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Skin Whitening Capability of Shikimic Acid Pathway Compounds

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Skin Whitening Capability of Shikimic Acid Pathway Compounds European Review for Medical and Pharmacological Sciences 2016; 20: 1214-1220 Skin whitening capability of shikimic acid pathway compounds Y.-H. CHEN1, L. HUANG1, Z.-H. WEN5, C. ZHANG2, C.-H. LIANG3, S.-T. LAI3, L.-Z. LUO4, Y.-Y. WANG4, G.-H. WANG1 1Department of Pharmacy and Research Center of Natural Cosmeceuticals Engineering (RCNCE), Xiamen Medical College, Xiamen, China 2Department of Research Engineering, Xiamen TRIZ Laboratories Limited, Xiamen, China 3Department of Cosmetic Science, Chia Nan University of Pharmacy and Science, Tainan, Taiwan 4Department of Pharmacy, Xiamen Medical College, Xiamen, China 5Department of Marine Biotechnology and Resources and Asia-Pacific Ocean Research Center, National Sun Yat-sen University, Kaohsiung, Taiwan Yung-Husan Chen, Lisen Huang, Zhi-Hong Wen and Chunyi Zhang contributed equally to this work Abstract. – OBJECTIVE: To examine the skin Introduction whitening capabilities of shikimic acid pathway compounds and find the most effective mole- Nowadays, skin-caring and anti-aging cos- cule to be used as the active ingredient for skin metics are in the center of attention in differ- whitening products. ent societies in countries around the world and MATERIALS AND METHODS: Skin whitening is the practice of using chemical substances to Asia there is a boom in this industry. Over- lighten skin tone by the lessening the concen- exposure to the sun may result in some unde- tration of melanin. The whitening efficacy of shi- sirable effects on the skin health. Ultraviolet kimic acid pathway compounds was evaluated. ray (UV) in sunlight has a disordering effect Eight compounds in the shikimic acid pathway on the sebaceous glands and damages healthy were chosen for this study: benzoic acid, p-cou- skin cells. UV stimulates tyrosinase activity maric acid, vanillic acid, syringic acid, quinic ac- id, shikimic acid, orcinol monohydrate, and phe- in melanophores and accelerates the formation nyl pyruvic acid. We measured the tyrosinase of dark spots on the skin. UV also accelerates inhibitory capacity of the compounds in the an- the dermal tissue degradation and speed up the imal model of zebrafish and also evaluated the skin oxidation due to the formation of free rad- compounds’ anti-oxidant activities using the icals and stimulation of reactions converting DPPH radical scavenging, and ABTS+ free rad- dopaquinone to melanin in the melanocytes1. ical scavenging tests. Compounds’ cytotoxicity Tyrosinase inhibitors in medications and cos- effects were also evaluated. RESULTS: Amongst eight shikimic acid path- metics can reduce the accumulation of melanin way compounds used in this study, shikimic ac- pigments in the skin tissue and prevent hyper- id was the most potent tyrosinase-inhibitor and pigmentation. Tyrosinase (polyphenol oxidase, the most efficient compound to be used as an EC 1.14.18.1), a copper-containing oxidase, is the active ingredient for skin whitening. Shikimic rate-limiting enzyme in melanin biosynthesis. Ty- acid revealed a good radical scavenging activi- rosinase catalyzes the first two steps in mamma- ty (RAS) with low cell toxicity. CONCLUSIONS: Promising results obtained lian melanogenesis: i) transformation of the hy- in this study may open a new window of opportu- droxylation of tyrosine to Dopa (3, 4-dihydroxy- nity to introduce another compound to be used phenylalanine) and ii) the oxidization of Dopa to in the skin-whiting cosmetics industry. Dopaquinone2,3. The number of studies focusing on tyrosinase inhibitory activity of various com- Key Words: Tyrosinase, Zebrafish, Shikimic acid pathway, Shi- pounds is growing; this momentum is generated kimic acid. due to the fact that there is a substantial industri- al and economic interest in these inhibitors. Our 1214 Corresponding Author: Guey-Horng Wang, MD; e-mail: [email protected] Skin whitening capability of shikimic acid pathway compounds study was designed to study compounds that hy- Previous studies13,14,16 showed that some pheno- pothetically would be good tyrosinase inhibitors. lics compounds, such as caffeic acid and ferulic Melanin in human skin is a major defense mecha- acid were tyrosinase inhibitors. Eight compounds nism against UV ray. Melanin is a biopolymer mole- in the shikimic acid pathway were chosen for this cule synthesized within epidermal melanocytes and study: benzoic acid, p-coumaric acid, vanillic is packaged in organelles called melanosomes. Skin acid, syringic acid, quinic acid, shikimic acid, color is determined primarily by this pigment. In the orcinol monohydrate, and phenyl pyruvic acid absence of tyrosinase activity, the melanin synthetic (Figure 1). We used zebra fish as our animal mod- pathway is blocked, and the result is the formation of el to verify the whitening capability of synthetic albino phenotype characterized by red eyes and un- compounds in the shikimic acid pathway. Zebraf- pigmented skin and hair4-7. Knowledge of melano- ish have similar developmental