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Identification and quantitation of allelochemicals from the lichen Lethariella canariensis: phytotoxicity and antioxidative activity.

Phytotoxicity-based extraction and fractionation were employed to separate allelochemicals contained in an extract of Lethariella canariensis. Twelve phenolic substances were isolated from the phytotoxic fraction "Letharal" of the thalli. These were identified by spectroscopic methods, physicochemical constants, and HPLC chemical correlation, and determined to be atranol (2), chloroatranol (3), hematommic acid (4), chlorohematommic acid (5), methyl hematommate (6), methyl chlorohematommate (7) (new compound), ethyl hematommate (8), ethyl chlorohematommate (9), methyl beta-orsellinate (10), atranorin (11), chloroatranorin (12), and (+)-usnic acid (13). Further identification and quantification of these allelochemicals in the environment were conducted by HPLC. Several phenolic compounds showed moderate antimicrobial activity. The cytostatic activity of the polyphenols was investigated on U937 and HL-60 cells. All compounds were assayed, with the exception of 10. The "Letharal" mixture decreased cell viability in both cell lines. Protection against lipid peroxidation was investigated using brain homogenates. Compounds 2, 3, 6, 8, 11, and Letharal decreased H2O2/Fe+2 induced lipid peroxidation in a concentration-dependent manner, while 10 and 13 were unable to protect tissue against oxidative stress.

Animals↗

Mutagenicity of lichen constituents.

Usnic acid (the most abundant lichen constituents), physodic, and physodalic acids isolated from Hypogymnia enteromorph (Ach.) Nyl. were tested for mutagenicity in the Ames Salmonella/microsome assay. Physodalic acid exhibited clear dose-related mutagenicity against Salmonella typhimurium strain TA 100 with or without S9 mix in both plate-incorporation and preincubation assays. The addition of S9 mix increased the number of revertants approximately threefold and fourfold in preincubation and plate-incorporation assays, respectively.

Animals↗

The significance of lichens and their metabolites.

Lichens, symbiontic organisms of fungi and algae, synthesize numerous metabolites, the "lichen substances," which comprise aliphatic, cycloaliphatic, aromatic, and terpenic compounds. Lichens and their metabolites have a manifold biological activity: antiviral, antibiotic, antitumor, allergenic, plant growth inhibitory, antiherbivore, and enzyme inhibitory. Usnic acid, a very active lichen substance is used in pharmaceutical preparations. Large amounts of Pseudevernia furfuracea and Evernia prunastri are processed in the perfume industry, and some lichens are sensitive reagents for the evaluation of air pollution.

Air Pollution↗

Antimycobacterial activity of lichen metabolites in vitro.

Several compounds, whose structures represent the most common chemical classes of lichen metabolites, were screened for in vitro activity against Mycobacterium aurum, a non-pathogenic organism with a similar sensitivity profile to M. tuberculosis. Of the compounds tested, usnic acid from Cladonia arbuscula exhibited the highest activity with an MIC value of 32 microg/ml. Atranorin and lobaric acid, both isolated from Stereocaulon alpinum, salazinic acid from Parmelia saxatilis and protolichesterinic acid from Cetraria islandica all showed MIC values >/=125 microg/ml.

4-Butyrolactone↗

Protection against UVB irradiation by natural filters extracted from lichens.

Natural substances extracted from lichens and boldo tree were tested in vivo and in vitro as possible UV-light filters. The protection factors were compared with that found for the references: Nivea sun Spray LSF 5, octylmethoxycinnamate (OMC) and 4-tert.-butyl-4'-methoxy dibenzoylmethane (BM-DBM). The stability of the single compounds was studied through UV-Vis spectroscopy. Usnic acid resulted to be the best UVB filter, with an in vivo protection factor similar to Nivea sun Spray LSF 5. Most of the single compounds studied in vitro resulted to have higher or similar filtering power than octylmethoxycinnamate. The protection factors as well as the good UV-light absorption of their photo-products suggest that these natural substances may be useful as new filters in sun-screen preparations.

Aporphines↗

Alectosarmentin, a new antimicrobial dibenzofuranoid lactol from the lichen, Alectoria sarmentosa.

From the alcoholic extract of the lichen Alectoria sarmentosa, four compounds showing antimicrobial activity were isolated. Of these, (-)-usnic acid and physodic acid are well known lichen products, 8'-O-ethyl-beta-alectoronic acid [2] is believed to be an artifact formed during isolation and fractionation, and alectosarmentin [1] is a new natural product whose structure was shown, by spectroscopy and chemical transformations, to be that of a dibenzofuranoid lactol. The antimicrobial activity of these substances accounts for the activity of the lichen.

Anti-Bacterial Agents↗

Euplectin and coneuplectin, new naphthopyrones from the lichen Flavoparmelia euplecta.

