ArticlePDF Available

Abstract and Figures

Besides powerful antioxidant activity, increasing collagen production and prevention of premature aging, caffeic acid has demonstrated antimicrobial activity and may be promising in the treatment of dermal diseases. The relevance of this study is based on the use of caffeic acid that has become increasingly common in humans. Thus, studies that demonstrate and clarify the functions of this substance are very important.
Content may be subject to copyright.
Caeic acid: a review of its potential use in
medications and cosmetics
C. Magnani,*V. L. B. Isaac, M. A. Correa and H. R. N. Salgado*
Besides powerful antioxidant activity, increasing collagen production and prevention of premature aging,
caeic acid has demonstrated antimicrobial activity and may be promising in the treatment of dermal
diseases. The relevance of this study is based on the use of caeic acid that has become increasingly
common in humans. Thus, studies that demonstrate and clarify the functions of this substance are very
Characteristics of caeic acid
Phenolic compounds occur universally in the plant kingdom
and are part of a large and complex group of organic
substances. Higher plants synthesize and accumulate a wide
variety of phenolic compounds, which confer protection against
the attacks of free radicals, which are by-products from the
process of photosynthesis, and against tissue injuries.
The phenolic compounds can be classied into two groups: the
group of simple phenolic compounds and the group of poly-
phenolic compounds which can be observed through the frame
shown in Fig. 1.
Cinnamic acid derivatives, also called phenylpropanoids, are
nine carbon structures (Fig. 2). Caeic acid (3,4-dihydroxycin-
namic) is representative of this group.
Modern consumers increasingly demand products and foods
with high quality. Cosmetics may not have as many health
implications as pharmaceutical products or food, but they are
chemical products that people use daily and apply on skin, hair,
nails and even teeth or mouth.
Allied to this, legislation is
increasingly strict about quality and safety, which has chal-
lenged the industries.
For this reason, natural antimicrobial
compounds, such as polyphenols,
are being widely used.
Caeic acid (3,4-dihydroxycinnamic) is one of the hydroxy-
cinnamate and phenylpropanoid metabolites more widely
distributed in plant tissues. This polyphenol is present in many
food sources, including coee drinks, blueberries, apples and
Besides food, caeic acid is present in several medica-
tions of popular use, mainly based on propolis.
Besides acting
as a carcinogenic inhibitor,
it is also known to possess anti-
oxidant and antibacterial activity in vitro, and can contribute to
the prevention of atherosclerosis and other cardiovascular
Antioxidant activity
Antioxidants are compounds that inhibit or reduce the eects
triggered by free radicals and oxidizing compounds.
Phenolic antioxidants act as free radical scavengers and
sometimes as metal chelators. They act both in the initiation
step and in the propagation of the oxidative process. The
products are relatively stable due to the resonance of the
aromatic ring shown by these substances. The phenolic acids
Fig. 1 Chemical classication of phenolic compounds.
Fig. 2 Chemical structure of the main cinnamic acids. Cinnamic acid
R1 ¼R2 ¼R3 ¼R4 ¼H, o-coumaric acid: R2 ¼OH, p-coumaric acid:
R3 ¼OH; caeic acid: R2 ¼R3 ¼OH; ferulic acid: R2 ¼OCH
R3 ¼OH.
UNESP Universidade Estadual Paulista, Faculdade de Ciˆ
encias Farmacˆ
Departamento de F´
armacos e Medicamentos, Araraquara, SP, Brazil. E-mail: carol.;
Cite this: Anal. Methods,2014,6,3203
Received 15th October 2013
Accepted 22nd February 2014
DOI: 10.1039/c3ay41807c
This journal is © The Royal Society of Chemistry 2014 Anal. Methods,2014,6, 32033210 | 3203
Published on 25 February 2014. Downloaded by UNESP-ARAIQ on 28/04/2014 12:08:04.
View Article Online
View Journal
| View Issue
are characterized by the presence of a benzene ring, a carboxylic
acid group and one or more hydroxyl or methoxy groups, which
confers antioxidant properties.
The phenylpropanoids act as antioxidants by eliminating
oxygen free radicals
and chelating pro-oxidant metal ions,
especially iron.
The hydroxyl groups of these molecules
confer antioxidant activity, but they are not the only factors in
determining the potency of their activities. There is a single
hydroxyl group para-substituted in an aromatic ring that is
linked to a side chain conjugate in the case of ferulic acid. This
substitution allows the phenoxy radical free electrons to
become delocalized over the entire molecule, and therefore
The ortho substitution to the methoxy group, an elec-
tron donor, is also a contributing factor to the stability of the
phenoxy radical and thus increases the antioxidant e-
The presence of a second hydroxyl group in the ortho
position, besides the para position, is known to increase the
antioxidant activity due to an additional resonance stabilization
and formation of o-quinone (Fig. 3).
This characteristic
can be used to explain the fact that the eciency of antioxidants
such as caeic acid is greater than that of ferulic acid.
Caeic acid has been shown to have protective eects on a-
tocopherol in low-density lipoprotein (LDL).
Furthermore, its
combination with other products, such as chlorogenic and
caaric acids, showed more potent antioxidant activity in a
variety of dierent systems.
Natural phenolic antioxidants including caeic and ferulic
acids gained remarkable attention as promising photo-
protective agents
which have also been used in skin care
products due to their antioxidant activity. However the litera-
ture shows little evidence about the usefulness of hydroxycin-
namic acids in protecting the skin from photo-oxidative
The normal cellular metabolism produces free radicals,
including reactive species of oxygen and nitrogen, which are
derived from both normal metabolic processes and essential
metabolic processes in the body (endogenous), and they can be
derived from exposure to environmental factors (exogenous)
such as pollution, radiation, pesticides, and tobacco, among
others. Free radicals can cause benecial or deleterious eects
to health.
The importance of reactive oxygen species (ROS) and free
radicals has attracted increasing attention over the last decade.
ROS include free radicals such as superoxide anion radicals
), hydroxyl radicals (OHc) and reactive oxygen species such
as H
and singlet oxygen (1O
). These molecules exacerbate
factors of cell damage and aging.
ROS are continuously produced during normal physiological
events and they can easily initiate the peroxidation of
membrane lipids, leading to the accumulation of lipid perox-
However antioxidant cells have developed mechanisms
to protect themselves from free radical toxicity. The agents
considered to be antioxidants include catalytic enzymes that
remove radicals such as superoxide dismutase (SOD); proteins
which minimize the availability of pro-oxidants, such as iron
ions and copper ions, for example, transferrins, ferritins, met-
allothionein and haptoglobines; and low molecular weight
molecules that have the ability to capture reactive oxygen
species through autoxidation such as, for example, those with
glutathione and thiol groups (SH) or vitamins such as a-
tocopherol, ascorbic acid and b-carotene.
When there is an imbalance between pro and antioxidant
systems, with a predominance of oxidants, the oxidative stress
This stress can be associated with damage to lipids,
proteins and genes and is implicated in a great variety of human
diseases as well as aging.
The free radicals also aect the skin tissue, which originate
mainly from exogenous actions, such as ultraviolet radiation.
Depending on the dose, exposure time, wavelength and area
exposed, the ultraviolet radiation can cause skin burns,
premature skin aging and even skin cell DNA damage and skin
Thus, the natural aging of the skin associated with the action
of free radicals causes a reduction in skin hydration, pigmen-
tation, ne wrinkles, signals from sagging and increased
possibility of the occurrence of neoplasm diseases. Another
change is the reduction of dermal collagen that makes the skin
thinner. These changes are even more evident aer menopause,
where there is a rapid decrease in the levels of collagen in skin
and bone, suggesting that estrogen inuences the collagen
synthesis in the skin as much as bone mass.
In order to maintain the skin healthier and younger-looking,
thereby mitigating the eects of aging, more strategies have
been suggested.
The use of natural or synthetic antioxidants in
foods, cosmetics, beverages and also medicine is one of the
defence mechanisms against free radicals.
Photoaging of the skin is one of the most common derma-
tological concerns and can become a major health concern
because it is correlated with an increased risk of skin cancer.
UVA radiation can cause clinical, biochemical and histological
changes in the skin through changes in cells and in extracel-
lular matrix proteins, including collagen, responsible for the
structural integrity of the skin.
