A New Nonpeptide Tachykinin NK1 Receptor Antagonist Isolated from the Plants of Compositae.

Yamamoto, Atsushi; Nakamura, Ko; Furukawa, K.; Konishi, Yoko; Ogino, Takashi; Higashiura, Kunihiko; Yago, Hisashi; Okamoto, Kaoru; Otsuka, Masanori

doi:10.1248/cpb.50.47

Cited by 41 publications

(42 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Its content varied widely between 0.075 -1.517 mg/g DW (Table I). Unlike in the work of Yamamoto et al (2002) no considerable amount of 1N,5N,10N-tris[3-(4-hydroxyphenyl)-2-propenoyl]-1,5,10,14-tetraazatetradecane (triscoumaroyl spermine) was found in fresh methanol extracts. However, tetracoumaroyl spermine was quiet unstable in the extract, and several degradation products appeared after longer storage.…”

Section: Resultscontrasting

confidence: 62%

“…Because tetracoumaroyl spermine is a new and promising natural medical compound (Yamamoto et al, 2002), possible factors affecting the tetracoumaroyl spermine accumulation were examined.…”

Section: Resultsmentioning

confidence: 99%

“…All analyses were performed with fresh extracts, because of the low stability of tetracoumaroyl spermine. Calibration was done with isolated tetracoumaroyl spermine using semipreparative HPLC with the compound identity verifi ed by 1 H NMR spectra (Yamamoto et al, 2002) measured on a 300 MHz Varian Mercury Plus NMR spectrometer (Palo Alto, CA, USA), at room temperature.…”

Section: Analyses Of Tetracoumaroyl Sperminementioning

confidence: 99%

“…Spermine hydroxycinnamoyl transferase links the CoA-activated carboxy group of a phenolic acid with a spermine amino group (Hedberg et al, 1996;Martin-Tanguy, 2001). Polyamine conjugates with phenolic compounds have been found in a wide range of plant species of several families such as Fabaceae, Asteraceae, Amaryllidaceae, and Araceae (Walters, 2003;Yamamoto et al, 2002;Youhnovski et al, 2001). They are the predominant phenolic compounds in the reproductive organs, pollen, and seeds, but have also been identifi ed in roots, stems, or leaves in small amounts (Edreva et al, 2007).…”

Section: Introductionmentioning

confidence: 99%

“…1) was discovered by Yamamoto et al (2002), who isolated it from chamomile tubular fl owers and pollen and found it in fl ower extracts of six species of Asteraceae. The identifi ed compound belongs to the group of conjugated polyamines that are non-peptide antagonists of tachykinin NK 1 receptors and have positive effects against depression and anxiety.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Accumulation of Tetracoumaroyl Spermine in Matricaria chamomilla during Floral Development and Nitrogen Deficiency

Eliašová

Poracká

Paľove-Balang

et al. 2012

Zeitschrift Für Naturforschung C

View full text Add to dashboard Cite

The new natural polyamine conjugate 1N,5N,10N,14N-tetracoumaroyl spermine (tetracoumaroyl spermine) recently isolated from chamomile (Matricaria chamomilla L.) flower heads is applicable for the treatment of several human disorders such as depression and anxiety. High variability in the level of tetracoumaroyl spermine is found in commercial tisanes. Accumulation of tetracoumaroyl spermine was tested during fl oral development, and nitrogen deficiency was chosen as its putative limiting environmental factor. It was observed that tetracoumaroyl spermine is present mainly in tubular flowers, reaching its maximal content during the 3rd phase of flowering when the corollae of tubular flowers start to open. The later observed decrease could result from a release of pollen that also contains a considerable amount of tetracoumaroyl spermine. It is likely that tetracoumaroyl spermine plays an important role in pollen development, and so, despite overall N-deficiency in the plants, tetracoumaroyl spermine is accumulated at the same or even higher rate than in the flowers of the N-sufficient control.

show abstract

Section: Resultscontrasting

confidence: 62%

“…Because tetracoumaroyl spermine is a new and promising natural medical compound (Yamamoto et al, 2002), possible factors affecting the tetracoumaroyl spermine accumulation were examined.…”

