Fuligopyrones from the Fruiting Bodies of Myxomycete Fuligo septica Offer Short-Term Protection from Abiotic Stress Induced by UV Radiation.

The myxomycete Fuligo septica, colloquially referred to as "dog vomit fungus", forms vibrant yellow fruiting bodies (aethalia) on wood chips during warm and humid conditions in spring. In 2018, ideal climatic conditions in Sydney, Australia, provided a rare opportunity to access abundant quantities of F. septica aethalia, which enabled the isolation, purification, structure elucidation, and biological screening of two avenalumamide pyrones, fuligopyrone (1) and fuligopyrone B (2). While 1 and 2 did not exhibit any appreciable biological activity, their significant UV absorption at 325 nm suggested they may be acting as transient sunscreens to help protect the fruiting mass from exposure to sunlight. In support of this hypothesis, exposing a solution of 2 to direct sunlight for 5 min resulted in rapid equilibration with a mixture of 2E,4Z-fuligopyrone B (10) and 2Z,4E-fuligopyrone B (11) photoisomers.

An exceptionally stable and widespread hydrated amorphous calcium carbonate precipitated by the dog vomit slime mold Fuligo septica (Myxogastria).

Biogenic amorphous calcium carbonate (ACC) is typically metastable and can rapidly transform through aging, dehydration, and/or heating to crystalline calcium carbonate. Gaining insight into its structure and properties is typically hampered by its tendency to crystallize over short time periods once isolated from the host organism, and also by the small quantities that are usually available for study. Here we describe an exceptionally stable hydrated ACC (HACC) precipitated by the cosmopolitan slime mold Fuligo septica (L.) F.H. Wigg. (1780). A single slime mold can precipitate up to a gram of HACC over the course of one night. Powder x-ray diffraction (XRD) patterns, transmission electron microscopy images, infrared absorption spectra, together with the lack of optical birefringence are consistent with an amorphous material. XRD simulations, supported by thermogravimetric and evolved gas analysis data, are consistent with an intimate association of organic matter with ~ 1-nm-sized ACC units that have monohydrocalcite- and calcite-like nano-structural properties. It is postulated that this association imparts the extreme stability of the slime mold HACC by inhibiting loss of H2O and subsequent crystallization. The composition, structure, and thermal behavior of the HACC precipitated by F. septica collected over 8000 km apart and in markedly different environments, suggests a common structure, as well as similar biochemical and biomineralization mechanisms.

Laboratory culture and bioactive natural products of myxomycetes.

Myxomycetes, one of the lowest classes of eukaryote (true slime molds), are an unusual group of primitive organisms. Their life cycle consists of two stages, namely the free-living plasmodium and the fruiting body with unique structures and colors. The chemical studies on the secondary metabolites of the myxomycetes are limited due to a lack of understanding of their laboratory cultivation. In this review, 93 natural products from myxomycetes, including their chemical structures and bioactivities were described. We also provided a conceptual overview over five culture methods of myxomycetes, including moist chamber culture, feeding culture, pure culture, liquid culture and hanging drop culture.

Identification of a consistent polyene component of purple pigment in diseased sclerites of Caribbean corals across region, species, and insult agent.

Gorgonians respond to insult (damage and disease) by producing sclerites containing a purple pigment as opposed to the normal white sclerites. Raman microscopy is used to study the purple areas of three species of diseased coral, Gorgonia ventalina, Pseudoplexaura porosa, and Eunicea laciniata obtained from Puerto Rico. These spectra were compared to Gorgonia ventalina samples previously reported that were obtained from San Salvador, Bahamas. Spectra from two samples of G. ventalina that had been infected by different agents, Aspergillus sydowii and a slime mold, were also obtained. The results indicate that the purple compounds (polyenes) generated by the coral in response to infection are similar regardless of region from which the coral were harvested, of species of coral, and of the infective agent. A discussion of the Raman spectra of G. ventalina and the other coral species is presented.

Dibenzofurans and derivatives from lichens and ascomycetes.

Covering: up to 2016.When looking for dibenzofuran in the biochemical databases, most papers and reviews deal with pollutants and polychlorinated dibenzofurans like dioxins. But dibenzofurans are also biosynthetized by a wide diversity of organisms in nature. Even if dibenzofurans from natural sources represent a small class of secondary metabolites, compared to flavonoids, xanthones or terpenoids, they are often endowed with interesting biological properties which have been recently described. This review provides an update on papers describing dibenzofurans from lichens, ascomycetes and cultured mycobionts. Other sources, such as basidiomycetes, myxomycetes or plants produce sporadically interesting dibenzofurans in terms of structures and activities.