UVA radiation (315400 nm) has been shown to elevate
matrix metalloproteinase-1 extracellular (collagenase MMP-1)
and most proteolytic enzymes produced by the skin cells,
including keratinocytes and broblasts.
This activation is
related to oxidative stress, which occurs when there is excessive
production of reactive oxygen species and/or depletion of anti-
oxidant defence in cells.
Natural and synthetic antioxidants act as scavengers of free
radicals and have been shown to promote skin photo protection
Fig. 3 Chemical structure of caeic acid and formation of ortho-
3204 |Anal. Methods,2014,6, 32033210 This journal is © The Royal Society of Chemistry 2014
Analytical Methods Minireview
Published on 25 February 2014. Downloaded by UNESP-ARAIQ on 28/04/2014 12:08:04.
View Article Online
by inhibiting the induction of MMP-1 activity mediated by
UVA radiation and expression of keratinocytes and skin
Ultraviolet A (UVA) plays a fundamental role in the patho-
genesis of premature skin aging through cytotoxicity to kera-
tinocytes and degradation of collagen, a major component of
the extracellular matrix that provides structural support.
Protection against UVA damage mediated through the anti-
oxidant defence systems has been proposed as a possible
mechanism by which plant compounds decrease the process
of premature aging.
Furthermore, under stimulation by UVA and UVB sunlight,
keratinocytes from human skin can secrete nitric oxide (a
radical involved in oxidation reactions). Nitric oxide (NO)
appears to have great interest in the formation of erythema and
skin inammation.
Both caeic and ferulic acids act as
sequestering agents for radical NO.
In light of these observa-
tions, the topical administration of antioxidants found
considerable interest, since it represents an eective strategy to
protect the skin against oxidative damage mediated by UV.
The extension of erythema caused by UVB radiation may be
monitored through reectance spectrophotometry, which is
considered one of the most suitable models for the in vivo study
of skin damage aer acute exposure to UV.
Caeic and
ferulic acids, dissolved in saturated aqueous solutions at pH
7.2, proved to provide signicant photo-protection to the skin
against UV-induced erythema.
Anti-aging products are being increasingly used in recent
years and those with active antioxidants in their composition
are highlighted.
There are various methods for determining the in vitro
antioxidant activity of substances, such as: ferric thiocyanate
method, method of inhibition of ABTSc
and DPPHc, the
superoxide anion radical and metal chelating activity. In all
these methods, caeic acid proved to be an eective antioxidant
when compared with conventional antioxidants such as BHA,
BHT, a-tocopherol, and Trolox, a water soluble analogue of
Through the permeation study of caeic acid, chlorogenic
acid and oraposide, it was found that the caeic and chloro-
genic acids are able to permeate all the skin layers of pig ear,
which have a systemic activity, whereas oraposide remained in
the upper layer of the skin surface.
Permeation studies on
human skin also conrm the ability of caeic acid and ferulic
acid to permeate into the skin, a characteristic independent of
the pH of the receptor solution being 3.0 or 7.2.
As the solar radiation penetrates deeply into the skin, it is
necessary to ensure that topically applied substances are able to
penetrate through the stratum corneum, the main barrier against
permeation of foreign substances through the skin and reach
the deepest layers to promote satisfactory photo-protection.
The absorption of a compound in the skin is determined by
its physicochemical characteristics, and on the permeation
process, the lipophilicity is one of the most important
Thus, the high lipophilicity of caeic and ferulic
acids may explain the fact that they permeate through the
stratum corneum.
The ferulic and caeic acids also demonstrate protective
eects against phosphatidylcholine peroxidation induced by UV
radiation, which is important since the phosphatidylcholine is a
major constituent of the lipid bilayers of cell membranes.
Antimicrobial activity
Every day more consumers seek more eective cosmetics, which
approximate the denition of cosmeceuticals, or actually having
some biological eects, particularly in the prevention of
premature aging and diseases such as cancers caused by the
action of free radicals in the genes of cells. Therefore, similar to
drugs, these products should also provide security to the
consumer. Allied to this, legislation is becoming increasingly
stringent, which has challenged the industries.
cosmetic companies are required to control the optimal pres-
ervation of their commercial products, since microbial
contamination in cosmetics represents an important risk for
consumer health.
For this reason, natural antimicrobial
compounds are widely used.
Besides its remarkable antioxidant activity, in vitro studies
have demonstrated antimicrobial properties of propolis against
various oral pathogens. Several components of propolis have been
analysed in dierent countries, and caeic acid, phenethyl ester
of caeic acid and avonoids are the main ingredients respon-
sible for the antibiotic power of this resin.
Thus, a thorough
search of the antimicrobial activity of caeic acid is promising
targeting the treatment of dermal diseases, such as acne.
Some phenylpropanoids, including caeic acid, p-coumaric
acid and ferulic acid, are able to inhibit the growth of bacteria,
including E. coli,Staphylococcus aureus,Bacillus cereus,Listeria
monocytogenes and some yeasts.
The antimicrobial activity of these substances depends not
only on their structure but also on the environmental condi-
tions. Caeic acid has a reduced ability to inhibit Listeria
compared to other hydroxycinnamic acid derivatives due to the
presence of a high degree of hydroxylation.
Moreover, envi-
ronmental factors, including the pH and concentration of
sodium chloride, are important because they produce certain
physiological changes in the micro-organisms that make them
more sensitive to phenylpropanoids.
Antioxidant and antimicrobial activities of caeic acid are
pronounced in cosmetic emulsions with acidic pH (35). Caeic
acid showed, at this pH, antimicrobial eects against various
micro-organisms studied (E. coli,Pseudomonas aeruginosa,
Bacillus cereus,Kokuria rhizophila,Staphylococcus aureus,Listeria
monocytogenes,Candida albicans).
The mechanism of the antimicrobial activity of substances is
established considering one of the following three: (1) reaction
with the cell membrane causing increased permeability and
loss of cellular constituents, (2) inactivation of enzymatic
systems or essential enzymes, including those involved in the
production process energy and synthesis of structural compo-
nents, or (3) destruction or inactivation of functional genetic
The cytoplasm membrane of bacteria and the mitochondrial
membrane of yeasts are permeable barriers to passage of small
This journal is © The Royal Society of Chemistry 2014 Anal. Methods,2014,6, 32033210 | 3205
Minireview Analytical Methods
Published on 25 February 2014. Downloaded by UNESP-ARAIQ on 28/04/2014 12:08:04.
View Article Online
ions such as H
and Ca
, in addition to being
responsible for the input and output of dierent compounds.
This cell permeability is important for various cell functions
such as the maintenance of energy in the transduction process,
solute transport, metabolism regulation and pressure
There is a consensus that aromatic and phenolic
compounds, such as caeic acid, aect the cytoplasm
membrane, alter its structure and function, change the active
transport and coagulate cell content.
Caeic acid and its derivatives, such as caeic acid phenyl ester,
have action against colon and oral cancer, and they are inhib-
itors of cyclooxygenase II (COX-2).
These substances are
cytotoxic to tumours but not to normal cells.
An analysis by ow cytometry showed that the caeic acid
and its derivatives caused cellular entrapment of oral squamous
cell carcinoma cells, Meng-1 (OEC-M1) in the G2/M phase of cell
division. These dierential eects on cancer show that these
compounds may be useful in oral cancer chemotherapy.
Various natural antioxidants were tested, such as caeic
acid, catechin, epicatechin and quercetin, to evaluate the
reduction of the cytotoxicity induced by peroxynitrite in chon-
drosarcoma cells. This observation suggests that diets rich in
antioxidant compounds are able to limit cell cytotoxicity.
A derivative of caeic acid, the caeic acid phenyl ester, was
used and it was observed that it inhibited the growth and
secretion of interleucin-6, and it induced apoptosis in a dose
and time dependent manner on multiple myeloma cells ARH-
77. Therefore, both the caeic acid and its derivative deserve
further study as eective agents against multiple myeloma.
Treatment of mice with propolis, caeic acid phenyl ester
and caeic acid itself signicantly reduced the number of
tumour nodules in the lungs of animals whose lung nodules
were generated by injection of viable tumour cells intrave-
nously. In in vitro studies, the propolis did not aect the tumour
cell growth, while the phenyl ester of caeic acid and caeic
acid expressed strong cytotoxicity to cells.
