Abstract
Substituted pyrazinecarboxamides markedly influenced production of flavonolignans in Silybum marianum callus and suspension cultures. In this study the effect of two compounds, N-(3-iodo-4-methylphenyl)pyrazine-2-carboxamide (1) and N-(3-iodo-4-methylphenyl)-5-tert-butyl-pyrazine-2-carboxamide (2), as abiotic elicitors on flavono-lignan production in callus culture of S. marianum was investigated. Silymarin complex compounds have hepatoprotective, anticancer and also hypocholesterolemic activity. In vitro flavonolignan concentration in cells is very low and the elicitation is one of the methods to increase production. Elicitors were tested at three concentrations and at different culture times. In the case of elicitation with 1, the greatest increase of flavonolignan and taxifoline production was observed at concentration c1a after 6-hours of elicitation and after 24 and 72-hours at concentration c1b. However, increased production of silychristin, one of the compounds in the silymarin complex, was achieved after only 6-hours elicitation with c1a (2.95 × 10-4 mol/L). The content of silychristin was 2-times higher compared to the control sample. An increased production of silychristin was reached with compound 2 at the concentration c2 (2.53 × 10-3 mol/L) after 72 h of elicitation. The production of silychristin in this case was increased 12-times compared to control.
Highlights
Many polycyclic compounds of biological or industrial significance have the pyrazine ring in their structure
The detailed high-performance liquid chromatography (HPLC) analysis shows that in case of 6-hours’ elicitation with compound 1 at concentration c1a half of the detected content corresponded to taxifolin (0.04%), while the other half was the flavonolignan silychristin (0.04%), whereas after 24 and 72-hours of elicitation with concentration c1b almost the whole detected content was attributed to taxifolin
[12] There was testing the effect of two substituted amides of pyrazinecarboxylic acid and the results showed that they markedly influenced production of flavonolignans in an in vitro culture. [8]
Summary
Many polycyclic compounds of biological or industrial significance have the pyrazine ring in their structure. There is a high interest in these compounds due to the widespread occurrence of pyrazines in Nature, especially in the flavor compounds of many food systems, their effectiveness at very low concentrations, as well as the still increasing number of applications of synthetic pyrazines in the flavor, fragrance and pharmaceutical industries. Some ring substituted pyrazinecarboxamides, tested in vitro, showed high antimycobacterial activity. A simple pyrazine compound, 3-amino-6-chloropyrazine-6-carboxylic acid showed an anti auxin behavior [2,3]. The herbicidal and abiotic elicitation activity of novel pyrazine derivatives has been evaluated [2,4]. Substituted N-phenylpyrazine-2-carboxamides were already tested on callus culture Ononis arvensis L. All of them increased flavonoid production [5,6]
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