Psoromic Acid Research Articles

A New Species and a New Record of Byssoid Arthoniaceae (Lichenized Ascomycota) from Southern China

This paper illustrates two species in the lichen-forming family Arthoniaceae from southern China, including a new species of Herpothallon, H. fibrosum L.L. Liu & Lu L. Zhang and a new record of Cryptothecia, C. striata G. Thor for China. Herpothallon fibrosum has fluffy, cylindrical pseudoisidia, like a bundle of fiber, and psoromic acid and confluentic acid are present. Furthermore, the new record of Cryptothecia striata has been identified by morphological, anatomical, chemical, and molecular studies. The systematic position of the two species was clarified by the molecular sequence data from the small subunit of the mitochondrial ribosomal DNA (mtSSU). Detailed taxonomic descriptions, chemical characters, comparisons, and discussion of the characteristics of similar species are provided for the two species; the relationship between Cryptothecia and Herpothallon is also discussed here.

Notes on the genus Usnea (lichenized Ascomycota, Parmeliaceae). V.

Type material of twelve species of Usnea related to Asia and South Africa were studied and one species from North America is newly described. Holotype specimens of eight Chinese taxa described in 1975 were synonymized as follows: U. mengyangensis is lectotypified and synonymized with U. aciculifera. Usnea recurvata and U. subrectangulata are synonymized with U. baileyi. Usnea kirinensis is synonymized with U. barbata s.str. Usnea crassiuscula and U. yunnanensis (= U. australis J.D. Zhao et al., nom. illeg. non Fr.) are synonymized with U. bismolliuscula. Usnea iteratocarpa is synonymized with U. cristatula (new to Asia, China). Usnea decumbens is synonymized with U. intumescens (new to Asia, China). Usnea entoviolata and U. roseola are synonymized with U. fragilis (new to Asia, China, India, Japan). The lectotype of Usnea trichoideoides was found to belong to the Usnea pectinata aggr. and consequently U. montis-fuji was resurrected for U. trichodeoides sensu Ohmura. Usnea ceratina and U. trichodeoides are excluded from the Japan lichen flora. Usnea macaronesica a recently described Macaronesian and South American species is synonymized with the Asian taxa U. pycnoclada. Usnea chicitae is described as a new species endemic of the Southern Appalachian Mountains. It is characterized by stipitate efflorescent soralia, a tenuicorticata-type of CMA and the presence of salazinic and psoromic acid in the medulla.

Changes in Intracellular and Extracellular Metabolites of Mixed Lactobacillus Strains Enhance Inhibition of Pathogenic Bacterial Growth and Lipopolysaccharide-Induced Alleviation of RAW264.7 Cellular Inflammation.

It is important to explore whether there are antagonistic and synergistic effects between different strains of Lactobacillus when developing mixed Lactobacillus strain products. In this study, we investigated the antagonistic and symbiotic effects of co-cultured Lactobacillus strains, as well as their amelioratory effects on lipopolysaccharide (LPS)-induced inflammation and oxidative stress in RAW264.7 cells. The Lactobacillus strains tested in this paper showed no antagonism. Co-culture of Lactiplantibacillus plantarum Y44 and L. plantarum AKS-WS9 was found to show inhibiting effects on the growth of Escherichia coli and Staphylococcus aureus. Additionally, the co-cultured Lactiplantibacillus plantarum Y44 and L. plantarum AKS-WS9 relieved inflammation in RAW264.7 cells induced by LPS by inhibiting the activation of NF-κB and P38 signaling pathways and down-regulating the expression of pro-inflammatory cytokines NO, ROS, iNOs and TNF-α. And the co-cultured Lactobacillus strains activated the Nrf2 signaling pathway in the LPS-induced RAW264.7 cells to promote the expression of antioxidant enzymes in response to oxidative stress. There was a difference in intracellular and extracellular metabolites between single or co-cultured Lactobacillus strains, and the co-cultured Lactobacillus strains significantly increased extracellular metabolites 4-chlorobenzaldehyde, psoromic acid, and 2-dodecylbenzenesulfonic acid and intracellular metabolites 9(S)-HODE, pyocyanin, and LysoPA. We inferred that the better antibacterial and anti-inflammatory ability of the co-cultured Lactobacillus strains were related to the changes in the metabolites of the co-cultured Lactobacillus strains. The co-cultured L. plantarum Y44 and L. plantarum AKS-WS9 strains exhibited better anti-inflammatory abilities and had the potential to alleviate the symptoms of inflammatory diseases as mixed probiotics.