The p38, a mitogen-activated protein kinase (MAPK),
responds to stimuli such as heat, shock, cytokines, and UV and
is directly involved in cell proliferation and production of NO.
Caeic acid signicantly reduces the mRNA expression of
Interleucin-10 UVB-induced in murine and also inhibits the
activation of p38-MAPK.
The caeic acid also reduces the
migratory capacity of malignant keratinocytes.
Although many studies demonstrate the antitumoral activity
of caeic acid, others show opposite eects. The carcinogenicity
of low dietary levels of the antioxidants caeic acid, butylated
hydroxyanisole (BHA), sesamol, 4-methoxyphenol (4-MP) and
catechol was examined alone or in combination in a 2 year long-
term experiment. The results indicate that even at low dose
levels phenolic compounds can exert additive/synergistic eects
on carcinogenesis.
Furthermore, caeic acid is also listed
under some Hazard Data and the International Agency for
Research on Cancer has classied it in group 2B as a substance
that is possibly carcinogenic to humans.
As there are many controversial results about the protective
or carcinogenic potential of caeic acid, more studies should be
conducted to elucidate its therapeutic use.
Analytical methods
There is no method for determination and quantication of
caeic acid in ocial compendia, such as pharmacopoeias,
however most current articles recommend quantication of
the substance by High Performance Liquid Chromatography
For determination of rosmarinic and caeic acids in various
herbs such as rosemary, sage, thyme, mint, lemon balm and
lavender, a HPLC method was developed and validated. The
separation system consisted of a reversed phase C18 column, a
gradient elution system of methanolwater containing phos-
phoric acid and a photodiode array detector. The method
proved to be simple, sensitive, reproducible, fast and ideal for
routine analysis.
For quantitation of receptor solution in a permeation study,
the chromatography was performed on a Hypersil ODS column
(particle size: 5 mm25 cm 4.0 mm). The mobile phase was
acetonitrilewater (18 : 82) containing 2% acetic acid. The ow
rate was set at 1.0 mL min
. Each sample was ltered before
injection using a Millex lter and an aliquot (20 mL) was
injected onto the HPLC column. Detection was performed at
302 nm.
Marti-Mestres and co-workers (2007) conducted a perme-
ation study by applying 50 mL of test formulation 2% caeic acid
in propyleneglycoltranscutol (1 : 1) on the skin of the pig's ear
and used isotonic saline (NaCl 0.9%) with 1% gentamycin pH
7.0 as the receiver solution. This solution was maintained at
37 C and under these conditions the skin temperature is 32 C,
which corresponds to the temperature of the body surface in
vivo. The quantication of the receptor solution was also carried
out by HPLC with UV detection, column C-8 reverse phase
(5 mm, 250 mm 3 mm) at 40 C. The mobile phase was
acetonitrilewater (18 : 80) with 2% acetic acid and a ow rate of
0.5 mL min
. Detection was at 330 nm and the retention time
was approximately 6.0 min.
Chromatographic techniques are widely used in the separa-
tion, purication, identication and quantication of
substances. Although HPLC is a robust method, it is more
suitable for mixtures with known compositions. For identica-
tion of unknown substances in complex samples the most
suitable method is MS or LC-MS/MS. Many papers have been
published in recent years on the examination of caeic acid by
LC-MS/MS approaches.
An example of identication of caeic acid in a complex
matrix was done for simultaneous analysis of alkamides and
caeic acid derivatives from Echinacea purpurea extracts. The
analysis was carried out with reversed phase HPLC coupled to
electrospray ionization mass spectrometry (ESI-MS). The ow
rate was set to 0.2 mL min
and the eluents were A ¼water +
1% acetic acid and B ¼acetonitrile. The gradient conditions
were: 90% of A in B for 4 min; 9060% of A in B from 4 to
15 min; 6040% of A in B from 15 to 30 min; 100% B from 30 to
3206 |Anal. Methods,2014,6, 32033210 This journal is © The Royal Society of Chemistry 2014
Analytical Methods Minireview
Published on 25 February 2014. Downloaded by UNESP-ARAIQ on 28/04/2014 12:08:04.
View Article Online
35 min; 90% of A in B from 35 to 43 min. The outlet of the HPLC
column was directly connected to the electrospray ionization
source of an ion trap mass spectrometer. The mass spectrom-
eter was operated in the negative ion mode for the rst 15 min
of the analysis, then switched to the positive ion mode for the
remainder. The total analysis time was 43 min. This new
method was considered eective for the quality control of these
extracts that require rapid methods to determine their chemical
Another method was developed and validated to assess the
qualitative and quantitative proles of Myrcia bella hydro-
alcoholic extract. In total, 24 constituents were characterized,
including phenolic acids such as caeic acid, by means of
extensive preparative chromatographic analyses, along with
mass spectroscopy and Nuclear Magnetic Resonance (NMR)
techniques. And it shows that the mass spectroscopy technique
is a powerful tool for direct and rapid identication of the
constituents aer isolation and NMR characterization.
Plasma is another type of complex matrix in which caeic
acid may be found. A validated method was developed for the
simultaneous determination of the hydroxycinnamates caeic
acid, dihydrocaeic acid, ferulic acid, dihydroferulic acid, and
isoferulic acid in human plasma as metabolites derived from
coee consumption. It was possible using high-performance
liquid chromatography coupled to negative electrospray ioni-
zation tandem mass spectrometry.
These same techniques
were used in conjunction to develop a simple, rapid and
sensitive method for the simultaneous quantication of
chlorogenic acid and caeic acid in rat plasma.
This review was carefully prepared to prove the potential of
caeic acid used in cosmetics and pharmaceutical preparations
and to encourage more studies to elucidate the activity of this
substance on the human body.
We thank FAPESP, CNPq and PADC-FCF-UNESP for their
nancial support.
1 S. E. Soares, ´
Acidos fen´
olicos como antioxidantes, Rev. Nutr.,
2002, 15,7181.
2 E. A. Melo and N. B. Guerra, Aç˜
ao antioxidante de compostos
olicos naturalmente presentes em alimentos, Bol. SBCTA,
2002, 36,111.
3 J. Burns, P. T. Gardner, D. Matthews, G. G. Duthie, M. E. Lean
and A. Crozier, Extraction of phenolics and changes in
antioxidant activity of red wines during vinication, J.
Agric. Food Chem., 2001, 49, 57975808.
4 A. Chisvert and A. Salvador, Cosmetic ingredients: from the
cosmetic to the human body and the environment, Anal.
Methods, 2013, 5, 309.
5 A. I. Nazer, A. Kobilinsky, J. L. Tholozan and F. Dubois-
Brissonnet, Combinations of food antimicrobials at low
levels to inhibit the growth of Salmonella sv. typhimurium:a
synergistic eect?, Food Microbiol., 2005, 22, 391398.
6 A. M. Wen, P. Delaquis, K. Stanich and P. Toivonen,
Antilisterial activity of selected phenolic acids, Food
Microbiol., 2003, 20, 305311.
7M.N.Cliord, Chlorogenic acids and other cinnamates-
nature, occurrence, dietary burden, absorption and
metabolism, J. Sci. Food Agric., 2000, 80, 10331043.
8 S. R. Lustosa, A. B. Galindo, L. C. C. Nunes, K. P. Randau and
P. J. Rolim Neto, Propolis: atualizaç˜
oes sobre a qu´
ımica e a
farmacologia, Rev. Bras. Farmacogn., 2008, 18, 447454.
9 M. T. Huang and T. Ferraro, Phenolic-compounds in food
and cancer prevention, ACS Symp. Ser., 1992, 507,834.
10 P. Greenwald, Clinical trials in cancer prevention: current
results and perspectives for the future, J. Nutr., 2004, 134,
11 C. Sanchez-Moreno, A. Jimenez-Escrig and F. Saura-Calixto,
Study of low-density lipoprotein oxidizability indexes to
measure the antioxidant activity of dietary polyphenol,
Nutr. Res., 2000, 20, 941953.
12 J. A. Vinson, K. Teufel and N. Wu, Red wine, dealcoholized
red wine, and especially grape juice, inhibit atherosclerosis
in a hamster model, Atherosclerosis, 2001, 156,6772.
13 Worldwide Chemical Information, Trading & Advertising,
20acid.htm, accessed in February 1st 2014.
