ABSTRACT
MAIN CONCLUSION: Rainwater most probably constitutes a relatively effective solvent for lichen substances in nature which have the potential to provide for human and environmental needs in the future. The aims were (i) to test the hypothesis on the potential solubility of lichen phenolic compounds using rainwater under conditions that partly reflect the natural environment and (ii) to propose new and effective methods for the water extraction of lichen substances. The results of spectrophotometric analyses of total phenolic metabolites in rainwater-based extracts from epigeic and epiphytic lichens, employing the Folin-Ciocalteu (F.-C.) method, are presented. The water solvent was tested at three pH levels: natural, 3, and 9. Extraction methods were undertaken from two perspectives: the partial imitation of natural environmental conditions and the potential use of extraction for economic purposes. From an ecological perspective, room-temperature water extraction ('cold' method) was used for 10-, 60-, and 120-min extraction periods. A variant of water extraction at analogous time intervals was an 'insolation' with a 100W light bulb to simulate the heat energy of the sun. For economic purposes, the water extraction method used the Soxhlet apparatus and its modified version, the 'tea-extraction' method ('hot' ones). The results showed that those extractions without an external heat source were almost ineffective, but insolation over 60- and 120-min periods proved to be more effective. Both tested 'hot' methods also proved to be effective, especially the 'tea-extraction' one. Generally, an increase in the concentration of phenolic compounds in water extracts resulted from an increasing solvent pH. The results show the probable involvement of lichen substances in biogeochemical processes in nature and their promising use for a variety of human necessities.
Subject(s)
Lichens , Phenols , Solubility , Spectrophotometry , Water , Lichens/chemistry , Lichens/metabolism , Phenols/metabolism , Phenols/analysis , Water/chemistry , Solvents/chemistry , Hydrogen-Ion Concentration , Rain/chemistryABSTRACT
Dibenzofurans are a small class of natural products with versatile biological activities that used to be thought to come mainly from lichens and ascomycetes. In fact, they are also distributed widely in higher plants, especially in the families Rosaceae and Myrtaceae. Dibenzofurans and derivatives from lichens and ascomycetes have been well reviewed, but dibenzofurans from all biological sources in nature have not been reviewed. In this review, dibenzofurans from all natural sources have been comprehensively reviewed, and a total of 211 dibenzofurans isolated and identified from organisms between 1843 and March 2023 are categorized and discussed, including their biosynthesis, structural diversity, sources, and bioactivities.
Subject(s)
Ascomycota , Lichens , Humans , Dibenzofurans , Lichens/chemistryABSTRACT
Parmotrema perlatum, a lichen belonging to the family Parmeliaceae, is well known for its culinary benefits and aroma used as a condiment in Indian homes is also known as the "black stone flower" or "kalpasi" in India. This research intends to analyze the antioxidant power of the crude extracts using four pH-based buffers solubilized proteins/peptides and RP-HPLC fractions of P. perlatum obtained by purification. The proteins that were extracted from the four different buffers were examined using LC-MS/MS-based peptide mass fingerprinting. When compared to the other buffers, the 0.1 M of Tris-HCl buffer pH 8.0 solubilized proteins/peptides had the strongest antioxidant capacity. The sequential purification of the peptide was carried out by using a 3-kDa cut-off membrane filter and semipreparative RP-HPLC. Additionally, the purified fractions of the peptide's antioxidant activity were assessed, and effects were compared with those of the crude and 3 kDa cut--off membrane filtrates. The peptide fractions were sequenced by LC-MS/MS, which reveals that fraction 2 from RP-HPLC with the sequence LSWFMVVAP has shown the highest antioxidant potential in comparison with other fractions which can serve as the potential natural antioxidant drug. Further, fraction 2 also showed antibacterial activity against the selected microorganisms.
