Effects of resveratrol, oxyresveratrol, and their acetylated derivatives on cellular melanogenesis

Abstract

Resveratrol and oxyresveratrol are naturally occurring phenolic compounds with various bioactivities, but their uses in cosmetics have been partly limited by their chemical instabilities. This study was performed to examine the anti-melanogenic effects of the acetylated derivatives from resveratrol and oxyresveratrol. Resveratrol and oxyresveratrol were chemically modified to triacetyl resveratrol and tetraacetyl oxyresveratrol, respectively. The acetylated compounds were less susceptible than the parent compounds to oxidative discoloration. The acetylated compounds inhibited the activities of tyrosinases less than parent compounds in vitro, but they were as effective at cellular melanogenesis inhibition, indicating bioconversion to parent compounds inside cells. Supporting this notion, the parent compounds were regenerated when the acetylated compounds were digested with cell lysates. Although resveratrol and triacetyl resveratrol inhibited tyrosinase activity less effectively than oxyresveratrol and tetraacetyl oxyresveratrol in vitro, they inhibited cellular melanogenesis more effectively. This discrepancy was explained by strong inhibition of tyrosinase expression by resveratrol and triacetyl resveratrol. Experiments using a reconstituted skin model indicated that resveratrol derivatives can affect melanin synthesis and cell viability to different extents. Collectively, this study suggests that acetylated derivatives of resveratrol have great potential as anti-melanogenic agents for cosmetic use in terms of efficacy, safety, and stability.

Resveratrol-Enriched Rice Down-Regulates Melanin Synthesis in UVB-Induced Guinea Pigs Epidermal Skin Tissue

“…Recent reports have shown that resveratrol produced therapeutic effects against hyperplastic skin disorders by inhibiting keratinocyte proliferation , inhibited skin photoaging by acting as a Sirt-1 agonist (Lee et al, 2010), and showed anti-cancer effects in human melanoma cell lines (Niles et al, 2003). The anti-melanogenic effects of resveratrol and resveratrol analogs have already been reported by many other groups (Ohguchi et al, 2003;Song et al, 2012;Bae et al, 2013;Park and Boo, 2013;Park et al, 2014). We previously demonstrated the depigmentation effects of resveratrol in UVB-treated guinea pigs , too.…”

“…Interestingly, RR shows synergistic effects in comparison that of each resveratrol or rice alone (Baek et al, 2013;Baek et al, 2014). Several reports show that resveratrol decreases the expression of tyrosinase (Franco et al, 2012;Zheng et al, 2012;Bae et al, 2013;Park and Boo, 2013;Park et al, 2014), and Jun et al reported that gamma-oryzanol from rice extract dually inhibited cellular melanogenesis, too (Jun et al, 2012). Because each of resveratrol and rice had anti-melanogenic effects, we expected that RR would produce synergistic antimelanogenic effects and thus have some advantages over treatment with rice or resveratrol alone.…”

Relevance of Natural Phenolics from Grape and Derivative Products in the Formulation of Cosmetics

“…The cosmetic use of resveratrol and oxyresveratrol has been partly limited by their chemical instabilities. The acetylated derivatives triacetyl resveratrol and tetraacetyl oxyresveratrol are less susceptible to oxidative discoloration than resveratrol and oxyresveratrol, respectively, less active tyrosinase inhibitors and are as effective as the original compounds for cellular melanogenesis inhibition [49]. However, it is possible that topical application of resveratrol-containing products to skin exposed to sunlight could produce potential hazardous action [43].…”

Use of Polyphenolic Compounds in Dermatologic Oncology

“…Moreover, it has anti-inflammatory effects on macrophage, adipocyte, cultured adipocytes, and adipose tissue [162], as well as down-regulating tyrosinase [168] on melanocytes [166–171]. …”