Herpothallon rubrogranulosum, a new species with granular pseudoisidia from the Mid-Atlantic Coastal Plain of southeastern North America1

Herpothallon rubrogranulosum is described from forested wetlands in the Mid-Atlantic Coastal Plain of southeastern North America. It appears to be infrequent throughout its range, but locally abundant on bald cypress trees in areas of Francis Marion National Forest, South Carolina, USA. The species is characterized by a cream colored, ecorticate thallus with small, coarse granular pseudoisidia that are covered with variable amounts of orange-red pigment that reacts K+ red-pink, and the production of abundant psoromic acid. It was previously confused with H. rubroechinatum, which is a rarer tropical species that differs markedly in having large, conspicuous pseudoisidia.

Lecanora moniliformis sp. nov. from China

A new multispored Lecanora species from China is proposed as L. moniliformis, which is similar to L. japonica but differs by its crenate apothecial margin and the presence of psoromic acid. A detailed taxonomic description, ecological and chemical characters, and illustrations are provided for the new taxon, and a key to the multispored species of Lecanora is presented.

Sarcogyne similis (Acarosporaceae) produces psoromic acid and is confirmed to be widespread in North America

Sarcogyne similis is found to produce psoromic acid, a substance previously known from only one other species in the family Acarosporaceae. Study of more than one hundred specimens from throughout the range of S. similis confirms the species is widely distributed from Nova Scotia, Canada, south throughout much of the eastern United States, and westward through the Sonoran Desert to southern California, where it occurs on non-calcareous rocks, especially sandstone. The recently proposed synonymy with S. reebiae is confirmed. Sarcogyne similis f. convexa is lectotypified with material that contains psoromic acid. The type of S. californica, currently treated as a synonym of S. similis, does not produce psoromic acid and may belong to a separate taxon. The distribution of S. dakotensis, which produces norstictic acid, appears to be nearly allopatric with S. similis.

Two New Fumarprotocetraric Acid Lactones Identified and Characterized by UHPLC-PDA/ESI/ORBITRAP/MS/MS from the Antarctic Lichen Cladonia metacorallifera

Lichens are symbiotic organisms between algae and fungi, which are makers of secondary compounds named as lichen substances. Hyphenated techniques have significantly helped natural product chemistry, especially UHPLC/ESI/MS/MS in the identification, separation, and tentative characterization of secondary metabolites from natural sources. Twenty-five compounds were detected from the Antarctic lichen Cladonia metacorallifera for the first time using UHPLC-PDA/ESI/Orbitrap/MS/MS. Compounds 5 and 7 are reported as new compounds, based on their MS/MS fragmentation routes, and considered as fumarprotocetraric acid derivatives. Besides, ten known phenolic identified as orsellinic acid, ethyl 4-carboxyorsellinate, psoromic acid isomer, succinprotocetraric acid, siphulellic acid, connorstictic acid, cryptostictic acid, lecanoric acid, lobaric acid and gyrophoric acid are noticed for the first time in the Cladonia genus.

A new species of Mazosia (lichenised Ascomycetes: Roccellaceae) from Tasmania

Two species of Mazosia occur in Tasmania: the foliicolous, pantropical M. phyllosema and M. corticola, here described as new to science. The new species is characterised by a corticolous thallus containing psoromic acid and three-septate ascospores, 17–27 × 4–6.5 μm; it occurs in Tasmanian and Victoria.