Subject(s)
Anti-Bacterial Agents , Antioxidants , Tandem Mass Spectrometry , Antioxidants/pharmacology , Antioxidants/chemistry , Antioxidants/isolation & purification , Chromatography, High Pressure Liquid , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/isolation & purification , Peptide Mapping , Peptides/chemistry , Peptides/pharmacology , Peptides/isolation & purification , Lichens/chemistry , Parmeliaceae/chemistry , Antimicrobial Peptides/chemistry , Antimicrobial Peptides/pharmacology , Antimicrobial Peptides/isolation & purification , Liquid Chromatography-Mass SpectrometryABSTRACT
The endolichenic fungi are an unexplored group of organisms for the production of bioactive secondary metabolites. The aim of the present study is to determine the antibacterial potential of endolichenic fungi isolated from genus Parmotrema. The study is continuation of our previous work, wherein a total of 73 endolichenic fungi were isolated from the lichenized fungi, which resulted in 47 species under 23 genera. All the isolated endolichenic fungi were screened for preliminary antibacterial activity. Five endolichenic fungi-Daldinia eschscholtzii, Nemania diffusa, Preussia sp., Trichoderma sp. and Xylaria feejeensis, were selected for further antibacterial activity by disc diffusion method. The zone of inhibition ranged from 14.3 ± 0.1 to 23.2 ± 0.1. The chemical composition of the selected endolichenic fungi was analysed through GC-MS, which yielded a total of 108 compounds from all the selected five endolichenic fungi. Diethyl phthalate, 1-hexadecanol, dibutyl phthalate, n-tetracosanol-1, 1-nonadecene, pyrrol[1,2-a] pyrazine-1,4-dione, hexahydro-3-(2-methyl) and tetratetracontane were found to be common compounds among one or the other endolichenic fungi, which possibly were responsible for antibacterial activity. GC-MS data were further analysed through Principal Component Analysis which showed D. eschscholtzii to be with unique pattern of expression of metabolites. Compound confirmation test revealed coumaric acid to be responsible for antibacterial activity in D. eschscholtzii. So, the study proves that endolichenic fungi that inhabit lichenized fungal thalli could be a source of potential antibacterial compounds.
Subject(s)
Anti-Bacterial Agents , Microbial Sensitivity Tests , Secondary Metabolism , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/metabolism , Lichens/microbiology , Lichens/chemistry , Bacteria/drug effects , Bacteria/classification , Bacteria/metabolism , Ascomycota/metabolism , Ascomycota/chemistry , Gas Chromatography-Mass SpectrometryABSTRACT
Lichens are symbiotic associations of algae and fungi. They are edible as food and have been used in traditional medicine for years. It is aimed to screen Peltigera praetextata (Flörke ex Sommerf.) Zopfand and Peltigera elisabethae Gyeln. phytochemically by LC/QTOF/MS and according to the constituents to evaluate the antioxidant, tyrosinase inhibitory, and antibacterial activities. In total 54 of metabolites detected by LC/QTOF/MS were common in both species. According to LC/QTOF/MS scanning results, alkaloids, iridoid glycosides, phenolics, cyanogenetic glycosides, and terpenic structures were detected. DPPH, ABTS, superoxide radical scavenging activities, and metal chelating capacity IC50 values were 84.55, 9.349; 51.27, 9.127; 95.01, 58.65 and 20.57, 70.08 µg/mL., respectively. The CUPRAC reducing power was determined as 4.69 and 9.57 TEACCUPRAC, respectively. Tyrosinase inhibitor activity were found to be 86.95 and 196.7 µg/mL. Both lichens did not show antimicrobial effects. As a result of the antioxidant and tyrosinase inhibitor activities it was seen that their activities were significant and further in vivo studies could be carried out on this lichens.
Subject(s)
Antioxidants , Lichens , Phytochemicals , Lichens/chemistry , Antioxidants/pharmacology , Antioxidants/analysis , Phytochemicals/pharmacology , Phytochemicals/analysis , Phytochemicals/chemistry , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/analysis , Anti-Bacterial Agents/chemistry , Monophenol Monooxygenase/antagonists & inhibitors , Chromatography, Liquid/methods , Mass Spectrometry/methodsABSTRACT
The use of natural dyes in several areas is regulated by current European and non-European legislation, due to various problems with synthetic dyes. The analysis revealed that the lichen studied: Xanthoria parietina has potential natural dye sources and provides bright colors for extraction solvents. Furthermore, dyed wool and toile fabric have good fastness properties in ammonia fermentation and boiling water, both with and without mordants. The sample dyes with Xanthoria parietina were characterized by several analytical techniques: high-performance liquid chromatography with diode array detection (HPLC-DAD) and electrospray ionization with tandem mass spectrometry (HPLC-ESI-Q-ToF). As compounds from Xanthoria parietina form a complex with mordants and tissues, it is impossible to identify the molecules responsible for coloring using chromatographic techniques. However, we have evaluated the dyeing power of their major molecule, parietin. To further confirm the coloring power of the isolated parietin molecule, we performed a dye test with pure parietin. Thus, CIALAB analyses have shown parietin is the molecule responsible for the coloring obtained by Xanthoria parietina. The utilization of parietin derived from lichens facilitates the development of sustainable dyes for textile coloring, presenting an environmentally friendly alternative to synthetic dyes while simultaneously enriching lichen biodiversity.