14 D. G. Soares, A. C. Andreazza and M. Salvador, Avaliaç˜
ao de
compostos com atividade antioxidante em c´
elulas da
levedura Sacharomyces cerevisae,Rev. Bras. Cienc. Farm.,
2005, 1,95100.
15 Dossiˆ
e de Antioxidantes. Os Antioxidantes, http://, accessed in February
1st 2014.
16 J. H. Chen and C. T. Ho, Antioxidant activities of caeic acid
and its related hydroxycinnamic acid compound, J. Agric.
Food Chem., 1997, 45, 23742378.
17 A. S. Meyer, J. L. Donovan, D. A. Pearson, A. L. Waterhouse
and E. N. Frankel, Fruit hydroxycinnamic acids inhibit low
density lipoprotein oxidation in vitro,J. Agric. Food Chem.,
1998, 46, 17831787.
18 F. Paiva-Martins and M. H. Gordon, Eects of pH and ferric
ions on the antioxidant activity of olive polyphenols in oil-in-
water emulsions, J. Am. Oil Chem. Soc., 2002, 79, 571576.
19 M. J. Hynes and W. O. Coinceanainn, The kinetics and
mechanisms of reactions of iron(III) with caeic acid,
chlorogenic acid, sinapic acid, ferulic acid and naringin, J.
Inorg. Biochem., 2004, 98, 14571464.
20 E. Graf, Antioxidant potential of ferulic acid, Free Radical
Biol. Med., 1992, 13, 435448.
21 M. E. Cuvelier, H. Richard and C. Berset, Antioxidative
activity and phenolic composition of pilot-plant and
commercial extracts of sage and rosemary, J. Am. Oil Chem.
Soc., 1996, 73, 645652.
22 J. Terao, H. Karasawa, H. Arai, A. Nagao, T. Suzuki and
K. Takawa, Peroxyl radical scavenging activity of caeic
This journal is © The Royal Society of Chemistry 2014 Anal. Methods,2014,6,32033210 | 3207
Minireview Analytical Methods
Published on 25 February 2014. Downloaded by UNESP-ARAIQ on 28/04/2014 12:08:04.
View Article Online
acid and its related phenolic compounds in solution, Biosci.,
Biotechnol.,Biochem., 1973, 57, 12041205.
23 W. Brand-Willams, M. E. Cuvelier and C. Berset, Use of free
radical method to evaluate antioxidant activity, Food Sci.
Technol., 1995, 28,2530.
24 J. Laranjinha, O. Vierira, L. Almeida and V. Madeira,
Inhibition of metmyoglobin/H
-dependent low density
lipoprotein lipid peroxidation by naturally occurring
phenolic acids, Biochem. Pharmacol., 1996, 51, 395402.
25 L. R. Fukumoto and G. Mazza, Assessing antioxidant and
prooxidant activities of phenolic compounds, J. Agric. Food
Chem., 2000, 48, 35973604.
26 Y. Yamada, H. Yasui and H. Sakurai, Suppressive eect of
caeic acid and its derivatives on the generation of UVA-
induced reactive oxygen species in the skin of hairless
mice and pharmacokinetic analysis on organ distribution
of caeic acid in ddY mice, Photochem. Photobiol., 2006,
82, 16681676.
27 J. C. Murray, J. A. Burch, R. D. Streilein, M. A. Iannacchione,
R. P. Hall and S. R. Pinnell, A topical antioxidant solution
containing vitamins C and E stabilized by ferulic acid
provides protection for human skin against damage
caused by ultraviolet irradiation, J. Am. Acad. Dermatol.,
2008, 59, 418425.
28 M. I. Hadshiew, M. S. Eller and B. A. Gilchrest, Skin aging
and photoaging: the role of DNA damage and repair, Am. J.
Contact Dermat., 2000, 11,1925.
29 M. Yaar and B. A. Gilchrest, Skin aging: postulated
mechanisms and consequent changes in structure and
function, Clinics in Geriatric Medicine, 2001, vol. 17, pp.
30 K. G. Menon, L. Dryer and R. Kalafsky, Approaches to the
development of cosmetic products to counter the eects of
skin aging, Skin Aging Handbook, 2009, pp. 265290.
31 B. Halliwell and J. M. Gutteridge, Free Radicals in Biology and
Medicine, Clarendon Press, Oxford, New York, 2007.
32 I. G¨
ulçin, M. E. B¨
ukokuroglu, M. Oktay and
O. I. K¨
ufrevioglu, On the in vitro antioxidant properties of
melatonin, J. Pineal Res., 2002, 33, 167171.
33 P. D. Duh, Y. Y. Tu and G. C. Yen, Antioxidant activity of
water extract of harng jyur (Chrysanthemum morifolium
Ramat), Lebensm.-Wiss. Technol., 1999, 32, 269277.
34 M. E. B¨
ukokuroglu, I. G¨
ulçin, M. Oktay and
O. I. K¨
ufrevioglu, In vitro antioxidant properties of
dantrolene sodium, Pharmacol. Res., 2001, 44, 491495.
35 E. Cadenas, Biochemistry of oxygen toxicity, Annu. Rev.
Biochem., 1989, 58,79110.
36 C. M. Berra, C. F. M. Menck and P. Di Mascio, Estresse
oxidativo, les˜
oes no genoma e processos de sinalizaç˜
ao no
controle do ciclo celular, Quim. Nova, 2006, 29, 13401344.
37 F. Q. Schafer and G. R. Buettner, Redox environment of the
cell as viewed through the redox state of the glutathione
disulde/glutathione couple, Free Radical Biol. Med., 2001,
30, 11911212.
38 T. Finkel and N. J. Holbrook, Oxidative stress and aging:
catalase is a longevity determinant enzyme, Nature, 2000,
408, 239.
39 M. Valko, D. Leibfritz, J. Moncol, M. T. Cronin, M. Mazur and
J. Telser, Free radicals and antioxidants in normal
physiological functions and human disease, Int. J. Biochem.
Cell Biol., 2007, 39,4484.
40 K. Scharetter-Kochanek, M. Wlaschek, P. Brenneisen,
M. Schauen, R. Blaudschun and J. Wenk, UV-induced
reactive oxygen species in photocarcinogenesis and
photoaging, Biol. Chem., 1997, 378, 12471257.
41 Y. Matsumura and H. N. Ananthaswamy, Short-term and
long-term cellular and molecular events following UV
irradiation of skin: implications for molecular medicine,
Expert Rev. Mol. Med., 2002, 2,122.
42 M. Yaar and B. A. Gilchrest, Photo ageing: mechanism,
prevention and therapy, Br. J. Dermatol., 2007, 157, 874877.
43 J. H. Doroshow, Eect of anthracycline antibiotics on oxygen
radical formation in rat heart, Cancer Res., 1983, 43, 460472.
44 B. Halliwell, R. Aeschbach, J. L¨
olinger and O. I. Aruoma, The
characterization on antioxidants, Food Chem. Toxicol., 1995,
33, 601617.
45 N. I. Weijl, F. J. Cleton and S. Osanto, Free radicals and
antioxidants in chemotherapy-induced toxicity, Cancer
Treat. Rev., 1997, 23, 209240.
46 G. J. Fisher, Z. Q. Wang, S. C. Datta, J. Varani, S. Kang and
J. J. Voorhees, Pathophysiology of premature skin aging
induced by ultraviolet light, N. Engl. J. Med., 1997, 337,
47 M. Brennan, H. Bhatti, K. C. Nerusu, N. Bhagavathula,
S. Kang, G. J. Fisher, J. Varani and J. J. Voorhees, Matrix
metalloproteinase-1 is the major collagenolytic enzyme
responsible for collagen damage in UV-irradiated human
skin, Photochem. Photobiol., 2003, 78,4348.
48 N. Philips, J. Smith, T. Keller and S. Gonzalez, Predominant
eects of Polypodium leucotomos on membrane integrity,
lipid peroxidation, and expression of elastin and
matrixmetalloproteinase-1 in ultraviolet radiation exposed
broblasts, and keratinocytes, J. Dermatol. Sci., 2003, 32,19.
49 T. Polte and R. M. Tyrrell, Involvement of lipid peroxidation
and organic peroxides in UVA-induced matrix
metalloproteinase-1 expression, Free Radical Biol. Med.,
2004, 36, 15661574.
