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Role of Anthocyanins in Skin Aging and UV Induced Skin Damage

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The visible changes associated with chronological aging and chronic sun exposure, especially to the face, head, and neck areas, are particularly concerning for a significantpercentage of the general population. This fact, along with the powerful influence of advertisement and the popular press, has led to an increasing demand for natural and efficient cosmetic ingredients that claim to reduce manifestations of skin aging. More importantly, while skin cancers account for up to 40% of the newly diagnosed cancers in the United States, there are no natural preventive methods to avoid cutaneous malignancies associated with chronic sunlight exposure for individuals with pigmentary traits associated with high cancer risk. Consequently, new effective antiaging and chemopreventive agents are in high demand. Although many of the skin-protective claims attributed to botanical products still lack sufficient scientific evidence, the use of natural bioactives with potential antiaging and/or skin-protective properties continues to receive attention from consumers. During the last decade, a substantial body of knowledge has been produced in this area. Polyphenols and most recently, anthocyanins ave been reported as potentially effective agents to prevent signs of skin aging and protect the skin from external injuries caused by ultraviolet (UV) radiation role of UV radiation, reactive oxygen species (ROS), inflammation, and extracellular matrix (ECM) remodeling in skin pathophysiology has allowed researchers to propose the specific molecular targets for anthocyanins and/or anthocyanin-rich extracts. Although some of the current research describes promising skin-protective effects for anthocyanins, most of the proposed dermatological applications still await clinical validation. This chapter reviews the current scientific literature on the potential of anthocyanins in preserving skin health and preventing skin aging.
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307
Role of Anthocyanins
inSkin Aging and UV-
Induced Skin Damage
Leonel E. Rojo, Diana E. Roopchand, Brittany Graf,
Diana M. Cheng, David Ribnicky, Bertold
Fridlender, and Ilya Raskin
11.1 INTRODUCTION
The visible changes associated with chronological aging and chronic sun exposure,
especially to the face, head, and neck areas, are particularly concerning for a sig-
nicant percentage of the general population. This fact, along with the powerful
inuence of advertisement and the popular press, has led to an increasing demand for
natural and efcient cosmetic ingredients that claim to reduce manifestations of skin
aging (Baumann etal., 2009). More importantly, while skin cancers account for up
to 40% of the newly diagnosed cancers in the United States (Afaq etal., 2005a), there
are no natural preventive methods to avoid cutaneous malignancies associated with
chronic sunlight exposure for individuals with pigmentary traits associated with
high cancer risk (Zanetti etal., 1996). Consequently, new effective antiaging and
chemopreventive agents are in high demand. Although many of the skin-protective
claims attributed to botanical products still lack sufcient scientic evidence, the
use of natural bioactives with potential antiaging and/or skin-protective properties
continues to receive attention from consumers. During the last decade, a substantial
body of knowledge has been produced in this area (Chiu and Kimball, 2003, Afaq
etal., 2002, 2005a, Afaq, 2011).
Polyphenols (Afaq etal., 2005a, Afaq and Katiyar, 2011, Kao etal., 2007, Kim
etal., 1998) and most recently, anthocyanins (Afaq etal., 2009, 2011, Lila, 2004,
11
CONTENTS
11.1 Introduction ..................................................................................................307
11.2 Skin Aging ....................................................................................................308
11.3 Anthocyanins and Skin Protection ...............................................................309
11.4 Current and Future Work .............................................................................. 312
11.5 Conclusions ................................................................................................... 315
Acknowledgments .................................................................................................. 316
References .............................................................................................................. 316
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308 Anthocyanins in Health and Disease
Schmidt et al., 2008, Schreckinger et al., 2010, Tsoyi et al., 2008d) have been
reported as potentially effective agents to prevent signs of skin aging and protect the
skin from external injuries caused by ultraviolet (UV) radiation (Afaq etal., 2011,
2010, Schreckinger etal., 2010, Tsoyi etal., 2008c). A better understanding of the
role of UV radiation, reactive oxygen species (ROS), inammation, and extracel-
lular matrix (ECM) remodeling in skin pathophysiology has allowed researchers
to propose the specic molecular targets for anthocyanins and/or anthocyanin-rich
extracts. Although some of the current research describes promising skin-protective
effects for anthocyanins, most of the proposed dermatological applications still await
clinical validation. This chapter reviews the current scientic literature on the poten-
tial of anthocyanins in preserving skin health and preventing skin aging.
11.2 SKIN AGING
Skin aging affects the dermis, epidermis, and hypodermis of the skin (Gomez and
Berman, 1985, Giangreco et al., 2008). It not only makes the skin look different
but also makes it more vulnerable to external injuries (Giangreco etal., 2008). The
epidermis, the most external layer of the skin, is mainly composed of keratinocytes
and is directly exposed to environmental aggressions (Figure 11.1). The dermis, rich
in connective tissues (structural proteins), such as collagen and elastin, is under the
epidermis and gives the young skin its characteristic strength, extensibility, and elas-
ticity (Figure 11.1). Skin aging is an intrinsic biological process, which inevitably
starts once a person reaches puberty (Farage etal., 2009) and is manifested by the
appearance of skin wrinkles, dryness, thinning of the skin, loss of subcutaneous fat,
and uneven pigmentation (Giacomoni, 2008). Each individuals genetic background
Oxidative
damage
Ultraviolet
radiation
Overexpression
of MMP's
Activation of NF-
κB/AP-1
Inflammation
Oxidative
damage
Overexpression
of MMP's
Activation of NF-
κB/AP-1
Inflammation
Merkel cells
Fibroblasts
Keratinocytes
Melanocyte
Collagen fibers
Elastin fibers
Sensory neuron
Langerhans cell
Epidermis
Dermis
FIGURE 11.1 (See color insert.) Schematic representation of the skin architecture and
mechanisms of skin damage.