Subject(s)
Ascomycota , Emodin/analogs & derivatives , Lichens , Animals , Lichens/chemistry , Ascomycota/chemistry , Coloring AgentsABSTRACT
A bio-guided isolation was applied to the Vietnamese lichen Roccella montagnei based on alpha-glucosidase inhibition. Six compounds were isolated and structurally elucidated, including a new ortho depside, montagneside A (1), together with five known compounds, sekikaic acid (2), lanost-7-en-3ß-ol (3), ethyl orsellinate (4), D-montagnetol (5), and D-erythrin (6). Their chemical structures were identified by extensive 1D and 2D NMR analysis, high-resolution mass spectroscopy, and comparisons with those reported in the literature. D-Erythrin (6), a major component, was selected for further modification using Smiles rearrangement. Three erythritol derivatives 6a-6c were synthesized. Compounds 1-3, 6, and 6a-6c were evaluated for alpha-glucosidase inhibition. Compounds 2 and 6a-6c showed significant alpha-glucosidase inhibition with IC50 values ranging from 7.9 to 149â µM, respectively. Molecular docking was applied to the most active compound 6a to clarify the inhibitory mechanism.
Subject(s)
Glycoside Hydrolase Inhibitors , Lichens , alpha-Glucosidases , alpha-Glucosidases/metabolism , Depsides/isolation & purification , Depsides/chemistry , Depsides/pharmacology , Dose-Response Relationship, Drug , Glycoside Hydrolase Inhibitors/chemistry , Glycoside Hydrolase Inhibitors/pharmacology , Glycoside Hydrolase Inhibitors/isolation & purification , Lichens/chemistry , Molecular Docking Simulation , Molecular Structure , Structure-Activity Relationship , VietnamABSTRACT
Lichens are a symbiotic association of algae and fungus, belonging to the family Parmeliaceae. Some lichen species are edible and used as an active ingredient for preparation of exotic spices as well as folklore medicine to cure different kinds of ailments. A specimen of lichen was collected from Munner in the Kerala State of South India for chemical profiling. Chemical analyses of the diethyl ether extract of the defatted lichen led to the isolation of six phenols 1-6 with variation of relative abundance. Amongst them, the relative abundance of compound 3 was the greatest (1 % of crude extract) and it was identified as atranorin. The structures of known compounds were confirmed by comparison of their 1H-NMR, 13C NMR, and mass data with published values available in the literature. In vitro bioassay for anti-proliferative activity of these compounds has been conducted against various human cancer cell lines in comparison with paclitaxel as control using SRB assay. Interestingly, a new compound 5 was found along with previously reported compounds from this lichen. This new compound was designated as fluoroatranorin 5 which was reported for the first time herein. The structural characterization of a new depside was determined by spectral methods such as 1H-NMR, 13C NMR, 19F NMR, IR, LC-HRESI-MS, and LC-MS/MS study. Its structure was confirmed by single crystal X-ray diffraction study. This new compound was designated as fluoroatranorin 5 which was reported first time herein. Anti-proliferative activity of all these compounds was evaluated against six different cancer cell lines. The inhibitory activity, IC50 value of compounds 1-3 and 5 exhibited at 99.64, 102.04, 109.20, 53.0 and 2.4â µM on cancer cell lines HT-29 (colon), Hela (cervical), HT-29, HPAC (pancreas) and A2780 (ovarian cancer cell line) respectively in comparison with paclitaxel as control. The new compound 5 exhibited significant activity with IC50 value 2.4â µM on A2780 ovarian cancer cell line.
