Secondary metabolites of the lichen Cladonia stellaris

Половинка, М. П.; Комарова, Н. И.; Корчагина, Д. В.; Sokolov, D. N.; Luzina, O. A.; Vlasenko, N. G.; Malyuga, A. A.; Романова, Е. В.; Salakhutdinov, N. F.

doi:10.1007/s10600-012-0259-4

Cited by 7 publications

(4 citation statements)

References 9 publications

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“…Based on 1D 1 H, 13 C, HSQC, and HMBC experiments, the aromatic protons (H-3 and H-5) and aromatic carbons (C-1, C-2, C-3, C-4, C-5, and C-6) were unambiguously assigned. The 1 H NMR and 13 C NMR chemical shifts for the starting materials, olivetolic acid and its ester (ethyl or benzyl), were similar to those previously published. − Briefly, the 1 H NMR chemical shift of H-3 and H-5 of the aromatic ring was first distinguished by proving that H-5 is the only one correlating to the C-1″ chain carbon in HMBC. Then, the correlation of H-5 to only C-4 and not C-2 was proven using the HMBC spectrum.…”

Section: Resultssupporting

confidence: 72%

Synthetic Biology of Cannabinoids and Cannabinoid Glucosides in Nicotiana benthamiana and Saccharomyces cerevisiae

Gülck

Booth

Carvalho³

et al. 2020

J. Nat. Prod.

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Phytocannabinoids are a group of plant-derived metabolites that display a wide range of psychoactive as well as health-promoting effects. The production of pharmaceutically relevant cannabinoids relies on extraction and purification from cannabis (Cannabis sativa) plants yielding the major constituents, Δ9-tetrahydrocannabinol and cannabidiol. Heterologous biosynthesis of cannabinoids in Nicotiana benthamiana or Saccharomyces cerevisiae may provide cost-efficient and rapid future production platforms to acquire pure and high quantities of both the major and the rare cannabinoids as well as novel derivatives. Here, we used a meta-transcriptomic analysis of cannabis to identify genes for aromatic prenyltransferases of the UbiA superfamily and chalcone isomerase-like (CHIL) proteins. Among the aromatic prenyltransferases, CsaPT4 showed CBGAS activity in both N. benthamiana and S. cerevisiae. Coexpression of selected CsaPT pairs and of CHIL proteins encoding genes with CsaPT4 did not affect CBGAS catalytic efficiency. In a screen of different plant UDP-glycosyltransferases, Stevia rebaudiana SrUGT71E1 and Oryza sativa OsUGT5 were found to glucosylate olivetolic acid, cannabigerolic acid, and Δ9-tetrahydrocannabinolic acid. Metabolic engineering of N. benthamiana for production of cannabinoids revealed intrinsic glucosylation of olivetolic acid and cannabigerolic acid. S. cerevisiae was engineered to produce olivetolic acid glucoside and cannabigerolic acid glucoside.

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Section: Resultssupporting

confidence: 72%

Synthetic Biology of Cannabinoids and Cannabinoid Glucosides in Nicotiana benthamiana and Saccharomyces cerevisiae

Gülck

Booth

Carvalho³

et al. 2020

J. Nat. Prod.

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“…Atranorin was already fragmented in the ion source; therefore, fragment ions m / z 179.03389 (C 9 H 7 O 4 + ) and m / z 163.04007 (C 9 H 7 O 3 − ) were used for identification. Identification of perlatoric acid [ 64 ], rangiformic acid [ 65 ], and 4-O-methylolivetoric acid [ 66 ] were confirmed in reference to data presented in the cited publications.…”

Section: Methodsmentioning

confidence: 73%

Microbial Communities of Cladonia Lichens and Their Biosynthetic Gene Clusters Potentially Encoding Natural Products

et al. 2021

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Lichens have been widely used in traditional medicine, especially by indigenous communities worldwide. However, their slow growth and difficulties in the isolation of lichen symbionts and associated microbes have hindered the pharmaceutical utilisation of lichen-produced compounds. Advances in high-throughput sequencing techniques now permit detailed investigations of the complex microbial communities formed by fungi, green algae, cyanobacteria, and other bacteria within the lichen thalli. Here, we used amplicon sequencing, shotgun metagenomics, and in silico metabolomics together with compound extractions to study reindeer lichens collected from Southern Finland. Our aim was to evaluate the potential of Cladonia species as sources of novel natural products. We compared the predicted biosynthetic pathways of lichen compounds from isolated genome-sequenced lichen fungi and our environmental samples. Potential biosynthetic genes could then be further used to produce secondary metabolites in more tractable hosts. Furthermore, we detected multiple compounds by metabolite analyses, which revealed connections between the identified biosynthetic gene clusters and their products. Taken together, our results contribute to metagenomic data studies from complex lichen-symbiotic communities and provide valuable new information for use in further biochemical and pharmacological studies.

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“…Column chromatography and analytical techniques were successful in isolating, purifying and unambiguously characterising the major four lichenic acids, and this is the first report on the isolation of 1 and 2 and identification of 3 and 4 in Cladonia portentosa . Compounds 1 and 2 found in lichenic acids have been reported in Cladonia stellaris and Cladonia macaronesica [ 34 , 51 , 52 ], while 3 has been reported in C. stellaris and other Cladonia spp. (discussed earlier) [ 43 ].…”

Section: Discussionmentioning

confidence: 99%

Unravelling Novel Phytochemicals and Anticholinesterase Activity in Irish Cladonia portentosa

et al. 2023

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Acetylcholinesterase inhibitors remain the mainstay of symptomatic treatment for Alzheimer’s disease. The natural world is rich in acetylcholinesterase inhibitory molecules, and research efforts to identify novel leads is ongoing. Cladonia portentosa, commonly known as reindeer lichen, is an abundant lichen species found in Irish Boglands. The methanol extract of Irish C. portentosa was identified as an acetylcholinesterase inhibitory lead using qualitative TLC-bioautography in a screening program. To identify the active components, the extract was deconvoluted using a successive extraction process with hexane, ethyl acetate and methanol to isolate the active fraction. The hexane extract demonstrated the highest inhibitory activity and was selected for further phytochemical investigations. Olivetolic acid, 4-O-methylolivetolcarboxylic acid, perlatolic acid and usnic acid were isolated and characterized using ESI-MS and two-dimensional NMR techniques. LC-MS analysis also determined the presence of the additional usnic acid derivatives, placodiolic and pseudoplacodiolic acids. Assays of the isolated components confirmed that the observed anticholinesterase activity of C. portentosa can be attributed to usnic acid (25% inhibition at 125 µM) and perlatolic acid (20% inhibition at 250 µM), which were both reported inhibitors. This is the first report of isolation of olivetolic and 4-O-methylolivetolcarboxylic acids and the identification of placodiolic and pseudoplacodiolic acids from C. portentosa.

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Secondary metabolites of the lichen Cladonia stellaris

Cited by 7 publications

References 9 publications

Synthetic Biology of Cannabinoids and Cannabinoid Glucosides in Nicotiana benthamiana and Saccharomyces cerevisiae

Synthetic Biology of Cannabinoids and Cannabinoid Glucosides in Nicotiana benthamiana and Saccharomyces cerevisiae

Microbial Communities of Cladonia Lichens and Their Biosynthetic Gene Clusters Potentially Encoding Natural Products

Unravelling Novel Phytochemicals and Anticholinesterase Activity in Irish Cladonia portentosa

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