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, UV spectra and RR, values of /J-orcinol depsides having different substituents, namely methyl (squamatic acid), aldehyde (baeomycesic acid) and carboxyl (barbatic acid) groups at the 3 position of the benzene ring. T f" Diffractaic acid 10.49 Barbaric acid 21.96
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Secondary metabolites from Lichen, mainly phenolic compounds, have been analysed and identified using high performance liquid chromatography with a photodiode array detector. Components of lichen thalli were detected by characteristic ultraviolet spectra and relative retention times. Some new minor components have been found in several lichens.
Citations
... Lecanoric acid was eluted with absolute benzene and 5% ethyl acetate in benzene. Lecanoric acid was purified by re-crystallizing in 50% acetone after the elute solvents had been evaporated in a vacuum [32]. ...
Lichens are symbiotic organisms that are composed of fungal partners and photosynthetic algal partners. During the symbiotic process in lichen thallus, the fungus synthesizes certain secondary metabolites in which lecanoric acid is very important in terms of antibiotic properties. Considering the vital importance of lecanoric acid, the present study aimed to produce lecanoric acid from the thallus of Parmotrema austrosinense lichen using Modified Bold’s basal salt medium and evaluate the bio-efficacy against tea fungal pathogens. Lecanoric acid was purified and confirmed by micro-crystallization method and subsequently bioassayed against tea fungal pathogens. The results revealed that lecanoric acid registered a significant antifungal activity in terms of the growth inhibition of test pathogens. Companion systemic and botanical fungicides were found to be inferior to lecanoric acid in the percentage of growth inhibition. The inhibition rate varied among tea pathogens. Of the tea pathogens tested, tea leaf disease-causing pathogens including Cercospora theae (C. theae), Glomerella cingulata (G. cingulate), and Phomopsis theae (P. theae) showed the highest percentage of growth inhibition followed by stem and root rot diseases. The present study suggests that lecanoric acid showed an inhibitory effect against tea pathogens, which might be due to antibiotic properties and fungicidal action of lecanoric acid.
... Running conditions included: a mobile gradient phase [1% orthophosphoric acid in milli-Q water (A)/methanol (B)]; a flow rate of 0.6 mL/min; a column temperature of 40 • C and a UV spectrum between 190 and 400 nm. Secondary metabolites of lichens were identified by comparing the retention time and UV absorption spectra with standard compounds (commercialized and isolated previously by our research team) and other lichen species [9,54]. ...
Oxidative stress is involved in the pathophysiology of many neurodegenerative diseases. Lichens have antioxidant properties attributed to their own secondary metabolites with phenol groups. Very few studies delve into the protective capacity of lichens based on their antioxidant properties and their action mechanism. The present study evaluates the neuroprotective role of Dactylina arctica, Nephromopsis stracheyi, Tuckermannopsis americana and Vulpicida pinastri methanol extracts in a hydrogen peroxide (H2O2) oxidative stress model in neuroblastoma cell line “SH-SY5Y cells”. Cells were pretreated with different concentrations of lichen extracts (24 h) before H2O2 (250 µM, 1 h). Our results showed that D. arctica (10 µg/mL), N. stracheyi (25 µg/mL), T. americana (50 µg/mL) and V. pinastri (5 µg/mL) prevented cell death and morphological changes. Moreover, these lichens significantly inhibited reactive oxygen species (ROS) production and lipid peroxidation and increased superoxide dismutase (SOD) and catalase (CAT) activities and glutathione (GSH) levels. Furthermore, they attenuated mitochondrial membrane potential decline and calcium homeostasis disruption. Finally, high-performance liquid chromatography (HPLC) analysis revealed that the secondary metabolites were gyrophoric acid and lecanoric acid in D. artica, usnic acid, pinastric acid and vulpinic acid in V. pinastri, and alectoronic acid in T. americana. In conclusion, D. arctica and V. pinastri are the most promising lichens to prevent and to treat oxidative stress-related neurodegenerative diseases.