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309Role of Anthocyanins inSkin Aging and UV- Induced Skin Damage
dictates when and how quickly the so-called “intrinsic aging process” unfolds
(Koehler etal., 2008). A number of factors can accelerate the intrinsic skin-aging
process, which includes weakened deoxyribonucleic acid (DNA)-repairing mech-
anisms, alterations of the mitochondrial function, slower repair of the ECM, and
alterations in cell cycle regulation. The most important extrinsic (accelerating) factor
of skin aging is exposure to UV radiation, although diet and smoking can also play a
key role in enhancing the appearance of signs of skin aging (Fazio etal., 1989, Fisher
etal., 2002, Sakuraoka etal., 1996). It is well known that the acute exposure to high
doses of UV radiation triggers the various inammatory pathways and oxidative
damage in the epidermis, dermis, and adnexal organs of the skin, especially UVB
radiation (290320 nm) (Afaq etal., 2005a, Fisher etal., 2002, Ting etal., 2003).
The UVA radiation (320400 nm) is less powerful than UVB, but can penetrate
deeper into the skin. In addition, the chronic exposure to high levels of UV radia-
tion can lead to accelerated skin aging (photoaging), hyperkeratosis or atrophy, and
precancerous lesions, such as squamous cell carcinomas (Afaq etal., 2005a, Farage
etal., 2009). One of the key molecular alterations associated with UV-induced skin
damage is the overexpression of metalloproteinases (MMPs), a family of zinc-depen-
dent endopeptidases capable of degrading proteins of the ECM, primarily collagen
and elastin. MMPs play an important physiological role in skin regeneration and
cell migration (adhesion/dispersion). However, repeated exposure to UV radiation
induces the overexpression of specic MMPs (e.g., MMP-9 and MMP-2) leading to
the degradation of skin collagen and elastin, incomplete repair of the ECM, loss of
skin elasticity and resilience, and the appearance of skin wrinkles. UV radiation also
triggers the increase in redox-sensitive transcription factors, including nuclear fac-
tor kappa-B, (NF-ĸB) and activator protein-1 (AP-1). Consequently, researchers are
actively looking for natural compounds or mixtures capable of blocking UV radia-
tion, suppressing UV-mediated oxidative damage, inhibiting UV-induced overexpres-
sion of MMPs, modulating NF-ĸB/AP-1 pathways, and decreasing skin inammation
(Figure 11.1).
11.3 ANTHOCYANINS AND SKIN PROTECTION
The known antioxidant power of anthocyanins has led researchers to study their
potential in preventing noncommunicable chronic diseases (Cao et al., 2000,
Chirinos et al., 2006, Grace et al., 2009, Prior and Wu, 2006, Rojo et al., 2012,
Schreckinger et al., 2010). However, the potential of anthocyanins in preventing
oxidative skin damage such as UV-induced erythema, skin cancer, and photoag-
ing have received less attention and only a relatively limited number of reports has
addressed this question (Afaq etal., 2005b, 2007, 2010, 2011). As the overexposure
to UVB radiation is among the most relevant risk factors for oxidative damage to
the skin, researchers have used various chemical and biological models to explore
the potential of anthocyanins in preventing UVB-induced skin damage. A recent in
vitro chemical study showed that a cosmetic formulation containing anthocyanins
from TNG73 purple sweet potato, at a concentration of 0.61 mg/100 g of cream,
could absorb up to 46% of the incident UV radiation (Chan etal., 2010). Although
this study was not performed using cellular or animal models of skin damage and
K14214_C011.indd 309 5/3/2013 7:15:27 PM
310 Anthocyanins in Health and Disease
has not been clinically conrmed, the results suggest that the topical application
of anthocyanins from TNG73 purple sweet potato at very low doses may prevent
UV-induced skin damage by decreasing the amount of UVB radiation reaching
the epidermis. This mechanism of skin protection is not unexpected, considering
that anthocyanins also attenuate UV damage in plants (Woodall and Stewart, 1998,
Harvaux and Kloppstech, 2001). Anthocyanins absorb strongly in the visible and UV
spectrums, with maximum absorbances in the ranges of 500–550 and 280–320 nm
(Harborne, 1958). The UV absorption capacity of anthocyanins varies depending on
their specic aglycones, sugar conjugation, and acylation patterns. Consequently, in
some colored plant species, other C6C3C6 avonoids, but not anthocyanins, are
responsible for the UV protection (Woodall and Stewart, 1998). More importantly,
for anthocyanin-rich UV-blocking formulations, it has been reported that acylated
anthocyanins containing coumaric acid, caffeic acid, and ferulic acid display the
enhanced adsorption of UVB radiation (Harborne, 1958). Chan et al. (2010) also
concluded that acidic ethanol-extracted anthocyanins have better radical scavenging
ability, higher total phenolic content, and stronger reducing ability than acidic water-
extracted anthocyanins from TNG73 purple sweet potato.
A variety of cellular and animal models have been used to elucidate the phar-
macological mechanism by which anthocyanins prevent UV-induced damage to the
skin (Table 11.1). A recent study using the reconstituted human skin (EpiD5erm(TM)
FT-200) showed that pomegranate-derived extracts and juices rich in anthocyanins
prevented UVB-induced damage to the dermal structures (Afaq etal., 2009). In this
study, the pomegranate-derived products were applied to reconstituted human skin
1 h prior to a 12-h UVB (60 mJ/cm
2
) irradiation period. The pomegranate-derived
products signicantly inhibited protein oxidation, elevation of cyclobutane pyrimi-
dine dimers (CPD), and 8-dihydro-2-deoxyguanosine (8-OHdG), suggesting the
protective effects against the oxidative damage to proteins and DNA. According to
the authors, anthocyanin-rich products from pomegranate also protected the ECM
of the skin by ameliorating the UVB-induced overexpression of various MMPs,
such as collagenase (MMP-1), gelatinase (MMP-2, MMP-9), stromelysin (MMP-3),
marilysin (MMP-7), and elastase (MMP-12). Similarly, another study showed that an
extract from the blueberry (Vaccinium uliginosum L.), rich in cyanidin-3-glucoside,
petunidin-3-glucoside, malvidin-3-glucoside, and delphinidin-3-glucoside, prevented
UVB-induced overexpression of MMPs and upregulated the UVB-induced suppres-
sion of collagen synthesis in human broblasts (Bae etal., 2009). These results sug-
gest that anthocyanins from the blueberry may offer protection against photoaging.