Two new naphthopyrones, euplectin (1) and coneuplectin (2), have been isolated from the lichen Flavoparmelia euplecta and their structures elucidated using multidimensional NMR spectroscopic methods, including highfield (600 MHz) gHMBC and gNOE experiments. Cytotoxicity of the more abundant naphthopyrone (1) against the murine P-815 mastocytoma cell line (IC(50) ca. 1.67 microg/mL) has also been evaluated. These compounds are the first lichen metabolites known to contain indenone or indanone moieties in their structure. F. euplecta was also found to contain the known metabolites usnic acid, protocetraric acid, and skyrin.

Cell Division↗

Raman spectroscopy of hot desert, high altitude epilithic lichens.

Twenty-three highly-coloured lichen specimens belonging to the genera Candelariella, Aspicilia and Xanthoria from high altitude sites in the Atacama Desert, Chile, 2300-4500 metres, have been analysed non-destructively by Raman spectroscopy. The vibrational band assignments in the spectra of the specimens, which were still attached to their limestone or sandstone substrata, were accomplished by comparison with the chemical compositions obtained from wet chemical extraction methods. Carotenoids and chlorophyll were found in all specimens as major components and the characteristic spectral signatures of calcium oxalate monohydrate (whewellite) and dihydrate (weddellite) could be identified; chemical signatures were found for these materials even in lichen thalli growing on the non-calcareous substrata, indicating probably that the calcium was provided here from wind- or rain-borne sources. The Raman spectral biomarkers for a variety of protective biomolecules and accessory pigments such as usnic acid, calycin, pulvinic acid dilactone and rhizocarpic acid have been identified in the lichens, in broad agreement with the chemical extraction profiles. The present study indicates that some form of non-destructive taxonomic identification based on Raman spectroscopy was also possible.

Altitude↗

Alysinol--a new triterpene from Alysicarpus monolifer.

A new triterpene named as alysinol 3alpha, 22beta-dihydroxyolean-12-ene [structure: see text] along with known compounds usnic acid, methyl 2,4-dihydroxy-3,6-dimethyl benzoate, 3-hydroxy benzoic acid, stigmasterol, poriferasterol and ursolic acid have been isolated from Alysicarpus monolifer. The structure of [structure: see text] has been established through spectroscopic techniques.

Acetylation↗

Growth and phage production of B. megatherium. I. Growth of cells after infection with C phage. II. Rate of growth, phage yield, and RNA content of cells. III. Effect of various substances on growth rate and phage production.

I. Lysogenic B. megatherium 899a (de Jong, 1931) produces two types of phage (Gratia, 1936 c) T and C. The T phage forms cloudy plaques and gives rise to fresh lysogenic strains (Gratia, 1936 b) when added to the sensitive strain of megatherium. It may or may not cause lysis, depending on the media (Northrop, 1951). The C phage occurs very rarely) forms clear plaques, does not give rise to lysogenic strains, and causes complete lysis of the sensitive strain under all conditions tested, provided infection occurs. If C phage is added to the sensitive strain, and the mixture allowed to stand, or made into a hanging drop preparation, the infected cells stop growing and lyse completely after 60 to 80 minutes with the liberation of from 50 to 200 phage particles per cell. If, however, C phage is added to a rapidly growing culture of B. megatherium and the suspension shaken at 34 degrees , the cells continue to grow and divide for 50 to 60 minutes, after infection has occurred. They then lyse, with the liberation of from 1000 to 2500 phage particles per cell. II. The following determinations have been made on megatherium sensitive cells growing in 5 per cent peptone at different stages of growth. (1) Growth rate of infected and uninfected cells; (2) RNA, DNA, and protein content; (3) volume of the cell; (4) phage yield per cell by plaque count; (5) phage yield per cell by cell and plaque count; (6) lysis time. The growth rate decreases as the cell concentration increases. The lysis time and the protein N per cell are nearly independent of the growth rate; all the other values increase as the growth rate increases. The ratio See PDF for Equation is nearly constant. RNA and DNA per cell increase less rapidly than the volume, so that NA per unit volume is not constant, but decreases as the size of the cell increases. The phage yield measured under conditions in which the infected cells do not grow (by plaque count) is very nearly proportional to the size of the cell. The phage yield per cell, under conditions in which the infected cells do grow, increases more rapidly than the size of the cells. The phage yield per cell under these conditions may be calculated by the equation See PDF for Equation The determining factor for the variation in phage yield is the growth rate of the cells. This, in turn, is determined by the composition of the medium. III. The growth and phage production of megatherium 899a have been determined in the presence of the following substances: aureomycin, bacitracin, chloromycetin, gramicidin, Merck AB631, Merck AB191, Merck AB624, penicillin, streptomycin, terramycin, tyrothricin, usnic acid, acetone, chloroform, ethyl alcohol, formaldehyde, gentian violet, glycerin, maleic hydrazide, methyl alcohol, phenyl mercuric acetate, sodium fluoride, sulfanilamide, toluene, and urethane. In every case, the lowest concentration of the substance which completely inhibits growth, is also the lowest concentration which completely inhibits phage production. One antibiotic, Merck AB81, causes increased phage production in concentrations which partially inhibit growth, and low phage production in concentrations which completely inhibit growth (as determined by turbidity). Short exposure to ultraviolet light also decreases the growth rate, with increase in phage production. Longer exposure, which completely inhibits growth (as determined by turbidity) results in lysis and phage liberation.

