants

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