Secondary metabolites of the lichen Hypogymnia physodes (L.) Nyl. and their presence in spruce (Picea abies (L.) H. Karst.) bark

Latkowska, Ewa; Bober, Beata; Chrapusta, Ewelina; Adamski, Michał; Kamiński, Ariel; Białçzyk, Jan

doi:10.1016/j.phytochem.2015.08.016

Cited by 21 publications

(20 citation statements)

References 20 publications

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“…[27] [29] The main daughter ions at m/z 167.0344 and 149.0238 are due to the cleavage of ester bond. This fragmentation pathway was consistent with the one described by Latkowska et al [35] Herein, further decarboxylation of m/z 163.0405 led to the fragment ion at m/z 119.0504. Based on an equivalent characterization process, compound 9 (m/z 389.0870, C 19 H 17 O 9 ) only detected in C. rangiformis, might correspond to squamatic acid, a common depside already found in C. uncialis.…”

Section: Depsidessupporting

confidence: 90%

UHPLC‐HRMS/MS Based Profiling of Algerian Lichens and Their Antimicrobial Activities

Rafika

Ahmed

Burger

et al. 2018

Chemistry & Biodiversity

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Lichens are complex symbiotic organisms able to produce a vast array of compounds. The Algerian lichen diversity has only prompted little interest even given the 1085 species listed. Herein, the chemodiversity of four Algerian lichens including Cladonia rangiformis, Ramalina farinaceae, R. fastigiata, and Roccella phycopsis was investigated. A dereplication strategy, using ultra high performance liquid chromatography-high resolution-electrospray ionization-mass spectrometry (UHPLC-HRMS/MS), was carried out for a comprehensive characterization of their substances including phenolics, depsides, depsidones, depsones, dibenzofurans, and aliphatic acids. Some known compounds were identified for the first time in some species. Additionally, the lichenic extracts were evaluated for their antifungal and antimicrobial activities on human pathogenic strains (Candida albicans, C. glabrata, Aspergillus fumigatus, Staphylococcus aureus, and Escherichia coli). Cyclohexane extracts were found particularly active against human pathogenic fungi with MIC values ranging from 8 to 62.5 μg/mL, without cytotoxicity. This study highlights the therapeutic and prophylactic potential of lichenic extracts as antibacterial and antifungal agents.

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Section: Depsidessupporting

confidence: 90%

UHPLC‐HRMS/MS Based Profiling of Algerian Lichens and Their Antimicrobial Activities

Rafika

Ahmed

Burger

et al. 2018

Chemistry & Biodiversity

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“…Metabolites have been characterized in previous studies and were therefore identified by their molecular mass, fragmentation patterns and comparison with reference MS data [18,20,41]. A list of major metabolites is presented in Table 1.…”

Section: Resultsmentioning

confidence: 99%

“…However, the secondary metabolite profiles of the genus Melanelia have not been fully studied apart from thin layer chromatography profiling [16,17]. Rapid instrumental development has rendered liquid chromatography coupled to mass spectrometry (LC-MS) a useful tool to investigate lichen secondary metabolites for ecological [18], biological [19] and chemotaxonomical purposes [20,21]. Moreover, chemometrics using principal component analysis (PCA) of large datasets has shown great potential in the classification of lichen taxa and discovery of novel secondary metabolites [22].…”

Section: Introductionmentioning

confidence: 99%

DNA barcoding and LC-MS metabolite profiling of the lichen-forming genus Melanelia: Specimen identification and discrimination focusing on Icelandic taxa

