New eudesmane sesquiterpenes from the marine-derived fungus Penicillium thomii

Afiyatullov, Shamil Sh.; Leshchenko, Elena V.; Sobolevskaya, M. P.; Денисенко, В. А.; Киричук, Н. Н.; Khudyakova, Yuliya V.; Hoai, Trinh P. T.; Dmitrenok, Pavel S.; Menchinskaya, Ekaterina S.; Pislyagin, Еvgeny А.; Бердышев, Д. В.

doi:10.1016/j.phytol.2015.10.011

Cited by 20 publications

(12 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A BLAST search result indicated that the sequence is similar 100% to the sequence of A. flocculosus (compared with NRRL 5224). In order to search for bioactive secondary metabolites of the strain, the fungus was grown stationary at 22 °C for 21 days in 100 Erlenmeyer flasks (500 mL), each containing 20 g of rice, 20 mg of yeast extract, 10 mg of KH 2 PO 4 , and 40 mL of natural sea water [ 25 ].…”

Section: Methodsmentioning

confidence: 99%

Suppression of RANKL-Induced Osteoclastogenesis by the Metabolites from the Marine Fungus Aspergillus flocculosus Isolated from a Sponge Stylissa sp.

et al. 2018

View full text Add to dashboard Cite

A new α-pyrone merosesquiterpenoid possessing an angular tetracyclic carbon skeleton, ochraceopone F (1), and four known secondary metabolites, aspertetranone D (2), cycloechinulin (3), wasabidienone E (4), and mactanamide (5), were isolated from the marine fungus Aspergillus flocculosus derived from a sponge Stylissa sp. collected in Vietnam. The structures of Compounds 1–5 were elucidated by analysis of 1D and 2D NMR spectra and MS data. All the isolated compounds were evaluated for anti-proliferation activity and their suppression effects on receptor activator of nuclear factor κB ligand (RANKL)-induced osteoclast differentiation using tartate-resisant acid phosphatase (TRAP). Compounds 1–5 had no anti-proliferative effect on human cancer cell lines up to 30 μg/mL. Among these compounds, aspertetranone D (2) and wasabidienone E (4) exhibited weak osteoclast differentiation inhibitory activity at 10 μg/mL. However, mactanamide (5) showed a potent suppression effect of osteoclast differentiation without any evidence of cytotoxicity.

show abstract

Section: Methodsmentioning

confidence: 99%

Suppression of RANKL-Induced Osteoclastogenesis by the Metabolites from the Marine Fungus Aspergillus flocculosus Isolated from a Sponge Stylissa sp.

et al. 2018

View full text Add to dashboard Cite

show abstract

“…[201]; a oxygenated steroid derivative (186), isolated from the Vietnamese starfish Protoreaster nodosus [202]; a new spirobisnaphthalene rhytidenone C (187), isolated from an extract of a cultured fungal endophyte Rhytidhysteron sp. AS21B isolated from a Thailandese mangrove area [203]; a known terpenoid sarcocrassocolide E (188), isolated from a Taiwanese soft coral Sarcophyton crassocaule [204]; a new cembrane diterpenoid sinulacembranolide A (189), isolated from the Taiwanese soft coral Sinularia gaweli [205]; a new eudesmane-type sesquiterpene thomimarine B (190), isolated from the fungus Penicillium thomii KMM 4667 isolated from the Japanese sea grass Zostera marina [206]; and a novel diterpenoid tortuosene A (191), isolated from the Taiwanese soft coral Sarcophyton tortuosum [207].…”

Section: Anti-inflammatory Activitymentioning

confidence: 99%

“…As shown in Table 2 and Figure 2, in 2014-2015, the preclinical marine nervous system pharmacology of compounds (196)(197)(198)(199)(200)(201)(202)(203)(204)(205)(206)(207)(208)(209)(210)(211) described several mechanism of action: at the nicotinic acetylcholine receptor and potassium channels, with conopeptides, and in models of antinociception and neuroprotection.…”

Section: Marine Compounds Affecting the Nervous Systemmentioning

confidence: 99%

“…Furthermore, detailed signaling studies revealed the "activation of mitogen-activated protein kinase signaling pathway" [221]. Cassiano and colleagues, using chemical proteomics, noted that the terpenoid heteronemin (206), isolated from the marine sponge Hyrtios sp., targeted TDP-43, a major component of inclusions that characterize amyotrophic lateral sclerosis and front-temporal lobar degeneration, by lowering its affinity "towards nucleic acids", and thus becoming a "relevant chemical tool in the study of TDP-43 related processes" [222]. Shimizu and colleagues provided the "first report" that the pro-electrophilic sesquiterpene zonarol (211), isolated from the Japanese brown alga Dictyopteris undulata, provided neuroprotection by activating the nuclear factor (erythroid-derived-2)-like 2/antioxidant responsive element Nrf2/ARE pathway, inducing phase-2 enzymes and providing oxidative stress protection to cerebrocortical neurons in vitro, concluding that the compound "represents a lead compound for the treatment of chronic neurodegenerative diseases associated with oxidative stress" [228].…”

