Benefits Of Skin Application Of Piceatannol—A Minireview

Abstract

The skin is the largest organ of the human body and has several functions such as a barrier against external agents, the maintenance of temperature and homeostatic functions. Skinageing is a natural process that can be influenced by environmental factors, intrinsic skin factors and lifestyle. UV light plays an important role in skin ageing and can cause spots, requiring the use of depigmenting agents. Nowadays,  there is a great demand for ingredients that prevent skin ageing, with natural agents occupying a promising position. Among the natural agents, polyphenols,  such as resveratrol and piceatannol, found in grapes, passion fruits and other fruits, have a huge relevance. Great benefits of piceatannol have been reported,  so thus, this work focuses specifically on a review of the literature regarding the application of this polyphenol in skin care products. This polyphenol can be used in a wound-healing, or as an anti-ageing, antioxidant, anti-acne and skin whitening,  among other effects.

Glycoside of cistanche can also increase the activity of SOD in heart and liver tissues, and significantly reduce the content of lipofuscin and MDA in each tissue, effectively scavenging various reactive oxygen radicals (OH-, H₂O₂, etc.) and protecting against DNA damage caused by OH-radicals. Cistanche phenylethanoid glycosides have a strong scavenging ability of free radicals, a higher reducing ability than vitamin C, improve the activity of SOD in sperm suspension, reduce the content of MDA, and have a certain protective effect on sperm membrane function. Cistanche polysaccharides can enhance the activity of SOD and GSH-Px in erythrocytes and lung tissues of experimentally senescent mice caused by D-galactose, as well as reduce the content of MDA and collagen in lung and plasma, and increase the content of elastin, have a good scavenging effect on DPPH, prolong the time of hypoxia in senescent mice, improve the activity of SOD in serum, and delay the physiological degeneration of lung in experimentally senescent mice With cellular morphological degeneration, experiments have shown that Cistanche has the good antioxidant ability and has the potential to be a drug to prevent and treat skin aging diseases. At the same time, echinacoside in Cistanche has a significant ability to scavenge DPPH free radicals and has the ability to scavenge reactive oxygen species and prevent free radical-induced collagen degradation, and also has a good repair effect on thymine free radical anion damage.

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KEYWORDS 

antioxidant, piceatannol, polyphenol, skin

INTRODUCTION

Over the years our skin structure changes, the epidermal layer becomes thinner, wrinkles and spots may appear, and there is a major trans epidermal water loss,  especially in elderly individuals, resulting in dryness (xerosis). In addition, there is a reduction in skin elasticity, with decreased collagen and elastin. Nowadays, there is a great demand for agents that prevent skin ageing and skin darkening, and natural compounds occupy a  promising position.1

Piceatannol (3,3′,4′,5-trans-tetrahydroxystilbene) (Figure 1) is a stilbenoid compound and a resveratrol  analogue.2

A search was performed in PubMed from 2010 to 2019  concerning piceatannol and resveratrol (Figure 2).

It is possible to verify a growing interest in these phenolic compounds of natural origin. Only 473 articles about piceatannol and 10,986 about resveratrol were reported in the literature over the study time. It is possible to verify a much lower number of articles about piceatannol than resveratrol. It is less studied but displays a wide spectrum of biological activity, and some studies reveal better activity than resveratrol.2,3

NATURAL SOURCES OF  PICEATANNOL

Piceatannol can be found mainly in grapes. However,  there are already studies that report the presence of piceatannol in passion fruit, white tea and rhubarb, among others. As shown in Table 1, in some species, piceatannol can be found in seeds, while in other plants, it can found in leaves or rhizomes.

Regarding the piceatannol extraction from plants, there are some methods described in the literature, such as ultrasound, Soxhlet, maceration, microwave and supercritical fluid extraction. The extraction time, the solvent used and the temperature employed are some of the characteristics that must be taken into consideration in the selection of the piceatannol extraction method from the plant.

