Antiproliferative, Antimicrobial and Antiviral Activity of β-Aryl-δ-iodo-γ-lactones, Their Effect on Cellular Oxidative Stress Markers and Biological Membranes

Włoch, Aleksandra; Stygar, Dominika; Bahri, Fouad; Bażanów, Barbara; Kuropka, Piotr; Chełmecka, Elżbieta; Pruchnik, Hanna; Gładkowski, Witold

doi:10.3390/biom10121594

Cited by 11 publications

(11 citation statements)

References 67 publications

(85 reference statements)

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“…For example, a synthetic α -amino- γ -lactone ketolide (Entry 19) showed excellent antibacterial activity against erythromycin-susceptible Streptococus pyogenes [ 45 ]. Additionally, hydrazonothiazolyl derivative (Entry 20) [ 46 ], β -cyclocitral derivative (Entry 21) [ 47 ], and α -methylene- γ -butyrolactone (Entry 22) [ 48 ] displayed potent antibacterial activities and a synthetic β -aryl- δ -iodo- γ -butyrolactone (Entry 23) exhibited bactericidal activity against Proteus mirabilis [ 49 , 50 ].…”

Section: Pharmacological Activities Of γ -Butyrmentioning

confidence: 99%

A Review of the Pharmacological Activities and Recent Synthetic Advances of γ-Butyrolactones

Hur

Jang

Sim

2021

IJMS

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γ-Butyrolactone, a five-membered lactone moiety, is one of the privileged structures of diverse natural products and biologically active small molecules. Because of their broad spectrum of biological and pharmacological activities, synthetic methods for γ-butyrolactones have received significant attention from synthetic and medicinal chemists for decades. Recently, new developments and improvements in traditional methods have been reported by considering synthetic efficiency, feasibility, and green chemistry. In this review, the pharmacological activities of natural and synthetic γ-butyrolactones are described, including their structures and bioassay methods. Mainly, we summarize recent advances, occurring during the past decade, in the construction of γ-butyrolactone classified based on the bond formation in γ-butyrolactone between (i) C5-O1 bond, (ii) C4-C5 and C2-O1 bonds, (iii) C3-C4 and C2-O1 bonds, (iv) C3-C4 and C5-O1 bonds, (v) C2-C3 and C2-O1 bonds, (vi) C3-C4 bond, and (vii) C2-O1 bond. In addition, the application to the total synthesis of natural products bearing γ-butyrolactone scaffolds is described.

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Section: Pharmacological Activities Of γ -Butyrmentioning

confidence: 99%

A Review of the Pharmacological Activities and Recent Synthetic Advances of γ-Butyrolactones

Hur

Jang

Sim

2021

IJMS

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“…The increase observed in the amount of hemolyzed cells in the presence of compounds ( 5 ) was negligible and did not exceed 3.4% (± 0.61) for 100 μM concentration. This means that the tested compounds are not toxic.The compounds are considered to be slightly toxic when they achieve hemolysis above 10%, toxic when hemolysis is above 50%, and highly toxic with hemolysis exceeding 90% 19 , 20 . These results are compatible with the hemolytic activity studies conducted by Cyboran et al for green tea supplement (GP), epigallocatechin-3-gallate (EGCG), and gallic acid (GA), measured after 1, 2 and 3 h of incubation 21 .…”

Section: Resultsmentioning

confidence: 99%

“…Amide I is located within the range of 1610–1695 cm –1 and amide II appears within the range of 1480–1575 cm −1 . Amide I and amide II is used for determining the type of protein secondary structure 20 , 36 . An analysis demonstrated that chalcone, flavanone, and flavones are able to shift the maximum of both amide I and amide II bands, e.g.…”

Section: Resultsmentioning

confidence: 99%

“…Detailed procedures for the preparation of RBCMs and PC are described in ealier. The procedure of sample preparation has been described in our previous papers 3 , 20 , 57 . Briefly, after to remove the water the spectrum of the control (RBCMs or liposomes) and tested samples (RBCMs or PC with tested compounds) at concentration 50 and 25 µM was taken.…”

Section: Methodsmentioning

confidence: 99%

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Interaction of 4′-methylflavonoids with biological membranes, liposomes, and human albumin