Another report by Cimino et al. (2006) showed that the anthocyanin cyanidin-3-
O-glucoside (C3G) inhibited UV-induced translocation of the transcription factors
NF-ĸB and AP-1 and other inammatory responses in keratinocytes. According to
these data, C3G could provide multifaceted protection against skin damage since
NF-ĸB and AP-1 are the key modulators of several cellular survival programs of
skin cells, including the synthesis of inammatory mediators, and effectors of both
innate and adaptive immunity. C3G was also found to prevent the UV-induced over-
expression of IL-8, caspase-3 activation, and DNA fragmentation in human kerati-
nocytes (Cimino etal., 2006). This evidence points to a potential protective role of
C3G-rich extracts, not only against UVB accumulative skin damage, but also against
K14214_C011.indd 310 5/3/2013 7:15:27 PM
311Role of Anthocyanins inSkin Aging and UV- Induced Skin Damage
TABLE 11.1
Skin-Protective Effects Reported for Anthocyanins
Anthocyanin(s)
Tested Reported Mode of Action
Type of
Study
Associated Skin
Disease Reference
Anthocyanins
(+reduced
glutathione)
Reduction of erythema after
radiation therapy in patients
with breast cancer
Clinical/
human
Radiation of
dermatitis,
discomfort
associated with
breast irradiation
Enomoto
etal.
(2005)
Cyanidin-3-O-β-
glucopyranoside
Protection against UVA-
induced oxidative stress in
human keratinocytes
In vitro Photoaging,
hyperkeratosis,
skin atrophy,
precancerous
lesions, and skin
cancer
Tarozzi
etal.
(2005)
C3G Reduction of UVB-induced
translocation of NF- B and
AP-1, overexpression of the
cytokines IL-8, apoptosis, and
DNA fragmentation in
cultured human keratinocytes.
In vitro Photoaging,
UV-induced
erythema
Cimino
etal.
(2006)
Anthocyanins (+
proanthocyanidin)
from Jacquez
grapes
Reduction of IL-1α and PGE2,
malondialdehyde/4-
hydroxynonenal, protein
carbonyl groups, and oxidized
glutathione, in human
reconstructed dermis
In vitro Photoaging,
UV-induced
erythema
Tomaino
etal.
(2006)
Delphinidin Protection of human HaCaT
keratinocytes and mouse skin
against UVB-mediated
oxidative stress and apoptosis
In vitro
and
invivo
Photoaging and
skin cancer
Afaq et al.
(2007)
Anthocyanin-rich
extract from red
orange
Reduction of UVB-induced
translocation of NF- B and
AP-1, anti-inammation in
cultured human keratinocytes.
In vitro Photoaging,
UV-induced
erythema
Cimino
etal.
(2007)
Black soybean seed
anthocyanins
Prevention of UVB-induced
apoptotic cell death,
inammation, COX-2, and
PGE2. Decreased production
of NF- B and inhibition of
phosphatidylinositol 3-kinase/
Akt pathway
In vitro
and
invivo
Photoaging,
hyperkeratosis,
skin atrophy,
precancerous
lesions, and skin
cancer
Tsoyi etal.
(2008)
Blueberry
anthocyanins
Amelioration of UVB-induced
damage to human dermal
broblasts
In vitro Photoaging,
precancerous
lesions, and skin
cancer
Bae etal.
(2009)
(continued)
K14214_C011.indd 311 5/3/2013 7:15:27 PM
312 Anthocyanins in Health and Disease
psoriasis, characterized by hyperactive NF-ĸB in keratinocytes. A similar effect was
documented using anthocyanins from bilberry and human keratinocytes as a model
of dermal UV-induced damage (Svobodova etal., 2008). This latter study showed
that anthocyanins from bilberry reduce UVA-stimulated ROS formation and lipid
peroxidation.
Analogous skin-protective mechanisms were documented in two separate publi-
cations from the same research group (Tsoyi etal., 2008a,b). According to these stud-
ies, anthocyanins from black soybean coats may offer protection against UV-induced
damage not only to cultured keratinocytes, but also in vivo to hairless mice skin.
At least two different modes of action were identied in these reports: (i) a reduc-
tion of UVB-induced elevation of cyclooxygenase-2 (COX-2) and prostaglandin E2
(PGE(2)) through a NF-ĸB-dependent pathways (Tsoyi et al., 2008b) and (ii) the
prevention of apoptotic cell death by inhibiting caspase-3 activation and reduction
of proapoptotic Bax protein levels (Tsoyi etal., 2008a). Delphinidin, an ubiquitous
anthocyanin, commonly found in edible berries (Escribano-Bailon et al., 2006,
Rojo etal., 2012, Schreckinger etal., 2010) has also shown the protective effect to
human HaCaT keratinocytes and mouse skin against UVB-mediated oxidative stress
and apoptosis (Afaq etal., 2009). Similarly, another anthocyanin, cyanidin-3-O-β-
glucopyranoside, was found to prevent UVA-induced damage to human keratino-
cytes (Tarozzi etal., 2005).
11.4 CURRENT AND FUTURE WORK
It is well known that oxidative damage, inammation, apoptotic cell death, and over-
expression of MMPs play a key role in skin aging and certain forms of UV-induced
skin damage. The accumulated scientic evidence suggests that anthocyanins may
offer the protection against UV-induced precancerous lesions and possibly delay the
appearance of signs of skin aging (Table 11.1). The protective effect of anthocyanins
and mode of action have been partially described in several in vitro and in vivo
TABLE 11.1 (continued)
Skin-Protective Effects Reported for Anthocyanins
Anthocyanin(s)
Tested Reported Mode of Action
Type of
Study
Associated Skin
Disease Reference
Bilberry
anthocyanins
Reduction of UVA-stimulated
oxidative damage to
keratinocytes
In vitro Photoaging,
hyperkeratosis,
skin atrophy,
precancerous
lesions, and skin
cancer
Bae et al.
