olivetoric-acid and physodic-acid

Topics: Depsides; Dibenzoxepins; Fungi; Genomics; Lactones; Lichens; Multigene Family; Parmeliaceae; Salicylates

The present study aims at assessing the efficacies of olivetoric acid (OA) and physodic acid (PA) isolated from Pseudevernia furfuracea (L.) Zopf (Parmeliaceae) in human lymphocytes (HLs) in vitro. 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide and lactate dehydrogenase assays were performed to establish cytotoxicity in HLs. Besides, oxidative stress and genotoxicity were monitored by estimating the changes of total oxidative stress (TOS) and 8-hydroxy-2'-deoxyguanosine (8-OH-dG) levels, respectively, in HLs. At the same time, OA- and PA-induced total antioxidant capacity (TAC) levels in HLs were determined. Although especially low concentrations of OA (IC50=109.94 mg/L) and PA (IC50=665.49 mg/L) did not show cytotoxic effect at high levels in HLs, it was revealed that cytotoxicity was significantly (p<0.05) associated with oxidative stress and genotoxicity via correlation analysis. While TOS level in HLs did not statistically (p>0.05) increase in the presence of all treatments (0.5-100 mg/L) of PA, TAC level was increased by PA applications in certain concentrations (0.5-10 mg/L). Overall, the obtained data indicate that OA and especially PA as lichen compounds that do not cause oxidative stress can be a new resource of therapeutics as recognized in the present study with their high antioxidant features.

Topics: 8-Hydroxy-2'-Deoxyguanosine; Adult; Cells, Cultured; Deoxyguanosine; Dibenzoxepins; Dose-Response Relationship, Drug; Humans; Lymphocytes; Molecular Structure; Oxidative Stress; Parmeliaceae; Salicylates; Secondary Metabolism; Young Adult

It is known that lichens are utilized for the treatment of many diseases including ulcer, diabetes, and cancer for many years. Secondary metabolites in the structure of the lichens provide various activity properties for them. In the present study, cytotoxic and oxidative effects of main constituents of Pseudevernia furfuracea (L.) Zopf (Parmeliaceae), olivetoric acid (OA), and physodic acid (PA) were investigated on cultured human amnion fibroblasts (HAFs). OA and PA were isolated from P. furfuracea using column chromatography and their structures were determined by proton nuclear magnetic resonance and carbon-13 nuclear magnetic resonance. HAFs were incubated during 48 h in the presence of OA and PA, at different concentrations from 6.25 mg/L to 200 mg/L. OA showed higher cytotoxicity than PA. In fact, median inhibitory concentration values of OA and PA were 571.27 and 3373.69 mg/L, respectively. The lower concentrations (<50 mg/L) of OA and PA did not cause oxidative stress and genotoxicity; furthermore, they supported anti-oxidative capacity of HAFs. Therefore, all these data suggested that both tested metabolites, especially PA might be developed as natural health medicine to protect human body against oxidative stress and genotoxicity. As far as we know, this is the first report on the cytotoxic and anti-oxidative activities of OA and PA on HAFs.

Topics: Amnion; Antioxidants; Cell Survival; Cells, Cultured; Deoxyadenosines; Dibenzoxepins; DNA Damage; Fibroblasts; Humans; Lichens; Oxidative Stress; Salicylates

Context Since methods utilised in the treatment of glioblastoma multiforme (GBM) are inadequate and have too many side effects, usage of herbal products in the treatment process comes into prominence. Lichens are symbiotic organisms used for medicinal purposes for many years. There are various anticancer treatments about components of two lichen species used in the present study. Objective Antitumor potential of three lichen secondary metabolites including olivetoric acid (OLA) and physodic acid (PHA) isolated from Pseudevernia furfuracea (L.) Zopf (Parmeliaceae) and psoromic acid (PSA) isolated from Rhizoplaca melanophthalma (DC.) Leuckert (Lecanoraceae) were investigated on human U87MG-GBM cell lines and primary rat cerebral cortex (PRCC) cells for the first time. Materials and methods PRCC cells used as healthy brain cells were obtained from Sprague-Dawley rats. The treatments were carried out on the cells cultured for 48 h. Cytotoxic effects of different concentrations (2.5, 5, 10, 20 and 40 mg/L) of metabolites on the cells were determined via 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and lactate dehydrogenase (LDH) analyses. Total antioxidant capacity (TAC) and total oxidant status (TOS) parameters were used for assessing oxidative alterations. Oxidative DNA damage potentials of metabolites were investigated via evaluating 8-hydroxy-2'-deoxyguanosine (8-OH-dG) levels. Results Median inhibitory concentration (IC50) values of OLA, PHA and PSA were 125.71, 698.19 and 79.40 mg/L for PRCC cells and 17.55, 410.72 and 56.22 mg/L for U87MG cells, respectively. It was revealed that cytotoxic effects of these metabolites showed positive correlation with concentration, LDH activity and oxidative DNA damage. Discussion and conclusion The present findings obtained in this study revealed that primarily OLA and then PSA had high potential for use in the treatment of GBM.

Topics: 8-Hydroxy-2'-Deoxyguanosine; Animals; Antineoplastic Agents, Phytogenic; Benzoxepins; Biomarkers; Brain Neoplasms; Carboxylic Acids; Cell Line, Tumor; Cell Proliferation; Cerebral Cortex; Deoxyguanosine; Dibenzoxepins; DNA Damage; Dose-Response Relationship, Drug; Glioblastoma; Humans; L-Lactate Dehydrogenase; Lichens; Neurons; Oxidative Stress; Plant Extracts; Rats, Sprague-Dawley; Salicylates; Time Factors

A chemical race of the lichen Cetraria ciliaris Ach., known to produce the depside olivetoric acid, contains the corresponding depsidone, physodic acid, as well. Physodic acid may form by an intramolecular coupling of olivetoric acid.

Topics: Ascomycota; Biphenyl Compounds; Depsides; Dibenzoxepins; Lactones; Lichens; Research; Salicylates