Terretonin M: A new meroterpenoid from the thermophilic <i>Aspergillus terreus</i> TM8 and revision of the absolute configuration of penisimplicins

Shaaban, Mohamed; El-Metwally, Mohammad Magdy; Laatsch, Hartmut

doi:10.1080/14786419.2017.1419230

Cited by 27 publications

(25 citation statements)

References 33 publications

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“…Later, new terpenoid, terretonin O (442), was isolated from thermophilic Aspergillus terreus TM8 and marine Aspergillus terreus LGO13 [287]. Presumably, compound (442) is a biosynthetic precursor of the recently isolated terretonins M (441) [288] and N (443) [289]. These compounds are oxidized at the C-11 position, which is not typical BARANOVA et al A new ergostan, sarocladione (444), is the first steroid that contains the unique 5,10:8,9-diketo motif.…”

Section: Terpenoids Steroids and Related Compoundsmentioning

confidence: 99%

Antibiotics from Extremophilic Micromycetes

et al. 2020

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Extremophilic microorganisms, which are capable of functioning normally at extremely high or low temperatures, pressure, and in other environmental conditions, have been in the focus of microbiologists’ attention for several decades due to the biotechnological potential of enzymes inherent in extremophiles. These enzymes (also called extremozymes) are used in the production of food and detergents and other industries. At the same time, the inhabitants of extreme econiches remained almost unexplored for a long time in terms of the chemistry of natural compounds. In recent years, the emergence of new antibiotic-resistant strains of pathogens, which affect humans and animals has become a global problem. The problem is compounded by a strong slowdown in the development of new antibiotics. In search of new active substances and scaffolds for medical chemistry, researchers turn to unexplored natural sources. In recent years, there has been a sharp increase in the number of studies on secondary metabolites produced by extremophiles. From the discovery of penicillin to the present day, micromycetes, along with actinobacteria, are one of the most productive sources of antibiotic compounds for medicine and agriculture. Many authors consider extremophilic micromycetes as a promising source of small molecules with an unusual mechanism of action or significant structural novelty. This review summarizes the latest (for 2018–2019) experimental data on antibiotic compounds, which are produced by extremophilic micromycetes with various types of adaptation. Active metabolites are classified by the type of structure and biosynthetic origin. The data on the biological activity of the isolated metabolites are summarized.

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Section: Terpenoids Steroids and Related Compoundsmentioning

confidence: 99%

Antibiotics from Extremophilic Micromycetes

et al. 2020

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“…The soil-derived thermophilic fungal strain Aspergillus terreus TM8 collected from a hot desert place (~50 °C) in South Egypt produced a new highly oxygenated tetracyclic meroterpenoid, terretonin M ( 245 ) ( Figure 43 ). The crude extract of the mass mycelium and solid rice meida could slightly inhibit the growth of Proteus sp., Candida albicans, and Streptococcus pyogenes , while authors failed to isolate the active ingredient [ 80 ].…”

Section: Thermophilic Fungimentioning

confidence: 99%

Novel Natural Products from Extremophilic Fungi

Zhang

et al. 2018

Marine Drugs

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“…In the course of this work, two interesting compounds, terretonin N (1) [ 10 ] and butyrolactone I (2) [ 11 ], obtained recently from our investigation into thermophilic fungus Aspergillus terreus TM8 [ 12 ], were examined as anticancer agents against prostate adenocarcinoma (PC-3) and ovary adenocarcinoma (SKOV3) human cell lines. The chemical structures of the two compounds were fully identified and characterized in our recently published data [ 11 , 12 , 13 ]. In addition, our team reported the full taxonomy of the producing thermophilic Aspergillus terreus TM8 previously [ 10 , 11 , 12 , 13 ].…”

Section: Introductionmentioning

confidence: 99%

“…The chemical structures of the two compounds were fully identified and characterized in our recently published data [ 11 , 12 , 13 ]. In addition, our team reported the full taxonomy of the producing thermophilic Aspergillus terreus TM8 previously [ 10 , 11 , 12 , 13 ]. The structure of the isolated metabolites, shown in Figure 1 , were assigned by comparison of their 1D and 2D NMR spectroscopy and ESI HR mass measurements with our recently published data [ 10 , 11 , 12 , 13 ].…”

Section: Introductionmentioning

confidence: 99%

Production of Terretonin N and Butyrolactone I by Thermophilic Aspergillus terreus TM8 Promoted Apoptosis and Cell Death in Human Prostate and Ovarian Cancer Cells

et al. 2021

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The anticancer activity of terretonin N (1) and butyrolactone I (2), obtained from the thermophilic fungus Aspergillus terreus TM8, was intensively studied against prostate adenocarcinoma (PC-3) and ovary adenocarcinoma (SKOV3) human cell lines. According to this study, both compounds showed potent cytotoxicity towards ovarian adenocarcinoma cells (SKOV3) with IC50 1.2 and 0.6 μg/mL, respectively. With respect to metastatic prostate cells (PC-3), the two compounds 1 and 2 showed a significantly promising cytotoxicity effect with IC50 of 7.4 and 4.5 μg/mL, respectively. The tested fungal metabolites showed higher rates of early and late apoptosis with little or no necrotic apoptotic pathway in all treated prostate adenocarcinoma (PC-3) and ovary adenocarcinoma (SKOV3) human cell lines, respectively. The results reported in this study confirmed the promising biological properties of terretonin N (1) and butyrolactone I (2) as anticancer agents via the induction of cellular apoptosis. However, further studies are needed to elucidate the molecular mechanism by which cellular apoptosis is induced in cancer cells.

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Terretonin M: A new meroterpenoid from the thermophilic Aspergillus terreus TM8 and revision of the absolute configuration of penisimplicins

Cited by 27 publications

References 33 publications

Antibiotics from Extremophilic Micromycetes

Antibiotics from Extremophilic Micromycetes

Novel Natural Products from Extremophilic Fungi

Production of Terretonin N and Butyrolactone I by Thermophilic Aspergillus terreus TM8 Promoted Apoptosis and Cell Death in Human Prostate and Ovarian Cancer Cells

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