Variation in the Composition of Secondary Metabolites in Flavocetraria Lichens from Western Siberia

Prokopiev, I. A.; Poryadina, L. N.; Konoreva, L. A.; Chesnokov, S. V.; Шаварда, А. Л.

doi:10.1134/s1067413618050107

Cited by 7 publications

(4 citation statements)

References 12 publications

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“…The suite of compounds is relatively steady for a given lichen species and are used for species authentication. However, chemotypes within a species have been identified that may be induced by nutrients, ecological parameters, biotic and abiotic stressors, light intensity, and by the presence of other microorganisms . Based on our findings, we suggest that these four compounds represent a part of the principal set of specialized metabolites in E. prunastri , which are important for its function as a multi‐member microbial community and may be involved in protecting that community from abiotic and biotic stressors.…”

Section: Discussionmentioning

confidence: 55%

Structure and Chemical Analysis of Major Specialized Metabolites Produced by the Lichen Evernia prunastri

Staples

LaDuca

Roze

et al. 2020

Chemistry & Biodiversity

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We performed comparative profiling of four specialized metabolites in the lichen Evernia prunastri, collected at three different geographic locations, California and Maine, USA, and Yoshkar Ola, Mari El, Russia. Among the compounds produced at high concentrations that were identified in all three specimens, evernic acid, usnic acid, lecanoric acid and chloroatranorin, evernic acid was the most abundant. Two depsidones, salazinic acid and physodic acid, were detected in the Yoshkar-Ola collection only. The crystalline structure of evernic acid (2hydroxy-4-[(2-hydroxy-4-methoxy-6-methylbenzoyl)oxy]-6-methylbenzoate) (hmb) revealed two crystallographically and conformationally distinct hmb anions, along with two monovalent sodium atoms. One hmb moiety contained an exotetradentate binding mode to sodium, whereas the other exhibited an exohexadentate binding mode to sodium. Embedded edge-sharing {Na 2 O 8 } n sodium-oxygen chains connected the hmb anions into the full three-dimensional crystal structure of the title compound. The crystal used for single-crystal X-ray diffraction exhibited non-merohedral twinning. The data suggest the importance of the acetyl-polymalonyl pathway products to processes of maintaining integrity of the lichen holobiont community.[a] Data for one replicate.

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Section: Discussionmentioning

confidence: 55%

Structure and Chemical Analysis of Major Specialized Metabolites Produced by the Lichen Evernia prunastri

Staples

LaDuca

Roze

et al. 2020

Chemistry & Biodiversity

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“…Phenolic compounds have a similar effect as chelators of transition metals and have an ability to quenching of free radical reactions (Foti, 2007;Kulbat, 2016). Thus, the presence of phenols and flavonoids in bark can be a substitution for lichen metabolites such as melanins, lecanoric, and usnic acid (Solhaug and Gauslaa, 1996;Luo et al, 2009;Prokopiev et al, 2018) in prevention thalli from a damage from reactive oxygen species under high UV-B levels. A close contact of crustose epiphytes with their substrates and a variability in an amount of phenols and flavonoids in bark may be a reason for a lower dependence of a secondary chemistry of crustose species on bark pH.…”

Section: Discussionmentioning

confidence: 99%

The Role of Secondary Metabolites and Bark Chemistry in Shaping Diversity and Abundance of Epiphytic Lichens

Paukov

Teptina

Ermoshin

et al. 2022

Front. For. Glob. Change

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Diversity of secondary lichen metabolites was studied in epiphytic lichens on six phorophytes—spruce, pine, birch, alder, aspen and poplar in the Middle Urals of Russia. Atranorin, usnic, fumarprotocetraric acid, zeorin, and gyrophoric acid were found in 31, 24, 23, 18, and 14 species, respectively, of 237 taxa collected. Seventy-seven species (i.e., 32% of total species documented) contained no secondary metabolites. Spectra of secondary metabolites of fruticose and foliose lichens varied on different phorophytes, while in crustose species the strong dependence on the tree species was not detected. This is different to the pH dependence of saxicolous lichens where crustose lichens were more susceptible to the rock chemistry. The results of Canonical Correspondence Analysis reveal the affinity of species containing depsides, depsidones or usnic acid to acidic substrata and those lacking secondary metabolites or containing terpenes and antraquinones to the pH-neutral bark. We suppose that phenolic compounds and flavonoids, as chemical constituents of bark, may interact with lichen symbioses and elements in phellem, and similarly to the lichen acids shape the affinity of species to the substrata.

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“…Localities with limestones represent a separate group with high Ca and Sr. Sites with granites group with quartzite and one locality with 'basalt.' Habitats with serpentinized rocks are subdivided into groups with apoharzburgite serpentinites (1,11,12,15) and apoharzburgite antigorite-talc-carbonate slates (6,9,17). The rocks regarded as 'basalts' are chemically not uniform and appeared to be close to granites or serpentinized rocks in some locations.…”

Section: Chemical Properties Of Rock Substratesmentioning

confidence: 99%

“…Lichen secondary metabolites, including pigments, have a number of known functions. Some substances are biologically active and act as allelopathic agents [3,4], while others affect herbivore palatability [5,6], increase permeability of the cell membrane of phycobionts [7,8] and protect photobionts from excessive ultraviolet (UV)-B light [3,[6][7][8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

The Effects of Edaphic and Climatic Factors on Secondary Lichen Chemistry: A Case Study Using Saxicolous Lichens

et al. 2019

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Diversity of secondary lichen metabolites and their relationship to substrate and environmental parameters were studied in saxicolous lichens in the Middle and South Urals of Russia. Atranorin, usnic acid, gyrophoric acid, zeorin, norstictic acid, antraquinones and stictic acid were found in 73, 42, 41, 37, 36, 35 and 32 species, respectively, of 543 taxa collected. One hundred and ninety six species (i.e., 36% of total species documented) contained no secondary metabolites. Spectra of secondary metabolites of crustose lichens varied on different rock types, while in fruticose and foliose groups only those species without lichen acids were dependent on the substrate type. In Canonical Correspondence Analysis, secondary lichen metabolites were subdivided into groups depending on the concentration of Ca and metals in the substrate. Gyrophoric, lobaric, psoromic, rhizocarpic and stictic acids were common in crustose lichens in metal-poor habitats; species with antraquinones and lichens without any secondary metabolites were most abundant on limestone (alkalic and metal-poor), while other common lichen metabolites had no to minimal dependence on the chemistry of the substrate. The two additional abiotic factors affecting the composition of secondary metabolites were the maximum temperature of the warmest month and elevation. Our results suggest a range of possible relationships exist among lichen acids, rocks and climatic parameters. Furthermore, the same metabolite may affect both accumulation of metals and stress tolerance under unfavorable conditions.

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Variation in the Composition of Secondary Metabolites in Flavocetraria Lichens from Western Siberia

Cited by 7 publications

References 12 publications

Structure and Chemical Analysis of Major Specialized Metabolites Produced by the Lichen Evernia prunastri

Structure and Chemical Analysis of Major Specialized Metabolites Produced by the Lichen Evernia prunastri

The Role of Secondary Metabolites and Bark Chemistry in Shaping Diversity and Abundance of Epiphytic Lichens

The Effects of Edaphic and Climatic Factors on Secondary Lichen Chemistry: A Case Study Using Saxicolous Lichens

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