Bacillus↗

Occupational allergic contact dermatitis from lichens in present-day Finland.

Lichens are abundant in forests, living on trees, soil, stones and rocks. They contain usnic acid and other lichen acids that are contact allergens. Lichens and liverworts cause woodcutter's dermatitis, eczema that appears in the forest on the bare skin areas, especially in cold and wet weather. Occupational allergic contact dermatitis from lichens occurs in forestry and horticultural workers and in lichen pickers. Lichens can cause immediate allergy, contact urticaria, rhinitis and asthma and probably also photoallergic contact dermatitis. Lichens are used for the manufacture of oak moss absolute, a fragrance constituent. Oak moss absolute contains lichen acids and is one of the commonest contact allergens. Lichen acid allergy develops either from contact with lichens or from fragrances. We describe 4 cases of occupational allergic contact dermatitis from lichens during the past decade: 2 were farmers and 2 gardeners. 3 of them had allergic reactions to fragrance mix and oak moss absolute. Lichen contact allergy is an old, partly forgotten, syndrome that should be remembered for symptoms in contact with barked wood or wood dust.

Agricultural Workers' Diseases↗

Perfume allergy due to oak moss and other lichens.

During a period of 2 1/2 years, 7 of 2000 patients routinely tested at our laboratory revealed contact allergy to oak moss in perfumes. All reacted to a mixture of different lichens and to some specific lichen compounds. The sensitivity was probably induced by cosmetics containing lichen substances. The following 3 compounds caused reactions in all patients tested: atranorin, evernic and usnic acids. 3 patients were photosensitive, but stronger reactions were elicited by prolonged contact during occlusion of the patches and complete protection against light, rather than by irradiation alone. The data suggest that the sensitizing capacity of the lichen compounds is primarily of a contact rather than of a photocontact nature.

Adult↗

Cytotoxic and apoptotic effects on hepatocytes of secondary metabolites obtained from lichens.

There are a large number of species of Antarctic lichens, and several studies describing the secondary metabolites present in these lichens, as well as the advances in understanding the chemistry of these metabolites, have been reported. In addition, some derivatives displaying interesting antibacterial effects have been described. The cytotoxic and apoptotic effects of 15 secondary metabolites (depsides, depsidones and usnic acid) obtained from Continental (Chilean) and Antarctic lichens were evaluated in primary cultures of rat hepatocytes. Intracellular lactate dehydrogenase release, caspase 3 activation and DNA fragmentation were measured. In this study, we have evaluated a set of markers associated with pivotal steps in the execution phase of apoptosis, in order to detect compounds with apoptotic effects on hepatocytes before significant necrosis takes place. Flow cytometric analysis of DNA fragmentation revealed an increase in apoptotic nuclei with sub-diploid DNA content after the exposure of hepatocytes to sub-cytotoxic concentrations of the compounds. Among these, salazinic acid, stictic acid and psoromic acid displayed significant apoptotic activities.

Animals↗

Some lichen products have antimicrobial activity.

Antimicrobial activity in some lichens from south Spain has been studied. Some lichenical substances are also identified. The structures of all compounds were elucidated by physical, spectral and chemical methods. A very high activity against Gram-positive bacteria has been observed in lichens containing usnic acid.

Anti-Bacterial Agents↗

Contact allergy from Frullania and respiratory allergy from Thuja.

Occupational allergic contact dermatitis in 52 forest-workers was caused by sesquiterpene lactones from liverworts (Frullania) and by usnic acid from lichens which grow on various trees including cedar (Thuja). Occupational asthma and rhinitis in 35 wood-workers was caused by wood dust of western red cedar (Thuja plicata). Characteristically, the respiratory symptoms occurred in the evening and at night and not during working hours; inhalation challenge with plicatic acid from the wood provoked immediate, late or dual (combined immediate and late) asthmatic reactions. Another class of compounds, tropolones, derived from Thuja plicata wood, was responsible for dermatitis in a wood-worker. These distinct industrial hazards in two groups of workers at the tree-felling and wood-working levels in the forest-products industry can be identified by clinical history and examination supplemented by specific cutaneous or respiratory clinical investigation.

Alcohols↗