(2009)
Anthocyanins from
TNG73 purple
potato
Absorption of 46% incident
UV radiation (0.61 mg/100 g
of cream)
In vitro Sun burns,
photoaging, and
UV-induced
erythema
Chan et al.
(2010)
K14214_C011.indd 312 5/3/2013 7:15:27 PM
313Role of Anthocyanins inSkin Aging and UV- Induced Skin Damage
models of skin damage. However, the current preclinical evidence is seemingly
insufcient to conclude that anthocyanins are solely responsible for the skin-protec-
tive properties observed in vitro and in vivo (Table 11.1) because various polyphenols
that are different from anthocyanins may be present in the test materials used for
these studies.
Additional work is needed to address another important innovation gap”; the
development of chemically stable and clinically effective anthocyanin-rich formula-
tions for dermatological applications. Only one clinical study was available at the
time this chapter was written. It reported that a multicomponent formulation con-
taining anthocyanins and glutathione signicantly reduced skin erythema after radi-
ation therapy in patients with breast cancer (Enomoto etal., 2005). Unfortunately,
the report provided very scarce information regarding the specic group of antho-
cyanins and doses used for topical applications.
Our research group has recently reported that anthocyanins, along with other
polyphenols, can be efciently separated from highly polar carbohydrates, bound,
concentrated, and stabilized into protein-rich, food matrixes, such as defatted soy-
bean our (DSF) and soy protein isolate (SPI), while preserving their pharmaco-
logical effects (Roopchand etal., 2012). The stability of anthocyanins captured in
this type of protein-rich matrices was veried up to 50 weeks (Figure 11.2) at 37°C.
This form of stabilized anthocyanins opens challenging avenues to develop stable
0
20
40
60
80
100
120
140
SPI Blueberry-SPI Maqui berry-SPI Cranberry-SPI
Relative MMP-9 activity (%)
*
*
*
FIGURE 11.2 Effect of anthocyanin-rich protein matrix on MMP-9 activity in vitro. The
polyphenols including anthocyanins from different sources were concentrated and stabilized
in SPI. The concentrations of anthocyanins bound to SPI are shown in Table 11.2. The SPI-
enriched matrices were suspended in water mixed with recombinant human MMP-9 (1 µg/
mL in PBS) and dye-quenched (DQ) gelatin (1 mg/mL in PBS), a uorescent quenched sub-
strate of MMP-9. Anthocyanin-enriched matrices (1.5 mg/mL) were incubated with 0.4 µg/
mL MMP-9, and 50 µg/mL DQ gelatin at 37°C for 30 min, centrifuged to precipitate solids,
and the supernatant was transferred to a 96-well plate to measure MMP-9 activity. The data
are reported as the percentage of the inhibition of MMP-9 activity relative to control (SPI).
The values correspond to the mean of the three replicates ± SD (*), P < 0.05, and t-test.
K14214_C011.indd 313 5/3/2013 7:15:28 PM
314 Anthocyanins in Health and Disease
dermatological and cosmetic anthocyanin-rich formulations with the application
in cosmetics and food products. We also evaluated whether the SPI with electro-
statically bound and concentrated anthocyanins and other polyphenols from maqui
berry, blueberry, and cranberry retains the antioxidant capacity and human MMP-9
inhibitory activity of its components. According to our results, these anthocyanin-
rich matrices not only displayed a powerful antioxidant capacity (Table 11.2), but
also inhibited collagen degradation by human MMP-9 (Figure 11.3), a collagenase
known to participate in UV-induced skin damage. The molecular mechanisms by
TABLE 11.2
ORAC Antioxidant Capacity of Different Anthocyanin- Rich Soy Protein
Matrices from Fruits
Anthocyanins
(mg/g)
Phenolics
(mg/g)
ORAC
a
(Trolox
Equivalents
(µmol/g)
Representative Kinetic Curve of
AAPH
b
-induced Fluorescence
Decay
Maqui
berry–SPI
32 80
1090 ± 130
30
20
10
Fluorescence
0
10 20 30 40
Min
50 60 70
Blueberry–
SPI
29 251
1380 ± 360
30
Fluorescence
20
10
0
10 20 30 40
Min
50 60 70
Cranberry–
SPI
16 290
1550 ± 200
30
20
10
Fluorescence
0
10 20 30 40
Min
50 60 70
SPI
230 ± 110
30
20
10
Fluorescence
0
10 20 30 40
50
Min
60 70
Note: SPI, Soy protein isolate.
a
ORAC, Oxygen radical absorbance capacity.
b
AAPH, 2,2-Azobis (2-amidinopropane) hydrochloride.
K14214_C011.indd 314 5/3/2013 7:15:31 PM
315Role of Anthocyanins inSkin Aging and UV- Induced Skin Damage
which polyphenols bound to SPI inhibit MMP-9 activity remain to be elucidated; our
hypothesis is that the specic and nonspecic mechanisms may explain this inhibi-
tion and are worthy of further investigations.
11.5 CONCLUSIONS
The previous publications and the presented data suggest that anthocyanins from
plants can prevent skin aging and UV-induced skin damage, particularly in formula-
tions that enhance their stability to temperature, pH, and light (Gironés-Vilaplana
etal., 2012, Roopchand etal., 2012, Schreckinger etal., 2010). For example, acyl-
ated anthocyanins have shown increased stability to pH offering a natural and safer
alternative to synthetic dyes for food and cosmetics (Giusti and Wrolstadb, 2003).
However, the skin-protective properties of acylated anthocyanins from plants are
scarcely studied (Schreckinger etal., 2010). Other authors have addressed this prob-
lem by stabilizing anthocyanins from Aristotelia chilensis in beverages using lemon
juice (Gironés-Vilaplana etal., 2012). Stabilizing anthocyanins by electrostatically
binding them to protein matrices may provide another strategy for protecting their
structural integrity, function, and color (Roopchand etal., 2012). We hope that in the
150
Anthocyanins
(a)
(b)
Total polyphenols
125
100
75
mg/Lmg/L
50
25
0
400
300
200
100
0
0 2 4 8 12 16
Weeks
22 24 28 38 50
FIGURE 11.3 Stability of blueberry anthocyanins and polyphenols bound to DSF. The con-
centration of (a) monomeric anthocyanins and (b) total polyphenols are eluted from blue-
berry polyphenol-enriched DSF after the indicated number of weeks postincubation at 37°C.
