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Article

Efficacy, Stability, and Safety Evaluation of New Polyphenolic Xanthones Towards Identification of Bioactive Compounds to Fight Skin Photoaging

by
Diana I. S. P. Resende
1,2,
Mariana C. Almeida
1,2,
Bruna Maciel
3,
Helena Carmo
4,
José Sousa Lobo
5,
Carlotta Dal Pozzo
6,
Sara M. Cravo
1,2,
Gonçalo P. Rosa
7,8,
Aida Kane-Pagès
8,
Maria do Carmo Barreto
7,8,
Isabel F Almeida
5,*,
Maria Emília de Sousa
1,2,* and
Madalena M. M. Pinto
1,2
1
Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, 4050-313 Porto, Portugal
2
CIIMAR-Centro Interdisciplinar de Investigação Marinha e Ambiental, Avenida General Norton de Matos, S/N, 4450-208 Matosinhos, Portugal
3
Laboratório de Tecnologia Farmacêutica, Departamento do Medicamento, Faculdade de Farmácia, Universidade do Porto, 4050-313 Porto, Portugal
4
UCIBIO, REQUIMTE, Laboratório de Toxicologia, Departamento de Ciências Biológicas, Faculdade de Farmácia, Universidade do Porto, 4050-313 Porto, Portugal
5
UCIBIO/REQUIMTE, MedTec-Laboratório de Tecnologia Farmacêutica, Departamento de Ciências do Medicamento, Faculdade de Farmácia, Universidade do Porto, 4050-313 Porto, Portugal
6
University of Ferrara, Dept. of Life Sciences and Biotechnology, Via Fossato di Mortara 17/1944121 Ferrara, Italy
7
cE3c–Centre for Ecology, Evolution and Environmental Changes / Azorean Biodiversity Group, 9500-321 Ponta Delgada, Portugal
8
Faculdade de Ciências e Tecnologia, Universidade dos Açores, 9500-321 Ponta Delgada, Portugal
*
Authors to whom correspondence should be addressed.
Molecules 2020, 25(12), 2782; https://doi.org/10.3390/molecules25122782
Submission received: 22 May 2020 / Revised: 12 June 2020 / Accepted: 15 June 2020 / Published: 16 June 2020
(This article belongs to the Special Issue Natural and Artificial Photoprotective Agent)
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Abstract

Antioxidants have long been used in the cosmetic industry to prevent skin photoaging, which is mediated by oxidative stress, making the search for new antioxidant compounds highly desirable in this field. Naturally occurring xanthones are polyphenolic compounds that can be found in microorganisms, fungi, lichens, and some higher plants. This class of polyphenols has a privileged scaffold that grants them several biological activities. We have previously identified simple oxygenated xanthones as promising antioxidants and disclosed as hit, 1,2-dihydroxyxanthone (1). Herein, we synthesized and studied the potential of xanthones with different polyoxygenated patterns as skin antiphotoaging ingredients. In the DPPH antioxidant assay, two newly synthesized derivatives showed IC50 values in the same range as ascorbic acid. The synthesized xanthones were discovered to be excellent tyrosinase inhibitors and weak to moderate collagenase and elastase inhibitors but no activity was revealed against hyaluronidase. Their metal-chelating effect (FeCl3 and CuCl2) as well as their stability at different pH values were characterized to understand their potential to be used as future cosmetic active agents. Among the synthesized polyoxygenated xanthones, 1,2-dihydroxyxanthone (1) was reinforced as the most promising, exhibiting a dual ability to protect the skin against UV damage by combining antioxidant/metal-chelating properties with UV-filter capacity and revealed to be more stable in the pH range that is close to the pH of the skin. Lastly, the phototoxicity of 1,2-dihydroxyxanthone (1) was evaluated in a human keratinocyte cell line and no phototoxicity was observed in the concentration range tested.
Keywords: skin; photoaging; antioxidants; xanthones; 1,2-dihydroxyxanthone; DPPH; elastase; collagenase; tyrosinase; phototoxicity skin; photoaging; antioxidants; xanthones; 1,2-dihydroxyxanthone; DPPH; elastase; collagenase; tyrosinase; phototoxicity

Share and Cite

MDPI and ACS Style

Resende, D.I.S.P.; Almeida, M.C.; Maciel, B.; Carmo, H.; Sousa Lobo, J.; Dal Pozzo, C.; Cravo, S.M.; Rosa, G.P.; Kane-Pagès, A.; do Carmo Barreto, M.; et al. Efficacy, Stability, and Safety Evaluation of New Polyphenolic Xanthones Towards Identification of Bioactive Compounds to Fight Skin Photoaging. Molecules 2020, 25, 2782. https://doi.org/10.3390/molecules25122782

AMA Style

Resende DISP, Almeida MC, Maciel B, Carmo H, Sousa Lobo J, Dal Pozzo C, Cravo SM, Rosa GP, Kane-Pagès A, do Carmo Barreto M, et al. Efficacy, Stability, and Safety Evaluation of New Polyphenolic Xanthones Towards Identification of Bioactive Compounds to Fight Skin Photoaging. Molecules. 2020; 25(12):2782. https://doi.org/10.3390/molecules25122782

Chicago/Turabian Style

Resende, Diana I. S. P., Mariana C. Almeida, Bruna Maciel, Helena Carmo, José Sousa Lobo, Carlotta Dal Pozzo, Sara M. Cravo, Gonçalo P. Rosa, Aida Kane-Pagès, Maria do Carmo Barreto, and et al. 2020. "Efficacy, Stability, and Safety Evaluation of New Polyphenolic Xanthones Towards Identification of Bioactive Compounds to Fight Skin Photoaging" Molecules 25, no. 12: 2782. https://doi.org/10.3390/molecules25122782

APA Style

Resende, D. I. S. P., Almeida, M. C., Maciel, B., Carmo, H., Sousa Lobo, J., Dal Pozzo, C., Cravo, S. M., Rosa, G. P., Kane-Pagès, A., do Carmo Barreto, M., Almeida, I. F., de Sousa, M. E., & Pinto, M. M. M. (2020). Efficacy, Stability, and Safety Evaluation of New Polyphenolic Xanthones Towards Identification of Bioactive Compounds to Fight Skin Photoaging. Molecules, 25(12), 2782. https://doi.org/10.3390/molecules25122782

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