Stable isotope composition (δ(13)C and δ(15)N values) of slime molds: placing bacterivorous soil protozoans in the food web context.

RATIONALE: Data on the bulk stable isotope composition of soil bacteria and bacterivorous soil animals are required to estimate the nutrient and energy fluxes via bacterial channels within detrital food webs. We measured the isotopic composition of slime molds (Myxogastria, Amoebozoa), a group of soil protozoans forming macroscopic spore-bearing fruiting bodies. An analysis of largely bacterivorous slime molds can provide information on the bulk stable isotope composition of soil bacteria. METHODS: Fruiting bodies of slime molds were collected in a monsoon tropical forest of Cat Tien National Park, Vietnam, and analyzed by continuous-flow isotope ratio mass spectrometry. Prior to stable isotope analysis, carbonates were removed from a subset of samples by acidification. To estimate the trophic position of slime molds, their δ(13) C and δ(15) N values were compared with those of plant debris, soil, microbial destructors (litter-decomposing, humus-decomposing, and ectomycorrhizal fungi) and members of higher trophic levels (oribatid mites, termites, predatory macroinvertebrates). RESULTS: Eight species of slime molds represented by at least three independent samples were 3-6‰ enriched in (13) C and (15) N relative to plant litter. A small but significant difference in the δ(13) C and δ(15) N values suggests that different species of myxomycetes can differ in feeding behavior. The slime molds were enriched in (15) N compared with litter-decomposing fungi, and depleted in (15) N compared with mycorrhizal or humus-decomposing fungi. Slime mold sporocarps and plasmodia largely overlapped with oribatid mites in the isotopic bi-plot, but were depleted in (15) N compared with predatory invertebrates and humiphagous termites. CONCLUSIONS: A comparison with reference groups of soil organisms suggests strong trophic links of slime molds to saprotrophic microorganisms which decompose plant litter, but not to humus-decomposing microorganisms or to mycorrhizal fungi. Under the assumption that slime molds are primarily feeding on bacteria, the isotopic similarity of slime molds and mycophagous soil animals indicates that saprotrophic soil bacteria and fungi are similar in bulk isotopic composition.

RNA editing is absent in a single mitochondrial gene of Didymium iridis.

An open reading frame (ORF) was found in the mitochondrial genome of the Pan2-16 strain of Didymium iridis that showed high similarity to the NADH dehydrogenase subunit 3 (nad3) gene in other organisms. So far all other typical mitochondrial genes identified in this organism require RNA editing to generate ORFs capable of directing protein synthesis. The D. iridis sequence was compared to the putative nad3 gene in the related myxomycete Physarum polycephalum, which would require editing. Based on this comparison, editing sites could be predicted for the P. polycelphalum gene that would result in the synthesis of a highly conserved ND3 protein between the two organisms. To determine the editing status of the nad3 gene in other D. iridis strains, PCR was used to amplify this region from eight other independent isolates of the A1 Central American interbreeding series. In each case a 378 base pair ORF was detected by PCR amplification and sequencing. Three patterns of sequence variation were observed; however all base substitutions were in the third codon position and silent with respect to the amino acids encoded. The distribution of the sequence variants was mapped geographically. The requirement for RNA editing in all other typical mitochondrial genes of D. iridis and P. polycephalum and the presence of RNA editing in the nad3 gene of P. polycephalum suggest that the D. iridis nad3 gene might have been edited at one time. We propose that the D. iridis nad3 gene may have lost the requirement for RNA editing by reverse transcription of an edited transcript that subsequently was inserted into the genome.

A Bisindole Alkaloid with Hedgehog Signal Inhibitory Activity from the Myxomycete Perichaena chrysosperma.

6-Hydroxy-9'-methoxystaurosporinone (1), a new bisindole alkaloid, was isolated from field-collected fruiting bodies of the myxomycete Perichaena chrysosperma, together with two known compounds. The structure of the new alkaloid was elucidated from spectral data, and compound 1 was shown to have hedgehog signal inhibitory activity. A related new alkaloid, 6,9'-dihydroxystaurosporinone (4), was also isolated from Arcyria cinerea.