Section: Resultsmentioning

confidence: 99%

Section: Analyses Of Tetracoumaroyl Sperminementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Accumulation of Tetracoumaroyl Spermine in Matricaria chamomilla during Floral Development and Nitrogen Deficiency

Eliašová

Poracká

Paľove-Balang

et al. 2012

Zeitschrift Für Naturforschung C

View full text Add to dashboard Cite

show abstract

Totalsynthese von Albicidin – eine Leitstruktur aus Xanthomonas albilineans für potente antibakterielle Gyrase‐Inhibitoren

et al. 2014

View full text Add to dashboard Cite

Das Antibiotikum Albicidin wird von dem pflanzenpathogenen Bakterium Xanthomonas albilineans synthetisiert. Es zeigt eine bemerkenswerte Aktivität gegen Gram-positive und Gram-negative Mikroorganismen. Der Wildtypstamm wie auch der heterologe Expressionsstamm produziert Albicidin bislang in äußerst geringen Mengen, was die Untersuchung des biologischen Profils und die Ausarbeitung von Struktur-Aktivitäts-Beziehungen erschwert. Aus diesem Grund entwickelten wir eine konvergente Syntheseroute für Albicidin. Die unerwartet schwierige Knüpfung der Peptidbindungen zwischen aromatischen Aminosäuren konnte durch die Verwendung von Triphosgen als Kupplungsreagens ermçglicht werden. Die vorhergehende Strukturaufklärung und die außergewçhnliche antibakterielle Aktivität von Albicidin werden zudem durch die Totalsynthese bestätigt. Zudem ist es erstmals mçglich, Albicidin im Multigramm-Maßstab herzustellen, um das Potential einer kommerziellen Wirkstoffentwicklung eingehender zu untersuchen. Schema 1. Retrosyntheseschema von Albicidin (1 a) mit den strategisch gesetzten Schnittstellen (i) und (ii), die eine konvergente Totalsynthese aus den drei Fragmenten 2, 3 und 4, bestehend aus den einzelnen Bausteinen A-F, ermçglichen.

show abstract

Total Synthesis of Albicidin: A Lead Structure from Xanthomonas albilineans for Potent Antibacterial Gyrase Inhibitors

et al. 2014

View full text Add to dashboard Cite

The peptide antibiotic albicidin, which is synthesized by the plant pathogenic bacterium Xanthomonas albilineans, displays remarkable antibacterial activity against various Gram-positive and Gram-negative microorganisms. The low amounts of albicidin obtainable from the producing organism or through heterologous expression are limiting factors in providing sufficient material for bioactivity profiling and structure-activity studies. Therefore, we developed a convergent total synthesis route toward albicidin. The unexpectedly difficult formation of amide bonds between the aromatic amino acids was achieved through a triphosgene-mediated coupling strategy. The herein presented synthesis of albicidin confirms the previously determined chemical structure and underlines the extraordinary antibacterial activity of this compound. The synthetic protocol will provide multigram amounts of albicidin for further profiling of its drug properties.

show abstract

A New Nonpeptide Tachykinin NK1 Receptor Antagonist Isolated from the Plants of Compositae.

Abstract: Relative inhibitory activities of the eluted fractions on the contractile responses to SP (10 nM) and acetylcholine (ACh, 100 nM) of the guinea pig ileum are shown by black bars.

Cited by 41 publications

References 15 publications

Accumulation of Tetracoumaroyl Spermine in Matricaria chamomilla during Floral Development and Nitrogen Deficiency

Accumulation of Tetracoumaroyl Spermine in Matricaria chamomilla during Floral Development and Nitrogen Deficiency

Totalsynthese von Albicidin – eine Leitstruktur aus Xanthomonas albilineans für potente antibakterielle Gyrase‐Inhibitoren

Total Synthesis of Albicidin: A Lead Structure from Xanthomonas albilineans for Potent Antibacterial Gyrase Inhibitors

Contact Info

Product

Resources

About