Subject(s)
Antineoplastic Agents , Cell Proliferation , Depsides , Drug Screening Assays, Antitumor , Lichens , Humans , Lichens/chemistry , Cell Proliferation/drug effects , Depsides/pharmacology , Depsides/chemistry , Depsides/isolation & purification , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Cell Line, Tumor , Halogenation , Molecular Structure , Structure-Activity Relationship , Dose-Response Relationship, DrugABSTRACT
The aim of this work was to relate the contribution of mine-derived airborne particulate matter to Ca, Fe, Mn and S content and distribution in Punctelia hypoleucites transplanted to Bajo de la Alumbrera, an important open-pit mine in Catamarca, Argentina. Lichen samples were transplanted to four monitoring sites: two sites inside the mine perimeter and two sites outside the mine. After three months, elemental distribution in samples was analyzed by microparticle-induced X-ray emission (microPIXE), and elemental concentration was determined by specific techniques: Ca and Fe by instrumental neutron activation analysis, Mn by inductively coupled plasma atomic emission spectrometry and S by a turbidimetric method. A differential distribution of S and Ca in thalli transplanted in-mine sites was detected compared to that of samples transplanted outside-mine sites. An overlap of Fe and S in the upper cortex of the apothecium section was observed, leading to infer a mineral association of both elements. Similar association was observed for Ca and S. In addition to these results, the significantly higher concentration detected for S and Mn in in-mine site samples suggests a contribution of Fe, S, Ca and Mn of mining origin to the content and distribution of these elements in P. hypoleucites. MicroPIXE complemented with Mössbauer spectroscopy analysis determined the presence of pyrite particles together with other iron-bearing minerals displaying different degrees of oxidation. These results point to a mining origin of the airborne particulate matter trapped by the lichen thalli transplanted to Bajo de la Alumbrera. These findings indicate that P. Hypoleucites acts as an excellent air quality biomonitor in the Bajo de la Alumbrera mine area.
Subject(s)
Lichens , Parmeliaceae , Particulate Matter/analysis , Lichens/chemistry , Argentina , Minerals/analysis , Environmental Monitoring/methodsABSTRACT
Various studies have shown that Hypogymnia physodes are a source of many biologically active compounds, including lichen acids. These lichen-specific compounds are characterized by antioxidant, antiproliferative, and antimicrobial properties, and they can be used in the cosmetic and pharmaceutical industries. The main aim of this study was to optimize the composition of natural deep eutectic solvents based on proline or betaine and lactic acid for the extraction of metabolites from H. physodes. The design of the experimental method and the response surface approach allowed the optimization of the extraction process of specific lichen metabolites. Based on preliminary research, a multivariate model of the experiment was developed. For optimization, the following parameters were employed in the experiment to confirm the model: a proline/lactic acid/water molar ratio of 1:2:2. Such a mixture allowed the efficient extraction of three depsidones (i.e., physodic acid, physodalic acid, 3-hydroyphysodic acid) and one depside (i.e., atranorin). The developed composition of the solvent mixtures ensured good efficiency when extracting the metabolites from the thallus of H. physodes with high antioxidant properties.
