A new iridoid, verbascoside and derivatives with inhibitory activity against Taq DNA polymerase

Garro, Hugo Alejandro; García, Celina; Martı́n, Victor S.; Tonn, Carlos E.; Pungitore, Carlos Rodolfo

doi:10.1016/j.bmcl.2014.12.052

Cited by 15 publications

(9 citation statements)

References 16 publications

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“…The regioselective silylation of secondary saccharide alcohols can also be achieved either taking advantage of the inherent difference of reactivity among the hydroxy functions [24–32] or exploiting the activation effect of boron complexes [33]. …”

Section: Introductionmentioning

confidence: 99%

Orthogonal protection of saccharide polyols through solvent-free one-pot sequences based on regioselective silylations

Traboni¹,

Bedini²,

Iadonisi³

2016

Beilstein J. Org. Chem.

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tert-Butyldimethylsilyl (TBDMS) and tert-butyldiphenylsilyl (TBDPS) are alcohol protecting groups widely employed in organic synthesis in view of their compatibility with a wide range of conditions. Their regioselective installation on polyols generally requires lengthy reactions and the use of high boiling solvents. In the first part of this paper we demonstrate that regioselective silylation of sugar polyols can be conducted in short times with the requisite silyl chloride and a very limited excess of pyridine (2–3 equivalents). Under these conditions, that can be regarded as solvent-free conditions in view of the insolubility of the polyol substrates, the reactions are faster than in most examples reported in the literature, and can even be further accelerated with a catalytic amount of tetrabutylammonium bromide (TBAB). The strategy proved also useful for either the selective TBDMS protection of secondary alcohols or the fast per-O-trimethylsilylation of saccharide polyols. In the second part of the paper the scope of the silylation approach was significantly extended with the development of unprecedented “one-pot” and “solvent-free” sequences allowing the regioselective silylation/alkylation (or the reverse sequence) of saccharide polyols in short times. The developed methodologies represent a very useful and experimentally simple tool for the straightforward access to saccharide building-blocks useful in organic synthesis.

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Section: Introductionmentioning

confidence: 99%

Orthogonal protection of saccharide polyols through solvent-free one-pot sequences based on regioselective silylations

Traboni¹,

Bedini²,

Iadonisi³

2016

Beilstein J. Org. Chem.

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“…The reaction solution was diluted with methanol, then the reaction solution was dried by a rotary evaporator, and the reduction product of iridoid glycosides was obtained by silica gel column chromatography with dichloromethane and methanol. 13 4.2.5 Methyl(1S,4aS,7aS)-7-methyl-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl) oxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate (7). Yield, 40%; 1 H NMR (500 MHz, DMSO-d 6 ) d 7.46 (d, J = 1.0 Hz, 1H), 5.17 (d, J = 6.5 Hz, 1H), 5.05 (d, J = 5.3 Hz, 1H), 4.99 (d, J = 5.0 Hz, 1H), 4.95 (d, J = 5.4 Hz, 2H), 4.54 (d, J = 7.9 Hz, 2H), 4.49 (t, J = 5.7 Hz, 1H), 3.68-3.65 (m, 1H), 3.64 (s, 3H), 3.63 (d, J = 1.9 Hz, 1H), 3.42 (d, J = 5.7 Hz, 1H), 3.19-3.13 (m, 2H), 3.04 (dd, J = 15.9, 7.2, 3.7 Hz, 2H), 2.69-2.62 (m, 1H), 2.06-1.99 (m, 1H), 1.76 (s, 3H).…”

Section: Experimental Methodsmentioning

confidence: 99%

“…All reactions were performed in oven-dried glass ware and were monitored for completeness by thin-layer chromatography (TLC) using silica gel (visualized by UV light or developed by treatment with anisaldehyde stain or iodine stain). 1 H NMR and 13 C-NMR spectra were recorded on a Bruker AV-400 spectrometer at 500 and 125 MHz, in DMSO-d 6 , using DMSO-d 6 as the reference standard (2.50 ppm). Chemical shis are reported in ppm (d) relative to tetramethylsilane (TMS) as an internal standard.…”

Section: Reagents and Instrumentsmentioning

confidence: 99%

Study on the chemical reactivity difference of primary hydroxyl groups in iridoid glycosides

Kong,

Xu,

Zhu

et al. 2023

RSC Adv.

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“…As part of a programme to determine biological activities of natural products and derivatives (Pungitore 2008; Martin et al 2011; Garro et al 2015), 17 alkaloids previously reported were tested as biofilm forming inhibitors (Fig. 1) (Di Marco et al 2019).…”

Section: Methodsmentioning

confidence: 99%

Aporphinoid alkaloids inhibit biofilm formation of Yersinia enterocolitica isolated from sausages

Marco

Pungitore

Estrada

2020

J. Appl. Microbiol.

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Aims of the study The ability of Yersinia enterocolitica strains to form biofilms and the capacity of different alkaloids to inhibit biofilm formation were investigated. Methods and Results The capacity to form biofilm on polystyrene of 31 Y. enterocolitica strains was evaluated. Biofilm and quorum sensing (QS) inhibition of 17 alkaloids were assayed; furthermore, minimum biofilm inhibitory concentration (MBIC) was determined. The capacity to form biofilms among the examined strains seemed to be a strain‐related feature. The best biofilm inhibitors at 100 µmol l−1 were oliverine (1), guatterine (3), liriodenine (4), oliveridine (5) and pachypodanthine (6), which showed biofilm inhibition higher than 87%. Pachypodanthine (6) was the most effective compound with MBIC value of 12·5 µmol l−1 at subinhibitory concentration and also was able to inhibit QS system and reduce yenR expression at this concentration. Conclusion This is the first study to demonstrate that oliverine, liriodenine, and pachypodanthine are able to inhibit biofilm formation of Y. enterocolitica without critically disturbing its growing capacity. At MBIC, pachypodanthine inhibited biofilm formation and QS. Significance and Impact of the Study The use of aporphinoid alkaloids as biofilms inhibitory agents might potentially be useful to treat biofilm‐associated infections in the future.

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A new iridoid, verbascoside and derivatives with inhibitory activity against Taq DNA polymerase

Cited by 15 publications

References 16 publications

Orthogonal protection of saccharide polyols through solvent-free one-pot sequences based on regioselective silylations

Orthogonal protection of saccharide polyols through solvent-free one-pot sequences based on regioselective silylations

Study on the chemical reactivity difference of primary hydroxyl groups in iridoid glycosides

Aporphinoid alkaloids inhibit biofilm formation of Yersinia enterocolitica isolated from sausages

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