Secondary metabolites from lichen as potent inhibitors of advanced glycation end products and vasodilative agents

Schinkovitz, Andreas; Pogam, Pierre Le; Derbré, Séverine; Roy-Vessieres, E.; Blanchard, Paul T.; Thirumaran, Sangeetha-Laura; Bréard, Dimitri; Aumond, Marie-Chistine; Zehl, Martin; Urban, Ernst; Kaur, Amandeep; Jäger, Nathalie; Hofer, Stefanie; Kopp, Brigitte; Stuppner, Hermann; Baglin, Isabelle; Séraphin, Denis; Tomasi, Sophie; Henrion, Didier; Boustié, Joël; Richomme, Pascal

doi:10.1016/j.fitote.2018.10.015

Cited by 12 publications

(9 citation statements)

References 39 publications

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“…All exhibited IC 50 values in the range of 10.7 to 17.6 µM, which was more potent than the positive control (acarbose) (IC 50 449 µM). Depsidone, a unique class of lichen metabolites possess a wide variety of biological activities [19][20][21][22][23]. Up to now, over 22 lichen extracts, (i.e., from Parmotrema grayana or P. hababianum), have been studied for α-glucosidase inhibition or in vivo antihyperglycemic activity [19,24].…”

Section: Resultsmentioning

confidence: 99%

α-Glucosidase Inhibitory Depsidones from the Lichen Parmotrema tsavoense

et al. 2020

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Chemical investigation of the lichen Parmotrema tsavoense led to the isolation of 5 new depsidones, parmosidones F – J (1 – 5). These compounds were structurally elucidated using spectroscopic methods including HRESIMS and 2D NMR data. Compounds 1, 3, and 4 were evaluated for their inhibition of α-glucosidase. All exhibited potent α-glucosidase inhibitory activity with IC50 values ranging from 10.7 to 17.6 µM, which was much lower than that of the positive control acarbose (IC50 449 µM).

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Section: Resultsmentioning

confidence: 99%

α-Glucosidase Inhibitory Depsidones from the Lichen Parmotrema tsavoense

et al. 2020

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“…Nevertheless, many efforts have been made to reduce the toxicity of usnic acid, mainly through derivate compounds. In the study of Schinkovitz et al, 2018, where the in vitro capacity of several lichen secondary metabolites and semi-synthetic compounds for the inhibition of AGEs were tested, a synthetically modified molecule of usnic acid significantly inhibited the AGEs formation [70]. In relation to usnic acid, the triketone moiety of the molecule is attributed to the uncoupling activity of the oxidative phosphorylation; and the reaction of its carbonyl group with primary amines produces the enamine-type derivates.…”

Section: Discussionmentioning

confidence: 99%

“…• Anti-proliferative activity against melanoma and glioblastoma multiforme cell lines [94,112] • Concentration-dependent antioxidant activity towards free radicals [43] • Inhibitory activity of HMGR (non-competitive inhibition) and ACE (mixed inhibition) [43] Rhizocarpic acid Rhizocarpon geographicum • Inhibitory activity against AGEs [70] Sekikaic acid Protousnea malacea…”

