Rickenyls A–E, antioxidative terphenyls from the fungus Hypoxylon rickii (Xylariaceae, Ascomycota)

Kuhnert, Eric; Surup, Frank; Herrmann, Jennifer; Hüch, Volker; Müller, Rolf; Stadler, Marc

doi:10.1016/j.phytochem.2015.08.004

Cited by 49 publications

(51 citation statements)

References 39 publications

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“…In vitro cytotoxicity (IC50) was evaluated against mouse fibroblasts cell line L929 and HeLa (KB3.1) was carried out according to our previous papers [10,11].…”

Section: Cytotoxicity Assaymentioning

confidence: 99%

Skeletocutins M-Q, biologically active compounds from the fruiting bodies of the basidiomycete Skeletocutis sp. collected in Africa

Cheng¹,

Decock²,

Matasyoh³

et al. 2019

Preprint

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During the course of screening for new metabolites from basidiomycetes, we isolated and characterized five previously undescribed secondary metabolites skeletocutins M-Q (1-5) along with the known metabolite tyromycin A (6) from the fruiting bodies of the polypore Skeletocutis sp. The new compounds did not exhibit any antimicrobial, cytotoxic or nematicidal activities. However, compound 3 moderately inhibited the biofilm formation of Staphylococcus aureus, while compounds 3 and 4 performed moderately activity in the L-leucine-7-amido-4-methylcoumarin (L-Leu-AMC) inhibition assay. These compounds represent the first report of secondary metabolites occurring in the fruiting bodies of Skeletocutis. Interestingly, tyromycin A was found to be the only common metabolites in fruiting bodies and mycelial cultures of the fungus, and none of the recently reported skeletocutins from the culture of the same strain was detected in the basidiomes.

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“…In vitro cytotoxicity (IC50) was evaluated against mouse fibroblasts cell line L929 and HeLa (KB3.1) was carried out according to our previous papers [10,11].…”

Section: Cytotoxicity Assaymentioning

confidence: 99%

Skeletocutins M-Q, biologically active compounds from the fruiting bodies of the basidiomycete Skeletocutis sp. collected in Africa

Cheng¹,

Decock²,

Matasyoh³

et al. 2019

Preprint

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“…3, 28.0, 27.7, 27.5, 27.4, Table 1. 13 CS pectroscopic data for rickiols [1][2][3][4][5][6][7][8][9] 1166.7, C1 66.4, C1 66.2, C1 66.6, C166.9,C 166.4, C1 66.3,C 166.5, C166.3, C 2120 1;29.1;29.06,28.4;28.2;27.6;27.3;27.0;8 CH 2 27.9,CH 2 28.7;28.4;28.3;27.9;27.4;27.1;27.1;2 6.8;8 CH 2 24.6,C H 2 28.8;28.5;28.4;28.4;28.4;28.1;28.0;27.1;8 CH 2 28.9;28.6;28.5;28.4;28:0;27.7;27.7;27.4;27.2;27.1;10 CH 2 28.8;28.5;28.4;28.3;28.1;27.7;27.7;…”

Section: Isolation Of the Metabolitesunclassified

“…Besides the aforementionedantibacterial activity,m acrolides are utilized therapeutically for their immunosuppressive (FK506, rapamycin), antiparasitic (avermectin), antifungal (amphotericin B), and anticancer (epothilone) properties. [2] In the course of our ongoing search for novel fungal secondary metabolites, we identified Hypoxylon rickii (Hypoxylaceae) [3] as an exceptionally competent producer.P revious studies yieldedt he new botryane-, 14-noreremophilane-, abietane-, [4] silphiperfolene-, [5] and caryophyllane-type terpenoids [6] as well as new terphenyl representatives [7] from as ingle large scale fermentation. Recently investigation of remaining fractions led to the discoveryo fn ine new 20-, 22-, and 24-membered macrolides (1)(2)(3)(4)(5)(6)(7)(8)(9), which is the first discoveryo fl arger than 16-membered macrolides from fungi.…”

Section: Introductionmentioning

confidence: 99%

The Rickiols: 20‐, 22‐, and 24‐membered Macrolides from the Ascomycete Hypoxylon rickii