SKIN BENEFITS OF PICEATANNOL

Piceatannol has several beneficial effects on the skin,  namely skin whitening, antioxidant, anti-ageing, cutaneous wound-healing and anti-acne activity, and it presents anti-allergic effects and potential anti-cancer properties,  probably due to its ability to suppress the proliferation of a wide variety of tumour cells, including leukaemia, lymphoma, and breast and lung cancers.12,13

SKIN WHITENING ACTIVITY

Human skin colour originates from the outermost layer of the skin, the epidermis, where the pigment-producing cells, melanocytes, are localized to produce melanin. The distribution pattern of synthesized melanin by the melanocytes determines the actual colour of the skin. Melanin is formed by a process called melanogenesis through a combination of enzymatically catalysed and chemical reactions. The biosynthetic pathway of melanogenesis has been elucidated, where two types of melanin are synthesized within melanosomes: eumelanin and pheomelanin.14

Although melanin has mainly a photoprotective function, excess melanin production or abnormal distribution can cause irregular hyperpigmentation of the skin. Exposure to some drugs and chemicals, as well as the existence of certain diseases, can result in hyperpigmentation.15 For this reason, there is a high demand for melanogenesis inhibitors, which allowed for the reduction or prevent these hyperpigmented disorders.

The skin whitening agents appeared in the 60s of the 20th century with the discovery of hydroquinone to treat freckles, melasma, and senile lentigo, among others.16 As the  treatment of melasma is prolonged, the use of hydroquinone has its drawbacks, as it has various adverse effects,  such as irritation and loss of skin elasticity, contact dermatitis, nail pigmentation, sweat with bad odour, as well as  possible mutagenicity and carcinogenicity.17

In the last years, the studies regarding natural products have increased significantly, including natural depigmenting agents.18–20 Some researchers compared the effect of piceatannol and resveratrol, extracted from passion fruit seeds, on melanogenesis and collagen synthesis using cultivated human melanoma and fibroblast cells. It was verified that there was a significant increase in melanin synthesis inhibition, as well as an increase in collagen production in the samples tested with piceatannol and resveratrol, showing that piceatannol was superior to resveratrol in both cases, possibly due to the structure of the piceatannol, which presents one more hydroxyl group than resveratrol.8

The in vitro effect of passion fruit extract using human MNT-1 melanoma cells and human SF-TY fibroblast cells was studied for the inhibition of melanogenesis and the promotion of collagen synthesis. It  was demonstrated, due to the presence of polyphenols  such as piceatannol, resveratrol and curcumin B in passion fruit seed extract, that there was a strong inhibition  of melanin synthesis, as well as an increased collagen  synthesis.21

ANTIOXIDANT ACTIVITY

Antioxidants are regarded as promising agents that reduce skin oxidative stress. In recent years, naturally occurring compounds, such as phenolic acids, flavonoids and high molecular weight polyphenols, have gained considerable attention as beneficial protective agents. In vitro, the antioxidant activity of piceatannol in human fibroblast cells was investigated. It was demonstrated that piceatannol has  strong antioxidant activity even at low concentrations  and has a certain cytoprotective capacity.22

Piceatannol has a very strong antioxidant activity,  being similar to the antioxidant activity of ascorbic acid and superior to its analogue resveratrol.23 Piceatannol is more active than resveratrol due to the presence of an additional hydroxyl group at the 3′ position. The presence of an extra hydroxyl group in piceatannol makes it reactive and a more potent antioxidant when compared to resveratrol.3

Some researchers described the antioxidant effect of some polyphenols, including piceatannol, resveratrol and quercetin, using a porcine skin membrane-covered oxygen electrode (SCOE), an in vitro model to identify reactive oxygen species (ROS). The study was based on ROS  reactions that occur in the skin after topical application of piceatannol and other polyphenols, showing a great decrease in ROS effects.24

