Studies on the Regulatory Role of trans-Cinnamic Acid on the Activity of the Phenylalanine Ammonia-Lyase (PAL) in Suspension Cultures of Daucus carota L.
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In vivo and in vitro experiments were performed in order to study the regulatory role of trans- cinnamic acid and its hydroxylated derivatives (p-coumaric acid, caffeic acid) on the deamination of phenylalanine catalyzed by PAL (EC 4.3.1.5). Trans-cinnamic acid inhibits growth and reduces the content of soluble proteins of anthocyanin-containing carrot cells grown in suspension. There is strong evidence from the polysomal patterns and from the effect of trans-cinnamic acid on protein synthesis in vitro that protein synthesis is inhibited. The kinetic data of PAL clearly demonstrate that trans-cinnamic acid inhibits the enzyme by a noncompetitive mechanism. On the contrary, ʟ-α-aminooxy-β-phenylpropionic acid (ʟ-AOPP), a competitive inhibitor of PAL, does not affect protein metabolism.Keywords:
Cinnamic acid
Phenylalanine ammonia-lyase
Daucus carota
PAL activity and the anthocyanin content in strawberry fruits harvested at various stages of development were investigated. Concomitant increases in PAL activity and anthocyanin production were found, suggesting that a rise in PAL activity may be required for a high rate of anthocyanin synthesis.
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Cinnamic acid
Phenylalanine ammonia-lyase
Chlorogenic Acid
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Several carboxylic, phosphonic, phosphinic, boronic and nitro analogues of ( £ )-cinnamic acid were synthesized. These and other compounds related to (E)-cinnamic acid were evaluated as potential inhibitors of both phenylalanine ammonia-lyase and of anthocyanin biosynthesis in buckwheat. The most potent inhibition was found for 3-phenylprop-2-ynoic acid (21), however its K i is comparable to K M . The molecular modelling of the interaction of (E)-cinnamic acid (1) and 21 with PAL model suggests some similarities in the binding mode of both compounds.
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Anthocyanin content and the activities of polyphenol oxidase (PPO), peroxidase (POD) and phenylalanine ammonia-lyase (PAL) and their relationships were determined in the leaves of six lettuce (Lactuca sativa L.) cultivars, exposed for 6 weeks to alternating three different day/night temperatures. Anthocyanin content was found to be highest at 20/13°C, followed by 25/20°C and 30/25°C, showing accumulation of anthocyanin at low temperatures. Activities of PPO and PAL were also found to be highest at low day/night temperatures, whereas the POD activity was decreased at low day/night temperatures. The most significant positive correlation existed between anthocyanin content and PPO activity (r2 = 0.71). The results suggest that various day/night temperature regimes affect anthocyanin content and the activities of PPO, POD and PAL in lettuce.
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`Wonderful' Pomegranates ( Punica granatum L.) were placed in jars ventilated continuously with air or air enriched with 10 or 20 kPa CO 2 at 10 °C for 6 weeks. Samples were taken initially and after 1, 2, 4, and 6 weeks, and postharvest quality attributes were measured. The arils of the pomegranates stored in air were deeper red than the initial controls and than those stored in CO 2 -enriched atmospheres. This increased color was associated with increased anthocyanin concentration. Arils from fruit stored in air enriched with 10 kPa CO 2 had a lower anthocyanin concentration than air-stored fruit, and atmospheres enriched with 20 kPa CO 2 had even lower levels, possibly from suppressed anthocyanin biosynthesis. Anthocyanin concentration correlated well with the activity of phenylalanine ammonia lyase but not with glucosyltransferase activity. Moderate CO 2 atmospheres (10 kPa) prolong the storage life and maintain quality of pomegranates, including adequate red color intensity of the arils.
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The conversion of trans-cinnamic acid to phenylalanine using phenylalanine ammonia lyase (PAL) was examined. The optimum concentration of trans-cinnamic acid for the reaction was observed at 100 mM in cells and at 20 mM in cell free extracts, respectively. The production of L-phenylalanine was increased in both experiments as the concentration of ammonia was increased up to 10 M. The optimal pHs for the maximal conversion of trans-cinnamic acid to L-phenylalanine were 9.5 and 9.0 in experiments carried out with cells and with cell free extracts, respectively.
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Naturally occurring cinnamic acid derivatives are ubiquitously distributed in the plant kingdom, and it has been proposed that their consumption contributes to the maintenance of human health. However, the molecular mechanisms underlying their health keeping effects remain unknown. In the present investigation, we evaluated the capacity of several cinnamic acid derivatives (trans-cinnamic, p-coumaric, caffeic and ferulic acids, as well as caffeic acid-methyl and -propyl esters) to protect cells from oxidative stress-induced DNA damage. It was observed that effective protection was based on the ability of each compound to (i) reach the intracellular space and (ii) chelate intracellular "labile" iron. These results support the notion that numerous lipophilic iron chelating compounds, present abundantly in plant-derived diet components, may protect cells in conditions of oxidative stress and in this way be important contributors toward maintenance of human health.
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Biotransformations of capsaicinoids such as capsaicin and 8-nordihydrocapsaicin and phenylpropanoids such as cinnamic acid, p-coumaric acid, caffeic acid, and ferulic acid have been investigated using cultured plant cells. Capsain and 8-nordihydrocapsaicin were converted into the corresponding glycosides which are three glycosides respectively using the cultured cells of Catharanthus roseus. In a time-course study under sterile conditions, the changes in amounts of their reaction products were determined. Furthermore phenypropanoid, such as cinnamic acid, p-coumaric acid, caffeic acid and ferulic acid have been biotransformed using the cultured cells of the Eucalyptus perriniana, and then cinnamic acid was converted into two glycosides. In addition, p-coumaric acid, caffeic acid and ferulic acid were converted into four, four and three glycosides respectively. Then in time-course study under sterile conditions, the change in amounts of their reaction products were determined. Finally it was found that the cultured plant cells have the ability to glycosylate the phenolic group of capsacinoids and phenylpropanoids regioselectively.
Cinnamic acid
Coumaric acid
Phenylpropanoid
Phenolic acid
p-Coumaric acid
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Cinnamic acid
Phenylalanine ammonia-lyase
Lyase
Aminooxyacetic acid
1-Aminocyclopropane-1-carboxylic acid
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Phenylpropanoid pathway 생성물질은 식물의 self-defense에 관계하며 이러한 물질들은 UV뿐 아니라 wounding, pathogen과 같은 environmental stress에 의해 생성되는 것으로 알려져 있다. 벼에서 PAL mRNA 는 UV 조사 후 12시간에서 48시간까지는 증가하였으나 48시간부터 60시간까지는 점점 줄어드는 경향을 보였다. 한편 PAL의 활성은 UV 조사 후 24시간에서 가장 높았지만 상처에 의해서는 PAL의 활성이 벼에서는 증가하지 않았다. 그러나 고추에서는 UV조사와 상처를 준 후 24시간과 10시간에서 각각 높은 활성을 나타내었다. 벼와 고추 모두 cinnamic acid 4-hydroxylase의 활성은 상처를 준 후 12시간에서 증가하였지만 UV 조사는 C4H 활성에 영향을 주지 않았다. 이러한 결과로 볼 때 벼와 고추에서는 UV 조사와 상처가 모두 PAL, C4H 효소활성에 영향을 주는 것으로 나타났다.
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Cinnamic acid
Phenylpropanoid
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