Identification of photodegraded derivatives of usnic acid with improved toxicity profile and UVA/UVB protection in normal human L02 hepatocytes and epidermal melanocytes

Kwong, Sukfan P.; Wang, Hanxue; Shi, Liang; Huang, Zhenlin; Lü, Bin; Cheng, Xuemei; Chou, Gui‐Xin; Ji, Lili; Wang, Changhong

doi:10.1016/j.jphotobiol.2020.111814

Cited by 8 publications

(8 citation statements)

References 29 publications

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“…At the highest tested dose of 250 µg/mL, (+)usnic acid revealed 5.22% and 9.1% tyrosinase inhibition, (−)-usnic acid 1.4% and 4.09%, while IC 50 values for the control kojic acid were 1.1 µg/mL and 44.9 µg/mL, for monoand diphenolase activity, respectively. Similar observations were recently described for (+)-usnic acid, with no anti-tyrosinase activity up to 50 [23] and 200 µM [24], while no information was available on the activity of its left-handed enantiomer.…”

Section: None Of Usnic Acid Enantiomers Effectively Inhibited Tyrosinase Activitysupporting

confidence: 81%

A Comparative Survey of Anti-Melanoma and Anti-Inflammatory Potential of Usnic Acid Enantiomers—A Comprehensive In Vitro Approach

et al. 2021

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Usnic acid (UA) is a chiral lichen metabolite with an interesting pharmacological profile. The aim of this study was to compare the anti-melanoma effect of (+)-UA and (−)-UA in an in vitro model by studying their impact on the cells as well as the processes associated with cancer progression. The effect of UA enantiomers on the viability, proliferation, and invasive potential of three melanoma cell lines (HTB140, A375, WM793) was evaluated. Their interaction with a chemotherapeutic drug—doxorubicin was assessed by isobolographic analysis. Anti-inflammatory and anti-tyrosinase properties of (+)-UA and (−)-UA were also examined. Both UA enantiomers dose- and time-dependently decreased the viability of all three melanoma cell lines. Their synergistic effect with doxorubicin was observed on A375 cells. (+)-Usnic acid at a sub-cytotoxic dose strongly inhibited melanoma cells migration. Both UA enantiomers decreased the release of pro-inflammatory mediators. The cytotoxic effect of (+)-UA and (−)-UA depends greatly on the melanoma cell type; however, the overall anti-melanoma potential is perspective. Our results indicate that the strategy of combining usnic acid enantiomers with cytostatic drugs may be an interesting option to consider in combating melanoma; however, further studies are required.

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Section: None Of Usnic Acid Enantiomers Effectively Inhibited Tyrosinase Activitysupporting

confidence: 81%

A Comparative Survey of Anti-Melanoma and Anti-Inflammatory Potential of Usnic Acid Enantiomers—A Comprehensive In Vitro Approach

et al. 2021

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“…Similarly low toxicity of (+)-usnic acid towards fibroblasts was proven in our previous study, with an IC 50 > 40 µg/mL [24], and by [25] for HDF cells, with an IC 50 > 10 µM (about 3.5 µg/mL). Interestingly, the only published study on the impact of usnic acid on HEM cells revealed its high toxicity, with an IC 50 of 6.9 µM (about 2.4 µg/mL) [26], while our results suggest the opposite; thus, this problem requires further study. Our in vitro model, representing different skin layers, may mimic the complex nature of the skin itself.…”

Section: Discussioncontrasting

confidence: 68%

(+)-Usnic Acid as a Promising Candidate for a Safe and Stable Topical Photoprotective Agent