pattern and gene cyte biology and the processes underlying melanin homologies to those of mammals; therefore zebra synthesis has made significant progress, creating fish are often used in drug development proj- new opportunities in the pharmacologic methods ects7,11. Zebrafish is an alternativein vivo model to for skin darkening treatments. determine the effects of melanogenic inhibition. The shikimic acid pathway is a metabolic The security issue was crucial for this study pathway responsible for biosynthesis of aromatic and we analyzed the survival rates of murine mel- compounds in various groups of microorganisms, anoma B16 cells and human skin fibroblast Hs68 plants and parasites. The shikimic acid pathway cells to ensure the safety of the compounds to be consists of seven enzymatic reactions whose end potentially used in skin-care products18,19. product chorismate, is the precursor for the syn- thesis of the aromatic amino acids such as tyro- sine, phenylalanine and tryptophan. Other aro- Materials and Methods matic compounds such as coenzyme Q and vita- min K are also produced via this pathway8,9. The Chemical Teagents important branch point of shikimic acid pathway L-ascorbic acid (AA), p-coumaric acid, orci- begins with chorismic acid itself10-12. Natural oc- nol monohydrate, 1,1-Diphenyl-2-picrylhydra- curring or synthetic compounds can display in- zyl (DPPH•), 2,2-azinobis (3-ethylbenzothiazo- hibitory activity toward tyrosinase and effectively line-6-sulfonic acid) diammonium salt (ABTS•+), inhibit the formation of melanin13-16. These com- 4-Hydroxyphenylâ-D-glucopyranoside (arbutin), pounds may be used in skin care products as an mushroom tyrosinase (EC.1.14.18.1), 3,4-dihy- active ingredient for skin whitening17. droxy-L-phenylalanine (L-DOPA), potassium phosphate dibasic (KH2PO4), ferric chloride (Fe- Cl2) and potassium dihydrogen phosphate (KDP), were purchased form Sigma Chemical Co. (St. Louis, MO, USA). Arbutin and ascorbic acid were dissolved at a concentration of 10 mM in dimethyl sulfoxide (DMSO) stock solution. Benzoic acid, gallic acid, vanillic acid, syringic acid, quinic ac- id and shikimic acid were purchased from Alfa Aesar Co., Taiwan. All reagents used in this study were analytical grade. The water used was re-dis- tilled and was ion-free. Cell Culture Human Skin Fibroblast Hs68 cells were purchased from the American Type Culture Collection (Rockville, MD, USA). Human premalignant keratinocytic HaCaT cells were kindly provided by Prof. Hamm-Ming Sheu (National Cheng Kung University Medical Col- Figure 1. Eight shikimic acid biosynthesis pathway com- pounds employed in this study. Compounds include benzoic lege, Tainan, Taiwan). Cells were cultured in acid (1), p-coumaric acid (2), vanillic acid (3), syringic acid Dulbecco’s modified Eagle’s medium (DMEM) (4), quinic acid (5), shikimic acid (6), orcinol monohydrate (GIBCO, Grand Island, NY, USA) that was sup- (7), and phenylpyruvic acid (8). plemented with 10% fetal bovine serum (Ha- 1215 Y.-H. Chen, L. Huang, Z.-H. Wen, C. Zhang, C.-H. Liang, S.-T. Lai, L.-Z. Luo, et al. zelton Product, Denver, PA, USA) and 1% peni- struments, Inc., Winooski, VT, USA). The data cillin-streptomycin at 37°C in 5% CO2. were expressed as mean percentages and the ex- periments were conducted in triplicate17. Zebrafish Whitening Drug Screen Test The eight compounds from shikimate pathway Radical cation ABTS•+ were tested for their melanogenic inhibition capa- (2,2′-Azino-di[3-ethylbenzthiazoline bility on the pigmentation of zebrafish embryos. sulfonate]) Scavenging Activity Adult zebrafish were obtained from a commercial For DPPH·radical scavenging activity analysis we dealer (Seoul Aquarium, Seoul, South Korea) and added various compounds from shikimic acid bio- ten fish were kept in a 3-L acrylic tank at 28.5°C, synthesis pathway, in equal volumes, to the metha- with 14:10 hours light: dark cycle. Zebrafish were nol solution with different concentrations (1, 2, 4, 8, fed three times a day, 6 days a week, with Te- and 16 μM). After incubation at 25C for 30 min in tramin flake food supplemented with live brine dark, the absorbance (A) was measured at 517 nm shrimps (Artemia salina). Embryos were obtained (Hitachi U-2001, Japan). For ABTS•+ radical scav- from natural spawning that was induced in the enging activity analysis, we dissolved ABTS•+ in morning by turning on the light. A collection of water to 7 mM. ABTS•+ radicals were produced by embryos was completed within 30 mins18. Syn- reacting ABTS•+ stock solution and 2.45 mM po- chronized embryos were collected and arrayed tassium persulfate. Mixture was kept in the dark at by a pipette. We prepared 24-well plates contain- room temperature for 12–16 h. The ABTS•+ radi- ing 475 μL embryo medium with 10 to 15 em- cal solution was diluted to an absorbance of 0.70 ± bryos per well. Test compounds were dissolved 0.02 at 734 nm at 30C. Each agent reacted with 2.9 in 1% dimethylsulfoxide and then added to the ml of diluted ABTS•+ radical solution for 20 min embryo medium from 9 to 35 hours post-fertil- at 30°C (100 μg/ml), and then the absorbance was ization (hpf).
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