... Lecanoric acid (Gaia Chemical Corp., New Milford, CT, USA), usnic acid (Sigma-Aldrich, St. Louis, MO, USA), and vulpinic acid (Toronto Research Chemicals Inc., North York, ON, Canada) were purchased from the commercial vendors. Chemical identities of all the purified and purchased lichen substances were confirmed by comparing their relative retention time and the UV spectra to those in our in-house lichen substance database (Yoshimura et al., 1994). Thirty microliters of lichen substances (1 mg/ml) were injected for HPLC analysis. ...
... Usnic acid is a product of dimerization of two methylphloroacetophenone molecules, and vulpinic acid is a product of dimerization of two aro-matic amino acids. The authenticity and purity of the eight lichen substances compounds were confirmed by HPLC analyses in which the relative retention time and UV spectra of lichen substances were compared to those in our inhouse lichen substance database (Yoshimura et al., 1994) (Fig. 1). ...
Plant pathogens pose major threats on agriculture and horticulture, causing significant economic loss worldwide. Due to the continuous and excessive use of synthetic pesticides, emergence of pesticide resistant pathogens has become more frequent. Thus, there is a growing needs for environmentally-friendly and selective antimicrobial agents with a novel mode of action, which may be used in combination with conventional pesticides to delay development of pesticide resistance. In this study, we evaluated the potentials of lichen substances as novel biopesticides against eight bacterial and twelve fungal plant pathogens that have historically caused significant phytopathological problems in South Korea. Eight lichen substances of diverse chemical origins were extracted from axenic culture or dried specimen, and further purified for comparative analysis of their antimicrobial properties. Usnic acid and vulpinic acid exhibited strong antibacterial activities against Clavibacter michiganensis subsp. michiganensis. In addition, usnic acid and vulpinic acid were highly effective in the growth inhibition of fungal pathogens, such as Diaporthe eres, D. actinidiae, and Sclerotinia sclerotiorum. Intriguingly, the growth of Rhizoctonia solani was specifically inhibited by lecanoric acid, indicating that lichen substances exhibit some degrees of selectivity to plant pathogens. These results suggested that lichen substance can be used as a selective biopesticide for controlling plant disease of agricultural and horticultural significance, minimizing possible emergence of pesticide resistant pathogens in fields.
... This information's are principally basis on some features such as morphology and anatomy, phenology. Then in the current era, Phylogenetic evaluation is needed for all biological organisms (Yoshimura et al., 1994). On the examination of 1000 taxa, 19 species not found on American Herbaria. ...
... The sample was kept for complete drying under shade before examination of morphology. Chemo syndrome was performed as spot test and Thin Layer Chromatography (TLC) as common Solvent System A (Dioxane: Toluene: Acetic acid); with the acetone extract (Culberson and Culberson, 1976;Rogers, 1989;Yoshimura et al., 1994). The geomorphology and anatomy characteristic features were examined by the Indian Lichenologist, with the use of artificial keys. ...
Recent explorations in Megamalai Tiger reserve and Wildlife sanctuary in Tamil Nadu has resulted in the documentation of new bloodstain lichen, Haematomma collatum Haematommone with UV negative taxonomic species. It has been collected for the first time and hence it forms a new record for India. A detailed description of Haematommaceae, Taxonomical keys and Photographs are provided for rapid identification.
... LC/UV-DAD (Huber and George 1993) was utilized, in several labs, detecting metabolites (Bramley 1992;Yoshimura et al. 1994). LC/UV-DAD gives complementary information for different metabolites owing to strong chromophores. ...
Steroids are a cluster of secondary metabolites owning a range in their structure and biological activities. Natural products are often linked with harmful effects on health and have many medicinal applications. Secondary metabolites can potentially drive drug design or discovery. The prime information about such steroids has risen systematically. Advancement in biotechnological approaches affects the disciplines of biochemistry, botany, conservation biology, and toxicology. The genetic markers are a beneficial tool that provides more insight into pathways. Genetic markers accompanied by PTC can supply more insight into the path of steroid products. We will here highlight the biological effects of steroids and the biosynthesis pathways. Studies on steroid extraction and in vitro production will also be included. Besides, the bioreactor of steroids will be scaled up.
