Putrescine, spermidine, spermine, and related polyamine alkaloids

Bienz, Stefan; Detterbeck, Richard; Ensch, Corinne; Guggisberg, Armin; Häusermann, Ursula A.; Meisterhans, Christian; Wendt, Barbara; Werner, Christa; Hesse, Manfred

doi:10.1016/s0099-9598(02)58003-2

Cited by 39 publications

(33 citation statements)

References 435 publications

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“…The detailed knowledge of acylpentamine fragmentation mechanisms is essential for the correct characterization of isomeric compounds, particularly for coeluting compounds within complex mixtures such as spider venoms. P olyamines and polyamine-containing alkaloids are widely found throughout the plant and animal kingdom [1,2]. Over the past decades, spider venoms, particularly their fractions containing acylpolyamine derivatives [1,3,4], have increasingly attracted the attention of scientists.…”

Section: Tandem Mass Spectrometric Investigation Of Acylpolyamines Ofmentioning

confidence: 99%

“…In reality, however, the CID spectra derived from the two quasi-molecular ions of synthetic IndAc4333 and IndAc3433 also showed signals at m/z 129 and 112, which should be indicative for a terminal PA34 or PA43 unit; [PA34 stands for a linear triamine with 3 and 4 methylene units (in this succession) between the terminal and internal N-atoms [2]. The nomenclature is also used for more extended polyamines.]…”

Section: Tandem Mass Spectrometric Investigation Of Acylpolyamines Ofmentioning

confidence: 99%

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Tandem mass spectrometric investigation of acylpolyamines of spider venoms and their ¹⁵N-labeled derivatives

Tzouros

Manov

Bienz

et al. 2004

J. Am. Soc. Mass Spectrom.

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The fragmentation mechanism of the acylpentamine toxins 1-4 found in the venom of the spider Agelenopsis aperta has been investigated in detail. To identify the origin of the two doublets of unexpected fragment ions at m/z 129/112 and m/z 115/98, three synthetic 15N-labeled analogs 5-7 have been prepared and subjected to CID fragmentation on a triple quadrupole mass spectrometer. It appears that the unexpected doublet of fragment ions arises from an internal portion of the polyamine backbone after either a transaminative Zip reaction or a sequential fragmentation of the quasi-molecular ion. The second option has been proven by in-source CID experiments. The detailed knowledge of acylpentamine fragmentation mechanisms is essential for the correct characterization of isomeric compounds, particularly for coeluting compounds within complex mixtures such as spider venoms.

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Section: Tandem Mass Spectrometric Investigation Of Acylpolyamines Ofmentioning

confidence: 99%

Section: Tandem Mass Spectrometric Investigation Of Acylpolyamines Ofmentioning

confidence: 99%

Tandem mass spectrometric investigation of acylpolyamines of spider venoms and their ¹⁵N-labeled derivatives

Tzouros

Manov

Bienz

et al. 2004

J. Am. Soc. Mass Spectrom.

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“…Polyamine alkaloids are widely distributed throughout the animal and plant kingdoms (as a review, see [1,2] ), and they exhibit a variety of important and interesting biological activities. [3] It is not surprising thus, that new and efficient methods for their synthesis as well as more sensitive and selective analytical methods for the identification and structural elucidation of new examples from natural sources are searched for.…”

Section: Introductionmentioning

confidence: 99%

Structure Elucidation of Polyamine Toxins in the Venom of the Spider Larinioides folium

