High-performance liquid chromatographic analysis and separation of N-feruloylserotonin isomers

Pavlı́k, Milan; Laudová, Věra; Grüner, Karel; Vokáč, Karel; Harmatha, Juraj

doi:10.1016/s1570-0232(02)00018-1

Cited by 18 publications

(10 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…26,27 Important therapeutic compounds of L. carthamoides were shown in the first four fractions (A-D) by TLC. 19,21 The results showed a high arsenic content (57.4% of total content) in these fractions. The fractions (A-D) were also important for copper (38.9%) and lead (29.8%).…”

Section: Resultsmentioning

confidence: 90%

“…According to the IR spectrum there are ecdysteroids present: the band at 1653 cm −1 is typical of a ketone on the sixth carbon with a conjugated C C bond of 7-cholesten. The band at 1763 cm −1 belongs to a γ -lactone corresponding to lignans, 33 and bands at 1516 and 1512 cm −1 correspond to aromatic substances similar to four N-feruloylserotonin isomers 21 (Table 3). Oil seeds contain fatty acids and lipids, mainly phospholipids (e.g.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Separation of organic compounds binding trace elements in seeds of Leuzea carthamoides (Willd.) DC

Pavlı́ková

Pavlı́k

Vašíčková

et al. 2004

Applied Organom Chemis

Self Cite

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Separation of organic compounds binding trace elements in seeds of Leuzea carthamoides (Willd.) DC

Pavlı́ková

Pavlı́k

Vašíčková

et al. 2004

Applied Organom Chemis

Self Cite

View full text Add to dashboard Cite

show abstract

“…Using Leuzea seeds, we isolated a crystalline fraction containing N-feruloylserotonin isomers, which are phenylpropanoids conjugated with serotonin, and are structurally similar to melatonin (Harmatha et al, 2007). The structural features and quantitative composition of this fraction, which contains four isomeric compounds (geometric E and Z isomers of N-feruloylserotonin and N-iso-feruloylserotonin), have been fully characterized (Pavlík et al, 2002;Harmatha et al, 2007). This crystalline fraction, containing N-(E)-iso-feruloylserotonin as the major component, was used in our experiments.…”

Section: Introductionmentioning

confidence: 99%

The selective effect of N-feruloylserotonins isolated from Leuzea carthamoides on nociception and anxiety in rats

Yamamotová

Pometlová

Harmatha

et al. 2007

Journal of Ethnopharmacology

View full text Add to dashboard Cite

“…They have been reported to be antioxidants (Zhang et al, 1996) and to inhibit injury associated with ischemiareperfusion (Hotta et al, 2002). These serotonin derivatives have only been detected in certain families of plant seeds or in the twigs of the diseased bamboo (Pavlik et al, 2002;Tanaka et al, 2003), and the pathway for their biosynthesis has not been identified.…”

mentioning

confidence: 99%

Production of Coumaroylserotonin and Feruloylserotonin in Transgenic Rice Expressing Pepper Hydroxycinnamoyl-Coenzyme A:Serotonin N-(Hydroxycinnamoyl)transferase

Jang

Ishihara²,

Back³

2004

Plant Physiology

View full text Add to dashboard Cite

Transgenic rice (Oryza sativa) plants were engineered to express a N-(hydroxycinnamoyl)transferase from pepper (Capsicum annuum), which has been shown to have hydroxycinnamoyl-CoA:tyramine N-(hydroxycinnamoyl)transferase activity, a key enzyme in the synthesis of hydroxycinnamic acid amides, under the control of constitutive maize (Zea mays) ubiquitin promoter. The transgenic rice plants require foliar application of amines to support synthesis of hydroxycinnamic acid amides, suggestive of limiting amine substrates in rice shoots. In addition, when T 2 homozygous transgenic rice plants were grown in the presence of amines or phenolic acids, two novel compounds were exclusively identified in the leaves of the transgenic plants. These compounds eluted earlier than p-coumaroyltyramine and feruloyltyramine during HPLC chromatography and were identified as p-coumaroylserotonin and feruloylserotonin by liquid chromatography/mass spectrometry and other methods. To test whether the unpredicted production of serotonin derivatives is associated with the pepper N-(hydroxycinnamoyl)transferase, the substrate specificity of the pepper enzyme was analyzed again. Purified recombinant pepper N-(hydroxycinnamoyl)transferase exhibited a serotonin N-hydroxycinnamoyltransferase (SHT) activity, synthesized p-coumaroylserotonin and feruloylserotonin in vitro, and demonstrated a low K m for serotonin. SHT activity was inhibited by 10 to 50 mM tyramine. In addition, SHT activity was predominantly found in the root tissues of wild-type rice in parallel with the synthesis of serotonin derivatives, suggesting that serotonin derivatives are synthesized in the root of rice. This is the first report of SHT activity and the first demonstration, to our knowledge, that serotonin derivatives can be overproduced in vivo in transgenic rice plants that express serotonin N-(hydroxycinnamoyl)transferase.Hydroxycinnamic acid amides (HCAA) are thought to play a role in plant defense against pathogen attacks (Clarke, 1982;Hahlbrock and Scheel, 1989;Von Roepenack-Lahaye et al., 2003). Consistent with this idea, HCAA are synthesized in the cytosol and transported into the cell wall, where they undergo peroxidative polymerization (Negrel and Martin, 1984;Negrel and Jeandet, 1987;Negrel and Lherminier, 1987;Negrel et al., 1993). The accumulation of HCAA in the cell wall creates a resilient barrier against pathogens by reducing cell wall digestibility and/or by directly inhibiting the growth of fungal hyphae (Grandmaison et al., 1993). Accordingly, the synthesis of HCAA is induced in response to various stresses, including physical injury, pathogen infection, and elicitor treatment. These responses have been observed in Solanaceae plants such as potato (Solanum tuberosum), tobacco (Nicotiana tabacum), tomato (Lycopersicon esculentum), and grass plants such as maize (Zea mays;Clarke, 1982;Negrel and Martin, 1984;Miyagawa et al., 1998;Pearce et al., 1998;Ishihara et al., 2000).Hydroxycinnamoyl-CoA:tyramine N-(hydroxycinnamoyl)transferase (THT; EC 2.3.1.110) is...

show abstract

High-performance liquid chromatographic analysis and separation of N-feruloylserotonin isomers

Cited by 18 publications

References 13 publications

Separation of organic compounds binding trace elements in seeds of Leuzea carthamoides (Willd.) DC

Separation of organic compounds binding trace elements in seeds of Leuzea carthamoides (Willd.) DC

The selective effect of N-feruloylserotonins isolated from Leuzea carthamoides on nociception and anxiety in rats

Production of Coumaroylserotonin and Feruloylserotonin in Transgenic Rice Expressing Pepper Hydroxycinnamoyl-Coenzyme A:Serotonin N-(Hydroxycinnamoyl)transferase

Contact Info

Product

Resources

About