<p><strong><em>Lecanographa atlantica</em> (Arthoniales, Lecanographaceae), a widespread and conspicuous but still undescribed lichen-forming fungus</strong></p>

Lecanographa farinosa was considered to be a lichen inhabiting coastal rocks of the Mediterranean region and to possess psoromic and conpsoromic acids as major secondary metabolites. A revision of its type specimen from Germany proved that the species has been misunderstood. In this paper, L. farinosa is shown to have a thallus containing confluentic and 2’-O-methylmicrophyllinic acids and to have a different ecology and distribution. A revision of previous reports of L. farinosa from continental Portugal and the study of recent specimens of Lecanographa cf. farinosa from the Azores, Canary Islands, Cape Verde and continental Portugal revealed a new species described as L. atlantica. Moreover, reports of L. dialeuca from France (Brittany) and of L. subgrumulosa from the Azores are considered misidentifications of L. atlantica. This latter has thus a widespread distribution ranging from the Azores to the Atlantic coast of the European continent where it inhabits volcanic rocks near the sea. Lecanographa atlantica is characterized by a whitish to cream coloured thallus, usually rounded or oblong to shortly lirelliform and white pruinose ascomata with a widely exposed hymenial disc and thin margin, (3–)5–7-septate ascospores of (16–)18.9–23(–26) × (3–)3.4–4(–4.5) µm, and a chemistry including at least 2’-O-methylperlatolic acid but lacking confluentic and 2’-O-methylmicrophyllinic acids. Psoromic acid is sometimes present in L. atlantica but its origin is unclear. Phylogenetic analyses using nuLSU sequences place L. atlantica as sister to L. hypothallina.

A new species of Synarthonia from Luxembourg, and a new combination in the genus Reichlingia (Arthoniaceae)

AbstractA new species of Synarthonia, S. leproidica, is described from Luxembourg. Phylogenetic analyses of mtSSU and RPB2 sequences were used to determine the generic affiliation of this sterile species. Synarthonia leproidica differs from all other species of the genus by the combination of a leproid thallus and the production of psoromic acid. It is the sister species to S. muriformis in our phylogenetic analyses. The discovery of the new species suggests that other strictly sorediate lichen species might have been overlooked in Europe, even in intensely explored countries such as Luxembourg. Phylogenetic analyses further confirm the placement of Reichlingia anombrophila in the genus Reichlingia and of Synarthonia astroidestera in the genus Synarthonia. Arthonia atlantica is transferred to the genus Reichlingia as R. dendritica.

Cytotoxic Activity of Compounds from Lichens of the Cerrado Biome in Brazil

Lichens are sources of numerous biologically active compounds and many of these have demonstrated antitumor potential. The purposes of this study were to evaluate the antiproliferative activity and selectivity of the following compounds isolated from lichens: atranorin and diffractaic, divaricatic, perlatolic, psoromic, norstictic, and protocetraric acids. Cytotoxicity tests based on sulforhodamine B were performed on normal cells (NIH/3T3, fibroblast) and cancer cell lines 786-0 (renal), MCF7 (breast), HT-29 (colon), PC-3 (prostate), and HEp2 (laryngeal). Diffractaic acid exhibited GI 50 values in the 58.6-98.9 µM range. Divaricatic and perlatolic acids were the most active compounds, with GI 50 values of 9.8 and 15.5 µM for PC-3 and MCF7 cells, respectively. Protocetraric acid proved active only against HEp2 cells (GI 50 = 41.4 µM). Atranorin, psoromic acid, and norstictic acids were inactive against all the cells tested. Chemometrics was used to evaluate the effect of the compounds against the cell lines tested. PCA (Principal Component Analysis) based on GI 50 values ​​separated compounds into two groups compared to doxorubucin, while HCA (Hierarchical Cluster Analysis) separated them into three groups based on SI values. DOI: http://dx.doi.org/10.17807/orbital.v12i1.1397

Bioactive constituents, vitamin analysis, antioxidant capacity and α-glucosidase inhibition of Canna indica L. rhizome extracts

Rhizomes of Canna indica were studied to determine their potential use as a functional food, a source of vitamins, nutritional and nutraceutical ingredients. Biomass and nutrient characterization showed the rhizomes were a good source of fiber (25.1%), starch (28.5%), crude protein (4.72%), and lipids (5.75%) with a total estimated caloric value of 423 Kcal/100 g dry weight. The rhizome also had considerable amounts of minerals and vitamins. Acetone extracts of rhizomes showed significantly higher antioxidant properties. The IC50 values with DPPH, ABTS+. and O2.- radicals were 21, 23 and 170 μg/ml, respectively. The reducing properties (FRAP and CUPRAC) and DNA protection assay were correlated with the total phenolic and flavonoid content of the rhizome extracts. Acetone and methanol extracts showed protection against free radical-induced DNA and protein degradation. In a β-carotene-linoleic acid model, the acetone extracts significantly decreased the bleaching of β-carotenoids. In a meat model system, the acetone extracts minimized the thiobarbituric acid reactive substance of ground pork meat. α-Glucosidase activity was significantly inhibited using water extracts (IC50 2.35 μg/ml) and acetone extracts (IC50 27.1 μg/ml). HR-LCMS/MS analysis of different extracts showed the occurrence of different bioactive compounds such as rosmarinic acid, psoromic acid, usnic acid, isoeugenitol, ellagic acid, coumaric acid and swietenine. The results suggested that C. indica rhizomes might be a potential source of nutrients and metabolites with health benefits.