Eichenberger¹,

Bigler²,

Bienz³

2007

Chimia

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The lyophilized venom of the spider Larinioides folium (Araneidae) was analyzed by highperformance liquid chromatography, coupled on-line to electrospray ionization mass spectrometry (HPLC-ESI-MS) and tandem mass spectrometry (HPLC-ESI-MS/MS), as well as UV-DAD analysis. In combination with amino acid analysis, high-resolution mass spectrometry and on-column H/D-exchange experiments, the structures of 41 new acylpolyamines contained in the complex venom of the spider L. folium were elucidated. Data interpretation in detail and the efficiency of this combined set of analytical method is exemplified by the structural elucidation of one of the toxins, namely of LF503a. Abstract: The lyophilized venom of the spider Larinioides folium (Araneidae) was analyzed by high-performance liquid chromatography, coupled on-line to electrospray ionization mass spectrometry (HPLC-ESI-MS) and tandem mass spectrometry (HPLC-ESI-MS/MS), as well as UV-DAD analysis. In combination with amino acid analysis, high-resolution mass spectrometry and on-column H/D-exchange experiments, the structures of 41 new acylpolyamines contained in the complex venom of the spider L. folium were elucidated. Data interpretation in detail and the efficiency of this combined set of analytical method is exemplified by the structural elucidation of one of the toxins, namely of LF503a.

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“…-Hydroxycinnamic acid amide (HCAA) derivatives are widely distributed in the plant kingdom in families as Asteraceae, Liliaceae, Rosaceae, Solanaceae, or Fabaceae [1]. Physiological and phytochemical studies on the flowering plants of these families have shown that HCAAs are mostly accumulated in the reproductive organs as pollen [2].…”

mentioning

confidence: 99%

“…They may also protect plants from viral, bacterial, or fungal infestations [9], and may be produced as phytoalexins [10]. Mono-, di-, and trisubstituted spermidines have been found as derivatives of hydroxycinnamic acids (p-coumaric, ferulic, caffeic, or sinapic acid) [1].…”

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confidence: 99%

N1,N5,N10-Tris(4-hydroxycinnamoyl)spermidines fromMicrodesmis keayana Roots

Zamblé

Şahpaz

Hennebelle

et al. 2006

C&B

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Three new N1,N5,N10-tris(4-hydroxycinnamoyl)spermidines were isolated from a methanolic root extract of Microdesmis keayana. They were identified as N5,N10-di(p-coumaroyl)-N1-feruloylspermidine,N5-(p-coumaroyl)-N1,N10-diferuloylspermidine, and N1,N5,N10-triferuloylspermidine, and were named keayanidines A, B, and C (1-3), respectively. Their structures were established by spectral techniques(electrospray mass spectrometry, one- and two-dimensional NMR). A 4',4'',4'''-trimethylated derivative was prepared by methylation of keayanidine C, and the same compound was synthesized fromspermidine and 3,4-dimethoxycinnamic acid to confirm the spectral attributions of the NMR data of the natural compounds. Radical-scavenging properties of all compounds were evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical spectrophotometric assay.

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Putrescine, spermidine, spermine, and related polyamine alkaloids

Cited by 39 publications

References 435 publications

Tandem mass spectrometric investigation of acylpolyamines of spider venoms and their ¹⁵N-labeled derivatives

Tandem mass spectrometric investigation of acylpolyamines of spider venoms and their ¹⁵N-labeled derivatives

Structure Elucidation of Polyamine Toxins in the Venom of the Spider Larinioides folium

N1,N5,N10-Tris(4-hydroxycinnamoyl)spermidines fromMicrodesmis keayana Roots

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Putrescine, spermidine, spermine, and related polyamine alkaloids

Cited by 39 publications

References 435 publications

Tandem mass spectrometric investigation of acylpolyamines of spider venoms and their 15N-labeled derivatives

Tandem mass spectrometric investigation of acylpolyamines of spider venoms and their 15N-labeled derivatives

Structure Elucidation of Polyamine Toxins in the Venom of the Spider Larinioides folium

N1,N5,N10-Tris(4-hydroxycinnamoyl)spermidines fromMicrodesmis keayana Roots

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Tandem mass spectrometric investigation of acylpolyamines of spider venoms and their ¹⁵N-labeled derivatives

Tandem mass spectrometric investigation of acylpolyamines of spider venoms and their ¹⁵N-labeled derivatives