Usnic acid: from an ancient lichen derivative to promising biological and nanotechnology applications

Macedo, Daniel C.; Almeida, F. J. F.; Wanderley, Marcela Silvestre Outtes; Ferraz, Milena Sales; Santos, N. P. S.; López, Ana Maria Queijeiro; Santos-Magalhães, Nereide Stela; Nogueira, Mariane Cajubá de Britto Lira

doi:10.1007/s11101-020-09717-1

Cited by 34 publications

(23 citation statements)

References 126 publications

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“…Usnic acid (2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2 H ,9b H )-dibenzo-furandione); C 18 H 16 O 7 , MW of 344.32 is a molecule metabolized by several species of lichens (symbiotic organisms composed of a fungus (mycobiont) in association with one or more photosynthetic partners (photobiont) which may be green algae, cyanobacteria or both), of the genera Cladonia , Usnea , Lecanora , Ramalina , Parmelia , and Evernia , widely distributed, present in the arctic, tropical and subtropical countries and the Antarctic [ 1 , 2 , 3 , 4 , 5 ]. Usnic acid is found naturally in two enantiomeric forms, such as (−) levogyrous and (+) dextrogyrous, due to the angular projection of the methyl group located in position 9b [ 6 , 7 ] being still characterized as a yellow pigmented substance; its forms can be varied, that is, depending directly on the solvent used in its recrystallization [ 8 , 9 ].…”

Section: Introductionmentioning

confidence: 99%

“…Although usnic acid is a molecule with an initial report available in the literature in the 1950s, whose purpose was the search for new antibiotics [ 10 ], even nowadays this molecule is used in pharmaceutical industry applications [ 11 , 12 , 13 ], with a breakthrough and hundreds of scientific papers to demonstrate the efficacy of the various biological activities and toxicity attributed to usnic acid [ 4 , 9 ]. Antibacterial action [ 14 ], gastroprotective effect [ 15 ], immunostimulatory [ 16 ], antiviral [ 17 ], antifungal [ 18 ], anti-inflammatory [ 19 ], antiparasitic [ 20 ] and antitumor activity [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

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The Natural Compound Hydrophobic Usnic Acid and Hydrophilic Potassium Usnate Derivative: Applications and Comparisons

et al. 2021

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Usnic acid is the best-studied lichen metabolite, presenting several biological activities, such as antibacterial, immunostimulating, antiviral, antifungal, anti-inflammatory, and antiparasitic agents; despite these relevant properties, it is a hydrophobic and toxic molecule. In this context, scientific research has driven the development of innovative alternatives, considering usnic acid as a source of raw material in obtaining new molecules, allowing structural modifications (syntheses) from it. The purpose is to optimize biological activities and toxicity, with less concentration and/or response time. This work presents a literature review with an analogy of the hydrophobic molecule of usnic acid with its hydrophilic derivative of potassium usnate, emphasizing the elucidation and structural characteristics, biological activities, and toxicological aspects of both molecules, and the advantages of using the promising derivative hydrophilic in different in vitro and in vivo assays when compared to usnic acid.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The Natural Compound Hydrophobic Usnic Acid and Hydrophilic Potassium Usnate Derivative: Applications and Comparisons

et al. 2021

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“…Usnic acid is class of dibenzofuran functional group and it has multiple biological activities. It shows antitumor activity against Lewis Lung carcinoma and P388 leukaemia through the mechanism of mitosis inhibition and apoptotic induction (Galanty et al 2019;Macedo et al 2020). Interestingly, depside and depsidone series, for example 1 1 -chloropannarin and sphaerophorin have shown higher cytotoxicity than colchicine against cell cultures of lymphocytes.…”

Section: Antitumour and Antimutagenic Activitymentioning

confidence: 99%

Mycorrhiza and Lichens as Two Models of Fungal Symbiosis

Elkhateeb¹,

Somasekhar²,

Thomas³

et al. 2021

J microb biotech food sci

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Fungi have evolved many symbioses including different eukaryotes and prokaryotes. Mutualism is one of the symbioses and here both symbionts benefit from the interaction. The most common mutualistic relationships involving fungi are mycorrhiza and lichens. A mycorrhiza is a symbiotic relationship between a roots of a plant and a fungus while lichen associates between a fungus and an algae. Many studies have performed to investigate these symbiotic relationships in depth, however, still have some debates on them, though many taxonomists rely on genetic analyses besides with traditional morphological data. In our study, it highlights the nature, importance, nutritional and pharmaceutical uses, and applications of these mysterious dual between fungi and plant and/or algae.

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“…The question regarding differences in the activity of both enantiomeric forms is still open, as the evidence supporting the advantages of one form over the other is scarce and unambiguous, as recently reviewed in our previous work [ 1 ]. Although usnic acid reveals marked cytotoxic, anti-inflammatory, and antibacterial properties [ 2 ], some studies pointed to its hepatotoxicity [ 3 , 4 ], which may limit the internal administration of this compound. On the other hand, a few case studies have reported on contact allergy to usnic acid, but extracts with its compounds have been successfully used in antiperspirants [ 1 ].…”

Section: Introductionmentioning

confidence: 99%

(+)-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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Usnic acid: from an ancient lichen derivative to promising biological and nanotechnology applications

Cited by 34 publications

References 126 publications

The Natural Compound Hydrophobic Usnic Acid and Hydrophilic Potassium Usnate Derivative: Applications and Comparisons

The Natural Compound Hydrophobic Usnic Acid and Hydrophilic Potassium Usnate Derivative: Applications and Comparisons

Mycorrhiza and Lichens as Two Models of Fungal Symbiosis

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

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