α-Glucosidase Inhibition Kinetics and Molecular Docking Studies with the Bioactive Constituents from Canna indica L. Rhizome Extract

The present study investigated the phytochemical constituents from Canna indica rhizome acetone extract, which was earlier reported to possess α-glucosidase inhibiting potential. Different fractions were collected from column chromatography of the acetone extract and the in vitro enzyme inhibition and the kinetic study was performed with the active fraction. The active fraction exhibited competitive inhibition of α-glucosidase. HRLC-MS/MS technique was used to identify the lead compounds from the active fraction. The major compounds were psoromic acid, usnic acid and rosmarinic acid. Molecular docking study of the compounds with the crystal structure of α-glucosidase was performed using ParDOCK. Psoromic acid and usnic acid exhibited strong binding affinity with the active site nucleophiles Asp349 and Asp212, respectively. Usnic acid also stabilized the catalytic residue Glu274. Rosmarinic acid formed multiple hydrogen bonds with the catalytic residue Glu274 and also bonded to non-catalytic residues Gln276, Arg312 and Glu408. The study illustrated informative data on the phytochemical constituents from Canna indica rhizome as α-glucosidase inhibitor and as potential candidates for the development of antidiabetic drugs.

A new Ocellularia (lichenized Ascomycota: Graphidaceae) from New Zealand indicates small-scale differentiation of an Australasian species complex

ABSTRACT Ocellularia (Graphidaceae) is a genus of crustose lichens comprising c.200 species, four known from Australia and New Zealand. Based on recent collections from northern North Island, we describe a fifth species Ocellularia jacinda-arderniae, which is a member of the O. bicuspidata complex. This complex is characterised by peculiar, appendiculate ascospores and a psoromic acid chemistry. Two further undescribed species of this complex, one from North Island and one from South Island, are discussed but left undescribed pending further study. Based on our findings, we provide a revised assessment of New Zealand Ocellularia. Of the four species included in the most recent Flora of New Zealand Lichens from 2007, three do not belong in that genus and the identification of the fourth is incorrect; instead, the following four taxa are recognised: O. jacinda-arderniae, O. aff. dolichotata, O. aff. bicuspidata (a) (South Island; OTA 58820) and O. aff. bicuspidata (b) (North Island; UNITEC 10818). This leads to the somewhat unusual situation that a presumably known genus biota in New Zealand is entirely replaced by names of a new species and three provisional identifications. The following new combination is introduced: Schizotrema concentricum (Stirt.) Lücking comb. nov. In addition, the name Thelotrema manosporum (C. Knight.) Hellb. is given as the correct name for the New Zealand taxon previously identified as T. monosporum Nyl., and the name T. monosporoides Nyl. [syn.: O. monosporoides (Nyl.) Hale] is established as a taxonomic synonym of T. manosporum, leaving two New Zealand species of Thelotrema with large, brown ascospores, namely T. manosporum and T. saxatile C. Knight. The situation of the genus Ocellularia highlights the need for detailed taxonomic revision of understudied lichen groups in New Zealand, especially as these and related genera in the Graphidaceae are excellent indicators of forest health and can be used for monitoring purposes.

Psoromic Acid, a Lichen-Derived Molecule, Inhibits the Replication of HSV-1 and HSV-2, and Inactivates HSV-1 DNA Polymerase: Shedding Light on Antiherpetic Properties.

