Extraction and theoretical study on complexation of the strontium cation with antamanide

Makrlík, Emanuel; Vaňura, Petr; Böhm, Stanislav; Ruzza, Paolo

doi:10.1007/s10967-014-3098-x

Cited by 7 publications

(2 citation statements)

References 15 publications

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“…Antamanide is a cyclic decapeptide isolated from the lipophilic fraction of an extract of the green toadstool Amanite phalloides , able to form complexes of high stability with different metal ions [ 4 , 5 , 6 , 7 , 8 , 9 ]. In order to improve the hydrophilicity of this peptide, the Phe residue at either the six or nine positions was replaced with a Gly residue.…”

Section: Resultsmentioning

confidence: 99%

“…In the past years, we evaluated the chemical and biological activities of the cyclic decapeptide antamanide, firstly isolated from the lipophilic fraction of an extract of Amanite phalloides by the T. Wieland’s group in 1962 [ 3 ]. A characteristic of this peptide is its ability to form complexes of high stability with metal ions, including Na + , K + , Ca 2+ , Tl 3+ , and others [ 4 , 5 , 6 , 7 , 8 ]. A close correlation has been found between the ion binding properties and the selectivity for Na + over K + with its antitoxic activity against phallotoxins and the prevention of their accumulation in the liver cells [ 9 ].…”

Section: Introductionmentioning

confidence: 99%

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Antamanide Analogs as Potential Inhibitors of Tyrosinase

Honisch¹,

Gazziero²,

Dallocchio³

et al. 2022

IJMS

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The tyrosinase enzyme, which catalyzes the hydroxylation of monophenols and the oxidation of o-diphenols, is typically involved in the synthesis of the dark product melanin starting from the amino acid tyrosine. Contributing to the browning of plant and fruit tissues and to the hyperpigmentation of the skin, leading to melasma or age spots, the research of possible tyrosinase inhibitors has attracted much interest in agri-food, cosmetic, and medicinal industries. In this study, we analyzed the capability of antamanide, a mushroom bioactive cyclic decapeptide, and some of its glycine derivatives, compared to that of pseudostellarin A, a known tyrosinase inhibitor, to hinder tyrosinase activity by using a spectrophotometric method. Additionally, computational docking studies were performed in order to elucidate the interactions occurring with the tyrosinase catalytic site. Our results show that antamanide did not exert any inhibitory activity. On the contrary, the three glycine derivatives AG9, AG6, and AOG9, which differ from each other by the position of a glycine that substitutes phenylalanine in the parent molecule, improving water solubility and flexibility, showed tyrosinase inhibition by spectrophotometric assays. Analytical data were confirmed by computational studies.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Antamanide Analogs as Potential Inhibitors of Tyrosinase

Honisch¹,

Gazziero²,

Dallocchio³

et al. 2022

IJMS

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Contribution to the interaction of antamanide with the trivalent terbium cation

2014

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Complex of antamanide with the nitrate anion

Vaňura

Sýkora

Uhlíková

2023

J Incl Phenom Macrocycl Chem

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Anionic complex of antamanide with the nitrate anion has been proven by electrospray ionization mass spectrometry (ESI-MS) method. Further, applying quantum chemical DFT calculations, the most probable structure of this complex was derived. The nitrate anion is embedded in the molecule of antamanide and its oxygens atoms are bonded by seven bonds to the hydrogen atoms of the ligand. Finally, the interaction energy, E(int), of the antamanide-NO3− complex was calculated as E(int) = -175.9 kJ/mol.

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Extraction and theoretical study on complexation of the strontium cation with antamanide

Cited by 7 publications

References 15 publications

Antamanide Analogs as Potential Inhibitors of Tyrosinase

Antamanide Analogs as Potential Inhibitors of Tyrosinase

Contribution to the interaction of antamanide with the trivalent terbium cation

Complex of antamanide with the nitrate anion

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