Galanty

Popiół

Paczkowska-Walendowska

et al. 2021

Molecules

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The study aimed to examine whether usnic acid—a lichen compound with UV-absorbing properties—can be considered as a prospective photoprotective agent in cosmetic products. Moreover, a comparison of two usnic acid enantiomers was performed to preselect the more effective compound. To meet this aim, an in vitro model was created, comprising the determination of skin-penetrating properties via skin-PAMPA assay, safety assessment to normal human skin cells (keratinocytes, melanocytes, fibroblasts), and examination of photostability and photoprotective properties. Both enantiomers revealed comparable good skin-penetrating properties. Left-handed usnic acid was slightly more toxic to keratinocytes (IC50 80.82 and 40.12 µg/mL, after 48 and 72 h, respectively) than its right-handed counterpart. The latter enantiomer, in a cosmetic formulation, was characterized by good photoprotective properties and photostability, comparable to the UV filter octocrylene. Perhaps most interestingly, (+)-usnic acid combined with octocrylene in one formulation revealed enhanced photoprotection and photostability. Thus, the strategy can be considered for the potential use of (+)-usnic acid as a UV filter in cosmetic products. Moreover, the proposed model may be useful for the evaluation of candidates for UV filters.

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“…Natural substances extracted from lichens have been tested in vivo and in vitro as possible UV filters and the protective factors of natural substances have been compared with those of Nivea sunscreen spray LSF 5, octyl methoxycinnamate, and 4-tert-butyl-4′-dibenzoylmethane [ 29 ]; the results showed that usnic acid was the best UVB filter and its body-protective factors were similar to those of Nivea sunscreen spray LSF 5. In another study, after 21 days of exposure to natural sunlight, four of five photodegraded derivatives of usnic acid showed significant protective activity against UV and lower toxicity to human liver L02 cells and melanocytes than usnic acid [ 27 ].…”

Section: Biological Activitymentioning

confidence: 99%

“…Modern pharmacological studies have confirmed that the many secondary metabolites of Usnea have various biological activities, specifically antimicrobial activities against Mycobacterium tuberculosis and Gram-positive bacteria [ 16 ] and antipyretic-analgesic [ 17 ], anti-inflammatory [ 18 ], antitumor [ 19 , 20 ], and antiviral [ 21 , 22 ] activities; promote wound healing [ 23 , 24 , 25 ]; exert photoprotection [ 26 , 27 , 28 , 29 ]; and induce antioxidative enzymes and alleviate mucosal damage [ 18 , 30 , 31 , 32 ]. All these biological activities are related to the chemical components contained in Usnea , such as dibenzofuran compounds, including (+/−) usnic acid ( Figure 2 ), longiusnine, and (−)-placodiolic acid, and phenolic acids, including evernic acid, barbatic acid, diffractaic acid, and ramalic acid [ 4 ].…”

Section: Introductionmentioning

confidence: 99%

Advances in Research on Bioactivity, Toxicity, Metabolism, and Pharmacokinetics of Usnic Acid In Vitro and In Vivo

2022

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Lichens are among the most widely distributed plants on earth and have the longest growth cycle. Usnic acid is an abundant characteristic secondary metabolite of lichens and the earliest lichen compound used commercially. It has diverse pharmacological activities, such as anti-inflammatory, antibacterial, antiviral, anticancer, antioxidant, and photoprotective effects, and promotes wound healing. It is widely used in dietary supplements, daily chemical products (fodder, dyes, food, perfumery, and cosmetics), and medicine. However, some studies have found that usnic acid can cause allergic dermatitis and drug-induced liver injury. In this paper, the bioactivity, toxicity, in vivo and in vitro metabolism, and pharmacokinetics of usnic acid were summarized. The aims were to develop and utilize usnic acid and provide reference for its future research.

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Identification of photodegraded derivatives of usnic acid with improved toxicity profile and UVA/UVB protection in normal human L02 hepatocytes and epidermal melanocytes

Cited by 8 publications

References 29 publications

A Comparative Survey of Anti-Melanoma and Anti-Inflammatory Potential of Usnic Acid Enantiomers—A Comprehensive In Vitro Approach

A Comparative Survey of Anti-Melanoma and Anti-Inflammatory Potential of Usnic Acid Enantiomers—A Comprehensive In Vitro Approach

(+)-Usnic Acid as a Promising Candidate for a Safe and Stable Topical Photoprotective Agent

Advances in Research on Bioactivity, Toxicity, Metabolism, and Pharmacokinetics of Usnic Acid In Vitro and In Vivo

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