Psoromic acid (PA), a bioactive lichen-derived compound, was investigated for its inhibitory properties against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2), along with the inhibitory effect on HSV-1 DNA polymerase, which is a key enzyme that plays an essential role in HSV-1 replication cycle. PA was found to notably inhibit HSV-1 replication (50% inhibitory concentration (IC50): 1.9 μM; selectivity index (SI): 163.2) compared with the standard drug acyclovir (ACV) (IC50: 2.6 μM; SI: 119.2). The combination of PA with ACV has led to potent inhibitory activity against HSV-1 replication (IC50: 1.1 µM; SI: 281.8) compared with that of ACV. Moreover, PA displayed equivalent inhibitory action against HSV-2 replication (50% effective concentration (EC50): 2.7 μM; SI: 114.8) compared with that of ACV (EC50: 2.8 μM; SI: 110.7). The inhibition potency of PA in combination with ACV against HSV-2 replication was also detected (EC50: 1.8 µM; SI: 172.2). Further, PA was observed to effectively inhibit HSV-1 DNA polymerase (as a non-nucleoside inhibitor) with respect to dTTP incorporation in a competitive inhibition mode (half maximal inhibitory concentration (IC50): 0.7 μM; inhibition constant (Ki): 0.3 μM) compared with reference drugs aphidicolin (IC50: 0.8 μM; Ki: 0.4 μM) and ACV triphosphate (ACV-TP) (IC50: 0.9 μM; Ki: 0.5 μM). It is noteworthy that the mechanism by which PA-induced anti-HSV-1 activity was related to its inhibitory action against HSV-1 DNA polymerase. Furthermore, the outcomes of in vitro experiments were authenticated using molecular docking analyses, as the molecular interactions of PA with the active sites of HSV-1 DNA polymerase and HSV-2 protease (an essential enzyme required for HSV-2 replication) were revealed. Since this is a first report on the above-mentioned properties, we can conclude that PA might be a future drug for the treatment of HSV infections as well as a promising lead molecule for further anti-HSV drug design.

Biogenic Trichoderma harzianum-derived selenium nanoparticles with control functionalities originating from diverse recognition metabolites against phytopathogens and mycotoxins

Selenium nanoparticles (SNP) were generally utilized as chemotherapeutic agents and environmental ameliorants, but without simultaneous biocontrol functionalities against fungal pathogens and mycotoxins, plus unknown recognition mechanism. Selenium nanoparticles derived from Trichoderma harzianum JF309 (TSNP) were herein synthesized, contrast to traditional SNP, where diverse metabolites co-occurred in TSNP including organic acids and their derivates, such as psoromic acid, β-decyloxybenzoic acid, glucaric acid lactone, etc., revealed by Triple TOF UPLC/HRMS. As hypothesized, this interaction of diverse recognition metabolites and selenium nanoparticles in TSNP might change the arrangement and movement of original state, form random, nondirective to regulated, directional, thus contributing to better antifungal effects and dramatically increasing control functionalities against Alternaria toxins (83% of TeA and 79% of AOH reduction), fumonisin B1 (63% of FB1 reduction) and deoxynivalenol (76% of DON reduction), respectively. Meanwhile, expression of key biosynthetic genes of FUM1, PA, TRI5 and TRI6 were substantially decreased. Finally, as convinced, the obtained nanoparticles had no significant side effects to the selected three human cells. In total, the achieved data supports the biogenic nanoparticles as valuable functional materials with great potential for practical plant protection and food safety prevention.

The Effects of Edaphic and Climatic Factors on Secondary Lichen Chemistry: A Case Study Using Saxicolous Lichens

Diversity of secondary lichen metabolites and their relationship to substrate and environmental parameters were studied in saxicolous lichens in the Middle and South Urals of Russia. Atranorin, usnic acid, gyrophoric acid, zeorin, norstictic acid, antraquinones and stictic acid were found in 73, 42, 41, 37, 36, 35 and 32 species, respectively, of 543 taxa collected. One hundred and ninety six species (i.e., 36% of total species documented) contained no secondary metabolites. Spectra of secondary metabolites of crustose lichens varied on different rock types, while in fruticose and foliose groups only those species without lichen acids were dependent on the substrate type. In Canonical Correspondence Analysis, secondary lichen metabolites were subdivided into groups depending on the concentration of Ca and metals in the substrate. Gyrophoric, lobaric, psoromic, rhizocarpic and stictic acids were common in crustose lichens in metal-poor habitats; species with antraquinones and lichens without any secondary metabolites were most abundant on limestone (alkalic and metal-poor), while other common lichen metabolites had no to minimal dependence on the chemistry of the substrate. The two additional abiotic factors affecting the composition of secondary metabolites were the maximum temperature of the warmest month and elevation. Our results suggest a range of possible relationships exist among lichen acids, rocks and climatic parameters. Furthermore, the same metabolite may affect both accumulation of metals and stress tolerance under unfavorable conditions.