Subject(s)
Depsides , Lactones , Depsides/chemistry , Depsides/isolation & purification , Depsides/pharmacology , Lactones/chemistry , Lactones/isolation & purification , Lactones/pharmacology , Deep Eutectic Solvents/chemistry , Antioxidants/chemistry , Antioxidants/pharmacology , Antioxidants/isolation & purification , Proline/chemistry , Lichens/chemistry , Lactic Acid/chemistry , Green Chemistry Technology/methods , Betaine/chemistry , Betaine/analogs & derivatives , Betaine/pharmacology , Solvents/chemistry , Dibenzoxepins , HydroxybenzoatesABSTRACT
HIGHLIGHTS: Microplastics (MPs) and microrubbers (MRs) determined in lichens and mosses around Shiraz. In lichens, MPs mainly thin fibres up to 1 MP g-1; MRs were < 0.1 MP g-1. In mosses, abundances were similar but with a greater fraction of larger, non-fibrous particles. Larger MPs and MRs decreased in abundance with distance and elevation from Shiraz. Around Shiraz, the common moss, Grimmia critina, would be the most suitable biomonitor. Lichens and mosses have been employed as biomonitors of atmospheric particulate pollutants, like metals and industrial solids, for many decades. Here, we evaluated the potential of nine species of crustose and foliose lichens and a widely distributed moss (Grimmia critina) to act as biomonitors of airborne microplastics (MPs) and microrubbers (MRs). About 200 lichens and 40 mosses were sampled across different altitudinal transects in the vicinity of Shiraz City, southwest Iran, and MPs and MRs were quantified and characterised after sample peroxidation. In most species of lichen, MP and MR abundance overall was < 1 g-1 and < 0.1 g-1, respectively, and the majority of plastics were fibres of < 10 µm in diameter and < 1000 µm in length. Respective weight normalised abundances of MPs and MRs were similar in G. critina, but there were greater proportions of both larger (> 1000 µm) and non-fibrous particles among the MPs. In both lichens and moss, there was a greater number of larger MPs and MRs at locations closest to and at the same elevation as Shiraz than at more distant and elevated locations, suggesting an inverse relationship between particle size and distance travelled. Among the lichens, members of the genus Acarospora, with their areolated form, appeared to act as the most suitable biomonitors for MPs and MRs. Overall, however, the wide distribution of the moss, G. crinita, and its ability to intercept and accumulate a broader range of sizes and shapes of MPs and MRs make this species a better choice, at least in the type of environment studied.
Subject(s)
Air Pollutants , Bryophyta , Lichens , Microplastics , Lichens/chemistry , Iran , Microplastics/analysis , Air Pollutants/analysis , Bryophyta/chemistry , Environmental Monitoring/methods , Biological Monitoring/methods , Particle SizeABSTRACT
In Tunisia, urban air pollution is becoming a bigger problem. This study used a combined strategy of biomonitoring with lichens and satellite mapping with Sentinel-5 satellite data processed in Google Earth Engine (GEE) to assess the air quality over metropolitan Tunis. Lichen diversity was surveyed across the green spaces of the Faculty of Science of Tunisia sites, revealing 15 species with a predominance of pollution-tolerant genera. The Index of Atmospheric Purity (IAP) calculated from the lichen data indicated poor air quality. Spatial patterns of pollutants sulfur dioxide (SO2), ozone (O3), nitrogen dioxide (NO2), carbon monoxide (CO), and aerosol index across Greater Tunis were analyzed from Sentinel-5 datasets on the GEE platform. The higher values of these indices in the research area indicate that it may be impacted by industrial activity and highlight the considerable role that vehicle traffic plays in air pollution. The results of the IAP, IBL, and the combined ground-based biomonitoring and satellite mapping techniques confirm poor air quality and an environment affected by atmospheric pollutants which will enable proactive air quality management strategies to be put in place in Tunisia's rapidly expanding cities.
Subject(s)
Air Pollutants , Air Pollution , Environmental Monitoring , Lichens , Ozone , Sulfur Dioxide , Lichens/chemistry , Environmental Monitoring/methods , Air Pollutants/analysis , Air Pollution/statistics & numerical data , Tunisia , Ozone/analysis , Sulfur Dioxide/analysis , Nitrogen Dioxide/analysis , Cities , Satellite Imagery , Carbon Monoxide/analysisABSTRACT
The lichen natural products pulvinamide, rhizocarpic acid, and epanorin have been synthesized and characterized spectroscopically and by X-ray crystallography. The syntheses, by ring-opening of pulvinic acid dilactone (PAD), may well be biomimetic, given the well-known occurrence of PAD in lichen. The enantiomers, ent-rhizocarpic acid and ent-epanorin, and corresponding carboxylic acids, norrhizocarpic acid and norepanorin, were similarly prepared. All compounds were assessed for growth inhibitory activity against selected bacteria, fungi, a protist, a mammalian tumor cell line, and normal cells. Rhizocarpic acid is weakly antibacterial (Bacillus subtilis MIC = 50 µg/mL) and possesses modest but selective antitumor activity (NS-1 murine myeloma MIC = 3.1 µg/mL) with >10-fold potency relative to its enantiomer (MIC = 50 µg/mL).