50 M. J. Pygmalion, L. Ruiz, E. Popovic, J. Gizard, P. Portes,
X. Marat, K. Lucet-Levannier, B. Muller and J. B. Galey,
Skin cell protection against UVA by Sideroxyl, a new
antioxidant complementary to sunscreens, Free Radical
Biol. Med., 2010, 49, 16291637.
51 E. Venditti, F. Bruge, P. Astol, I. Kochevar and E. Damiani,
Nitroxides and a nitroxide-based UV lter have the potential
to photo protect UVA-irradiated human skin broblasts
against oxidative damage, J. Dermatol. Sci., 2011, 63,5561.
52 K. Wertz, N. Seifert, P. B. Hunziker, G. Riss, A. Wyss,
C. Lankin and R. Goralczyk, Beta-carotene inhibits UVA-
induced matrix metalloprotease 1 and 10 expression in
keratinocytes by a singlet oxygen-dependent mechanism,
Free Radical Biol. Med., 2004, 37, 654670.
53 T. Pluemsamran, T. Onkoksoong and U. Panich, Caeic acid
and ferulic acid inhibit UVA-induced matrix
metalloproteinase-1 through regulation of antioxidant
3208 |Anal. Methods,2014,6, 32033210 This journal is © The Royal Society of Chemistry 2014
Analytical Methods Minireview
Published on 25 February 2014. Downloaded by UNESP-ARAIQ on 28/04/2014 12:08:04.
View Article Online
defense system in keratinocyte HaCaT cells, Photochem.
Photobiol., 2012, 88, 961968.
54 G. Deliconstantinos, V. Villiotou and J. C. Stavrides, Nitric
oxide and peroxynitrite skin erythema and inammation,
Exp. Physiol., 1996, 81, 10211033.
55 C. Romero-Graillet, E. Aberdam, M. Clement, J. P. Ortonne
and R. Ballotti, Nitric oxide produced by ultraviolet-
irradiated keratinocytes stimulates melanogenesis, J. Clin.
Invest., 1997, 99, 635642.
56 A. Saija, A. Tomaino, R. Lo Cascio, D. Trombetta,
A. Proteggente, A. De Pasquale, N. Uccela and F. Bonina,
Ferulic and caeic acids as potential protective agents
against photooxidative skin damage, J. Sci. Food Agric.,
1999, 79, 476480.
57 A. Saija, A. Tomaino, D. Trombetta, M. Giacchi, A. De
Pasquale and F. Bonina, Inuence of dierent penetration
enhancers on in vitroskin permeation and in vivophoto
protective eect of avonoids, Int. J. Pharm., 1998, 175,85
58 J. B. Dawson, D. J. Barker, D. J. Ellis, E. Grassam,
J. A. Catterill, G. W. Fischer and J. W. Feather, A
theoretical and experimental study of light absorption and
scattering by in vivo skin, Phys. Med. Biol., 1980, 25, 696709.
59 P. H. Andersen, K. Abrams, P. Bjerring and H. A. Maibach, A
time-correlation study of ultraviolet B-induced erythema
measured by reectance spectroscopy and laser Doppler
owmetry, Photodermatol., Photoimmunol. Photomed., 1991,
8, 123128.
60 II Caderno de Tendˆ
encias, Higiene Pessoal, Perfumaria e
eticos, content/
uploads/2011/08/caderno_tendencias1.pdf., accessed in,
August 2013.
61 I. G¨
ulçin, Antioxidant activity of caeic acid (3,4-
dihydroxycinnamic acid), Toxicology, 2006, 217, 213220.
62 G. Marti-Mestres, J. P. Mestres, J. Bres, S. Martin, J. Ramos
and L. Viana, The in vitropercutaneous penetration of
three antioxidant compounds, Int. J. Pharm., 2007, 331,
63 A. Saija, A. Tomaino, D. Trombetta, A. De Pasquale,
N. Uccella, T. Barbuzzi, D. Paolino and F. Bonina, In vitro
and in vivo evaluation of caeic and ferulic acids as topical
photoprotective agents, Int. J. Pharm., 2000, 199,3947.
64 F. Bonina, M. Lanza, L. Montenegro, C. Puglisi, A. Tomaino,
D. Trombetta, F. Castelli and A. Saija, Flavonoids as
potential protective agents against photo-oxidative skin
damage, Int. J. Pharm., 1996, 94, 145187.
65 J. Zatz, Percutaneous absorption, Wiley, New York, 1985.
66 S. Shahrzad and I. Bitsch, Determination of some
pharmacology active phenolic acids in juices high-
perfomance liquid chromatography, J. Chromatogr. A, 1996,
742, 223231.
67 G. Alvarez-Rivera, T. Miguel, M. Llompart, C. Garcia-Jares,
T. G. Villa and M. Lores, A novel outlook on detecting
microbial contamination in cosmetic products: analysis of
biomarker volatile compounds by solid-phase
microextraction gas chromatography-mass spectrometry,
Anal. Methods, 2013, 5, 384.
68 B. Havsteen, Flavonoids, a class of natural products of high
pharmacological potency, Biochem. Pharmacol., 1983, 32,
69 M. C. Marcucci, Propriedades biol´
ogicas e terapˆ
euticas dos
constituintes qu´
ımicos da pr´
opolis, Quim. Nova, 1996, 19,
70 H. Menezes, Pr´
opolis: uma revis˜
ao dos recentes estudos de
suas propriedades farmacol´
ogicas, Arq. Inst. Biol., Sao
Paulo, 2005, 72, 405441.
71 F. M. Campos, J. A. Couto and T. A. Hogg, Inuence of
phenolic acids on growth and inactivation of Oenococcus
oeni and Lactobacillus hilgardii,J. Appl. Microbiol., 2003, 94,
72 N. Canillac and A. Mourey, Eects of several environmental
factors on the anti-Listeria monocytogenes activity of an
essential oil of Picea excels, Int. J. Food Microbiol., 2004,
73 M. P. Almajano, R. Carb'o, M. E. Delgado and M. H. Gordon,
Eect of pH on the Antimicrobial activity and oxidative
stability of oil-in-water emulsions containing caeic acid, J.
Food Sci., 2007, 72, C258C263.
74 A. L. Branen, Introduction to the use of antimicrobials, in
Antimicrobials in Foods, ed. P. P. Davidson and A. L.
Branen, Marcel Dekker, New York, 1993.
75 J. M. Kim, M. R. Marshall, J. A. Corneel, J. F. Preston and
C. I. Wei, Antibacterial activity of carvacrol, citral
and geraniol against Salmonella typhimurium in culture
medium and sh cubes, J. Food Sci., 1995, 60,1364
76 I. R. Booth, Regulation of cytoplasmatic pH in bacteria,
Microbiol. Rev., 1985, 49, 359378.
77 S. D. Cox, C. M. Mann, J. L. Markham, H. C. Bell,
J. E. Gustafson, J. R. Warmington and S. G. Wyllie, The
mode of antimicrobial action of essential oil of Melaleuca
alternifolia (tea tree oil), J. Appl. Microbiol., 2000, 88, 170
78 J. Sikkema, J. A. M. De Bont and B. Poolman, Mechanism of
membrane toxicityof hydrocarbons, Microbiol. Rev., 1995, 59,
79 S. Burt, Essential oils: theirs antibacterial properties and
potential applications in foods a review, Int. J. Food
Microbiol., 2004, 94, 223253.
80 G. C. Ceschel, P. Maei, A. Sforzini, B. S. Lombardi, A. Yasin
and C. Ronchi, In vitro permeation through porcine buccal
mucosa of caeic acid phenethyl ester (CAPE) from a
topical mucoadhesive gel containing propolis, Fitoterapia,
2002, 73,4452.
81 P. Michaluart, J. L. Masferrer, A. M. Carothers,
K. Subbaramaiah, B. S. Zweifel and C. Kobolt, Inhibitory
eects of caeic acid phenethyl ester on the activity and
expression of cyclooxygenase-2 in human oral epithelial
cells and in a rat model of inammation, J. Cancer Res.,
1999, 59, 23472352.
82 M. J. Weyant, A. M. Carothers, M. E. Bertagnolli and
M. M. Bertagnolli, Colon cancer chemo preventive drugs
modulate integrin-mediated signaling pathways, Clin.