Polyphenolic compounds were eluted from DSF with 75% methanol, 20% water, 5% acetic
acid solution, and the quantications were done as described elsewhere. (From Roopchand, D.
et al. 2012. Food Chemistry, 131, 1193–1200.)
K14214_C011.indd 315 5/3/2013 7:15:31 PM
316 Anthocyanins in Health and Disease
future, the intense and beautiful colors of free or stabilized anthocyanins may offer
a possibility for developing naturally colored cosmetics with skin-protecting and
antiaging properties.
ACKNOWLEDGMENTS
This work was supported in part by the NIH training grant T32 AT004094 (support-
ing DER) and by P50AT002776-01 and 2P50AT002776-06 grants from the National
Center for Complementary and Alternative Medicine (NCCAM) and the Ofce of
Dietary Supplements (ODS) that funds the Botanical Research Center of Pennington
Biomedical Research Center and the Department of Plant Biology and Pathology at
Rutgers University.
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Vilaplana et al. (2012)
... Their glycons are named anthocyanidins [5]. They are flavorless and odorless and vary in kind from purple, blue, red, orange, or in the coloration of different plant organs such as tubers, fruit, root, leaf, stem and flower [6][7][8][9]. The stability of anthocyanin is dependent on temperature, structure, light, and pH [10]. ...
... Anthocyanins have been shown to work as a "sunscreen" guarding cells from damage by UV light absorbing, additional to their ability to prevent the generation of free radicals by blue light and UV by their effective antioxidant property [9]. The current study aim is to detect the antioxidant features of the red petal (calyces) extract of Roselle and study its ability to conserve human DNA from damage by UV and free radicals. ...
Article
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The extract of Hibiscus sabdariffa calyces are a rich source of healthy benefit phytochemicals, especially anthocyanins, which are flavonoid plant pigments with antioxidant effects. Roselle (Hibiscus) extract was prepared and the functional groups of the main compounds were detected by UV-VIS spectrum and Fourier transform infrared spectroscopy (FT-IR). The extract's antioxidant capacity was detected using radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging action and ferric reducing antioxidant power. The human genomic DNA damage inhibition was tested and in-silico studied by docking of some Roselles anthocyanin compounds into the DNA. The main functional groups of Roselle anthocyanin compounds were detected by FT-IR and their peaks appeared at 282 nm and 520 nm UV-VIS spectrum. Additionally, the Roselle extract shows a powerful reducing power activity and antioxidant activity with IC 50 of about 105.9 ± 4.56 µg/ml besides the extract efficiently inhibits DNA damage by UV-radiant and free radicals. That was confirmed by the docking study of more common Hibiscus anthocyanin compounds, (Delphinidin 3 sambubioside) and (Cyanidin 3 sambubioside) into the DNA which formed docking conformations with stable bonds in the possible interaction of each of the compounds with the DNA as well as good binding energy (-5.62 and-6.74 kcal/mol) and lowest intermolecular energy (-10.69 and-11.24 kcal/mol) for them respectively. Therefore, Hibiscus calyces extract displayed potent human genomic DNA protection activity and can be used for DNA preservation and cancer inhibitors.
... Their glycons are named anthocyanidins [5]. They are flavorless and odorless and vary in kind from purple, blue, red, orange, or in the coloration of different plant organs such as tubers, fruit, root, leaf, stem and flower [6][7][8][9]. The stability of anthocyanin is dependent on temperature, structure, light, and pH [10]. ...
... Anthocyanins have been shown to work as a "sunscreen" guarding cells from damage by UV light absorbing, additional to their ability to prevent the generation of free radicals by blue light and UV by their effective antioxidant property [9]. The current study aim is to detect the antioxidant features of the red petal (calyces) extract of Roselle and study its ability to conserve human DNA from damage by UV and free radicals. ...
Article
Full-text available
The extract of Hibiscus sabdariffa calyces are a rich source of healthy benefit phytochemicals, especially anthocyanins, which are flavonoid plant pigments with antioxidant effects. Roselle (Hibiscus) extract was prepared and the functional groups of the main compounds were detected by UV–VIS spectrum and Fourier transform infrared spectroscopy (FT-IR). The extract's antioxidant capacity was detected using radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging action and ferric reducing antioxidant power. The human genomic DNA damage inhibition was tested and in - silico studied by docking of some Roselles anthocyanin compounds into the DNA. The main functional groups of Roselle anthocyanin compounds were detected by FT-IR and their peaks appeared at 282 nm and 520 nm UV-VIS spectrum. Additionally, the Roselle extract shows a powerful reducing power activity and antioxidant activity with IC50 of about 105.9 ± 4.56 µg/ml besides the extract efficiently inhibits DNA damage by UV-radiant and free radicals. That was confirmed by the docking study of more common Hibiscus anthocyanin compounds, (Delphinidin 3 sambubioside) and (Cyanidin 3 sambubioside) into the DNA which formed docking conformations with stable bonds in the possible interaction of each of the compounds with the DNA as well as good binding energy (-5.62 and-6.74 kcal/mol) and lowest intermolecular energy (-10.69 and - 11.24 kcal/mol) for them respectively. Therefore, Hibiscus calyces extract displayed potent human genomic DNA protection activity and can be used for DNA preservation and cancer inhibitors.
... Their glycons are named anthocyanidins [5]. They are flavorless and odorless and vary in kind from purple, blue, red, orange, or in the coloration of different plant organs such as tubers, fruit, root, leaf, stem and flower [6][7][8][9]. The stability of anthocyanin is dependent on temperature, structure, light, and pH [10]. ...
... Anthocyanins have been shown to work as a "sunscreen" guarding cells from damage by UV light absorbing, additional to their ability to prevent the generation of free radicals by blue light and UV by their effective antioxidant property [9]. The current study aim is to detect the antioxidant features of the red petal (calyces) extract of Roselle and study its ability to conserve human DNA from damage by UV and free radicals. ...