Section: Marine Compounds Affecting the Nervous Systemmentioning

confidence: 99%

See 1 more Smart Citation

Marine Pharmacology in 2014–2015: Marine Compounds with Antibacterial, Antidiabetic, Antifungal, Anti-Inflammatory, Antiprotozoal, Antituberculosis, Antiviral, and Anthelmintic Activities; Affecting the Immune and Nervous Systems, and Other Miscellaneous Mechanisms of Action

et al. 2019

View full text Add to dashboard Cite

The systematic review of the marine pharmacology literature from 2014 to 2015 was completed in a manner consistent with the 1998–2013 reviews of this series. Research in marine pharmacology during 2014–2015, which was reported by investigators in 43 countries, described novel findings on the preclinical pharmacology of 301 marine compounds. These observations included antibacterial, antifungal, antiprotozoal, antituberculosis, antiviral, and anthelmintic pharmacological activities for 133 marine natural products, 85 marine compounds with antidiabetic, and anti-inflammatory activities, as well as those that affected the immune and nervous system, and 83 marine compounds that displayed miscellaneous mechanisms of action, and may probably contribute to novel pharmacological classes upon further research. Thus, in 2014–2015, the preclinical marine natural product pharmacology pipeline provided novel pharmacology as well as new lead compounds for the clinical marine pharmaceutical pipeline, and thus continued to contribute to ongoing global research for alternative therapeutic approaches to many disease categories.

show abstract

“…Only a recent study by Kirichuk and Pivkin [13] reported the diversity of cultivable filamentous fungi associated with different parts of Z. marina collected in the Sea of Japan (Russia). A few filamentous fungi obtained from Z. marina leaves or rhizomes have been studied for isolation of their chemical constituents [14,15]. To our knowledge, no systematic study has been performed on the chemical profiles of cultivable mycobiota of Z. marina .…”

Section: Introductionmentioning

confidence: 99%

Rapid Metabolome and Bioactivity Profiling of Fungi Associated with the Leaf and Rhizosphere of the Baltic Seagrass Zostera marina

et al. 2019

View full text Add to dashboard Cite

Zostera marina (eelgrass) is a marine foundation species with key ecological roles in coastal habitats. Its bacterial microbiota has been well studied, but very little is known about its mycobiome. In this study, we have isolated and identified 13 fungal strains, dominated by Penicillium species (10 strains), from the leaf and the root rhizosphere of Baltic Z. marina. The organic extracts of the fungi that were cultured by an OSMAC (One-Strain–Many-Compounds) regime using five liquid culture media under both static and shaking conditions were investigated for their chemical and bioactivity profiles. All extracts showed strong anti-quorum sensing activity, and the majority of the Penicillium extracts displayed antimicrobial or anti-biofilm activity against Gram-negative environmental marine and human pathogens. HPLC-DAD-MS-based rapid metabolome analyses of the extracts indicated the high influence of culture conditions on the secondary metabolite (SM) profiles. Among 69 compounds detected in all Penicillium sp. extracts, 46 were successfully dereplicated. Analysis of SM relatedness in culture conditions by Hierarchical Cluster Analysis (HCA) revealed generally low similarity and showed a strong effect of medium selection on chemical profiles of Penicillium sp. This is the first study assessing both the metabolite and bioactivity profile of the fungi associated with Baltic eelgrass Z. marina.

show abstract

New eudesmane sesquiterpenes from the marine-derived fungus Penicillium thomii

Cited by 20 publications

References 15 publications

Suppression of RANKL-Induced Osteoclastogenesis by the Metabolites from the Marine Fungus Aspergillus flocculosus Isolated from a Sponge Stylissa sp.

Suppression of RANKL-Induced Osteoclastogenesis by the Metabolites from the Marine Fungus Aspergillus flocculosus Isolated from a Sponge Stylissa sp.

Marine Pharmacology in 2014–2015: Marine Compounds with Antibacterial, Antidiabetic, Antifungal, Anti-Inflammatory, Antiprotozoal, Antituberculosis, Antiviral, and Anthelmintic Activities; Affecting the Immune and Nervous Systems, and Other Miscellaneous Mechanisms of Action

Rapid Metabolome and Bioactivity Profiling of Fungi Associated with the Leaf and Rhizosphere of the Baltic Seagrass Zostera marina

Contact Info

Product

Resources

About