... Later gradient method was found suitable for separation of several lichen genera, Feige et al. [50] developed a standard method with a retention index (I) for the identification of 331 lichen compounds. However, by applying the isocratic method, Yoshimura et al. [51] demonstrated HPLC equipped with a photodiode array detector (PDA) to identify lichen compounds using UV spectral data and relative retention times (RR t ). In recent decades, several chemical studies on lichen mycobiont cultures have been investigated with HPLC-PDA for precise identification of compounds [6, 7, 9, 52-58] (Fig. 1). ...
Chromatography techniques facilitate separation, purification, and identification of secondary compounds (natural products) in lichens and their mycobiont cultures. In particular, high-performance liquid chromatography (HPLC) plays a vital role in the identification of lichen substances because of its high sensitivity, speed, and reliability with the minimal sample. Therefore, we describe the extraction and HPLC protocol for the investigation of secondary compounds with a special focus on lichen mycobiont cultures.
... The species belongs to the Ramalina farinacea complex. It is morphologically close to Ramalina farinacea, but it differs by the yellowish thallus tinge, the presence of minute linear pseudocyphellae, and the absence of protocetraric acid, salazinic acid, hypoprotocetraric acid, or norstictic acid(Yoshimura et al. 1994;Alvarez et al. 2001). It is also macroscopically close to Ramalina nervulosa, but R. dumeticola has K+ pink medulla and lacks divaricatic acid and stenosporic acid ...
A systematic survey of lichens was performed in 2019 in four of the five territories constituting the French Scattered Islands (Europa Island, Juan de Nova, Glorioso Islands, and Tromelin) focusing on the genus Ramalina. Species were characterized using morphological (macroscopic and microscopic) features and an accurate chemical profiling method based on high-performance liquid chromatography coupled with diode-array detection and electrospray ionization tandem mass spectrometry (HPLC-DAD-MS). Five species were found in these territories. Two of them, Ramalina dumeticola and R. ovalis, are already known. Three species are introduced here as new to science: Ramalina gloriosensis sp. nov., R. hivertiana sp. nov., and R. marteaui sp. nov. An identification key is provided for the species found in the area and morphologically closely related taxa.
... The purity of lichen compounds was checked by HPLC analyses on Waters Alliance 2690 using a reversed-phase Hibar ® LiChrospher ® 100 C-18 column (5 µm, 250 × 4 mm, Merck) coupled to a photodiodearray detector (Waters 996). The elution solvent MeOH-H 2 O-H 3 PO 4 at 80:20:0.9 was used in an isocratic mode at a flow rate of 1 ml/min according to the protocol of Yoshimura et al. (1994). ...
Lichens, due to their symbiotic nature (association between fungi and algae), constitute a chemical factory of original compounds. Polyphenolic compounds (depsides and depsidones) are the main constituents of lichens and are exclusively biosynthesized by these organisms. A panel of 11 polyphenols was evaluated for their anti-biofilm activity against Candida albicans biofilms on the maturation phase (anti-maturation) (MMIC50) as well as on preformed 24-h-old biofilm (anti-biofilm) (MBIC50) using the XTT assay. Minimum inhibitory concentrations of compounds (MICs) against C. albicans planktonic yeast were also determined using a broth microdilution method. While none of the tested compounds were active against planktonic cells (IC50 > 100 µg/ml), three depsides slowed the biofilm maturation (MMIC50 ≤12.5 µg/ml after 48 h of contact with Candida cells). Evernic acid was able to both slow the maturation and reduce the already formed biofilms with MBIC50 ≤12.5 µg/ml after 48 h of contact with the biofilm. This compound shows a weak toxicity against HeLa cells (22%) at the minimal active concentration and no hemolytic activity at 100 µg/ml. Microscopic observations of evernic acid and optimization of its solubility were performed to further study this compound. This work confirmed the anti-biofilm potential of depsides, especially evernic acid, and allows to establish the structure–activity relationships to better explain the anti-biofilm potential of these compounds.