Subject(s)
Lichens , Animals , Mice , Anti-Bacterial Agents/chemistry , Bacteria , Fungi , Lichens/chemistry , Malonates/metabolism , Mammals , Microbial Sensitivity TestsABSTRACT
The lichen Cetraria islandica is traditionally used as a demulcent for the symptomatic treatment of irritations of the mouth and throat and associated dry cough, as well as for the treatment of temporary loss of appetite. In addition to depsides and depsidones, thalli contain paraconic acids, a group of secondary metabolites commonly found in lichens and fungi. Among those, protolichesterinic acid has shown promising pharmacological activities. However, the efficient isolation of paraconic acids is quite complex due to their very similar chemical structures and their weak ultraviolet absorption. In the present work, a two-step isolation protocol of protolichesterinic acid and lichesterinic acid from a complex paraconic acid mixture is described using Sephadex LH20 column chromatography and fast centrifugal partition chromatography. Final purities higher than 95% and recoveries above 50% are achieved. Additionally, reliable qualitative techniques for detecting and differentiating paraconic acids are described. Finally, some data on compound stability and enantiomeric purity are shown.
Subject(s)
Lichens , Parmeliaceae , Parmeliaceae/chemistry , 4-Butyrolactone/metabolism , Lichens/chemistry , Lichens/metabolism , Chromatography, LiquidABSTRACT
This review provides information on the synthesis and revision of the structures of natural dimeric (poly)hydroxynaphthazarins, metabolites of echinoderms and lichens, and on the refinement of the direction and mechanism of reactions in the synthesis of some of these compounds.
Subject(s)
Lichens , Animals , Lichens/chemistry , EchinodermataABSTRACT
Marine organisms have gained considerable biotechnological interest in recent years due to their wide variety of bioactive compounds with potential applications. Mycosporine-like amino acids (MAAs) are UV-absorbing secondary metabolites with antioxidant and photoprotective capacity, mainly found in organisms living under stress conditions (e.g., cyanobacteria, red algae, or lichens). In this work, five MAAs were isolated from two red macroalgae (Pyropia columbina and Gelidium corneum) and one marine lichen (Lichina pygmaea) by high-performance countercurrent chromatography (HPCCC). The selected biphasic solvent system consisted of ethanol, acetonitrile, saturated ammonium sulphate solution, and water (1:1:0.5:1; v:v:v:v). The HPCCC process for P. columbina and G. corneum consisted of eight separation cycles (1 g and 200 mg of extract per cycle, respectively), whereas three cycles were performed for of L. pygmaea (1.2 g extract per cycle). The separation process resulted in fractions enriched with palythine (2.3 mg), asterina-330 (3.3 mg), shinorine (14.8 mg), porphyra-334 (203.5 mg) and mycosporine-serinol (46.6 mg), which were subsequently desalted by using precipitation with methanol and permeation on a Sephadex G-10 column. Target molecules were identified by HPLC, MS, and NMR.
Subject(s)
Lichens , Rhodophyta , Seaweed , Seaweed/chemistry , Lichens/chemistry , Countercurrent Distribution , Amino Acids/chemistry , Rhodophyta/chemistry , Plant Extracts/metabolism , Ultraviolet RaysABSTRACT
Due to the rapid increase in the novel coronavirus virulence, the entire world implemented the practice of lockdown along with the constraint of human movement. The obligation of quarantine halted most of the commercial and industrial movement that prominently disturbed the distinct key environmental parameters directly associated with the plant's and animal's health conditions. In this regard, the research aims to study the sudden shut-off of vehicular activity impact on the naturally growing lichen of the genus Pyxine cocoes. The results showed an increase in the pigments, Fv/Fm ratio, and phytohormones during the lockdown and concurrently the decreasing levels in the post-lockdown period. Interestingly, modulations in the phytohormones occur in the lockdown period as compared to the post-lockdown period. The metals Al, Cr, and Fe show the highest increasing trends in the unlocking period, whereas As, Cd, Pb, Cu, Hg, Mn, and Zn show very little variation during the running and post-lockdown phases. The lichen photosynthetic activity justifies further examination as initial biological indicators of the abrupt environmental variations prompted by such types of atmospheric situations and, to a greater extent, for the risk assessment in the near future. In conclusion, stress-phytohormone and amino acids play a significant role as stress reducers. Although lichens are well known for long environmental assessment, the present study will provide qualitative and quantitative variation in physiochemical changes in the short term and sudden environmental fluctuations. HIGHLIGHTS: ⢠Qualitative and quantitative variation in biochemical parameters in lichen during and post-lockdown period was analyzed. ⢠Stress-phytohormone and amino acids play a significant role as stress reducers. ⢠Selectivity sequence reflection in heavy metal accumulation may be used in future studies.