Włoch

Strugała

Pruchnik

et al. 2021

Sci Rep

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The aim of the study was to compare the impact of three synthesized chemical compounds from a group of methylated flavonoids, i.e. 2′-hydroxy-4-methylchalcone (3), 4′-methylflavanone (4), and 4′-methylflavone (5), on a red blood cell membranes (RBCMs), phosphatidylcholine model membranes (PC), and human serum albumin (HSA) in order to investigate their structure–activity relationships. In the first stage of the study, it was proved that all of the compounds tested do not cause hemolysis of red blood cells and, therefore, do not have a toxic effect. In biophysical studies, it was shown that flavonoids have an impact on the hydrophilic and hydrophobic regions of membranes (both RBCMs and PC) causing an increase in packing order of lipid heads and a decrease in fluidity, respectively. Whereas, on the one hand, the magnitude of these changes depends on the type of the compound tested, on the other hand, it also depends on the type of membrane. 4′-Methylflavanone and 4′-methylflavone are located mainly in the hydrophilic part of lipid membranes, while 2′-hydroxy-4-methylchalcone has a greater impact on the hydrophobic area. A fluorescence quenching study proved that compounds (3), (4) and (5) bind with HSA in a process of static quenching. The binding process is spontaneous whereas hydrogen bonding interactions and van der Waals forces play a major role in the interaction between the compounds and HSA.

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“…Sekine et al reported that the presence and difference of the isopropyl group in a ring of p -menthane monoterpenoids affected termite mortality [ 37 ]. Several studies have reported that the isopropyl group in the compound has biological effects, such as anti-mycobacterial [ 38 , 39 ], anti-amoebic [ 40 ], and anticancer [ 39 ] activities. Therefore, the isopropyl group arrangement is important for the pharmacological activity of the compounds.…”

Section: Discussionmentioning

confidence: 99%

Organic synthesis and anti-influenza A virus activity of cyclobakuchiols A, B, C, and D

et al. 2021

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Novel antiviral agents for influenza, which poses a substantial threat to humans, are required. Cyclobakuchiols A and B have been isolated from Psoralea glandulosa, and cyclobakuchiol C has been isolated from P. corylifolia. The structural differences between cyclobakuchiol A and C arise due to the oxidation state of isopropyl group, and these compounds can be derived from (+)-(S)-bakuchiol, a phenolic isoprenoid compound present in P. corylifolia seeds. We previously reported that bakuchiol induces enantiospecific anti-influenza A virus activity involving nuclear factor erythroid 2-related factor 2 (Nrf2) activation. However, it remains unclear whether cyclobakuchiols A–C induce anti-influenza A virus activity. In this study, cyclobakuchiols A, B, and C along with cyclobakuchiol D, a new artificial compound derived from cyclobakuchiol B, were synthesized and examined for their anti-influenza A virus activities using Madin-Darby canine kidney cells. As a result, cyclobakuchiols A–D were found to inhibit influenza A viral infection, growth, and the reduction of expression of viral mRNAs and proteins in influenza A virus-infected cells. Additionally, these compounds markedly reduced the mRNA expression of the host cell influenza A virus-induced immune response genes, interferon-β and myxovirus-resistant protein 1. In addition, cyclobakuchiols A–D upregulated the mRNA levels of NAD(P)H quinone oxidoreductase 1, an Nrf2-induced gene, in influenza A virus-infected cells. Notably, cyclobakuchiols A, B, and C, but not D, induced the Nrf2 activation pathway. These findings demonstrate that cyclobakuchiols have anti-influenza viral activity involving host cell oxidative stress response. In addition, our results suggest that the suitably spatial configuration between oxidized isopropyl group and phenol moiety in the structure of cyclobakuchiols is required for their effect.

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Antiproliferative, Antimicrobial and Antiviral Activity of β-Aryl-δ-iodo-γ-lactones, Their Effect on Cellular Oxidative Stress Markers and Biological Membranes

Cited by 11 publications

References 67 publications

A Review of the Pharmacological Activities and Recent Synthetic Advances of γ-Butyrolactones

A Review of the Pharmacological Activities and Recent Synthetic Advances of γ-Butyrolactones

Interaction of 4′-methylflavonoids with biological membranes, liposomes, and human albumin

Organic synthesis and anti-influenza A virus activity of cyclobakuchiols A, B, C, and D

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