Surup

Kuhnert

Böhm

et al. 2018

Chemistry A European J

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In preceding studies the neotropical ascomycete Hypoxylon rickii turned out to be a prolific source of new secondary metabolites, considering that we had obtained terpenoids with five different scaffolds along with a series of terphenyls. From the mycelial extracts of a 70 L scale fermentation of this strain we additionally isolated nine new macrolides (1-9) by RP-HPLC. The planar structures were elucidated by NMR spectroscopy complemented by HR-ESIMS. The relative configurations were assigned by J-based configuration analyses and confirmed by Kishi's Universal Database. Subsequently, the absolute configurations were assigned by Mosher's method using the shift analysis of a tetra-MTPA derivative. For rickiol A (1) and E (5) we observed transesterification of 20-membered ring structures to 22-membered isomers rickiol A2 (6) and E2 (7), and to 24-membered isomers rickiol A3 (8) and rickiol E3 (9), respectively. Cytotoxic effects and moderate antibiotic activity against Gram-positive bacteria were observed for 1-8 and 1-6 and 8, respectively. The total synthesis of rickiol E3 (9) established easier access to these compounds.

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“…In particular, the mycobiota of tropical countries are widely unexplored and can still yield a plethora of novel chemical entities. In recent years, many novel compounds with, for example, antimicrobial (Helaly et al 2016, 2017, Richter et al 2016, Kuephadungphan et al 2017), cytotoxic (Surup et al 2017) and antioxidative (Kuhnert et al 2015) effects were isolated in the authors’ laboratory from tropical fungi. Furthermore, fungi represent a rich source of nematicidal compounds because they are both prey and natural antagonists of nematodes.…”

Section: Introductionmentioning

confidence: 99%

New nematicidal and antimicrobial secondary metabolites from a new species in the new genus, Pseudobambusicola thailandica

Rupcic¹,

Hernández-Restrepo²,

Crous³

et al. 2018

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During the course of a study on the functional biodiversity of the mycobiota inhabiting rainforests in Thailand, a fungal strain was isolated from a plant sample and shown to represent an undescribed species, as inferred from a combination of morphological and molecular phylogenetic methods. Molecular phylogenetic analyses, based on four DNA loci, revealed a phylogenetic tree with the newly generated sequences clustering in a separate branch, together with members of the Sulcatisporaceae (Pleosporales, Ascomycota). The Thai specimen morphologically resembled Neobambusicola strelitziae in having pycnidial conidiomata with phialidic conidiogenous cells that produce both fusoid-ellipsoid macroconidia and subcylindrical microconidia. However, the new fungus, for which the name Pseudobambusicola thailandica is proposed, differs from N. strelitziae in having conidiomata with well-defined necks, the presence of globose to subglobose thick-walled cells adjacent to conidiomata and the production of chlamydospores in culture. When cultures of P. thailandica, growing on water agar, were confronted with Caenorhabditis elegans nematodes, worms approaching the fungal mycelia were killed. This observation gave rise to a study of its secondary metabolites and six novel and two known compounds were isolated from submerged cultures of P. thailandica. The structures of metabolites 1–6, for which the trivial names thailanones A–F are proposed, were elucidated using a combination of spectral methods, including extensive 1 and 2D NMR analysis and high resolution mass spectrometry. Compounds 4 and 8 showed strong nematicidal and weak antifungal activity, whereas all other tested compounds showed moderate to weak nematicidal activity but no significant effects in the serial dilution assay against various fungi and bacteria. Compounds 1 and 8 also inhibited growth of the pathogenic basidiomycete Phellinus tremulae in a plate diffusion assay.

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Rickenyls A–E, antioxidative terphenyls from the fungus Hypoxylon rickii (Xylariaceae, Ascomycota)

Cited by 49 publications

References 39 publications

Skeletocutins M-Q, biologically active compounds from the fruiting bodies of the basidiomycete Skeletocutis sp. collected in Africa

Skeletocutins M-Q, biologically active compounds from the fruiting bodies of the basidiomycete Skeletocutis sp. collected in Africa

The Rickiols: 20‐, 22‐, and 24‐membered Macrolides from the Ascomycete Hypoxylon rickii

New nematicidal and antimicrobial secondary metabolites from a new species in the new genus, Pseudobambusicola thailandica

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