Profiling and quantification of biogenic amines in wine by constant B2E linked scan mass spectrometry

Walther, Hansjörg; Schlunegger, U. P.; Friedli, Felix

doi:10.1002/bms.1200140506

Cited by 10 publications

(3 citation statements)

References 9 publications

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“…MSMS was performed in the positive as well as negative ion mode. In the positive FAB mode, major fragment ions for Dns-Gro-Cys at m/z 170 and 171 due to the (dimethylamino)naphthalene group were observed (Addeo et al, 1975;Walther et al, 1987) (our data not shown). The dansylated compounds gave stronger quasimolecular signal intensities in the negative ion mode, and this is exemplified by the negative ion FAB-MS of Dns-Gro-Cys shown in Figure 4.…”

Section: Resultsmentioning

confidence: 68%

Identification ofS-(2,3-Dihydroxypropyl)cystein in a Macrophage-Activating Lipopeptide fromMycoplasma fermentans

1996

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Mycoplasmas are capable of stimulating monocytes and macrophages to release cytokines, prostaglandins, and nitric oxide. The aim of this study was to characterize the chemical nature of the previously isolated [Mühlradt, P. F., & Frisch, M. (1994) Infect. Immun. 62, 3801-3807] macrophage-stimulating material "MDHM" from Mycoplasma fermentans. Mycoplasmas were delipidated, and MDHM activity was extracted with octyl glucoside and further purified by reversed-phase HPLC. Macrophage-stimulating activity was monitored by nitric oxide release from peritoneal macrophages from C3H/HeJ endotoxin low responder mice. HPLC-purified MDHM was rechromatographed on an analytic scale RP 18 column before and after proteinase K treatment. Proteinase treatment did not diminish biological activity but shifted MDHM elution toward higher lipophilicity, suggesting that the macrophage-stimulating activity might reside in the lipopeptide moiety of a lipoprotein. Proteinase K-treated MDHM was hydrolyzed, amino groups were dansylated, and the dansylated material was isolated by HPLC. Dansylated S-(2,3-dihydroxypropyl)cystein (glycerylcystein thioether), typical for Braun's murein lipoprotein, and Dns-Gly and Dns-Thr were identified by tandem mass spectrometry. These amino acids were isolated from biologically active but not from the neighboring inactive HPLC fractions. IR spectra from proteinase K-treated, HPLC-purified MDHM and those from the synthetic lipopeptide [2,3-bis(palmitoyloxy)-(2-RS)-propyl]-N-palmitoyl-(R)-CysSerSer AsnAla were very similar. The data, taken together, indicate that lipoproteins of a nature previously detected in eubacteria are expressed in M. fermentans and that at least one of these lipoproteins and a lipopeptide derived from it constitute the macrophage-activating principle MDHM from these mycoplasmas.

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Section: Resultsmentioning

confidence: 68%

Identification ofS-(2,3-Dihydroxypropyl)cystein in a Macrophage-Activating Lipopeptide fromMycoplasma fermentans

1996

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“…4A, insert). This peak is flanked by ions at m/z 169 and 171, which are described as being characteristic of dansylated amines (Walter et al 1987). In addition to this major peak, other peaks are observed at m/z 321, 304, 234, and 220.…”

Section: Structural Identification Of Putrescine As a Root Exudate Co...mentioning

confidence: 89%

Increased Uptake of Putrescine in the Rhizosphere Inhibits Competitive Root Colonization by Pseudomonas fluorescens Strain WCS365

Kuiper¹,

Bloemberg²,

Noreen³

et al. 2001

MPMI

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Sequence analysis of the chromosomal Tn5lacZ flanking regions of the Pseudomonas fluorescens WCS365 competitive root colonization mutant PCL1206 showed that the Tn5lacZ is inserted between genes homologous to bioA and potF. The latter gene is the first gene of the potF1F2GHI operon, which codes for a putrescine transport system in Escherichia coli. The position of the Tn5lacZ suggests an effect on the expression of the pot operon. A mutation in the potF1 gene as constructed in PCL1270, however, had no effect on competitive root colonization. The rate of uptake of [1,4-14C]putrescine by cells of mutant PCL1206 appeared to be increased, whereas cells of strain PCL1270 were strongly impaired in the uptake of putrescine. Dansylation of tomato root exudate and subsequent thin-layer chromatography showed the presence of a component with the same Rf value as dansyl-putrescine, which was identified as dansyl-putrescine by mass spectrometric analyses. Other polyamines such as spermine and spermidine were not detected in the root exudate. Growth of mutant strains, either alone or in competition with the wild type, was tested in media containing putrescine, spermine, or spermidine as the sole nitrogen source. The results show that mutant PCL1206 is strongly impaired in growth on putrescine and slightly impaired on spermine and spermidine. The presence of the polyamines had a similar effect on the growth rate of strain PCL1270 in the presence of putrescine but a less severe effect in the presence of spermine and spermidine. We conclude that an increased rate of putrescine uptake has a bacteriostatic effect on Pseudomonas spp. cells. We have shown that putrescine is an important tomato root exudate component and that root-colonizing pseudomonads must carefully regulate their rate of uptake because increased uptake causes a decreased growth rate and, therefore, a decreased competitive colonization ability.

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“…In a second type of experiment a product ion may be selected and all precursor ions determined. This approach allows the investigator to define homologous families or classes of compounds, e. g. terpenes in oil shale (63), biogenic amines in wine (64), and sulfated azo dyes in regulated products (65). In the third strategy, the two mass spectrometers are scanned in parallel to permit detection of all decompositions that proceed with elimination of neutral fragments of a predetermined mass.…”

Section: Scanning Strategiesmentioning

confidence: 99%

Tandem Mass Spectrometry: The Competitive Edge for Pharmacology

Fenselau¹

1992

Annu. Rev. Pharmacol. Toxicol.

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Profiling and quantification of biogenic amines in wine by constant B2E linked scan mass spectrometry

Cited by 10 publications

References 9 publications

Identification ofS-(2,3-Dihydroxypropyl)cystein in a Macrophage-Activating Lipopeptide fromMycoplasma fermentans

Identification ofS-(2,3-Dihydroxypropyl)cystein in a Macrophage-Activating Lipopeptide fromMycoplasma fermentans

Increased Uptake of Putrescine in the Rhizosphere Inhibits Competitive Root Colonization by Pseudomonas fluorescens Strain WCS365

Tandem Mass Spectrometry: The Competitive Edge for Pharmacology

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