Cancer Res., 2000, 6, 949956.
This journal is © The Royal Society of Chemistry 2014 Anal. Methods,2014,6, 32033210 | 3209
Minireview Analytical Methods
Published on 25 February 2014. Downloaded by UNESP-ARAIQ on 28/04/2014 12:08:04.
View Article Online
83 A. Russo, R. Longo and A. Vanella, Antioxidant activity of
propolis: role of caeic acid phenethyl ester and galangin,
Fitoterapia, 2002, 73,2129.
84 C. Chiao, A. M. Carothers, D. Grunberger, G. Solomon,
G. A. Preston and J. C. Barrett, Apoptosis and altered redox
state induced by caeic acid phenethyl ester (CAPE) in
transformed rat broblast cells, Cancer Res., 1995, 55,
85 Y. T. Lee, M. J. Don, P. S. Hung, Y. C. Shen, Y. S. Lo,
K. W. Chang, C. F. Chen and L. K. Ho, Cytotoxicity of
phenolic acid phenethyl esters on oral cancer cells, Cancer
Lett., 2005, 223,1925.
86 U. Ketsawatsakul, Modulation by bicarbonate of the
protective eects of phenolic antioxidants on peroxynitrite-
mediated cell cytotoxicity, ScienceAsia, 2007, 33, 273282.
87 O. Koru, F. Avcu, M. Tanyuksel, A. U. Ural, R. E. Araz and
K. S
¸ener, Cytotoxic eects of caeic acid phenethyl ester
(CAPE) on the human multiple myeloma cell line, Turk. J.
Med. Sci., 2009, 39, 863870.
88 I. Basic, N. Orsolic, Z. Tadic, N. M. F. Alcici, A. Brbot-
Saranovic, K. Bendelja, B. Krsnik and S. Rabatic,
Antimetastatic eects of propolis, caeic acid phenethyl
ester and caeic acid on mammary carcinoma of CBA
mouse, 17th International Cancer Congress, 1998, pp. 6375.
89 W. Ding, L. G. Hudson, X. Sun, C. Feng and K. J. Liu, As (III)
inhibits ultraviolet radiation-induced cyclobutane pyrimidine
dimer repair via generation of nitric oxide in human
keratinocytes, Free Radical Biol. Med., 2008, 45,10651072.
90 V. Staniforth, L. T. Chiu and N. S. Yang, Caeic acid
suppresses UVB radiation- induced expression of
interleukin-10 and activation of mitogen- activated protein
kinases in mouse, Carcinogenesis, 2006, 27, 18031811.
91 Y. Yang, Y. Li, K. Wang, Y. Wang and W. Yin, P38/NF-kB/
snail pathway is involved in caeic acid-induced inhibition
of cancer stem cells-like properties and migratory capacity
in malignant human keratinocyte, PLoS One, 2013, 8,18.
92 M. Hirose, Y. Takesada, H. Tanaka, S. Tamano, T. Kato and
T. Shirai, Carcinogenicity of antioxidants BHA, caeic acid,
sesamol, 4-methoxyphenol and catechol at low doses,
either alone or in combination, and modulation of their
eects in a rat medium-term multi-organ carcinogenesis
model, Carcinogenesis, 1998, 19, 207212.
93 H. Wang, G. J. Provan and K. Helliwell, Determination of
rosmarinic acid and caeic acid in aromatic herbs by
HPLC, Food Chem., 2004, 87, 307311.
94 N. B. Cech, M. S. Eleazer, L. T. Shoner, M. R. Crosswhite,
A. C. Davis and A. M. Mortenson, High performance liquid
chromatography/electrospray ionization mass spectrometry
for simultaneous analysis of alkamides and caeic
acidderivatives from Echinacea purpurea extracts, J.
Chromatogr. A, 2006, 1103, 219228.
95 L. L. Saldanha, W. Vilegas and A. L. Dokkedal,
Characterization of avonoids and phenolic acids in
Myrcia bella Cambess using FIA-ESI- IT-MSn and HPLC-
PAD-ESI-IT-MS combined with NMR, Molecules, 2013, 18,
96 P. A. Guy, M. Renouf, D. Barron, C. Cavin, F. Dionisi,
S. Kochhar, S. Rezzi, G. Williamson and H. Steiling,
Quantitative analysis of plasma caeic and ferulic acid
equivalents by liquid chromatography tandem mass
spectrometry, J. Chromatogr. B: Anal. Technol. Biomed. Life
Sci., 2009, 877, 39653974.
97 S. J. Wang, Z. Q. Zhang, Y. H. Zhao, J. X. Ruan and J. L. Li,
Simultaneous quantication of chlorogenic acid and
caeic acid in rat plasma aer an intravenous
administration of mailuoning injection using liquid
chromatography/mass spectrometry, Rapid Commun. Mass
Spectrom., 2006, 20, 23032308.
3210 |Anal. Methods,2014,6, 32033210 This journal is © The Royal Society of Chemistry 2014
Analytical Methods Minireview
Published on 25 February 2014. Downloaded by UNESP-ARAIQ on 28/04/2014 12:08:04.
View Article Online
... e extract of LSSM has antioxidant activity due to the presence of phenolic phytochemicals that act as scavengers of free radicals to interfere with lipid peroxidation and antimicrobial action on spoilage and pathogenic microorganisms [18][19][20]. e detailed inspection of the phenolic and flavonoid contents of LSSM is shown in (Table 1), which clarified the role of four phenolic acids in the process of oxidation reaction inhibition and antibacterial effect due to their elevated level [21,22]. For example, aside from the flavoring effect of gallic acid (3,4,5-trihydroxybenzoic acid), it also has the ability to inhibit the bioactivity of several bacteria. ...
... In addition, it can damage Gram-negative and Gram-positive bacterial cell membrane via interference with the membrane permeability, increase the accumulation of antibiotic in bacterial cell, and at the same time play an important role in the antioxidant scavenging process and metals chelation [23,24]. e same as for caffeic acid (3,4-dihydroxycinnamic), chlorogenic acid (hydroxycinnamic esters with quinic acid), and ferulic acid ([E]-3-[4-hydroxy-3-methoxyphenyl] prop-2-enoic acid) [21][22][23][24][25]. e LSSM components and their phytochemical constituents were illustrated to possess potent bioactivities, e.g., antioxidant and antimicrobial potentialities [19], which enabled their former usages for foodstuffs preservations [18], and capability for incorporation in functional foods due to LSSM biosafe nature and human-friendly attributes [26,27]. ...
Full-text available
Aiming to boost the catfish fillet quality, the consequences of their treatment with Lepidium sativum seeds mucilage (LSSM) and with LSSM-mediated selenium nanoparticles (LSSM-Se NPs) were investigated. The LSSM assessment for phenolic acids contents emphasized higher concentrations. Green-synthesized Se NPs were conjugated with LSSM to form LSSM-Se NPs and characterized; the NPs had spherical shapes, negatively charged with 15.47 nm mean diameters. Fish fillets were immersed in coating solutions for 2 min, drained, and stored for 25 days at 4°C. The fish groups (C: untreated samples, M: LSSM-treated, and G: LSSM-Se NPs treated) were assessed for their physicochemical, bacteriological, and sensorial attributes. On the 25th day, the samples’ pH values were 6.96, 6.6, and 6.3; TVB-N values were 38.8, 28.4, and 16.4 mg/100 g; TBARS values were 1.7, 0.97, and 0.68 malondialdehyde/kg; and overall acceptability scores were 3.9, 5.6, and 8.3, for C, M and G groups, respectively. At day 16, the psychrophilic bacterial count was 6.2, 4.0, and 3.6 log CFU/g for C, M, and G groups, respectively. The application of LSSM and LSSM-Se NPs is recommended to compose active coatings for quality boost and shelf-life extension of stored catfish fillet.
... Epigallocatechin reported to have antioxidant properties and associated in the prevention of cancer, diabetes, tooth decay, obesity, viral disease and cardiovascular diseases in humans [31,32] . Caffeic acid is known for its antioxidant and antibacterial activity that helps in the prevention of early aging, skin diseases and cardiovascular diseases such as atherosclerosis [33] . Quercetin shows numerous health benefit properties such as anti-inflammatory, anti-microbial, antidiabetic, anti-oxidant, anti-Alzheimer and anti-arthritic characteristics [34] . ...
