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 c(1a) after 6-hours of elicitation and after 24 and 72-hours at concentration c(1b). However, increased production of silychristin, one of the compounds in the silymarin complex, was achieved after only 6-hours elicitation with c(1a) (2.95 x 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 c(2) (2.53 x 10(-3) mol/L) after 72 h of elicitation. The production of silychristin in this case was increased 12-times compared to control.

• MeSH
• flavonolignany analýza   biosyntéza   chemie   MeSH
• ostropestřec mariánský účinky léků   metabolismus   MeSH
• pyraziny chemie   farmakologie   MeSH
• quercetin analogy a deriváty   analýza   chemie   MeSH
• techniky tkáňových kultur metody   MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• flavonolignany MeSH
• pyraziny MeSH
• quercetin MeSH
• taxifolin MeSH Prohlížeč

The condensation of substituted pyrazine-2-carboxylic acid chlorides with ring-substituted anilines yielded five substituted pyrazine-2-carboxylic acid amides. Thesynthesis, and analytical, lipophilicity and biological data of the newly synthesizedcompounds are presented in this paper. The photosynthesis inhibition, antialgal activityand the effect of a series of pyrazine derivatives as abiotic elicitors on the accumulation offlavonoids in a callus culture of Ononis arvensis (L.) were investigated. The most activeinhibitor of the oxygen evolution rate in spinach chloroplasts was 6-chloro-pyrazine-2-carboxylic acid (3-iodo-4-methylphenyl)-amide (2, IC(50) = 51.0 micromol.L(-1)). The highestreduction of chlorophyll content in Chlorella vulgaris was found for 5-tert-butyl-N-(4-chloro-3-methylphenyl)-pyrazine-2-carboxamide (3, IC(50) = 44.0 micromol.L(-1)). The maximalflavonoid production (about 900%) was reached after a twelve-hour elicitation processwith 6-chloropyrazine-2-carboxylic acid (3-iodo-4-methylphenyl)-amide (2).

• MeSH
• acetamidy chemická syntéza   chemie   farmakologie   MeSH
• Chlorella vulgaris účinky léků   MeSH
• chlorofyl metabolismus   MeSH
• chloroplasty účinky léků   MeSH
• flavonoidy metabolismus   MeSH
• herbicidy chemická syntéza   chemie   farmakologie   MeSH
• kyslík MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• acetamide MeSH Prohlížeč
• acetamidy MeSH
• chlorofyl MeSH
• flavonoidy MeSH
• herbicidy MeSH
• kyslík MeSH