ANTI-AGEING ACTIVITY

A study was performed in Japan with women using capsules containing passion fruit seed extract, rich in piceatannol (5 mg). The study was conducted for 8weeks, and several measurements were made on the skin of women's cheeks, such as viscoelasticity and transepidermal water loss (TEWL). It was shown a significant increase in skin hydration in the users of the extract from the placebo. About the TEWL, there was a decrease in the group of those who used the passion fruit extract. Finally, the study concluded that due to the high antioxidant activity of piceatannol and increase in the collagen synthesis, skin hydration can be improved, preventing skin ageing.25

CUTANEOUS WOUND-HEALING ACTIVITY

As aforementioned, the skin can act as a  natural barrier against external agents. Skin damage over a large area of the body can cause serious health problems and even death. Wound healing is a natural and complex process involving several physiological factors such as anti-inflammatory, antioxidant and antimicrobial activities, participating in this process several growth factors,  such as the vascular endothelial growth factor (VEGF),  the cytokines and several hormones. Annually, many people suffer skin injuries, such as burns and ulcers caused  by diabetes mellitus or pressure, having to make use of  wound-healing agents.26

Studies using grape seed extract, rich in resveratrol and piceatannol, when tested in vitro on HaCaT keratinocyte cells, demonstrated wound-healing activity. This possibly occurred due to the large amounts of antioxidants in the extract. In vitro, tests were also performed with 293T cells demonstrating the effect of polyphenols, including piceatannol, on the inhibition of endothelial migration during wound-healing assays.27

ANTI-ACNE PROPERTIES

Piceatannol can also be used against Propionibacterium acnes (P. acnes). Acne vulgaris affects many people mainly in adolescence, and about 85% of the population presents this dermatosis. One of the bacteria belonging to the human face microbiota is P. acnes, gram-positive anaerobic bacteria, which is responsible for acne vulgaris. Certain cases of acne can be considered serious, causing inflammatory problems, scars and psychosocial problems, so it is necessary to use isotretinoin in the treatment. Due to the serious side effects of isotretinoin, it is necessary to investigate new natural products to treat acne effectively and safely.28

A study was conducted for 28days, with seventeen volunteers with acne, at an average age of 17 years, being applied to the face of a group, twice a day, a gel with berries (Rhodomyrtus tomentosa), and in the other group, a  placebo gel was applied. The berries extract had organic acids, rhodomirtone, piceatannol (500ppm) and other polyphenols. After the study, it was verified in the volunteers who used the gel with the natural extract had a significant decrease in acne symptoms, as well as a decrease in papules and black spots.28

Some researchers reported the comparison of the in vitro anti-acne activity of purple passion fruit extract (Passiflora edulis Sims var. edulis) with clindamycin and erythromycin, two antibiotics that are widely used to treat acne. The extract was obtained from passion fruit seeds by maceration, containing a large amount of piceatannol. As a result, the passion fruit extract showed the same results as the other two antibiotics used, showing a great inhibitory effect of P. acnes. 29 Recent studies have also shown that piceatannol inhibited the proliferation of human keratinocyte cells (HaCaT cell line) induced by P. acnes and no in vitro cytotoxicity was observed in this cell line.30

CONCLUSION

This review allows us to demonstrate in vitro and in vivo the potential of piceatannol, a polyphenol that can be found naturally in some fruits, such as passion fruit and grapes.

Studies indicate that piceatannol presents a strong antioxidant activity, even superior to its resveratrol analogue, possibly because piceatannol has one more hydroxyl group than resveratrol. In addition, it can be used topically due to its wound healing, anti-acne and skin whitening properties.

Besides a few phytochemical investigations on piceatannol, it was verified that there is much less research on the cutaneous application of this compound. It would, therefore, be an interesting research topic.

ACKNOWLEDGEMENTS

This work was supported by the Applied Molecular Biosciences Unit-UCIBIO, which is financed by national funds from FCT/MCTES (UID/Multi/04378/2019).

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