Full-text available
Apricot is an outstanding source of natural acids, vitamins, carbohydrates, phenolic compounds and minerals. Apricot kernels have been used in folk medicine as a remedy for various diseases. It can hence be utilized for edible purpose in different forms in food industry. Besides being high in nutrition apricot kernels also contains cyanogenic glucoside 'Amygdalin' which on hydrolysis generates hydrogen cyanide and can be toxic to human beings. So, in order to make them feasible for edible purpose it is required to detoxify them first. Detoxification can be looked at from two perspectives. First is when a toxin is consumed or toxins have been released in the meal, which is detoxification of the body, and second is when toxins are removed from the food itself, which is detoxification of food. Various researchers have studied on apricot kernel detoxification and its use in various forms. Present review deals with the explanation of phenomenon of Amygdalin biosynthesis, catabolism, detoxification of kernels and their utilization in food and other areas.
... The antimicrobial activity may be caused by bioactive compounds, namely phenolics, flavonoids and alkaloids compounds 48 . Tentative identification of the various extracts by LC-MS investigated many compounds with antimicrobial potential, namely kaempferol 49 , quercetin 50 , germacrene D 51 , caffeic acid 52,53 and p-coumaric acid 54 . The minimum inhibitory concentration (MIC) performed the preliminary screening of antimicrobial activity. ...
Full-text available
Geranium wallichianum D. Don ex Sweet is a well-known medicinal plant in Kashmir Himalya. The evidence for its modern medicinal applications remains majorly unexplored. The present study was undertaken to elucidate the detailed antimicrobial promises of different crude extracts (methanolic, ethanolic, petroleum ether, and ethyl acetate) of G. wallichainum against common human bacterial and fungal pathogens in order to scientifically validate its traditional use. The LC-MS analysis of G. wallichainum yielded 141 bioactive compounds with the vast majority of them having therapeutic applications. Determination of minimum inhibitory concentrations (MICs) by broth microdilution method of G. wallichainum was tested against bacterial and fungal pathogens with MICs ranging from 0.39-400 µg/mL. Furthermore, virtual ligands screening yielded elatine, kaempferol, and germacrene-A as medicinally most active constituents and the potential inhibitor of penicillin-binding protein (PBP), dihydropteroate synthase (DHPS), elongation factor-Tu (Eu-Tu), ABC transporter, 1,3 beta glycan, and beta-tubulin. The root mean square deviation (RMSD) graphs obtained through the molecular dynamic simulations (MDS) indicated the true bonding interactions which were further validated using root mean square fluctuation (RMSF) graphs which provided a better understanding of the amino acids present in the proteins responsible for the molecular motions and fluctuations. The effective binding of elatine, kaempferol, and germacrene-A with these proteins provides ground for further research to understand the underlying mechanism that ceases the growth of these microbes
... Phenolic acid caffeine is prevalent in various food sources such as apple, cider, blueberries, etc., and beverages such as tea and coffee [26]. Caffeic acid is known to cross the brain barrier and is classified as an antioxidant, antibacterial and anti-cancer compound [27,28]. Similarly, Coumaric acid is an essential polyphenol that governs the synthesis of some other important polyphenolic compounds such as sinapinic, ferulic and caffeic acid [29,30]. ...
Full-text available
Alpha-amylase (α-amylase) is a key player in the management of diabetes and its related complications. This study was intended to have an insight into the binding of caffeic acid and coumaric acid with α-amylase and analyze the effect of these compounds on the formation of advanced glycation end-products (AGEs). Fluorescence quenching studies suggested that both the compounds showed an appreciable binding affinity towards α-amylase. The evaluation of thermodynamic parameters (ΔH and ΔS) suggested that the α-amylase-caffeic/coumaric acid complex formation is driven by van der Waals force and hydrogen bonding, and thus complexation process is seemingly specific. Moreover, glycation and oxidation studies were also performed to explore the multitarget to manage diabetes complications. Caffeic and coumaric acid both inhibited fructosamine content and AGE fluorescence, suggesting their role in the inhibition of early and advanced glycation end-products (AGEs). However, the glycation inhibitory potential of caffeic acid was more in comparison to p-coumaric acid. This high antiglycative potential can be attributed to its additional –OH group and high antioxidant activity. There was a significant recovery of 84.5% in free thiol groups in the presence of caffeic acid, while coumaric attenuated the slow recovery of 29.4% of thiol groups. In vitro studies were further entrenched by in silico studies. Molecular docking studies revealed that caffeic acid formed six hydrogen bonds (Trp 59, Gln 63, Arg 195, Arg 195, Asp 197 and Asp 197) while coumaric acid formed four H-bonds with Trp 59, Gln 63, Arg 195 and Asp 300. Our studies highlighted the role of hydrogen bonding, and the ligands such as caffeic or coumaric acid could be exploited to design antidiabetic drugs.
In this work, two novel selenium glycoconjugates are proposed as antioxidants to accelerate skin repair. These molecules, designed with more antioxidant sites and improved healing activity, are composed by a selenosugar covalently linked to the caffeic acid or a resveratrol residue. The selenium glycoconjugates have been synthesised and then loaded in a hydrogel flexible film, in order to obtain an active wound dressing. The chemical interaction between the hydrogel and the embedded selenium glycoconjugates can be modulated by the pH values, resulting in a pH-sensitive delivery system. In particular, the caffeic acid-containing compound is released at acute wounds’ pH (7.4), while the resveratrol-containing conjugate is released at pH 9.6, typical of chronic wounds. The specific characteristics of the hydrogel and the antioxidant features of the selenium glycoconjugates, as well as the proven controlled release, candidate the designed system at wound care practices.
Phytobased bioactive compounds are herbal scavengers and beneficial in skin disorders, aging and oxidative damage. Himalayan Cherry (Prinsepia utilis) is a good source of fatty acids; however, screening and optimization of polyphenolics in leftover waste of seeds after oil extraction have not been studied. The present study focuses on the optimization of antioxidant polyphenolics of leftover oil residue of Prinsepia utilis. The leftover oil residue optimized through Response Surface Model (RSM) using ultrasonic assisted extraction (UAE) with four-factors in Plackett-Burman (PBD) and three-factors in Central composite design (CCD). The model showed good fitness under optimum extraction conditions and total phenolics, flavonoids, tannins, and antioxidant activity were closely fit with the model predicted values. HPLC-PDA analysis detects ten polyphenolic compounds under optimized extraction conditions. The anti-aging activity by tyrosinase and hyaluronidase indicated that extract is good in inhibiting tyrosinase (IC50-1.81 ± 0.02 mg/mL) and hyaluronidase (IC50-0.90 ± 0.03 mg/mL) enzyme. The extract prevented UV damage and showed good sun protection (SP) at value of 11.00 ± 0.03 at a dose of 1000 μg/mL. The study provides the potential use of leftover residue in water for obtaining antioxidant activity and alleviating oxidative stress, which will be beneficial in the prospect of phyto-nutrients at the Industrial level. Also, the method of extraction was used to promote green extraction, which can be sustainably used for harnessing the waste residue in developing byproducts such as nutraceuticals and cosmeceuticals in a safer environment.
Colocasia esculenta var. Aquatilis Hassk, elephant ear (CF-EE) has been widely used as traditional food and medicine. It also shows other therapeutic properties, such as antimicrobial and anti-cancer activity. In this study, we aim to investigate the effect of CF-EE extract on apoptosis induction associated with ER stress in cervical cancer HeLa cells. Cell viability was determined by MTT assay. Assessments of nuclear morphological changes, mitochondrial membrane potential, and intracellular reactive oxygen species (ROS) production were conducted by hoeshst33342, JC-1, and DCFH-DA fluorescence staining, respectively. Sub-G1 DNA content was analyzed by flow cytometry, and protein expression was determined by Western blotting. The results demonstrate that CF-EE extract suppressed HeLa cell growth and induced nuclear condensation and apoptotic bodies. There was also a loss of mitochondrial membrane potential and increased apoptosis marker protein expression, including Bax, cleaved-caspase-7, and cleaved-PARP. In addition, the results show that CF-EE extract induced ROS, increased ER stress proteins (GRP78 and CHOP), enhanced p38 and c-Jun phosphorylation, and inhibited Akt expression in HeLa cells. In summary, CF-EE extract induced apoptotic cell death-associated ROS-induced ER stress and the MAPK/AKT signaling pathway. Therefore, CF-EE extract has anticancer therapeutic potential for cervical cancer treatment in the future.