Heiðmarsson

Þorsteinsdóttir

et al. 2017

PLoS ONE

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Taxa in the genus Melanelia (Parmeliaceae, Ascomycota) belong to a group of saxicolous lichens with brown to black foliose thalli, which have recently undergone extensive changes in circumscription. Taxa belonging to Parmeliaceae are prolific producers of bioactive compounds, which have also been traditionally used for chemotaxonomic purposes. However, the chemical diversity of the genus Melanelia and the use of chemical data for species discrimination in this genus are largely unexplored. In addition, identification based on morphological characters is challenging due to few taxonomically informative characters. Molecular identification methods, such as DNA barcoding, have rarely been applied to this genus. This study aimed to identify the Melanelia species from Iceland using DNA barcoding approach, and to explore their chemical diversity using chemical profiling. Chemometric tools were used to see if lichen metabolite profiles determined by LC-MS could be used for the identification of Icelandic Melanelia species. Barcoding using the fungal nuclear ribosomal internal transcribed spacer region (nrITS) successfully identified three Melalenlia species occurring in Iceland, together with Montanelia disjuncta (Basionym: Melanelia disjuncta). All species formed monophyletic clades in the neighbor-joining nrITS gene tree. However, high intraspecific genetic distance of M. stygia suggests the potential of unrecognized species lineages. Principal component analysis (PCA) of metabolite data gave a holistic overview showing that M. hepatizon and M. disjuncta were distinct from the rest, without the power to separate M. agnata and M. stygia due to their chemical similarity. Orthogonal partial least–squares to latent structures–discriminate analysis (OPLS-DA), however, successfully distinguished M. agnata and M. stygia by identifying statistically significant metabolites, which lead to class differentiation. This work has demonstrated the potential of DNA barcoding, chemical profiling and chemometrics in identification of Melanelia species.

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“…6 Las depsidonas son estructuralmente similares a los dépsidos, pero sus dos unidades monocíclicas están enlazadas tanto por enlaces ester como por éteres. 16 Como para la mayoría de las especies liquénicas, los metabolitos secundarios de H. tavaresii son fabricados por el hongo y depositados extracelularmente, en forma cristalina, en la superficie de las hifas -las depsidonas en la médula y los dépsidos en la corteza-. 15 Recientemente se ha aportado que estas sustancias se difunden más allá del talo liquénico llegando a penetrar las semillas de las plantas herbáceas 6 y las ramas de los árboles que epifitizan.…”

Section: Introduccionunclassified

“…15 Recientemente se ha aportado que estas sustancias se difunden más allá del talo liquénico llegando a penetrar las semillas de las plantas herbáceas 6 y las ramas de los árboles que epifitizan. 16 Es esta riqueza en polifenoles lo que nos llamó la atención, llevándonos a su reestudio con el objeto de analizar sus propiedades antioxidantes. Ya nuestro grupo había demostrado que los metabolitos fenólicos liquénicos -entre ellos la atranorina (1)-protegen a estos organismos de la peroxidación radicalaria provocada por el alto estrés oxidativo existente en las regiones de elevada irradiación solar.…”

Section: Introduccionunclassified

ANTIOXIDANT ACTIVITY OF POLYPHENOLS FROMHYPOGYMNIA TAVARESIID. HAWKSW. & P. JAMES

Pérez¹,

Marante²,

Hernández³

et al. 2016

Química Nova

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Recebido em 29/10/2015; aceito em 21/12/2015; publicado na web em 28/03/2016 ANTIOXIDANT ACTIVITY OF POLYPHENOLS FROM HYPOGYMNIA TAVARESII D. HAWKSW. & P. JAMES. Lichen substances have more than one phenolic hydroxyl group attached to one or more benzene rings, thus qualifying them as polyphenols. The secondary metabolites isolated from the lichen H. tavaresii have been studied in a bid to find compounds protective against oxidative stress and free radical-induced damage. The compounds were identified based on their MS and 1 H-NMR spectra as well as retention factors of TLC analysis. In addition to the previously described metabolites (atranorin, chloroatranorin, physodic and physodalic acids) of H. tavaresii, a further three were identified in its thalli: 2´-O-methylphysodone, isophysodic and ursolic acids. The newly identified compounds of H. tavaresii thalli may be useful in the chemotaxonomic classification of this species. Antioxidant effectiveness of the acetone extract's fractions was measured. The compounds of the active fractions were purified and exhibited 180-800 fold less radical scavenging activity than the reference substance α-(+)-tocopherol in a DPPH• model expressed by IC 50 values.

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Secondary metabolites of the lichen Hypogymnia physodes (L.) Nyl. and their presence in spruce (Picea abies (L.) H. Karst.) bark

Cited by 21 publications

References 20 publications

UHPLC‐HRMS/MS Based Profiling of Algerian Lichens and Their Antimicrobial Activities

UHPLC‐HRMS/MS Based Profiling of Algerian Lichens and Their Antimicrobial Activities

DNA barcoding and LC-MS metabolite profiling of the lichen-forming genus Melanelia: Specimen identification and discrimination focusing on Icelandic taxa

ANTIOXIDANT ACTIVITY OF POLYPHENOLS FROMHYPOGYMNIA TAVARESIID. HAWKSW. & P. JAMES

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