Biological activity of serotonin conjugates from the seeds of Centaurea nigra

Kumarasamy, Yashodharan; Middleton, Moira; Reid, R.G.; Nahar, Lutfun; Sarker, Satyajit D.

doi:10.1016/s0367-326x(03)00144-8

Cited by 47 publications

(31 citation statements)

References 9 publications

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“…Serotonin derivatives may function as antibacterial compounds, antioxidants, suppressors of proinflammatory cytokine production, antitumor compounds, or inhibitors of ischemia-reperfusion (Kawashima et al, 1998;Nagatsu et al, 2000;Hotta et al, 2002;Kumarasamy et al, 2003), but little is known about how their activities are regulated.…”

Section: Discussionmentioning

confidence: 99%

“…Additionally, for the first time to our knowledge, we have shown that serotonin derivatives are synthesized in the root tissues of rice in parallel with the high SHT activity. Further work will focus on elucidating the possible functions of serotonin derivatives against pathogen attack (Kumarasamy et al, 2003;Tanaka et al, 2003), as well as the kinetic analysis of a putative rice N-acetyltransferase.…”

Section: Discussionmentioning

confidence: 99%

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

Jang

Ishihara²,

Back³

2004

Plant Physiology

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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...

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

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

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“…[4,6] Members of Centaurea species were proposed to have antimicrobial, [5,[7][8][9][10] antifungal, [8,11] anti-inflammatory, [12] anti-ulcerogenic, [13] antioxidant, [14][15][16][17] antiplasmodial, [18] antiprotozoal, [8] antiviral [19] and cytotoxic [18,[20][21][22] activities. C. calcitrapa which grows up on northwestern Anatolia is used (2-6% infusion) as a fever reducer.…”

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confidence: 99%

Total Phenolic Contents, Antioxidant Activities Cytotoxicity of Three Centaurea Species: C. calcitrapa subsp. calcitrapa, C. ptosimopappa C. spicata

Erol-Dayi

Pekmez

Bona

et al. 2011

Free Radicals and Antioxidants

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Background: Many species of the genus Centaurea have been reported to be used in Anatolian folk medicine. In the present study, methanolic and aqueous extracts of three species of Centaurea L. (C. calcitrapa subsp. calcitrapa, C. ptosimopappa and C. spicata) have been assessed for antioxidant and cytotoxic activities. Materials and Methods: Antioxidant activity was investigated by DPPH and superoxide anion scavenging and anti-lipid peroxidation assays. Cytotoxic effect on HeLa and Vero cells were investigated by MTT assay. Results: Superoxide anion scavenging activities of aqueous extracts were higher than those of methanolic extracts, and the highest activity was detected in the aqueous extracts of C. calcitrapa subsp. calcitrapa with the IC 50 value of 25.91 µg/mL. The methanolic extract of C. ptosimopappa showed the strongest anti-lipid peroxidation activity. Total phenolic contents (mg gallic acid equivalent per gram) were ranged between 17.25 and 120.50 and the highest value was detected in aqueous extract of C. ptosimopappa. The highest cytotoxic activity was observed in the methanolic extract of C. calcitrapa subsp. calcitrapa on both cell lines with the IC 50 values of <100 µg/mL. Conclusions: According to the results of activity tests, the selected Centaurea species, especially C. calcitrapa subsp. calcitrapa can be regarded as a potential source of natural antioxidants in the prevention and treatment of diseases in which oxidants or free radicals are implicated.Key-words: Antioxidant activity; Centaurea; Cytotoxicity; Free radical scavenging.Key Messages: The selected Centaurea species showed an antioxidant activity and very low cytotoxic activity. Thus, Centaurea species might be a good candidate for further studies targeting the development of new antioxidants.

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“…Kumarasamy et al 3 found significant antimicrobial activity of serotonin conjugates from C. nigra against penicillin-resistant E. coli. However, little antimicrobial activity was observed against this bacterium in this study.…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, with the increasing acceptance of traditional medicine as an alternative way of health care, the screening of plants for active compounds has become very important. Many species of genus Centaurea L. (Asteraceae) have traditionally been used for the treatment of various ailments 3,4 . The genus Centaurea has been the subject of many antimicrobial and antioxidant activity properties [5][6][7][8][9][10][11][12][13][14][15][16][17] .…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial and Antioxidant Activities of Some Species of Centaurea Collected from Turkey

Uysal¹,

Çelik²,

Saglam³

et al. 2013

Asian J. Chem.

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The antimicrobial activity of the ethanol, acetone, ethyl acetate and chloroform extracts from Centaurea persica Boiss., C. polyclada DC. and C. consanguinea DC. (Asteraceae) were investigated by agar-well diffusion assay. All of the extracts exhibited an antimicrobial effect against most of the bacteria and all of the yeasts tested. The plant extracts were also screened for radical scavenging potential using a 1,1-diphenyl-2-picryl-hydrazyl (DPPH) in vitro model system for antioxidant activity. Ethyl acetate extracts showed the most significant inhibitory activity. Therefore, the minimal inhibitory concentration (MIC) of only ethyl acetate extracts of the samples was determined and C. consanguinea showed the highest antimicrobial effect. However, the ethanol extract of C. polyclada at 0.5 mg/mL concentration displayed the highest antioxidant activity. This activity was followed by ethanol extracts of. C. persica, ethyl acetate extracts of C. polclada, C. persica and C. consanguinea respectively.

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Biological activity of serotonin conjugates from the seeds of Centaurea nigra

Cited by 47 publications

References 9 publications

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

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

Total Phenolic Contents, Antioxidant Activities Cytotoxicity of Three Centaurea Species: C. calcitrapa subsp. calcitrapa, C. ptosimopappa C. spicata

Antimicrobial and Antioxidant Activities of Some Species of Centaurea Collected from Turkey

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