Full-text available
Coffee silverskin (CS) is the only byproduct of the roasting process for coffee beans and is rich in phenolic compounds with various bioactivities. This study proposes a valorization option for bioactive compounds (T-CQA) based on a subcritical water extraction (SWE) technique, which is known for its high efficiency and feasibility for use on an industrial scale. The use of water as a sole solvent requires a minimum number of cleaning steps and renders the extract safe for further applications, such as in either the cosmetic or food industry. Response surface methodology with a Box–Behnken design is effectively used to optimize and explain the individual and interactive process variables (i.e., extraction temperature, extraction time, and solid–liquid ratio) on the T-CQA content obtained from coffee silverskin by the SWE technique. The final model exhibits a precise prediction of the experimental data obtained for the maximum T-CQA content. Under the optimum conditions, the CS extract is found to contain a higher content of T-CQA and TPC than that reported previously. For antioxidant activity, up to 26.12 ± 3.27 mg Trolox equivalent/g CS is obtained.
Indian prickly ash [Zanthoxylum rhetsa (Roxb.) DC.] is a multipurpose, but lesser known underutilized spice of Western Ghats of India. The edible fruit pericarp is commonly used in culinary items in dried form to improve flavor and shelf life of culinary products especially fish curries. In the present study, we have identified 18 phenolic acids from Zanthoxyllum rhetsa fruit pericarp using LC–MS/MS. The main phenolic acid in fruit pericarp were observed to be Ferulic acid (2100 µg/g), Caffeic acid (404.60 µg/g), Sinapic acid (247.24 µg/g), p-Coumaric acid (177.56 µg/g), t-Cinnamic acid (119.20 µg/g) and Gentisic acid (104.24 µg/g). Out of 18 identified compounds Ferulic acid and Caffeic acid constituted 64.27% and 12.38%, respectively. Profiling of phenolic compounds in pericarp of Zanthoxylum rhetsa (Roxb.) DC could substantiate edible use of fruits as phenolic acids play an important role in health and funcional foods.
Plant-derived bioactive compounds have been extensively studied and used within food industry for the last few decades. Those compounds have been used to extend the shelf-life and improve physico-chemical and sensory properties on food products. They have also been used as nutraceuticals due to broad range of potential health-promoting properties. Unlike the synthetic additives, the natural plant-derived compounds are more acceptable and often regarded as safer by the consumers. This chapter summarizes the extraction methods and sources of those plant-derived bioactives as well as recent findings in relation to their health-promoting properties, including cardio-protective, anti-diabetic, anti-inflammatory, anti-carcinogenic, immuno-modulatory and neuro-protective properties. In addition, the impact of applying those plant-derived compounds on seafood products is also investigated by reviewing the recent studies on their use as anti-microbial, anti-oxidant, coloring and flavoring agents as well as freshness indicators. Moreover, the current limitations of the use of plant-derived bioactive compounds as well as future prospects are discussed. The discoveries show high potential of those compounds and the possibility to apply on many different seafood. The compounds can be applied as individual while more and more studies are showing synergetic effect when those compounds are used in combination providing new important research possibilities.
Microbial transformations of cyclic hydrocarbons have received much attention during the past three decades. Interest in the degradation of environmental pollutants as well as in applications of microorganisms in the catalysis of chemical reactions has stimulated research in this area. The metabolic pathways of various aromatics, cycloalkanes, and terpenes in different microorganisms have been elucidated, and the genetics of several of these routes have been clarified. The toxicity of these compounds to microorganisms is very important in the microbial degradation of hydrocarbons, but not many researchers have studied the mechanism of this toxic action. In this review, we present general ideas derived from the various reports mentioning toxic effects. Most importantly, lipophilic hydrocarbons accumulate in the membrane lipid bilayer, affecting the structural and functional properties of these membranes. As a result of accumulated hydrocarbon molecules, the membrane loses its integrity, and an increase in permeability to protons and ions has been observed in several instances. Consequently, dissipation of the proton motive force and impairment of intracellular pH homeostasis occur. In addition to the effects of lipophilic compounds on the lipid part of the membrane, proteins embedded in the membrane are affected. The effects on the membrane-embedded proteins probably result to a large extent from changes in the lipid environment; however, direct effects of lipophilic compounds on membrane proteins have also been observed. Finally, the effectiveness of changes in membrane lipid composition, modification of outer membrane lipopolysaccharide, altered cell wall constituents, and active excretion systems in reducing the membrane concentrations of lipophilic compounds is discussed. Also, the adaptations (e.g., increase in lipid ordering, change in lipid/protein ratio) that compensate for the changes in membrane structure are treated.
Since prehistoric times, chemicals have been added to preserve freshly harvested foods for later use. Drying, cooling, fermenting, and heating have always been the primary methods used to prolong the shelf life of food products. Whereas some chemical food preservatives, such as salt, nitrites, and sulfites, have been in use for many years, most others have seen extensive use only recently. One of the reasons for increased use of chemical preservatives has been the change in the ways foods are produced and marketed. Today, consumers expect foods to be readily available yearround, to be “free” of foodborne pathogens, and to have a reasonably long shelf life. Although some improvements have been made using packaging and processing systems to preserve foods without chemicals, antimicrobial preservatives play a significant role in protecting the food supply (Davidson et al., 2002). In addition, because of changes in the marketing for foods to a more global system, products seldom are grown and sold locally as in the past. Today, foods produced in one area are often shipped to another area for processing and to several other areas for distribution. Several months or years may elapse from the time food is produced until it is consumed. To accomplish the long-term shelf life necessary for such a marketing system, multiple effective means of preservation are often required. It is important to note that, with rare exceptions, food antimicrobials are not able to conceal spoilage of a food product (i.e., the food remains wholesome during its extended shelf life). In addition, because food antimicrobials are generally bacteriostatic or fungistatic, they will not preserve a food indefinitely.
Aim: Caffeic acid phenethyl ester (CAPE) has cytotoxic, apoptotic, and antiproliferative effects on various tumor cells, and is the most active component of propolis. This study aimed to examine the in vitro effects of CAPE on the human multiple myeloma cell line. Materials and methods: CAPE was added to the ARH-77 multiple myeloma cell line and the percentage of dead cells was measured using the 3-(4,5-dimethyl-thiazoyl)-2,5-diphenyl-SH-tetrazolium bromide (MTT) assay. The percentage of live cells and growth inhibition were determined using the Trypan blue test. The percentage of IL-6 cells was determined using ELISA. Results: ARH-77 cells treated with CAPE for 72 h at the 100 μg mL -1 concentration resulted in a growth inhibition effect of 90.4% and a cytotoxic effect of 80.4%. CAPE induced apoptosis in 92.3% of the cells in 22.5 μg mL-1 at 72 h. CAPE inhibited the secretion of IL-6 by ARH-77 multiple myeloma cells at LD50 concentrations. Conclusion: CAPE inhibited growth and secretion of IL-6, and induced apoptosis in a dose-dependent and time-dependent manner in ARH-77 multiple myeloma cells. We think that CAPE merits further study as an effective agent against multiple myeloma.
This chapter focuses mainly on the treatments for face, as facial beauty and appearance are the most significant and recognizable yardstick of youth and aging in human societies. Antiaging cosmetic products are being developed with the most sophisticated cell and molecular biology techniques, including gene arrays, SAGE, and proteomics in scientific laboratories the world over, using isolated skin cells to pinpoint the beneficial effects of active ingredients. Such studies are followed by testing on three-dimensional skin equivalents, which alleviates the need for animal testing. An array of noninvasive techniques utilizing instrumentation to measure a wide array of skin responses, parameters, and physiological functions has aided the cosmetic scientist and the dermatologist in quantifying the biological effects for claim substantiation of antiaging products. True antiaging efforts should have a holistic approach, addressing not only skin care, but nutrition, wellness, balanced lifestyle, and stress management. The cosmetic industry is embracing such an approach, and with increasing consumer awareness industry investments in research and development efforts to meet this need, antiaging is no more just a buzzword.