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Synthesis and Herbicidal Activity of New Hydrazide and Hydrazonoyl Derivatives.

Šeršeň F, Gregáň F, Peško M, Dvoranová D, Kráľová K, Matkovičová Z, Gregáň J, Donovalová J - Molecules (2015)

Bottom Line: IC50 values of these compounds varied in wide range, from a strong to no inhibitory effect.EPR spectroscopy showed that the active compounds interfered with intermediates Z•/D•, which are localized on the donor side of photosystem II.Fluorescence spectroscopy suggested that the mechanism of inhibitory action of the prepared compounds possibly involves interactions with aromatic amino acids present in photosynthetic proteins.

View Article: PubMed Central - PubMed

Affiliation: Institute of Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Bratislava 842 15, Slovakia. sersen@fns.uniba.sk.

ABSTRACT
Three new hydrazide and five new hydrazonoyl derivatives were synthesized. The chemical structures of these compounds were confirmed by 1H-NMR, IR spectroscopy and elemental analysis. The prepared compounds were tested for their activity to inhibit photosynthetic electron transport in spinach chloroplasts and growth of the green algae Chlorella vulgaris. IC50 values of these compounds varied in wide range, from a strong to no inhibitory effect. EPR spectroscopy showed that the active compounds interfered with intermediates Z•/D•, which are localized on the donor side of photosystem II. Fluorescence spectroscopy suggested that the mechanism of inhibitory action of the prepared compounds possibly involves interactions with aromatic amino acids present in photosynthetic proteins.

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Fluorescence emission spectra of untreated spinach chloroplasts and those treated with 5 μmol/dm3 of studied compounds (from top to bottom: 4f—olive; 2c—red; 2a—blue; control sample—black; 3c—wine; 3e—green; 3b—magenta; 3d—violet; 2b—cyan).
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Figure 1: Fluorescence emission spectra of untreated spinach chloroplasts and those treated with 5 μmol/dm3 of studied compounds (from top to bottom: 4f—olive; 2c—red; 2a—blue; control sample—black; 3c—wine; 3e—green; 3b—magenta; 3d—violet; 2b—cyan).

Mentions: Next, we attempted to determine the site of act ion of the studied compounds by studying the emission spectra of chlorophyll in spinach chloroplasts treated with the studied compounds. The fluorescence spectra of spinach chloroplasts treated with compounds under study are presented in Figure 1. We identified the emission peak at 684 nm corresponding to Chla, located in the pigment protein complexes of the photosystem PSII and a shoulder at 739 nm which corresponds to fluorescence of Chla located in the pigment protein complexes of the PSI [50]. This experiment showed that the compounds which inhibited the PET in spinach chloroplasts quenched the fluorescence of chlorophyll molecules present in the pigment protein complexes of both photosystems. On the other hand, the compounds which did not inhibit PET (2a, 2c and 4f) increased the fluorescence of chlorophyll. This effect may be caused by defects in photoreduction of QA. A similar effect has been observed by Haveman et al. [29] on PSII particles treated with hydrazobenzene. Based on these findings, we can assume that the sites of action of the studied compounds are both photosynthetic centers PSI and PSII.


Synthesis and Herbicidal Activity of New Hydrazide and Hydrazonoyl Derivatives.

Šeršeň F, Gregáň F, Peško M, Dvoranová D, Kráľová K, Matkovičová Z, Gregáň J, Donovalová J - Molecules (2015)

Fluorescence emission spectra of untreated spinach chloroplasts and those treated with 5 μmol/dm3 of studied compounds (from top to bottom: 4f—olive; 2c—red; 2a—blue; control sample—black; 3c—wine; 3e—green; 3b—magenta; 3d—violet; 2b—cyan).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4759945&req=5

Figure 1: Fluorescence emission spectra of untreated spinach chloroplasts and those treated with 5 μmol/dm3 of studied compounds (from top to bottom: 4f—olive; 2c—red; 2a—blue; control sample—black; 3c—wine; 3e—green; 3b—magenta; 3d—violet; 2b—cyan).
Mentions: Next, we attempted to determine the site of act ion of the studied compounds by studying the emission spectra of chlorophyll in spinach chloroplasts treated with the studied compounds. The fluorescence spectra of spinach chloroplasts treated with compounds under study are presented in Figure 1. We identified the emission peak at 684 nm corresponding to Chla, located in the pigment protein complexes of the photosystem PSII and a shoulder at 739 nm which corresponds to fluorescence of Chla located in the pigment protein complexes of the PSI [50]. This experiment showed that the compounds which inhibited the PET in spinach chloroplasts quenched the fluorescence of chlorophyll molecules present in the pigment protein complexes of both photosystems. On the other hand, the compounds which did not inhibit PET (2a, 2c and 4f) increased the fluorescence of chlorophyll. This effect may be caused by defects in photoreduction of QA. A similar effect has been observed by Haveman et al. [29] on PSII particles treated with hydrazobenzene. Based on these findings, we can assume that the sites of action of the studied compounds are both photosynthetic centers PSI and PSII.

Bottom Line: IC50 values of these compounds varied in wide range, from a strong to no inhibitory effect.EPR spectroscopy showed that the active compounds interfered with intermediates Z•/D•, which are localized on the donor side of photosystem II.Fluorescence spectroscopy suggested that the mechanism of inhibitory action of the prepared compounds possibly involves interactions with aromatic amino acids present in photosynthetic proteins.

View Article: PubMed Central - PubMed

Affiliation: Institute of Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Bratislava 842 15, Slovakia. sersen@fns.uniba.sk.

ABSTRACT
Three new hydrazide and five new hydrazonoyl derivatives were synthesized. The chemical structures of these compounds were confirmed by 1H-NMR, IR spectroscopy and elemental analysis. The prepared compounds were tested for their activity to inhibit photosynthetic electron transport in spinach chloroplasts and growth of the green algae Chlorella vulgaris. IC50 values of these compounds varied in wide range, from a strong to no inhibitory effect. EPR spectroscopy showed that the active compounds interfered with intermediates Z•/D•, which are localized on the donor side of photosystem II. Fluorescence spectroscopy suggested that the mechanism of inhibitory action of the prepared compounds possibly involves interactions with aromatic amino acids present in photosynthetic proteins.

Show MeSH