The first Hes1 dimer inhibitors from natural products.

In the present study, we developed a high-throughput screening system for small molecule-inhibitors of the basic helix-loop-helix (bHLH) transcriptional repressor factor Hes1. Successful dimerization of Hes1 immobilized on a microplate and fluorophore (Cy3)-labelled Hes1 was confirmed. Using this system, several natural products were identified as the first Hes1 dimer inhibitors. Of these, two compounds which were isolated from myxomycetes (true slime molds) inhibited Hes1 from N box-dependent suppression of the gene expression in C3H10T1/2 cells.

Cribrarione C, a naphthoquinone pigment from the myxomycete Cribraria meylanii.

Chemical investigation of field-collected fruit bodies of the myxomycete Cribraria meylanii resulted in the isolation of a naphthoquinone pigment, cribrarione C, and its structure was elucidated by spectral data as 2,5,6,7-tetrahydroxy-1,4-naphthoquinone (1). This compound (1) had been synthesized previously, while it was isolated here for the first time as a natural product, and its NMR and MS data are described in this study.

A habitat colonisation model for spore-dispersed organisms: does it work with eumycetozoans?

Spore productivities and establishment probabilities of eumycetozoans were estimated and compared with quantitative data obtained from field surveys, using series of cultures of a given substrate. Spore numbers per spore case were found to increase from one to four in protostelids to up to 10(5)-10(6) in myxomycetes, whereas average spore size decreased slightly from 14.8 microm for protostelids to 10.3 microm in myxomycetes. Spore numbers of fructifications calculated from dimensions of spores and fruit bodies were in good agreement with direct counts carried out for six species of myxomycetes. A colonisation model is presented that estimates frequencies (as a percent of successfully colonized habitat islands), which is independent of a given density of spore rain and the sexual system of the species being considered. Whereas asexual species need a minimum spore rain of ca 0.7 spores per habitat island to reach a frequency of 50%, this figure is at least 2.4-fold higher for sexual species, depending from the incompatibility system assumed. Data from cultures indicate that the maximum potential spore rain is usually three orders of magnitude higher than the minimum figure required to create the observed frequencies. Eumycetozoans seem to follow the evolutionary trends predicted by the model. Species with sexual reproductive systems produce often more spores than asexual ones; many morphospecies have sexual and asexual strains; and back-conversion from sexual to asexual reproduction occurs occasionally.

[Study on myxomycetes as a new source of bioactive natural products].

The Myxomycetes (true slime molds) are an unusual group of primitive organisms that may be assigned to one of the lowest classes of eukaryotes. As their fruit bodies are very small and it is very difficult to collect much quantity, few studies have been made on the chemistry of myxomycetes. We studied spore germination experiments of hundreds of field-collected myxomycetes collected in Japan, and succeeded in laboratory culture of plasmodia of several myxomycetes in a practical scale for natural products chemistry studies. Pyrroloiminoquinones, polyene yellow pigments, and a peptide lactone were isolated from cultured plasmodia of myxomycetes, while new naphthoquinone pigments, cycloanthranilylprolines, tyrosine-kinase inhibitory bisindoles, a cytotoxic triterpenoid aldehyde lactone, a dibenzofuran glycoside, and sterols possessing an unprecedented 2,6-dioxabicyclo[2.2.2] octan-3-one ring system, were also isolated from field-collected fruit bodies of myxomycetes.

Synthesis, determination of stereochemistry, and evaluation of new bisindole alkaloids from the myxomycete Arcyria ferruginea: an approach for Wnt signal inhibitor.

To determine the stereochemistry of dihydroarcyriarubin C (1), new bisindole alkaloid isolated from the myxomycete Arcyria ferruginea, cis- (2) and trans-dihydroarcyriarubin C (3) were synthesized. Comparison of their NMR characteristics allowed the trans stereochemistry of the natural product to be confirmed. Moreover, the Wnt signal inhibitory activities of 2 and 3 were compared with that of arcyriaflavin C (4), which is a natural product containing a bond between C-2 and C-2'. The cis-dihydroarcyriarubin C (2) showed moderate inhibition of Wnt signal transcription, which suggests that bisindole frameworks might be useful as small-molecule Wnt signal inhibitors.