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confidence: 99%

Bioactive Lichen Secondary Metabolites and Their Presence in Species from Chile

Poulsen-Silva,

Gordillo-Fuenzalida,

Atala

et al. 2023

Metabolites

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Lichens are symbiotic organisms composed of at least one fungal and one algal species. They are found in different environments around the world, even in the poles and deserts. Some species can withstand extreme abiotic conditions, including radiation and the vacuum of space. Their chemistry is mainly due to the fungal metabolism and the production of several secondary metabolites with biological activity, which have been isolated due to an increasing interest from the pharmaceutical community. However, beyond the experimental data, little is known about their mechanisms of action and the potential pharmaceutical use of these kinds of molecules, especially the ones isolated from lesser-known species and/or lesser-studied countries. The main objective of this review is to analyze the bibliographical data of the biological activity of secondary metabolites from lichens, identifying the possible mechanisms of action and lichen species from Chile. We carried out a bibliographic revision of different scientific articles in order to collect all necessary information on the biological activity of the metabolites of these lichen species. For this, validated databases were used. We found the most recent reports where in vitro and in vivo studies have demonstrated the biological properties of these metabolites. The biological activity, namely anticancer, antioxidant, and anti-inflammatory activity, of 26 secondary metabolites are described, as well as their reported molecular mechanisms. The most notable metabolites found in this review were usnic acid, atranorin, protolichesterinic acid, and lobaric acid. Usnic acid was the most investigated metabolite, in addition to undergoing toxicological and pharmacological studies, where a hepatotoxicity effect was reported due to uncoupling oxidative phosphorylation. Additionally, no major studies have been made to validate the pharmacological application of these metabolites, and few advancements have been made in their artificial growth in bioreactors. Despite the described biological activities, there is little support to consider these metabolites in pharmaceutical formulations or to evaluate them in clinical trials. Nevertheless, it is important to carry out further studies regarding their possible human health effects. These lichen secondary metabolites present a promising research opportunity to find new pharmaceutical molecules due to their bioactive properties.

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“…Nevertheless, most of the tested compounds were found with some activity, such as compounds 1 , 2 , 3 , 5 , 6 , 7 , and 13, which displayed mild to moderate enzyme inhibition ( p < 0.001). These results are to be pooled with the growing number of reports on the antidiabetic potential of lichen extracts or molecules [ 34 , 35 , 36 ]. The combination of activities with different mechanisms of action is of particular interest to develop potent antihyperglycemic effects.…”

Section: Biological Activitymentioning

confidence: 99%

Comprehensive Lichenometabolomic Exploration of Ramalina conduplicans Vain Using UPLC-Q-ToF-MS/MS: An Identification of Free Radical Scavenging and Anti-Hyperglycemic Constituents

et al. 2022

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In this study, we propose ultra-performance liquid chromatography coupled with quadrupole/time-of-flight mass spectrometry (UPLC-QToF-MS/MS)-guided metabolite isolation as a choice analytical approach to the ongoing structure–activity investigations of chemical isolates from the edible lichen, Ramalina conduplicans Vain. This strategy led to the isolation and identification of a new depside (5) along with 13 known compounds (1–4, 6–14), most of which being newly described in this lichen species. The structures of the isolates were established by detailed analysis of their spectral data (IR, NMR, and Mass). The acetone extract was further analyzed by UPLC-Q-ToF-MS/MS in a negative ionization mode, which facilitated the identification and confirmation of 18 compounds based on their fragmentation patterns. The antioxidant capacities of the lichen acetone extract (AE) and isolates were measured by tracking DPPH and ABTS free radical scavenging activities. Most isolates displayed marked radical scavenging activities against ABTS while moderate activities were observed against DPPH radical scavenging. Except for atranol (14), oxidative DNA damage was limited by all the tested compounds, with a marked protection for the novel isolated compound (5), as previously noted for the acetone extract (p < 0.001). Furthermore, compound (4) and acetone extract (AE) have inhibited intestinal α-glucosidase enzyme significantly (p < 0.01). Although some phytochemical studies were already performed on this lichen, this study provided new insights into the isolation and identification of bioactive compounds, illustrating interest in future novel analytical techniques.

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Secondary metabolites from lichen as potent inhibitors of advanced glycation end products and vasodilative agents

Cited by 12 publications

References 39 publications

α-Glucosidase Inhibitory Depsidones from the Lichen Parmotrema tsavoense

α-Glucosidase Inhibitory Depsidones from the Lichen Parmotrema tsavoense

Bioactive Lichen Secondary Metabolites and Their Presence in Species from Chile

Comprehensive Lichenometabolomic Exploration of Ramalina conduplicans Vain Using UPLC-Q-ToF-MS/MS: An Identification of Free Radical Scavenging and Anti-Hyperglycemic Constituents

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