Lichens as promising resources of enzyme inhibitors: A review

Inhibition of some enzymes seems to be one of the therapeutic strategies for the management of certain diseases or conditions such as diabetes, Alzheimer’s disease, cancer and obesity. In this review, an updated information on the enzyme inhibitory activity of lichen extracts and lichen compounds by an intensive literature survey is presented. Crude solvent extracts and isolated compounds from lichens were shown to be effective in causing inhibition of several enzymes such as amylase, lipase, lipoxygenase, aromatase, cyclooxygenase, trypsin, β-glucoronidase, prolyl endopeptidase, monoamine oxidase, urease, tyrosinase, xanthine oxidase, Thioredoxin reductase, glucosidase, topoisomerase, pancreatic elastase, phosphodiesterase, telomerase and acetylcholinesterase. Lichen metabolites such as usnic acid and its derivatives, lobaric acid, physodic acid, ramalin, protolichestrinic acid, salazinic acid, atranorin, evernic acid, zeorin, diffractic acid, psoromic acid, methyl β-orcinolcarboxylate, methylorsellinate, and anziaic acid were shown to be inhibitors of some enzymes. In conclusion, lichens can be employed as promising therapeutic agents in terms of their potential to inhibit the activity of certain enzymes that are involved in some diseases or disorders. In vitro culturing of lichen symbionts in optimized media can be carried out to isolate enzyme inhibitors in larger scale and to develop effective therapeutic agents. Keywords: Lichens, lichen substances, enzyme inhibitors, enzyme inhibitory activity

Anamylopsora altaica sp. nov. from Northwestern China

Anamylopsora altaica, collected from rocks in the Hot Spring Valley Forest Park in the Altay Mountains, Xinjiang, Northwestern China, is described as a new species, based on morphological and chemical characteristics, as well as ITS DNA sequence data. The new lichen species is characterized by its crowded, overlapping squamules with upturned margins, crowded globose apothecia with eight simple hyaline spores per ascus, and the presence of psoromic acid. A detailed description and colour photographs are provided.

Antimycobacterial, Enzyme Inhibition, and Molecular Interaction Studies of Psoromic Acid in Mycobacterium tuberculosis: Efficacy and Safety Investigations.

The current study explores the antimycobacterial efficacy of lichen-derived psoromic acid (PA) against clinical strains of Mycobacterium tuberculosis (M.tb). Additionally, the inhibitory efficacy of PA against two critical enzymes associated with M.tb, namely, UDP-galactopyranose mutase (UGM) and arylamine-N-acetyltransferase (TBNAT), as drug targets for antituberculosis therapy were determined. PA showed a profound inhibitory effect towards all the M.tb strains tested, with minimum inhibitory concentrations (MICs) ranging between 3.2 and 4.1 µM, and selectivity indices (SIs) ranging between 18.3 and 23.4. On the other hand, the standard drug isoniazid (INH) displayed comparably high MIC values (varying from 5.4 to 5.8 µM) as well as low SI values (13.0–13.9). Interestingly, PA did not exhibit any cytotoxic effects on a human liver hepatocellular carcinoma cell line even at the highest concentration tested (75 µM). PA demonstrated remarkable suppressing propensity against UGM compared to standard uridine-5'-diphosphate (UDP), with 85.8 and 99.3% of inhibition, respectively. In addition, PA also exerted phenomenal inhibitory efficacy (half maximal inhibitory concentration (IC50) value = 8.7 µM, and 77.4% inhibition) against TBNAT compared with standard INH (IC50 value = 6.2 µM and 96.3% inhibition). Furthermore, in silico analysis validated the outcomes of in vitro assays, as the molecular interactions of PA with the active sites of UGM and TBNAT were unveiled using molecular docking and structure–activity relationship studies. Concomitantly, our findings present PA as an effective and safe natural drug plausible for use in controlling tuberculosis infections.