Article
Full-text available
The extract of Hibiscus sabdariffa calyces are a rich source of healthy benefit phytochemicals, especially anthocyanins, which are flavonoid plant pigments with antioxidant effects. Roselle (Hibiscus) extract was prepared and the functional groups of the main compounds were detected by UV-VIS spectrum and Fourier transform infrared spectroscopy (FT-IR). The extract's antioxidant capacity was detected using radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging action and ferric reducing antioxidant power. The human genomic DNA damage inhibition was tested and in-silico studied by docking of some Roselles anthocyanin compounds into the DNA. The main functional groups of Roselle anthocyanin compounds were detected by FT-IR and their peaks appeared at 282 nm and 520 nm UV-VIS spectrum. Additionally, the Roselle extract shows a powerful reducing power activity and antioxidant activity with IC 50 of about 105.9 ± 4.56 µg/ml besides the extract efficiently inhibits DNA damage by UV-radiant and free radicals. That was confirmed by the docking study of more common Hibiscus anthocyanin compounds, (Delphinidin 3 sambubioside) and (Cyanidin 3 sambubioside) into the DNA which formed docking conformations with stable bonds in the possible interaction of each of the compounds with the DNA as well as good binding energy (-5.62 and-6.74 kcal/mol) and lowest intermolecular energy (-10.69 and-11.24 kcal/mol) for them respectively. Therefore, Hibiscus calyces extract displayed potent human genomic DNA protection activity and can be used for DNA preservation and cancer inhibitors.
... It is an excellent antioxidant. Currently, previous studies have reported that Aristotelia chilensis has anti-glycation, anti-inflammation, lipogenesis-inhibiting activities highly related to its anti-oxidation function, [16][17][18] but practical efficacy studies on immunological mechanisms of Aristotelia chilensis for skin related diseases, especially atopic dermatitis, have not been reported yet. ...
... The major component of the extract Aristotelia chilensis was known as anthocyanin, which contained the highest amount of delphinidin. 16 ...
Article
Background: Maqui berry (Aristotelia chilensis) has been reported to have anti-glycation, anti-inflammation, lipogenesis-inhibiting activities highly related to its anti-oxidation function, but practical efficacy studies on immunological mechanisms for atopic dermatitis, have not been reported yet. Objective: This study investigated the immune regulation mechanism of Aristotelia chilensis water extract (ACWE) related to atopic-like dermatitis . Methods: Antioxidant and anti-inflammatory effects of ACWE was assayed. Atopy inhibitory effect was evaluated using in vitro cell study and in vivo 2,4-dinitrochlorobenzene (DNCB)-induced mouse atopic-like dermatitis model. Results: ACWE has good antioxidant activities, and atopic indications were improved in ACWE group in DNCB-induced atopic-like dermatitis model of BALB/c mice. In spleen cells from mice, ACWE increased interferon-gamma (IFN-γ) levels, and decreased interleukin-4 (IL-4) levels compared with the DNCB control. Conclusions: ACWE was efficacious for atopic dermatitis which indicates that ACWE might have potential as an agent for atopic dermatitis.
... These anthocyanins play a major role in the activity of pomegranate as antioxidant and cancerprotective especially skin cancers (7,8). Anthocyanins also reported for their protective effect against UV-induced skin erythema and skin cancer (9). Furthermore, anthocyanins isolated from purple sweet potato prevented UV-induced skin damage at very low concentrations by decreasing the UV radiation reaching skin (9). ...
... Anthocyanins also reported for their protective effect against UV-induced skin erythema and skin cancer (9). Furthermore, anthocyanins isolated from purple sweet potato prevented UV-induced skin damage at very low concentrations by decreasing the UV radiation reaching skin (9). Also, anthocyanins through their effect as an antioxidant are improving the mitochondrial activity and useful in preventing oxidative damage of the skin (10). ...
Article
Background: Anthocyanins are antioxidant compounds constitute the primary dyes of the pomegranate arils. Anthocyanins could protect the aged skin induced by oxidant exposure as a major role in aging processing and skin degeneration. Purpose: The study aimed to evaluate the anti-aging activity of anthocyanins rich pomegranate (Punica granatum) after formulated into a topical cream. Also, its effect on human dermal fibroblast function and epidermal keratinocyte were evaluated. Method: Anthocyanins were extracted from fresh pomegranate arils using acidified methanol and were purified by Sephadex LH-20 gel-column chromatography. Further, the fusion method was used to prepare cold cream containing pomegranate anthocyanins. The formulated cream was evaluated for their compatibility study, irritation, homogeneity, drug content, drug release, and stability tests. Furthermore, permeation study through abdominal rabbits, as well as Human application was performed. Results: Compatibility study showed the absence of any interaction between anthocyanins and the used polymers. The formulated cream was nonirritant, homogenous and potentially reduced skin aging when applied to Human volunteers’ skin. Furthermore, the skin permeation displayed a good permeation of 43.16% after 210 min. Conclusion: Pomegranate anthocyanins could be used as a safe, stable, homogeneous, nonirritant and effective topical anti-aging drug formulation for aged human people.
... 39 These MMPs perform an important physiological role in skin regeneration and cell migration (adhesion/ dispersion). 40 Other studies also reported that the anthocyanin C3G inhibits UV-induced translocation of NF-ĸB and AP-1 and other inflammatory responses in keratinocytes. ...
Article
Full-text available
Background: Recently, emulgel has emerged as a potential hydrophobic drug delivery method. Therefore, this study aims to evaluate the phytochemical content of Oryza sativa extract and develop an emulgel formulation using Carbapol 940 as a gelling agent. Materials and Methods: The emulsion was placed in a gel basis after preparation and the formulations were evaluated for their rheology, pH, spreading coefficient, stability, and sun protection factor. Then, phytochemical analysis of O. sativa extract was used to determine the presence of alkaloids, flavonoids, polyphenols, quinones, monoterpenoids, and sesquiterpenoids, as well as triterpenoids and steroids. Results: The entire formulations of O. sativa emulgel extract filled the emulgel formulation criteria. Furthermore, O. sativa emulgel protects against UV radiation, as indicated by the SPF value in each formulation, which increases as the dose of O. sativa extract increases. Based on the results, formulations 2 and 3 have an SPF of 5.71±0.063 and 16.07±0.072, respectively. These suggest that they both fill the Indonesian National Standard, which requires a sunscreen preparation with a minimum of four protection. Conclusion: Consequently, O. sativa emulgel extract can serve as a novel sunscreen agent against UV radiation. However, further study is required to ascertain the mechanism of action of the active chemicals found in O. sativa that function as an antioxidant and give protection against UV radiation.
