Molecules derived from the extremes of life: a decade later

Wilson, Zoe E.; Brimble, Margaret A.

doi:10.1039/d0np00021c

Cited by 29 publications

(20 citation statements)

References 241 publications

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“…are capable of genetically segregating organisms due to their physical properties. Evolutionary adaptations to these extreme environments have generated novel biosynthetic pathways in extremophiles, giving novel structures that may find use in treating diseases [2][3][4]. Dermacoccus abyssi MT 1.1 T (Figure 1) is a piezotolerant Actinomycete isolated in 2006 from a Mariana Trench sediment, collected at a 10,898 m depth from the Challenger Deep by the remotely operated submersible Kaiko in 1998 [5].…”

Section: Introductionmentioning

confidence: 99%

Dermacozine N, the First Natural Linear Pentacyclic Oxazinophenazine with UV–Vis Absorption Maxima in the Near Infrared Region, along with Dermacozines O and P Isolated from the Mariana Trench Sediment Strain Dermacoccus abyssi MT 1.1T

et al. 2021

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Three dermacozines, dermacozines N–P (1–3), were isolated from the piezotolerant Actinomycete strain Dermacoccus abyssi MT 1.1T, which was isolated from a Mariana Trench sediment in 2006. Herein, we report the elucidation of their structures using a combination of 1D/2D NMR, LC-HRESI-MSn, UV–Visible, and IR spectroscopy. Further confirmation of the structures was achieved through the analysis of data from density functional theory (DFT)–UV–Visible spectral calculations and statistical analysis such as two tailed t-test, linear regression-, and multiple linear regression analysis applied to either solely experimental or to experimental and calculated 13C-NMR chemical shift data. Dermacozine N (1) bears a novel linear pentacyclic phenoxazine framework that has never been reported as a natural product. Dermacozine O (2) is a constitutional isomer of the known dermacozine F while dermacozine P (3) is 8-benzoyl-6-carbamoylphenazine-1-carboxylic acid. Dermacozine N (1) is unique among phenoxazines due to its near infrared (NIR) absorption maxima, which would make this compound an excellent candidate for research in biosensing chemistry, photodynamic therapy (PDT), opto-electronic applications, and metabolic mapping at the cellular level. Furthermore, dermacozine N (1) possesses weak cytotoxic activity against melanoma (A2058) and hepatocellular carcinoma cells (HepG2) with IC50 values of 51 and 38 μM, respectively.

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Section: Introductionmentioning

confidence: 99%

Dermacozine N, the First Natural Linear Pentacyclic Oxazinophenazine with UV–Vis Absorption Maxima in the Near Infrared Region, along with Dermacozines O and P Isolated from the Mariana Trench Sediment Strain Dermacoccus abyssi MT 1.1T

et al. 2021

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“…The frequent re-isolation of known metabolites from fungi has turned the interest of natural products chemists to hitherto less investigated ecological niches such as arctic glaciers, deep-sea hydrothermal vents or hypersaline lakes (Wilson and Brimble, 2009;. Fungi that live at elevated temperature, acidic or alkaline pH, high pressure, high salt concentration and /or low nutrient concentrations are called extremophiles.…”

Section: Introduction Introduction Introduction Introductionmentioning

confidence: 99%

Secondary metabolites of a marine-derived Penicillium ochrochloron

et al. 2021

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Extremophilic fungi have received considerable attention recently as new promising sources of biologically active compounds with potential pharmaceutical applications. This study investigated the secondary metabolites of a marine-derived Penicillium ochrochloron isolated from underwater sea sand collected from the North Sea in St. Peter-Ording, Germany. Standard techniques were used for fungal isolation, taxonomic identification, fermentation, extraction, and isolation of fungal secondary metabolites. Chromatographic separation and spectroscopic analyses of the fungal secondary metabolites yielded eight compounds: talumarin A (1), aspergillumarin A (2), andrastin A (3), clavatol (4), 3-acetylphenol (5), methyl 2,5-dihydro-4-hydroxy-5-oxo-3-phenyl-2-furanpropanoate (6), emodin (7) and 2-chloroemodin (8). After co-cultivation with Bacillus subtilis, the fungus was induced to express (-)-striatisporolide A (9). Compound 1 was evaluated for antibacterial activity against Staphylococcus aureus, Acinetobacter baumannii, Mycobacterium smegmatis, and M. tuberculosis, as well as cytotoxicity against THP-1 cells. The compound, however, was not cytotoxic to THP-1 cells and had no antibacterial activity against the microorganisms tested. The compounds isolated from P. ochrochloron in this study are well-known compounds with a wide range of beneficial biological properties that can be explored for pharmaceutical, agricultural, or industrial applications. This study highlights the bioprospecting potential of marine fungi and confirms co-cultivation as a useful strategy for the discovery of new natural products.

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“…Diverse groups of microorganisms have been isolated in the polar regions, including bacteria, actinomycetes, and fungi, which can adapt to the extreme environments [2][3][4]. Nowadays, most of the identified and investigated polar microorganisms belong to the Antarctic regions [5][6][7][8][9][10][11][12]. In contrast, only a few Arctic-derived microorganisms have been isolated and screened for secondary metabolites [13].…”

Section: Introductionmentioning

confidence: 99%

Cylindromicin from Arctic-Derived Fungus Tolypocladium sp. SCSIO 40433

et al. 2021

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The fungus strain SCSIO 40433 was isolated from an Arctic-derived glacier sediment sample and characterized as Tolypocladium cylindrosporum. A new compound, cylindromicin (1), and seven known secondary metabolites (2–8) were isolated from this strain. The chemical structures of these compounds were elucidated by comprehensive spectroscopic analyses. Cylindromicin (1) featured a 3,4-dihydro-2H-pyran skeleton. The absolute configuration of compound 1 was assigned via interpretation of key Nuclear Overhauser Effect Spectroscopy (NOESY) correlations and Electronic Circular Dichroism (ECD) calculation. Cylindromicin (1) exhibited significant tyrosinase inhibition activity. This study highlights Polar fungi as a potential resource for new bioactive natural products.

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Molecules derived from the extremes of life: a decade later

Abstract: Extremophiles continue to capture attention. This update highlights the structures of novel molecules isolated from extremophilic and extreme-tolerant microorganisms in the last decade.

Cited by 29 publications

References 241 publications

Dermacozine N, the First Natural Linear Pentacyclic Oxazinophenazine with UV–Vis Absorption Maxima in the Near Infrared Region, along with Dermacozines O and P Isolated from the Mariana Trench Sediment Strain Dermacoccus abyssi MT 1.1T

Dermacozine N, the First Natural Linear Pentacyclic Oxazinophenazine with UV–Vis Absorption Maxima in the Near Infrared Region, along with Dermacozines O and P Isolated from the Mariana Trench Sediment Strain Dermacoccus abyssi MT 1.1T

Secondary metabolites of a marine-derived Penicillium ochrochloron

Cylindromicin from Arctic-Derived Fungus Tolypocladium sp. SCSIO 40433

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