We describe here the extraction and identification of several classes of phenolic compounds from the lichens Parmotrema dilatatum (Vain.) Hale, Parmotrema tinctorum (Nyl.) Hale, Pseudoparmelia sphaerospora (Nyl.) Hale and Usnea subcavata (Motyka) and determined their anti-tubercular activity. The depsides (atranorin, diffractaic and lecanoric acids), depsidones (protocetraric, salazinic, hypostictic and norstictic acids), xanthones (lichexanthone and secalonic acid), and usnic acid, as well seven orsellinic acid esters, five salazinic acid 8',9'-O-alkyl derivatives and four lichexanthone derivatives, were evaluated for their activity against Mycobacterium tuberculosis. Diffractaic acid was the most active compound (MIC value 15.6mug/ml, 41.6 microM), followed by norstictic acid (MIC value 62.5 microg/ml, 168 microM) and usnic acid (MIC value 62.5 microg/ml, 182 microM). Hypostictic acid (MIC value 94.0 microg/ml, 251 microM) and protocetraric acid (MIC value 125 microg/ml, 334 microM) showed moderate inhibitory activity. The other compounds showed lower inhibitory activity on the growth of M. tuberculosis, varying from MIC values of 250 to 1370 microM.
Lichens produce phenolic compounds, such as depsides, depsidones, dibenzofuranes, usnic acids, depsones and others. Many of them are exclusive of lichens.1) These substances, as well as their derivatives obtained by structural modification, have shown an ample variety of pharmacological activities: antibiotic, antimycobacterial, antiviral, antitumour, analgesic, antipyretic and enzyme inhibitory.2-5) Although these activities continue to be investigated, both in lichen extracts and with pure substances, a number of others have been attributed to the compounds produced by lichens, such as anti-human immunodeficiency virus (anti-HIV) 6) and anti-herpes simplex virus 1 (anti-HSV-1). 7)Numerous studies on the biological activities of phenols have indicated that these substances are also potent antioxidants and free radical scavengers. 8) Although the free radicals perform an important role in the organism, their cumulative effects can promote the initiation and/or progression of several diseases, including atherosclerosis, inflammation, cancer, cardiovascular diseases, ischaemia, aging and other degenerative diseases. [9][10][11] The antioxidants are of interest in the treatment of several cellular degenerations, and they inhibit or delay the oxidation process by blocking the initiation or propagation of oxidizing chain reactions. 12) They are also used to preserve food by retarding rancidity, discoloration, or deterioration due to autoxidation.13) Due to the importance of antioxidants, many researches have been carried out with plants of several families and with simple phenolic substances, like those of the hydroxycinnamates group and the gallic acid derivatives. [14][15][16][17] Although the lichens are an important source of phenolic substances, studies of antioxidant activity with this group are more recent, and they have been performed mainly with extracts of some species. 12,[18][19][20][21] We have investigated lichens from the "cerrado" of the Mato Grosso do Sul State, in Brazil, through the isolation, structural elucidation, structural modifications and evaluation of biological activities of phenolic substances. The lecanoric acid isolated from the lichen Parmotrema tinctorum, and the orsellinates obtained through reactions of this acid with alcohols were evaluated against Artemia salina and microorganisms. [22][23][24] In continuing our investigations, we are relating here the results of the antioxidant activity of the lecanoric acid (1), orsellinic acid (2) and the methyl (3), ethyl (4), n-propyl (5), n-butyl (6), iso-propyl (7), sec-butyl (8) and tert-butyl (9) orsellinates. With the aim of establishing a qualitative correlation structure-activity we have also included the antioxidant activity of orcinol (10), resorcinol (11) and gallic acid (12). Results and Discussion2,2-Diphenyl-1-picrylhydrazyl (DPPH) Radical-Scavenging Activity Antioxidants are closely related to their biofunctionalities, such as the reduction of chronic diseases like DNA damage, mutagenesis, carcinogenesis and inhibition of pathog...
Recebido em 1/7/08; aceito em 19/12/08; publicado na web em 11/5/09The anti-Mycobacterium tuberculosis activity of Campomanesia adamantium fruits extracts were evaluated. Six compounds, identified as flavanones and chalcones were quantified by HPLC-DAD-UV. Promising antitubercular activity was observed with ethyl acetate extract (MIC 62.5 μg/mL) and their fractions (MIC values ranging from 39 to above 250 μg/mL). The better MIC result of 39 μg/mL was associated with two fractions that contain bigger amounts of 5,7-dihydroxy-6, 8-di-C-methylflavanone and 2',4'-dihydroxy-3',5'-dimethyl-6'-methoxychalcone. These compounds exhibited MICs >250 and 62.5 μg/mL, respectively, while their mixtures showed values ranging from 62.5 to 7.8 μg/mL, demonstrating a synergism between them.
Five flavanones and three chalcones were isolated from Campomanesia adamantium Berg. (Myrtaceae) leaves. The contents of these compounds were determined by HPLC. The phenolic contents were also determined. The monitoring of the antioxidant activity was carried out by inhibition of peroxidation using the linoleic acid system and radical-scavenging (DPPH). The plants were collected from 4 distinct cities of the Mato Grosso do Sul State, Brazil. The different samples exhibited a range of 4.67-232.35 mg/g chalcones and 15.62-50.71 mg/g flavanones and phenolic contents of the 7.24-21.19 mg/g gallic acid. All extracts showed high antioxidant activity with a wide range of the radical-scavenging (DPPH) from 52.0 to 92.2 % and inhibition oxidation of linoleic acid from 14.6 to 94.2%.
The antimicrobial activity of the hexanic extracts and fractions of fruits of Campomanesia pubescens pubescens (D.C) O. Berg and Campomanesia adamantium (Cambess.) O. Berg were assayed against six microorganisms. The hexanic extracts of C. pubescens and C. adamantium fruits were also investigated in their composition by gas chromatography-mass spectrometry and high-performance liquid chromatography with diode array detection. The results of this study showed the presence of 34 volatile compounds and flavonoids in the hexanic extract of C. pubescens and 33 volatile compounds and flavonoids in the hexanic extract of C. adamantium.
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