Nostotrebin 6, a bis(cyclopentenedione) with cholinesterase inhibitory activity isolated from <i>Nostoc</i> sp. str. Lukešová 27/97

Zelík, Petr; Lukešová, Alena; Čejka, Jan; Budêšínský, Miloś; Havlı́ček, Vladimı́r; Cegan, Alexander; Kopeckỳ, J.

doi:10.3109/14756360903213481

Cited by 12 publications

(29 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…2,2′-bis [4,5-bis(4-hydroxybenzyl)-2-(4-hydroxyphenyl)cyclopent-4-ene-1,3-dione], is a secondary phenolic metabolite produced by cyanobacterium Nostoc sp. strain Lukešová 27/ 97 [16], see Fig. 1.…”

Section: Introductionmentioning

confidence: 97%

“…1. Nostotrebin 6 is an effective inhibitor of acetylcholinesterase and butyrylcholinesterase [16], and its cytotoxic and pro-apoptotic properties have been previously reported [15]. Nostotrebin 6 has been obtained from the cyanobacterial biomass by using conventional separation methods, including solid-phase extraction and two HPLC steps [16].…”

Section: Introductionmentioning

confidence: 98%

“…The synthesis of novel CPDs is often devoted to modification of natural CPDs resulting in structure-activity relationship (SAR) studies and subsequent discoveries of novel bioactives with applicability in chemical technologies, biotechnology and biomedicine fields. Among well studied CPD representatives are lucidone and linderone with anti-inflammatory activities [2][3][4][5], cytostatic compound TX-1123 [6], involutone constituent of fungi Paxillus involutus [7][8][9], madindolines [10][11][12][13] and nostotrebin 6 [14][15][16] attributed to enzyme inhibitory effects. The novel synthetic approaches are primarily focused on total synthesis of above-mentioned CPDs and also on strategies for development of structurally simplified CPDs with biological, especially antibacterial and antifungal activities.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Dimeric cyanobacterial cyclopent-4-ene-1,3-dione as selective inhibitor of Gram-positive bacteria growth: Bio-production approach and preparative isolation by HPCCC

et al. 2016

Self Cite

View full text Add to dashboard Cite

a b s t r a c tThe need for new antimicrobial agents is greater than ever because of the emergence of multidrug resistance in common pathogens and incidence of new infections. Cyclopent-4-ene-1,3-diones (CPDs) have been reported as a new class of compounds with promising antimicrobial and antifungal properties. Herein we report the selective antibiotic properties of nostotrebin 6, a phenolic CPD produced biotechnologically by the culture of cyanobacterium Nostoc sp. str. Lukešová 27/97. High performance countercurrent chromatography (HPCCC) combined with gel permeation chromatography (GPC) was used for the isolation of nostotrebin 6 with a relatively high 0.53 ± 0.1% yield (calculated from dried biomass) and final purity higher than 96%. Nostotrebin 6 was tested for its antimicrobial and antifungal activities by using standard micro-dilution method, and the results were expressed as minimal inhibitory concentrations (MICs). Nostotrebin 6 unequivocally inhibited the growth of Gram-positive reference (Enterococcus faecalis CCM 4224, Staphylococcus aureus CCM 4223 and Staphylococcus aureus CCM 3953) and multidrug-resistant (Staphylococcus haemolyticus A/16568, Staphylococcus aureus MRSA 4591 and Enterococcus faecium VanA 419/ana) strains. Its strongest effect was exerted against the Gram-positive bacteria with MICs ranging between 6.25 and 15.6 μg/mL. There was no effect on Gram-negative strains tested and yeasts. Our results suggest that nostotrebin 6 could serve as basic nucleus for further design of novel antibiotic agents and demonstrate that the bio-production approach based on HPCCC/GPC isolation endpoint is an efficient methodology for obtaining nostotrebin 6 in multi-gram scale. Furthermore, the presented isolation method can be easily up-scaled to process kilograms of the cyanobacterial biomass.

show abstract

Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Dimeric cyanobacterial cyclopent-4-ene-1,3-dione as selective inhibitor of Gram-positive bacteria growth: Bio-production approach and preparative isolation by HPCCC

et al. 2016

Self Cite

View full text Add to dashboard Cite

show abstract

“…Routine methods for evaluation of biological activity in extracts from microalgal biomass as well as culture media have been applied. Lately, new test systems to identify drug candidates were applied for cellbased primary screening of several hundred microalgae strains for antibacterial, antioxidant, fungicidal, allelopathic, antitumoral, wound-healing, and anti-inflammatory compounds as well as enzyme (proteases, acetylcholine esterase) activity inhibitors [21,28,46,59,80,85,89,90].…”

Section: Microalgal Photosynthesis and Biotechnology After 1989mentioning

confidence: 99%

“…Compounds isolated from the cyanobacterium Nostoc spp. were structurally characterized [14,90]. In the field of antioxidant activity a new rapidresolution separation method was developed [59].…”

Section: Microalgal Photosynthesis and Biotechnology After 1989mentioning

confidence: 99%

The development of microalgal biotechnology in the Czech Republic

Masojídek

Prášil

2010

J Ind Microbiol Biotechnol

View full text Add to dashboard Cite

Microscopic algae and cyanobacteria are excellent sources of numerous compounds, from raw biomass rich in proteins, oils, and antioxidants to valuable secondary metabolites with potential medical use. In the former Czechoslovakia, microalgal biotechnology developed rapidly in the 1960s with the main aim of providing industrial, high-yield sources of algal biomass. Unique cultivation techniques that are still in use were successfully developed and tested. Gradually, the focus changed from bulk production to more sophisticated use of microalgae, including production of bioactive compounds. Along the way, better understanding of the physiology and cell biology of productive microalgal strains was achieved. Currently, microalgae are in the focus again, mostly as possible sources of bioactive compounds and next-generation biofuels for the 21st century.

show abstract

Pharmacological Applications of Lucidone: A Naturally Occurring Cyclopentenedione

Kumar

Wang

2016

Medicinal Plants - Recent Advances in Research and Development

View full text Add to dashboard Cite

Nostotrebin 6, a bis(cyclopentenedione) with cholinesterase inhibitory activity isolated from Nostoc sp. str. Lukešová 27/97

Cited by 12 publications

References 17 publications

Dimeric cyanobacterial cyclopent-4-ene-1,3-dione as selective inhibitor of Gram-positive bacteria growth: Bio-production approach and preparative isolation by HPCCC

Dimeric cyanobacterial cyclopent-4-ene-1,3-dione as selective inhibitor of Gram-positive bacteria growth: Bio-production approach and preparative isolation by HPCCC

The development of microalgal biotechnology in the Czech Republic

Pharmacological Applications of Lucidone: A Naturally Occurring Cyclopentenedione

Contact Info

Product

Resources

About