Efficacy, Stability, and Safety Evaluation of New Polyphenolic Xanthones Towards Identification of Bioactive Compounds to Fight Skin Photoaging
Autor(a) principal: | |
---|---|
Data de Publicação: | 2020 |
Outros Autores: | , , , , , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10400.3/5808 |
Resumo: | 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. |
id |
RCAP_5859c1eb9b61fe7938bc1f643ee92685 |
---|---|
oai_identifier_str |
oai:repositorio.uac.pt:10400.3/5808 |
network_acronym_str |
RCAP |
network_name_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository_id_str |
7160 |
spelling |
Efficacy, Stability, and Safety Evaluation of New Polyphenolic Xanthones Towards Identification of Bioactive Compounds to Fight Skin PhotoagingSkinPhotoagingAntioxidantsXanthones1,2-dihydroxyxanthoneDPPHElastaseCollagenaseTyrosinasePhototoxicityAntioxidants 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.This research was supported by national funds through FCT, Foundation for Science and Technology, within the scope of UIDB/04423/2020 and UIDP/04423/2020 under the project PTDC/SAU-PUB/28736/2017 (reference POCI-01-0145-FEDER-028736), cofinanced by COMPETE 2020, Portugal 2020 and the European Union through the ERDF and by FCT through national funds, as well as CHIRALBIOACTIVE-PI-3RL-IINFACTS-2019, and supported by the Applied Molecular Biosciences Unit-UCIBIO which is financed by national funds from FCT/MCTES (UID/Multi/04378/2019). Thanks are also due to FCT, the European Union, QREN, FEDER, COMPETE, by funding cE3c center (Ref. UID/BIA/00329/2019) and Direcao Regional da Ciencia e Tecnologia (Azores Government) by funding Azorean Biodiversity Group.MDPIRepositório da Universidade dos AçoresResende, Diana I. S. P.Almeida, Mariana C.Maciel, BrunaCarmo, HelenaLobo, José SousaDal Pozzo, CarlottaCravo, Sara M.Rosa, Gonçalo P.Kane-Pagès, AidaBarreto, Maria do CarmoAlmeida, Isabel F.Sousa, Maria Emília dePinto, Madalena M. M.2021-03-22T18:01:22Z2020-062020-06-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10400.3/5808engResende, D.I.S.P., Almeida, M.C., Maciel, B., Carmo, H., Lobo, J.S., Dal Pozzo, C., Cravo, S.M., Rosa, G.P., Kane-Pagès, A., Barreto, M.C., Almeida, I.F., 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, 1-16. DOI: 10.3390/molecules251227821420-304910.3390/molecules25122782http://europepmc.org/articles/PMC7356587https://www.ncbi.nlm.nih.gov/pubmed/32560201000550172100001info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2022-12-20T14:34:11Zoai:repositorio.uac.pt:10400.3/5808Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T16:28:00.918814Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
Efficacy, Stability, and Safety Evaluation of New Polyphenolic Xanthones Towards Identification of Bioactive Compounds to Fight Skin Photoaging |
title |
Efficacy, Stability, and Safety Evaluation of New Polyphenolic Xanthones Towards Identification of Bioactive Compounds to Fight Skin Photoaging |
spellingShingle |
Efficacy, Stability, and Safety Evaluation of New Polyphenolic Xanthones Towards Identification of Bioactive Compounds to Fight Skin Photoaging Resende, Diana I. S. P. Skin Photoaging Antioxidants Xanthones 1,2-dihydroxyxanthone DPPH Elastase Collagenase Tyrosinase Phototoxicity |
title_short |
Efficacy, Stability, and Safety Evaluation of New Polyphenolic Xanthones Towards Identification of Bioactive Compounds to Fight Skin Photoaging |
title_full |
Efficacy, Stability, and Safety Evaluation of New Polyphenolic Xanthones Towards Identification of Bioactive Compounds to Fight Skin Photoaging |
title_fullStr |
Efficacy, Stability, and Safety Evaluation of New Polyphenolic Xanthones Towards Identification of Bioactive Compounds to Fight Skin Photoaging |
title_full_unstemmed |
Efficacy, Stability, and Safety Evaluation of New Polyphenolic Xanthones Towards Identification of Bioactive Compounds to Fight Skin Photoaging |
title_sort |
Efficacy, Stability, and Safety Evaluation of New Polyphenolic Xanthones Towards Identification of Bioactive Compounds to Fight Skin Photoaging |
author |
Resende, Diana I. S. P. |
author_facet |
Resende, Diana I. S. P. Almeida, Mariana C. Maciel, Bruna Carmo, Helena Lobo, José Sousa Dal Pozzo, Carlotta Cravo, Sara M. Rosa, Gonçalo P. Kane-Pagès, Aida Barreto, Maria do Carmo Almeida, Isabel F. Sousa, Maria Emília de Pinto, Madalena M. M. |
author_role |
author |
author2 |
Almeida, Mariana C. Maciel, Bruna Carmo, Helena Lobo, José Sousa Dal Pozzo, Carlotta Cravo, Sara M. Rosa, Gonçalo P. Kane-Pagès, Aida Barreto, Maria do Carmo Almeida, Isabel F. Sousa, Maria Emília de Pinto, Madalena M. M. |
author2_role |
author author author author author author author author author author author author |
dc.contributor.none.fl_str_mv |
Repositório da Universidade dos Açores |
dc.contributor.author.fl_str_mv |
Resende, Diana I. S. P. Almeida, Mariana C. Maciel, Bruna Carmo, Helena Lobo, José Sousa Dal Pozzo, Carlotta Cravo, Sara M. Rosa, Gonçalo P. Kane-Pagès, Aida Barreto, Maria do Carmo Almeida, Isabel F. Sousa, Maria Emília de Pinto, Madalena M. M. |
dc.subject.por.fl_str_mv |
Skin Photoaging Antioxidants Xanthones 1,2-dihydroxyxanthone DPPH Elastase Collagenase Tyrosinase Phototoxicity |
topic |
Skin Photoaging Antioxidants Xanthones 1,2-dihydroxyxanthone DPPH Elastase Collagenase Tyrosinase Phototoxicity |
description |
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. |
publishDate |
2020 |
dc.date.none.fl_str_mv |
2020-06 2020-06-01T00:00:00Z 2021-03-22T18:01:22Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10400.3/5808 |
url |
http://hdl.handle.net/10400.3/5808 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Resende, D.I.S.P., Almeida, M.C., Maciel, B., Carmo, H., Lobo, J.S., Dal Pozzo, C., Cravo, S.M., Rosa, G.P., Kane-Pagès, A., Barreto, M.C., Almeida, I.F., 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, 1-16. DOI: 10.3390/molecules25122782 1420-3049 10.3390/molecules25122782 http://europepmc.org/articles/PMC7356587 https://www.ncbi.nlm.nih.gov/pubmed/32560201 000550172100001 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
MDPI |
publisher.none.fl_str_mv |
MDPI |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
instname_str |
Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
instacron_str |
RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository.name.fl_str_mv |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
repository.mail.fl_str_mv |
|
_version_ |
1799130737697357824 |