... H 3 PO 4 = 80:20:1; fl ow rate, 1 mL/min.; and detection wave length, 254 nm (190-800 nm). The retention times and UVspectra of peaks detected were compared with data from known compounds (Yoshimura et al. 1994), and the major components were identifi ed. ...
Chrismofulvea rubifaciens is reported as new for Japan, and C. dialyta is rediscovered in this country for the fi rst time in over a century, since Vainio (1918) described Buellia dialytoides (=B. dialyta) based on a specimen collected from Mt. Daisen in 1913. Chrismofulvea rubifaciens was collected only once on bark of Cryptomeria
japonica in Kochi-ken, Shikoku. Chrismofulvea dialyta was found on bark of conifers in the cool-temperate zone in Honshu. Detailed descriptions and illustrations are provided for the species based on the Japanese materials. Phylogenetic analyses support identifi cation of the Japanese specimens as C. dialyta./ Lichenology 19 (2): 47–64.
... F. Culberson and Culberson 1978;C. F. Culberson, Culberson, and Esslinger 1977), les études phytochimiques de S. Huneck, ainsi que les données d'analyse par LC-DAD et d'isolement de G. Feige (Feige et al. 1993), I. Yoshimura (Yoshimura et al. 1994) et J. Elix (Elix and Crook 1992;Elix and Gaul 1986;Elix, Jenie, and Parker 1987). Ce compendium donne un aperçu de ce qui était globalement connu dans la chimie des lichens à sa parution. ...
... Une grande gamme de techniques analytiques a pourtant été utilisée pour étudier les métabolites lichéniques (Le Pogam et al. 2015;Huovinen, Hiltunen, and Von Schantz 1982;Yoshimura et al. 1994;Le Corvec et al. 2016) et ces méthodes seraient à privilégier pour révéler la part d'inconnue dans leur métabolome. Des résultats récents ont par ailleurs démontré que certaines structures atypiques produites par les lichens restent à décrire, comme le montrent les squelettes originaux tsavoénones et sanctis, tous deux obtenus à partir d'espèces de Parmotrema collectées au Vietnam (T. ...
Les lichens sont des champignons symbiotiques dont la chimie est exploitée par l’Homme depuis l’antiquité. Ils n’ont cependant pas été intégrés aux études de métabolomique récentes ce qui a installé l’idée que les lichens sont pauvres en molécules. 1050 molécules leur sont classiquement attribuées, bien que ce décompte date et qu’il semble éloigné de ce qui pourrait être attendu pour un mode de vie concernant 19 387 espèces. En métabolomique, LC-MS et la déréplication à l’aide de bases de données sont régulièrement usitées pour permettre le profilage des échantillons. Ces bases de données ne sont cependant pas adaptées à l’étude des lichens, qui produisent principalement des molécules qui leur sont uniques. Dans cette optique, plusieurs bases de données spécifiques aux lichens ont été créées ici, en utilisant des données de la littérature ainsi qu’en produisant des données spectrales. Des outils ont été créées pour améliorer la déréplication par la prédiction des molécules contenues dans les extraits à partir des ions qu’elles produisent. Tout ceci a été appliqué à l’analyse de 300 échantillons de lichens pour mettre en évidence la diversité chimique de ces champignons à l’aide de techniques modernes. Ceci a permis de prédire quelque 8000 molécules avec des degrés de certitude variables. L’étude détaillée des résultats pour mettre à jour les connaissances sur les lichens reste à faire, mais ceux-ci permettent déjà d’avancer que ces organismes sont à l’origine d’une chimie sous-estimée et qui reste encore à explorer.