... Due to their previously stated physical-chemical characteristics, these compounds constitute a potential source of anti-aging modulators. In fact, several studies mostly using cellular and animal skin models have revealed promising and elucidating results about the pharmacological mechanisms by which anthocyanins prevent UV-induced skin damage [77]. ...
Article
Full-text available
Due to their physical and chemical characteristics, anthocyanins are amongst the most versatile groups of natural compounds. Such unique signature makes these compounds a focus in several different areas of research. Anthocyanins have well been reported as bioactive compounds in a myriad of health disorders such as cardiovascular diseases, cancer, and obesity, among others, due to their anti-inflammatory, antioxidant, anti-diabetic, anti-bacterial, and anti-proliferative capacities. Such a vast number of action mechanisms may be also due to the number of structurally different anthocyanins plus their related derivatives. In this review, we highlight the recent advances on the potential use of anthocyanins in biological systems with particular focus on their photoprotective properties. Topics such as skin aging and eye degenerative diseases, highly influenced by light, and the action of anthocyanins against such damages will be discussed. Photodynamic Therapy and the potential role of anthocyanins as novel photosensitizers will be also a central theme of this review.
... Topical applications of low-dose anthocyanins from purple sweet potato prevent UV-induced skin damage by decreasing the amount of UVB radiation reaching the epidermis. 7 Anthocyanins from blueberries inhibited photoaging in UV-Birradiated human dermal fibroblasts via reduction of collagenolytic matrix metalloproteinases. 8 Several by-products of purple corn (Zea mays L.), eg, silk, cob, and husk, are increasingly investigated for potential since they are rich in anthocyanins. ...
Article
Full-text available
Cob and silk of purple waxy corn ( Zea mays L. Ceratina Kulesh) are underutilized sources of anthocyanins, which could be extracted by various solvents: water, ethanol, methanol, 50% ethanol, and 50% methanol. Anthocyanin and melatonin levels were investigated. The quantifications of anthocyanins as cyanidin-3-glucoside, pelargonidin-3-glucoside, and peonidin-3-glucoside were determined by high-performance liquid chromatography combined with mass spectrometry (HPLC-MS/MS), and melatonin by HPLC-fluorescence. The ability of collagen production upon exposure to human skin fibroblasts from the different macerates of the cob and silk was also studied. All cob extracts showed higher level of anthocyanins than silk extracts. The 50% ethanol extract of cob showed the highest cyanidin-3-glucoside level at 2.42 ± 0.03 mg/g dried weight, whereas that of silk showed the highest content of cyanidin-3-glucoside at 1.95 ± 0.04 mg/g dried weight. Although cob extracts contained more anthocyanins than silk extracts, silk extracts could stimulate collagen production more than cob extracts. Therefore, the collagen production was likely due to the amount of melatonin in the silk extracts, which contained greater quantities than those of the cob, and the lipophilicity of melatonin or the hydrophilicity of anthocyanins also affected the ability of cell permeation. Thus, anthocyanins and melatonin levels should be considered for the biological activity study.
Article
Full-text available
Due to their physical and chemical characteristics, anthocyanins are amongst the most versatile groups of natural compounds. Such unique signature makes these compounds a focus in several different areas of research. Anthocyanins have well been reported as bioactive compounds in a myriad of health disorders such as cardiovascular diseases, cancer, and obesity, among others, due to their anti-inflammatory, antioxidant, anti-diabetic, anti-bacterial, and anti-proliferative capacities. Such a vast number of action mechanisms may be also due to the number of structurally different anthocyanins plus their related derivatives. In this review, we highlight the recent advances on the potential use of anthocyanins in biological systems with particular focus on their photoprotective properties. Topics such as skin aging and eye degenerative diseases, highly influenced by light, and the action of anthocyanins against such damages will be discussed. Photodynamic Therapy and the potential role of anthocyanins as novel photosensitizers will be also a central theme of this review.
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Full-text available
Until today, numerous studies evaluated the topic of anthocyanins and various types of cancer, regarding the anthocyanins’ preventative and inhibitory effects, underlying molecular mechanisms, and such. However, there is no targeted review available regarding the anticarcinogenic effects of dietary anthocyanins on skin cancers. If diagnosed at the early stages, the survival rate of skin cancer is quite high. Nevertheless, the metastatic form has a short prognosis. In fact, the incidence of melanoma skin cancer, the type with high mortality, has increased exponentially over the last 30 years, causing the majority of skin cancer deaths. Malignant melanoma is considered a highly destructive type of skin cancer due to its particular capacity to grow and spread faster than any other type of cancers. Plants, in general, have been used in disease treatment for a long time, and medicinal plants are commonly a part of anticancer drugs on the market. Accordingly, this work primarily aims to emphasize the most recent improvements on the anticarcinogenic effects of anthocyanins from different plant sources, with an in-depth emphasis on melanoma skin cancer. We also briefly summarized the anthocyanin chemistry, their rich dietary sources in flowers, fruits, and vegetables, as well as their associated potential health benefits. Additionally, the importance of anthocyanins in topical applications such as their use in cosmetics is also given.
