Structure and Cytotoxicity of Arnamial and Related Fungal Sesquiterpene Aryl Esters

Misiek, Mathias; Williams, J.M.; Schmich, Kathrin; Hüttel, Wolfgang; Merfort, Irmgard; Salomon, Christine; Aldrich, Courtney C.; Hoffmeister, Dirk

doi:10.1021/np900314p

Cited by 47 publications

(38 citation statements)

References 22 publications

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“…Sesquiterpene aryl esters from Armillaria sp. were already found to possess antibacterial [10,16], antifungal [28] and cytotoxic [29,30] effects and to inhibit the growth of lettuce [25]. Inhibition of degranulation of RBL-2H3 cells was observed for the first time in A. ostoyae, and all purified compounds were also isolated from the mycelium of A. ostoyae for the first time.…”

Section: Discussionmentioning

confidence: 96%

Untitled

2017

PMIO

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IntroductionDuring our investigations of biologically active fungi, Armillaria ostoyae (Romagn.) Herink [1], a basidiomycete belonging to the family Physalacriaceae, came into focus, as it affected degranulation in RBL-2H3 cells. The species is commonly known as edible mushroom, but it also occurs as a devastating pathogen of various tree species causing serious economic losses in forestry all over the world [2]. The mechanisms of host infection as well as hostpathogen interactions have been studied intensively [3][4][5][6][7]. In addition, Armillaria mushrooms attract a wider interest, for instance, as the worldʼs biggest living organism [8] or as a producer of bioluminescence [9]. A broad variety of antibacterial and cytotoxic sesquiterpene aryl esters were isolated from the genus Armillaria, especially Armillaria mellea [10][11][12][13][14][15][16][17][18][19][20], but also Armillaria novae-zelandiae [21] and Armillaria tabescens [22]. In this manuscript, degranulation inhibiting effects of extracts from fruiting bodies and cultivated mycelium as well as bioactivity-guided isolation of compounds from the mycelium of A. ostoyae are described. Degranulation is the process in which cells release secretory products stored in secretory granules by exocytosis. It is an important feature of many immune cells, e.g., for release of mediators [23]. Inhibition of degranulation can result in the blocking of inflammatory or allergic reactions.

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Section: Discussionmentioning

confidence: 96%

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2017

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“…The organic layer was evaporated in vacuo, then redissolved in methanol, and subjected to HPLC. Purification of individual aryl esters followed a published procedure (Misiek et al 2009). Analytical HPLC was performed on an Agilent 1200 instrument.…”

Section: Methodsmentioning

confidence: 99%

“…Preparative HPLC, liquid chromatography/mass spectrometry (LC/MS), and nuclear magnetic resonance spectroscopy were performed for melledonol, melledonal A, melledonal C, melleolide C, melleolide D, 10α-hydroxymelleolide, and arnamial ( Fig. 1; Table 1) as described (Misiek et al 2009). The total aryl ester content was quantified using a 1 μg/μl solution of pure melleolide D as external standard and injected in varied volumes (2-10 μl in 2-μl increments).…”

Section: Methodsmentioning

confidence: 99%

“…1) which represent biosynthetic chimera. Their protoilludanol alcohol is a sesquiterpene, while the orsellinic acid-derived aromatic moiety is assembled via the polyketide metabolism (Misiek et al 2009). Orsellinic acid and derivatives are known from numerous microorganisms, and protoilludanes are common homobasidiomycete secondary metabolites.…”

Section: Introductionmentioning

confidence: 99%

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Sesquiterpene aryl ester natural products in North American Armillaria species

Misiek

Hoffmeister

2010

Mycol Progress

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In the first comprehensive study on the secondary metabolism of all ten North American Armillaria species, we analyzed their capacity to produce sesquiterpene aryl ester natural products. All species were identified as producers. Species-specific trends were observed for some species, e.g., for Armillaria ostoyae and A. gemina (low diversity of aryl esters) or A. tabescens (very low number of chlorinated aryl esters). The crude extracts were assayed for antibiotic activity against wood-rotting basidiomycetes and ubiquitous soil fungi. Inhibitory effects were strongly dependent on the target organism, with basidiomycetes being more susceptible than other fungi. Tapinella panuoides and Omphalotus illudens were inhibited by extracts of all Armillaria species whereas the same extracts were completely inactive against Trichoderma harzianum, widely inactive against Mucor racemosus, and only moderately active against Aspergillus flavus and Penicillium oxalicum. Activity tests with seven purified aryl esters suggest that lipophilicity and the position of the double bond in the tricyclic sesquiterpene moiety impact upon bioactivity while the substitution pattern of the aromatic ring does not. Arnamial was the most active compound and showed a minimum inhibitory concentration of <5 μg/ml for all four basidiomycetes and Penicillium oxalicum, but did not inhibit Trichoderma harzianum and Mucor racemosus.

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“…7,8) It is likely that melleolide and its analogs show cell death activity against various types of cell, and that they show antiaging activity specifically as to budding yeast cells.…”

Section: )mentioning

confidence: 99%

Anti-aging and anti-microbial effects of melleolide on various types of yeast

Nakaya

Kobori

Sekiya

et al. 2014

Bioscience, Biotechnology, and Biochemistry

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The chronological lifespan (CLS) of the budding yeast Saccharomyces cerevisiae is a model for the aging of post-mitotic cells in higher eukaryotes. In this study, we found that the sesquiterpene aryl ester melleolide expands the CLS of budding yeast. In contrast, melleolide compromised the CLS of the fission yeast Schizosaccharomyces pombe. This indicates that melleolide might have a potential anti-aging activity against some types of cell, and that it might be useful as a selective anti-fungal drug.

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Structure and Cytotoxicity of Arnamial and Related Fungal Sesquiterpene Aryl Esters

Cited by 47 publications

References 22 publications

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Sesquiterpene aryl ester natural products in North American Armillaria species

Anti-aging and anti-microbial effects of melleolide on various types of yeast

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