Chemical Constituents of the Lichen Stereocaulon azoreum

González, Antonio G.; Pérez, Elsa M. Rodríguez; Padrón, Consuelo E. Hernández; Barrera, Jaime Bermejo

doi:10.1515/znc-1992-7-802

Cited by 17 publications

(13 citation statements)

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“…Dibenzofurans : Strepsilin, with an [M − H] − ion at m/z 269.0455, was evidenced as peak 12 [ 30 ]. The main daughter ions of peak 12 were at m / z 149.0238 and 123.0450 a.m.u.…”

Section: Resultsmentioning

confidence: 99%

Metabolomic Analysis of Two Parmotrema Lichens: P. robustum (Degel.) Hale and P. andinum (Mull. Arg.) Hale Using UHPLC-ESI-OT-MS-MS

et al. 2017

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Lichens are symbiotic associations of fungi with microalgae and/or cyanobacteria. Lichens belonging to the Parmeliaceae family comprise 2700 species of lichens, including the Parmotrema genus which is composed of 300 species. The metabolites of this genus include depsides, depsidones, phenolics, polysaccharides, lipids, diphenylethers and dibenzofurans, which are responsible for the biological activities reported including antidiabetic, antihelmintic, anticancer, antioxidant, antibacterial, anti-inflammatory, antimitotic, antitumoral, antifungal, and antioxidant enzyme inhibitory. Due to scarce knowledge of metabolomic profiles of Parmotrema species (P. andinum and P. robustum), a full metabolome study based on ultra-high performance liquid chromatography- diode array detector-electrospray ionization-quadrupole-orbitrap-mass-spectrometry (UHPLC-DAD-ESI-Q-orbitrap MS) was performed for a comprehensive characterization of their substances. From the methanolic extracts of these species, a total of 54 metabolites were identified for the first time using this hyphenated technique, including thirty compounds in P. andinum, and thirty-seven in P. robustum. Moreover, two compounds were not identified as known compounds, and could be new structures, according to our data. This report shows that this technique is effective and accurate for rapid chemical identification of lichen substances and the compounds identified could serve as chemotaxonomic markers to differentiate these ruffle lichens.

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“…Dibenzofurans : Strepsilin, with an [M − H] − ion at m/z 269.0455, was evidenced as peak 12 [ 30 ]. The main daughter ions of peak 12 were at m / z 149.0238 and 123.0450 a.m.u.…”

Section: Resultsmentioning

confidence: 99%

Metabolomic Analysis of Two Parmotrema Lichens: P. robustum (Degel.) Hale and P. andinum (Mull. Arg.) Hale Using UHPLC-ESI-OT-MS-MS

et al. 2017

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“…Stictic acid and its methylvinyl ketone derivative, isidiophorin, were isolated from the acetone extract. These two compounds have been consistently reported to be isolated simultaneously in the acetone fraction [ 22 – 24 ]. This suggests that, like compound 2 , isidiophorin was probably derived from stictic acid.…”

Section: Resultsmentioning

confidence: 99%

Depsides: Lichen Metabolites Active against Hepatitis C Virus

Lamer

Lalli

et al. 2015

PLoS ONE

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A thorough phytochemical study of Stereocaulon evolutum was conducted, for the isolation of structurally related atranorin derivatives. Indeed, pilot experiments suggested that atranorin (1), the main metabolite of this lichen, would interfere with the lifecycle of hepatitis C virus (HCV). Eight compounds, including one reported for the first time (2), were isolated and characterized. Two analogs (5, 6) were also synthesized, to enlarge the panel of atranorin-related structures. Most of these compounds were active against HCV, with a half-maximal inhibitory concentration of about 10 to 70 µM, with depsides more potent than monoaromatic phenols. The most effective inhibitors (1, 5 and 6) were then added at different steps of the HCV lifecycle. Interestingly, atranorin (1), bearing an aldehyde function at C-3, inhibited only viral entry, whereas the synthetic compounds 5 and 6, bearing a hydroxymethyl and a methyl function, respectively, at C-3 interfered with viral replication.

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“…Lobaric acid was isolated with a yield of 0.67 % from the MeOH extracts when fractionated via silica gel column using hexane/CH 2 Cl 2 to CH 2 Cl 2 /MeOH as solvents. The dentification of the compound was carried out by using spectral data and its comparison with the reported data (Gonzilez et al, 1992).…”

Section: Methodsmentioning

confidence: 99%

Enzyme inhibitory and immunomodulatory activities of the depsidone lobaric acid extracted from the lichen Heterodermia sp.

Thadhani¹,

Naaz²,

Choudhary³

et al. 2014

J. Natn. Sci. Foundation Sri Lanka

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This study evaluates the enzyme inhibitory and immunomodulatory activities of the lichen specific depsidone, lobaric acid. Lobaric acid was extracted with methanol from Heterodermia sp. found in Labukelle, Sri Lanka with a yield of 0.67 %. It was subjected to enzyme inhibition assays using acetyl and butyryl-cholinesterase, phosphodiesterase, β-glucuronidase, α-glucosidase and urease. In the β-glucuronidase inhibitory activity it showed an IC 50 value of 3.28 ± 0.05 µM, which was significantly lower than that of the standard, D-saccharic acid 1, 4-lactone (IC 50 = 48.4 ± 1.2 µM). Lobaric acid showed a significant inhibition of phosphodiesterase enzyme with an IC 50 = 313.7 ± 2.2, when compared with the two standards EDTA (IC 50 = 274.0 ± 0.1 µM) and cysteine (IC 50 = 748.0 ± 0.1 µM). Lobaric acid showed a moderate actyl and butyryl-cholinesterase inhibitory activity while it showed no activity against the enzymes α-glucosidase and urease. In the immunomodulatory assay, lobaric acid exhibited a potent oxidative burst inhibitory activity in human polymorphonuclear (PMN) cells. It suppressed both the myloperozidase dependant and myloperozidase independent reactive oxygen species (ROS) production of PMNs. The results indicate the pharmacological potential of lobaric acid as a lead compound for further studies.

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Chemical Constituents of the Lichen Stereocaulon azoreum

Cited by 17 publications

References 0 publications

Metabolomic Analysis of Two Parmotrema Lichens: P. robustum (Degel.) Hale and P. andinum (Mull. Arg.) Hale Using UHPLC-ESI-OT-MS-MS

Metabolomic Analysis of Two Parmotrema Lichens: P. robustum (Degel.) Hale and P. andinum (Mull. Arg.) Hale Using UHPLC-ESI-OT-MS-MS

Depsides: Lichen Metabolites Active against Hepatitis C Virus

Enzyme inhibitory and immunomodulatory activities of the depsidone lobaric acid extracted from the lichen Heterodermia sp.

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