Identification and synthesis of three cyclodidepsipeptides as potential precursors of enniatin B in Fusarium sporotrichioides

Šmelcerović, Andrija; Yancheva, Denitsa; Cherneva, Emiliya; Petronijević, Živomir; Lamshoeft, Marc; Herebian, Diran

doi:10.1016/j.molstruc.2010.11.029

Cited by 17 publications

(25 citation statements)

References 27 publications

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“…Test compounds: The synthesis of the 2 cyclodidepsipeptides used in the study, 1 and 2, was performed via N-(α-bromoacyl)-α-amino acids, as described in our previous study [6].…”

Section: Methodsmentioning

confidence: 99%

“…This fungus was isolated from the stem of fresh Hypericum barbatum Jacq. [6]. The role of compounds 1 and 2 for the producing organism is questionable.…”

Section: Cyclodidepsipeptidesmentioning

confidence: 99%

“…The role of compounds 1 and 2 for the producing organism is questionable. For identification and confirmation, those compounds were synthesized and studied by density functional theory calculations and infrared spectroscopy [6]. Those two 6-(propan-2-yl)-4-methyl-morpholine-2,5-diones were recently evaluated for antimicrobial, immunomodulatory [7], and antioxidant [8] activity, inhibitory activity toward xanthine oxidase (XO) in vitro and XO in rat liver homogenate, as well as for antiinflamatory response on human peripheral blood mononuclear cells (PBMCs) [9].…”

Section: Cyclodidepsipeptidesmentioning

confidence: 99%

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Effects on MC3T3-E1 Cells and In Silico Toxicological Study of Two 6-(Propan-2-yl)-4-methyl-morpholine-2,5-diones

Vukelić-Nikolić

Kolarevć

Tomovic

et al. 2015

Natural Product Communications

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Recently, we found that two cyclodidepsipeptides, 3,6-di-(propan-2-yl)-4-methyl-morpholine-2,5-dione (1) and 3-(2-methylpropyl)-6-(propan-2-yl)-4-methylmorpholine-2,5-dione (2), are excellent inhibitors of xanthine oxidase. In order to obtain more information about the toxicological potential of compounds 1 and 2 on bone cells, the current study was designed to evaluate the effect of these compounds on viability and proliferation of MC3T3-E1 cells. Compound 1 showed neither cytotoxic nor stimulatory effect on cell viability, while compound 2 showed a slight stimulatory effect on cell viability. Both studied compounds showed slight stimulatory effects on proliferation of MC3T3-E1 cells, in a dose dependent manner. Additionally, an in silico toxicological study of compounds 1 and 2 was performed, and the results indicate that they have a good probability of safe biological intake.

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“…Test compounds: The synthesis of the 2 cyclodidepsipeptides used in the study, 1 and 2, was performed via N-(α-bromoacyl)-α-amino acids, as described in our previous study [6].…”

Section: Methodsmentioning

confidence: 99%

“…This fungus was isolated from the stem of fresh Hypericum barbatum Jacq. [6]. The role of compounds 1 and 2 for the producing organism is questionable.…”

Section: Cyclodidepsipeptidesmentioning

confidence: 99%

Section: Cyclodidepsipeptidesmentioning

confidence: 99%

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Effects on MC3T3-E1 Cells and In Silico Toxicological Study of Two 6-(Propan-2-yl)-4-methyl-morpholine-2,5-diones

Vukelić-Nikolić

Kolarevć

Tomovic

et al. 2015

Natural Product Communications

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“…[63], the immunomodulator metacytofilin was obtained from the fungus Metarhizium sp. TA2759 [64], the compound lateritin, isolated from Gibberella lateritium W. C. Snyder & H. N. Hansen in 1993, was recently revised to beauvericin by extensive NMR and MS analyses [65], the cyclodidepsipeptides isolated as a mixture from the fungus Fusarium sporotrichioides Sherb., were identified by comparison with the synthetic series, and their stereostructure was studied by quantum chemical calculations [66], and, finally, PF1233 B was isolated from Aspergillus niveus Blochwitz in 2003 as a novel inhibitor of voltage-dependent sodium channels, and reported again as a new natural product with P-glycoprotein (Pgp) inhibitor properties in 2014 [67][68][69].…”

Section: Other Activitiesmentioning

confidence: 99%

Insights in Fungal Bioprospecting in Mexico

et al. 2018

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Fungi have consistently been one of the richest sources of natural products, with unprecedented chemical scaffolds and potent biological activities. During the last 20 years, pharmacognosy researchers in Mexico, in collaboration with mycologists, have discovered many novel bioactive fungi natural products and new fungal species. To date, more than 100 bioactive secondary metabolites from 20 fungi from different ecosystems throughout Mexico have been documented in peer-reviewed literature according to Scopus and SciFinder databases. These include compounds from different biosynthetic origins and structural cores with the potential for the development of anticancer, antidiabetic, and/or pesticide agents.

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“…Valine (Val) was selected as the N-terminal amino acid for the preparation of N-(α-bromoacyl)-α-amino esters based on our previous studies on the biological activities of valine-containing cyclic didepsipeptides. [20][21][22]24,30 At the C-terminal end of the dipeptide, three amino esters with aliphatic (norvaline) and aromatic (phenylglycine and phenylalanine) side chains were positioned in order to exhibit different physico-chemical properties. Cytotoxicity, [31][32][33] anti-inflammatory 34 and antibacterial 35 activity are some of the most commonly investigated biological activities of new compounds and therefore one of the aims of the present study was to investigate the above-mentioned activities of three synthesized N-(α-bromoacyl)-α-amino esters.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structure and biological activity screening of novel N-(α-bromoacyl)-α-amino esters containing valyl moiety

Yancheva

Cherneva

Quick

et al. 2015

ACSi

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Three novel N-(α-bromoacyl)-α-amino esters: methyl 2-(2-bromo-3-methylbutanamido)pentanoate (1), methyl 2-(2-bromo-3-methylbutanamido)-2-phenylacetate (2) and methyl 2-(2-bromo-3-methylbutanamido)-3-phenylpropanoate (3) were synthesized. Single crystal X-ray diffraction data are reported for compounds 1 and 2. The cytotoxicity, antiinflammatory and antibacterial activity of compounds 1-3 were investigated. Additionally, the physico-chemical properties of studied compounds were calculated and an in silico toxicological study of compounds 1-3 was performed. The low level of cytotoxicity and absence of antibacterial and anti-inflammatory activity of 1-3 in tested concentrations might be a beneficial prerequisite for their incorporation in prodrugs.

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Identification and synthesis of three cyclodidepsipeptides as potential precursors of enniatin B in Fusarium sporotrichioides

Cited by 17 publications

References 27 publications

Effects on MC3T3-E1 Cells and In Silico Toxicological Study of Two 6-(Propan-2-yl)-4-methyl-morpholine-2,5-diones

Effects on MC3T3-E1 Cells and In Silico Toxicological Study of Two 6-(Propan-2-yl)-4-methyl-morpholine-2,5-diones

Insights in Fungal Bioprospecting in Mexico

Synthesis, crystal structure and biological activity screening of novel N-(α-bromoacyl)-α-amino esters containing valyl moiety

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