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The present study demonstrated that defatted soybean flour (DSF) can sorb polyphenols from blueberry and cranberry juices while separating them from sugars. Depending on DSF concentration and juice dilution, the concentration of blueberry anthocyanins and total polyphenols sorbed to DSF ranged from 2 - 22 mg/g and 10 - 95 mg/g, respectively while the concentration of anthocyanins and proanthocyanidins in cranberry polyphenol-enriched DSF ranged from 2.5 - 17 mg/g and 21 - 101 mg/g, respectively. Blueberry polyphenols present in one serving of fresh blueberries (73g) were delivered in just 1.4 g of blueberry polyphenol-enriched DSF. Similarly, one gram of cranberry polyphenol-enriched DSF delivered the amount of proanthocyanidins available in three 240 ml servings of cranberry juice cocktail. The concentration of blueberry anthocyanins and total polyphenols eluted from DSF remained constant after 22 weeks of incubation at 37°C, demonstrating the high stability of the polyphenol-DSF matrix. LC-MS analysis of eluates confirmed DSF retained major cranberry and blueberry polyphenols remained intact. Blueberry polyphenol-enriched DSF exhibited significant hypoglycemic activities in C57bl/6J mice, and cranberry polyphenol-enriched DSF showed anti-microbial and anti-UTI activities in vitro, confirming its efficacy. The described sorption process provides a means to create protein-rich food ingredients containing concentrated plant bioactives without excess sugars, fats and water that can be incorporated in a variety of scientifically validated functional foods and dietary supplements.
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The biological function of juvenile leaves pigmented with anthocyanin is poorly understood. The role anthocyanins play in UV protection was assessed in juvenile leaves of two Syzygium species (S. luehmannii and S. wilsonii) which contain high anthocyanin concentrations. HPLC was used to separate UV-absorbing anthocyanins from other soluble UV-absorbing phenolic compounds. The isolated anthocyanins (predominantly malvidin-3,5-diglucoside) contributed little to the total absorbance of UV-A and UV-B radiation. This was because the non-acylated anthocyanins only effectively absorbed shortwave UV-B radiation and the strong absorbance by other compounds. These results suggest that the UV protection hypothesis is not valid for anthocyanins in juvenile Syzygium leaves.
Article
Polyphenols are a large family of naturally occurring plant products and are widely distributed in plant foods, such as, fruits, vegetables, nuts, flowers, bark and seeds, etc. These polyphenols contribute to the beneficial health effects of dietary products. Clinical and epidemiological studies suggest that exposure of the skin to environmental factors/pollutants, such as solar ultraviolet (UV) radiation induce harmful effects and leads to various skin diseases including the risk of melanoma and non-melanoma skin cancers. The incidence of non-melanoma skin cancer, comprising of squamous cell carcinoma and basal cell carcinoma, is a significant public health concern world-wide. Exposure of the skin to solar UV radiation results in inflammation, oxidative stress, DNA damage, dysregulation of cellular signaling pathways and immunosuppression thereby resulting in skin cancer. The regular intake of natural plant products, especially polyphenols, which are widely present in fruits, vegetables, dry legumes and beverages have gained considerable attention as protective agents against the adverse effects of UV radiation. In this article, we first discussed the impact of polyphenols on human health based on their structure-activity relationship and bioavailability. We then discussed in detail the photoprotective effects of some selected polyphenols on UV-induced skin inflammation, proliferation, immunosuppression, DNA damage and dysregulation of important cellular signaling pathways and their implications in skin cancer management. The selected polyphenols include: green tea polyphenols, pomegranate fruit extract, grape seed proanthocyanidins, resveratrol, silymarin, genistein and delphinidin. The new information on the mechanisms of action of these polyphenols supports their potential use in skin photoprotection and prevention of photocarcinogenesis in humans.
Article
Ultraviolet (UV) radiation can cause inflammatory changes and may further contribute to skin carcinogenesis. Anthocyanins are known to be powerful antioxidants that help protect plants from UV damage. Recently, we isolated anthocyanins from black soybean [Glycine max (L.) Merr] seed coats. Thus, we investigated the protective effect of anthocyanins from black soybean seed coats on UVB radiation-induced inflammatory responses and the molecular mechanism responsible for regulation of apoptosis and inflammatory responses. Anthocyanins inhibited UVB-induced cylooxygenase-2 (COX-2) and PGE 2 production through a nuclear factor-kappaB-dependent pathway and regulation of the PI3 kinase/Akt pathway activated by UVB in a human keratinocyte cell line, HaCaT. Topical application of anthocyanins prior to UVB irradiation of hairless mice also inhibited induction of COX-2 and PGE 2. In conclusion, it is suggested that anthocyanins from the seed coat of black soybeans can be used as a useful drug to modulate oxidative disorders including UVB-induced inflammation.
Article
The biological function of juvenile leaves pigmented with anthocyanin is poorly understood. The role anthocyanins play in UV protection was assessed in juvenile leaves of two Syzygium species (S. luehmannii and S. wilsonii) which contain high anthocyanin concentrations. HPLC was used to separate UV-absorbing anthocyanins from other soluble UV-absorbing phenolic compounds. The isolated anthocyanins (predominantly malvidin-3,5-diglucoside) contributed little to the total absorbance of UV-A and UV-B radiation. This was because the non-acylated anthocyanins only effectively absorbed shortwave UV-B radiation and the strong absorbance by other compounds. These results suggest that the UV protection hypothesis is not valid for anthocyanins in juvenile Syzygium leaves.
Article
We used a murine model of type II diabetes, which reproduces the major features of the human disease, and a number of cellular models to study the antidiabetic effect of ANC, a standardised anthocyanin-rich formulation from Maqui Berry (Aristotelia chilensis). We also isolated delphinidin 3-sambubioside-5-glucoside (D3S5G), a characteristic anthocyanin from Maqui Berry, and studied its antidiabetic properties. We observed that oral administration of ANC improved fasting blood glucose levels and glucose tolerance in hyperglycaemic obese C57BL/6J mice fed a high fat diet. In H4IIE rat liver cells, ANC decreased glucose production and enhanced the insulin-stimulated down regulation of the gluconeogenic enzyme, glucose-6-phosphatase. In L6 myotubes ANC treatment increased both insulin and non-insulin mediated glucose uptake. As with the ACN, oral administration of pure D3S5G dose-dependently decreased fasting blood glucose levels in obese C57BL/6J mice, and decreased glucose production in rat liver cells. D3S5G also increased glucose uptake in L6 myotubes and is at least partially responsible for ANC’s anti-diabetic properties.