Persistent and widespread occurrence of bioactive quinone pigments during post-Paleozoic crinoid diversification

Wolkenstein, Klaus

doi:10.1073/pnas.1417262112

Cited by 17 publications

(14 citation statements)

References 34 publications

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“…1 The fossil record indicates that crinoids are the most primitive of the present-day echinoderms, having flourished during both the Palaeozoic (544 -248 million years ago) and Mesozoic (248 -65 million years ago) Eras. 1,2 Their surviving descendants have hardly changed in their appearance. 1 Approximately 700 known species exist today, 3 typically existing in two forms: 'stalked' crinoids, or sea-lilies (representing approximately 100 known species, Fig.…”

Section: Introductionmentioning

confidence: 99%

Crinoids: ancient organisms, modern chemistry

2017

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Covering: 1877 to 2017The ancestors of present-day crinoids are thought to be some of the earliest echinoderms, with fossil records dating back to the early Paleozoic Era (Ordovician Period, 505-440 million years ago). Their bright colours have been noted for over 100 years, and are attributed to a series of polyketide-derived pigments. Some crinoid metabolites display a range of biological activities, including cytotoxicity and fish anti-feedant activity. This review is divided into two parts. Part 1 is encyclopedic in scope, collating information on the >50 known metabolites isolated from crinoids, including their taxonomic source, collection location, chemical structure and biological activities. During the compilation of this data, two distinct themes emerged. Firstly, there is little variation in the class of metabolites produced by crinoids, irrespective of their species or geographic origin. Secondly, the complete and unambiguous assignment of crinoid metabolite structures has been, in many cases, a difficult task. This has been due to a lack of spectroscopic technology available in the past, the presence of proton-poor chemical structures, or both. Thus, Part 2 provides a critical discussion of crinoid chemistry, including the biosynthetic origin of crinoid pigments, as well as the pitfalls and solutions experienced by ourselves and other chemists when elucidating the chemical structures of crinoid metabolites.

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Section: Introductionmentioning

confidence: 99%

Crinoids: ancient organisms, modern chemistry

2017

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“…) in the next several decades, and is still ongoing (e.g. and references therein). This field has hardly been “neglected” (, p.1); in fact, a cursory literature database search under “fossil pigment” yields hundreds of references from the late 1800s to the present.…”

Section: The Role Of Pigments In Biology and Evolutionmentioning

confidence: 99%

Melanosomes and ancient coloration re‐examined: A response to Vinther 2015 (DOI 10.1002/bies.201500018)

Schweitzer¹,

Moyer²

2015

BioEssays

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Round to elongate microbodies associated with fossil vertebrate soft tissues were interpreted as microbial traces until 2008, when they were re-described as remnant melanosomes -intracellular, pigment-containing eukaryotic organelles. Since then, multiple claims for melanosome preservation and inferences of organismal color, behavior, and physiology have been advanced, based upon the shape and size of these microstructures. Here, we re-examine evidence for ancient melanosomes in light of information reviewed in Vinther (2015), and literature regarding the preservation potential of microorganisms and their exopolymeric secretions. We: (i) address statements in Vinther's recent (2015) review that are incorrect or which misrepresent published data; (ii) discuss the need for caution in interpreting ''voids'' and microbodies associated with degraded fossil soft tissues; (iii) present evidence that microorganisms are in many cases an equally parsimonious source for these ''voids'' as are remnant melanosomes; and (iv) suggest methods/criteria for differentiating melanosomes from microbial traces in the fossil record.

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“…The occurrence of trehalose as a major saccharide and the presence of sucrose in some samples imply that disaccharides can survive in sedimentary rocks as old as the Cretaceous. Other compounds like: isoprenoidal GDGTs (Schouten et al, 2003;Littler et al, 2011;Jenkyns et al, 2012), sterols (Melendez et al, 2013), hypericinoid pigments (Wolkenstein et al, 2008;Wolkenstein, 2015), polyketide-derived spiroborate pigments , or polar diterpenoids (Marynowski et al, 2007b) have been reported in Palaeozoic and Mesozoic sedimentary deposits. These are other groups of compounds previously thought as unstable which were preserved in pre-Palaeogene strata.…”

Section: Implications For Differences In Saccharide Distribution and mentioning

confidence: 99%

Trehalose, mannitol and arabitol as indicators of fungal metabolism in Late Cretaceous and Miocene deposits

Marynowski

Goryl

Bucha

et al. 2019

International Journal of Coal Geology

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A B S T R A C TTrehalose, mannitol and arabitol are the main saccharides of extant fungal metabolism, but their occurrence and distribution in geological materials have rarely been considered. Here, we identify these sugars in Miocene lignites and for the first time in Late Cretaceous mudstones and coals. The co-occurrence of trehalose, mannitol and arabitol in the sedimentary rocks investigated suggests their fungal origin, because these three saccharides are major compounds present in most modern fungi, including the very common mycorrhizal and wood-rotting groups. Therefore, we conclude that these sugars should be treated as new fungal biomarkers (biomolecules) present in geological rocks. Trehalose and mannitol are major compounds in total extracts of the samples and a sum of their concentration reaches 4.6 μg/g of sample. The arabitol concentrations do not exceed 0.5 μg/g, but in contrast to trehalose, the concentration correlates well with mannitol (R 2 = 0.94), suggesting that they have the same, translocatory role in fungi. Based on the trehalose vs. mannitol and arabitol distributions in Cretaceous samples and their comparison with data for modern fungi, we preliminarily conclude that the coal seams from the Rakowice Małe (SW Poland) section were formed during warmer climatic periods than the overlying sediments. Furthermore, no DNA could be isolated from the samples of lignites and overlying sediments, whereas it was abundant in the control samples of maple, birch and oak wood degraded by fungi. This indicates an absence of recent fungi responsible for decay in lignites and implies that the saccharide origin is connected with ancient fungi.Other sugar alcohols and acids like D-pinitol, quinic acid and shikimic acid, were found for the first time in sedimentary rocks, and their source is inferred to be from higher plants, most likely conifers. The preservation of mono-and disaccharides of fungal origins in pre-Palaeogene strata implies that compounds previously thought as unstable can survive for tens to hundreds of millions of years without structural changes in immature rocks unaffected by secondary processes.Saccharides, ubiquitous biomolecules in both plant and animal kingdoms, are common in marine and terrestrial environments (Klok et al.

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Persistent and widespread occurrence of bioactive quinone pigments during post-Paleozoic crinoid diversification

Cited by 17 publications

References 34 publications

Crinoids: ancient organisms, modern chemistry

Crinoids: ancient organisms, modern chemistry

Melanosomes and ancient coloration re‐examined: A response to Vinther 2015 (DOI 10.1002/bies.201500018)

Trehalose, mannitol and arabitol as indicators of fungal metabolism in Late Cretaceous and Miocene deposits

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