Subject(s)
COVID-19 , Lichens , Humans , Lichens/chemistry , Lichens/metabolism , Plant Growth Regulators/metabolism , Communicable Disease Control , Amino Acids/metabolism , Environmental Monitoring/methodsABSTRACT
Polyhydroxy-anthraquinones bearing amino acids are found rather seldom in nature. Emodacidamides, isolated from a marine-derived fungus, Penicillium sp. SCSIO sof101 by Luo etâ al. (2017) are the first natural example of amino acid conjugated anthraquinone. In this study, O-methylated emodacidamides and emodinic acid-anilides were synthesized starting from parietin, extracted from the lichen Xanthoria parietina (L.) Th. Fr. The structural elucidations of prepared compounds were confirmed by 1D and 2D NMR analyses including HSQC and HMBC techniques. In addition, all newly synthesized compounds were evaluated for the antioxidant activities with free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH) scavenging. The synthesized compounds showed low to moderate antioxidant and DPPH scavenging activities. The antioxidant activities were supported within quantum chemical calculations using the DFT-B3LYP/6-311++G(d,p) level of theory. It is observed that the antioxidant activity of emodacidamides mostly depends on the phenolic groups on anthraquinone ring. The phenolic groups on other substituents help to improve antioxidant activity and also the position of hydroxy group is a decisive factor for antioxidant ability.
Subject(s)
Ascomycota , Lichens , Lichens/chemistry , Antioxidants/pharmacology , Antioxidants/metabolism , Anthraquinones/chemistryABSTRACT
A bioactivity-guided investigation of the lichen Parmotrema cristiferum (Taylor) Hale (Parmeliaceae) led to the isolation of two new depsidones, cristifones A and B (1 and 2). The structures of the isolated compounds were identified by spectroscopic methods and comparison with the literature data. Compound 1 showed the initial combined structures of depsidone and depside cores. The two isolated compounds were then evaluated for α-glucosidase inhibition. Compounds 1 and 2 were confirmed as potent, with IC50 values of 21.5 and 18.4â µM, respectively. Compound 2 was a non-competitive inhibitor against α-glucosidase, as indicated by the intersect in the second quadrant of each respective plot.
Subject(s)
Glycoside Hydrolase Inhibitors , Lichens , Parmeliaceae , alpha-Glucosidases/chemistry , alpha-Glucosidases/metabolism , Glycoside Hydrolase Inhibitors/pharmacology , Lichens/chemistry , Parmeliaceae/chemistryABSTRACT
Lichens are symbiotic organisms made up of alga/cyanobacterium and fungus. We investigated antioxidant, antibacterial and anticancer properties of two lichen compounds, atranorin and salazinic acid, and five lichen species: Heterodermia boryi, Heterodermia diademata, Heterodermia hypocaesia, Parmotrema reticulatum, and Stereocaulon foliolosum. Free radical scavenging, Ferric reducing potential, Nitric oxide scavenging, and Trolox equivalent capacity were used to measure antioxidant activity. Strong radical scavenging action was demonstrated by atranorin and salazinic acid, with IC50 values of 39.31â µM and 12.14â µM, respectively. The Minimum Inhibitory Concentration (MIC) assay based on resazurin, was used to measure antibacterial activity. Parmotrema reticulatum demonstrated significant antibacterial activity against Raoultella planticola with MIC of 7.8â µg/mL. Cytotoxicity assay on breast cancer cell line was used to assess anticancer activity. To further understand the binding locations on the target proteins Er (Estrogen Receptor alpha), EGFR (Epidermal Growth Factor Receptor), mTOR (Mammalian Target of Rapamycin), and PgR (Progesterone Receptor), molecular docking experiments were conducted. Docking study showed that the binding energies of atranorin and salazinic acid with mTOR were -5.31â kcal/mol and -3.43â kcal/mol, respectively. The results suggest that atranorin has the potential to be a multitargeted molecule with natural antioxidant, antibacterial, and anticancer properties.