Bisindole alkaloids from myxomycetes Arcyria denudata and Arcyria obvelata.

A new bisindole sulfate (1) and arcyroxocin B (2) were isolated from wild fruiting bodies of Arcyria denudate, along with three known bisindoles (4-6). Dihydroarcyriacyanin A (3) was obtained from wild fruiting bodies of Arcyria obvelata, along with a known bisindole (7). The structures of these compounds were elucidated on the basis of spectroscopic data, and this is the first report of full characterizations of arcyroxocin B (2) and dihydroarcyriacyanin A (3). Compounds 2, 3, and 6 showed cytotoxicity against Jurkat cells.

New bisindole alkaloids isolated from Myxomycetes Arcyria cinerea and Lycogala epidendrum.

Two new bisindole alkaloids, named cinereapyrrole A (1) and B (2), were isolated from wild fruit bodies of Arcyria cinerea and three new bisindole alkaloids (3-5) were isolated from wild fruit bodies of Lycogala epidendrum. Seven known bisindoles (6-12) were concomitantly obtained from them. The structures of the new compounds were elucidated by spectral data. Among these bisindole alkaloids, compound 12 showed cytotoxicity against cultured tumor cell lines.

New cytotoxic bisindole alkaloids with protein tyrosine kinase inhibitory activity from a myxomycete Lycogala epidendrum.

Two new bisindole alkaloids, 6-hydroxystaurosporinone (1) and 5,6-dihydroxyarcyriaflavin A (2) were isolated from field-collected fruit bodies of a myxomycete Lycogala epidendrum, along with eight known bisindoles (3-10). The structures of these new compounds were determined on the basis of spectroscopic data. Compounds 1 and 2 showed cytotoxicity against HeLa, Jurkat, and vincristine resistant KB/VJ300 cells, and compound 1, particularly, inhibited protein tyrosine kinase activity.

Isolation of bioactive natural products from myxomycetes.

The Myxomycetes (true slime molds) are an unusual group of primitive organisms that may be assigned to one of the lowest classes of eukaryotes. As their fruit bodies are very small and it is very difficult to collect much quantity of slime molds, few studies have been made on the chemistry of myxomycetes. Cultivation of the plasmodium of myxomycetes in a practical scale for natural products chemistry studies is known only for very limited species. Here is described a review on the recent results on isolation of bioactive natural products from myxomycetes obtained in these two years in the laboratories. Spore germination experiments were studied of hundreds of field-collected myxomycetes collected in Japan and succeeded in laboratory culture of plasmodia of several myxomycetes in a practical scale for natural products chemistry studies. As a result, pyrroloiminoquinones, polyene yellow pigments, and a peptide lactone from cultured plasmodia of Didymium iridis, Physarum rigidum and P. melleum, respectively were isolated. New naphthoquinone pigments, cycloanthranilylprolines, tyrosine-kinase inhibitory bisindoles, and a cytotoxic triterpenoid aldehyde lactone were also isolated from field-collected fruit bodies of Cribraria purpurea, Fuligo candida, Tubifera casparyi, and Tubifera dimorphotheca, respectively.

Cycloanthranilylproline-derived constituents from a myxomycete Fuligo candida.

Cycloanthranilylproline (1) and its derivatives (2--4) were isolated from field-collected fruit-bodies of a myxomycete Fuligo candida and their structures were elucidated by spectral data. Compound 4, which was contained in the water-soluble fraction of the extract of this myxomycete, was unstable and quite susceptible to decarboxylation to yield compound 2, which was a major constituent of the EtOAc-soluble fraction of this extract.

Enteridinines A and B from slime mold Enteridium lycoperdon.

Two novel deoxysugar esters, named enteridinines A and B, were isolated from the slime mold Enteridium lycoperdon. Their structures, including the absolute configurations of the hydroxyl and methyl groups, were determined by means of extensive spectroscopic data such as UV, IR, MS, 1D and 2D NMR spectra. Enteridinines A and B have unique structures containing 1,7-dioxaspiro[5.5]undecanes with an O-beta-D-mycarosyl-(1-->4)-beta-D-olivosyl and an O-beta-L-olivomycosyl-(1-->4)-beta-D-amicetosyl-(1-->4)-beta-L-digitoxosyl unit, respectively, and showed growth inhibitory activities against Gram positive bacteria.