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Cited by 15Skin Protection and AgingNatural Compound Pharmacology StudiesSynthesis of Organic Compounds

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

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Resende, Diana I. S. P., Almeida, Mariana C., Maciel, Bruna, Carmo, Helena, Sousa Lobo, José, Dal Pozzo, Carlotta, Cravo, Sara M., Rosa, Gonçalo P. +5 more·2020·Molecules
DOI 10.3390/molecules25122782PMC PMC7356587
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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.

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  • Xanthone 162 protects the skin against UV damage through DPPH scavenging action and UV-filter capacity, without phototoxicity in the HaCaT keratinocyte cell line.

    “Additionally, xanthone 162 showed a dual ability to protect the skin against UV damage, through DPPH scavenging action and UV-filter capacity, without phototoxicity in the HaCaT keratinocyte cell line [142].”

    From UV Filters: Challenges and Prospects (2022) · cites this paper as [142]

    The Conclusions (section 4; page unavailable) describe 1,2-dihydroxyxanthone (compound 1) as having antioxidant activity and UV-filter capacity, while section 2.2.1 reports its DPPH radical-scavenging activity. Section 2.5 finds it nonphototoxic in HaCaT cells up to 200 µM. The copy does not identify this compound as “xanthone 162,” and the claim omits the tested-concentration limit. (LLM, conf=0.82)

    Experimental — accuracy not yet measured

  • Compounds reported by Popiół et al. possess action against UVA and UVB radiation, in contrast to compounds with a simple xanthone scaffold reported by Resende et al.

    “Comparing these two groups of xanthones, the combination of the cinnamoyl and xanthonic moieties allows the correct electronic delocalisation, which improves the UV absorber properties and, because of that, compounds reported by Popiół et al. [26] possess action against UVA and UVB radiation, in contrast to compounds with a simple xanthone scaffold reported by Resende et al. [142].”

    From UV Filters: Challenges and Prospects (2022) · cites this paper as [142]

    In Results and Discussion §2.2 (page not provided), Resende et al. report that their xanthones have high absorbance in the UVB range. The passage does not establish that they lack UVA absorption or action, so it supports the UVB side of the contrast but not the implied absence of UVA action. (LLM, conf=0.83)

    Experimental — accuracy not yet measured

  • Three hydroxylated xanthone derivatives (162-164) have promising antioxidant activity and UV filtering characteristics.

    “Resende et al. (2020) reported three hydroxylated xanthone derivatives (162–164) with promising antioxidant activity and UV filtering characteristics [142].”

    From UV Filters: Challenges and Prospects (2022) · cites this paper as [142]

  • The combination of cinnamoyl and xanthonic moieties allows correct electronic delocalisation, which improves UV absorber properties.

    “Comparing these two groups of xanthones, the combination of the cinnamoyl and xanthonic moieties allows the correct electronic delocalisation, which improves the UV absorber properties and, because of that, compounds reported by Popiół et al. [26] possess action against UVA and UVB radiation, in contrast to compounds with a simple xanthone scaffold reported by Resende et al. [142].”

    From UV Filters: Challenges and Prospects (2022) · cites this paper as [142]

  • Compounds 162-164 absorb in the UVB range (280-320 nm).

    “Compounds 162–164 proved to absorb in the UVB range (280–320 nm).”

    From UV Filters: Challenges and Prospects (2022) · cites this paper as [142]

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Authors
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.
Affiliations
  • Universidade do Porto (PT)
  • UCIBIO/REQUIMTE, MedTec-Laboratório de Tecnologia Farmacêutica, Departamento de Ciências do Medicamento, Faculdade de Farmácia, Universidade do Porto, 4050-313 Porto, Portugal
  • University of Ferrara, Dept. of Life Sciences and Biotechnology, Via Fossato di Mortara 17/1944121 Ferrara, Italy
  • Universidade dos Açores (PT)
  • cE3c–Centre for Ecology, Evolution and Environmental Changes / Azorean Biodiversity Group, 9500-321 Ponta Delgada, Portugal
  • Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, 4050-313 Porto, Portugal
Corresponding author
Almeida, Isabel F
ORCID
Venue
Molecules
Publisher
MDPI AG
Published
2020-06-16
Volume
25
Issue
12
Pages
2782
ISSN
1420-3049 (ISSN-L)
DOI
10.3390/molecules25122782
PMC
PMC7356587
OpenAlex
W3034190025
Cited by
15
References
42
Citations by year
2026: 3 · 2025: 2 · 2024: 2 · 2023: 1 · 2022: 2 · 2021: 3 · 2020: 2
FWCI
1.64
Type
journal article
Language
en
Open access
Licence
Locations
  • Molecules (publishedVersion, cc-by)
  • PubMed Central (publishedVersion, cc-by)
  • PubMed (publishedVersion)
  • DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
  • Portuguese National Funding Agency for Science, Research and Technology (RCAAP Project by FCT) (submittedVersion, cc-by)
Funders
Fundação para a Ciência e a Tecnologia (PTDC/SAU-PUB/28736/2017 , UIDB/04423/2020 and UIDP/04423/2020)
Topics
  • Health Sciences › Medicine › Dermatology › Skin Protection and Aging
  • Life Sciences › Agricultural and Biological Sciences › Plant Science › Natural Compound Pharmacology Studies
  • Health Sciences › Medicine › Pharmacology › Synthesis of Organic Compounds
Keywords
xanthones, polyphenols, photoaging, antioxidants, tyrosinase inhibition, metal chelation, UV protection, photostability, phototoxicity, keratinocytes, cosmetic active ingredients, oxidative stress
MeSH terms
Antioxidants, Drug Evaluation, Preclinical, Humans, Skin, Sunscreening Agents, Ultraviolet Rays, Skin Aging, Keratinocytes, Xanthones

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