Quantitative analysis of trigonelline in some Annona species by proton NMR spectroscopy

Machado, Alan Rodrigues Teixeira; Lage, Gisele Avelar; Medeiros, Felipe da Silva; Filho, José Dias de Souza; Pimenta, Lúcia Pinheiro Santos

doi:10.1007/s13659-013-0051-6

Cited by 19 publications

(10 citation statements)

References 15 publications

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“…Signals at d H 8.08 ppm (1H, t, J = 7.37, H-5) and d H 8.84 ppm (2H, t, J = 8.8, H-4 and H-6) were detected. Additionally 1 H-13 C connectivities were determined based on HSQC assignments (Table 1) and values were consistent with those reported in the literature (Campo et al 2010;Machado et al 2013;Ö man et al 2014). This is the first report of trigonelline's presence in the genus Cymbopogon.…”

Section: Resultssupporting

confidence: 83%

NMR-based metabolomic analysis of wild, greenhouse, and in vitro regenerated shoots of Cymbopogon schoenanthus subsp. proximus with GC–MS assessment of proximadiol

Abdelsalam

Mahran

Chowdhury

et al. 2017

Physiol Mol Biol Plants

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subsp is a wild plant distributed in subtropical and east Africa extending from the north to the southern parts of Egypt. Widely used in folk medicine, it is the source of the diuretic sesquiterpene proximadiol. Nuclear magnetic resonance metabolomic analysis of polar extracts of shoots from wild, greenhouse, somatic embryos, and direct and indirect organogenic in vitro cultures was carried out. Metabolic profiling yielded 39 compounds, of which common metabolites were 15 (38.4%). Unique metabolites were trehalose (2.5%) in the wild plants, 2-hydroxylisobutyrate, galactarate and tyrosine (7.6%) in indirect organogenic shoots. Tartrate was found only in direct regenerated shoots (2.5%). Metabolites identified in greenhouse and embryogenic shoots showed no unique compounds. Multivariate analysis revealed significant differences between all tested shoots. 4-aminobutyrate, alanine, glutamine, glucose, fructose, and sucrose were the most significantly different metabolites. Proximadiol was identified and quantitatively measured from the non-polar extract of different types of shoots using gas chromatography and mass spectrometry (GC-MS). Concentrations ranged from 3.6 ± 0.03 to 198.6 ± 7.2 µg/100 mg dry weight in regenerated shoots from somatic embryogenesis and in wild plant shoots, respectively. Direct organogenesis yielded the highest in vitro concentration (20.3 ± 0.5 µg/100 mg dry weight). This study reported the metabolic profiling of polar extract and identified primary metabolites that are unique to the wild type and shoots regenerated from different in vitro cultures. Proximadiol was quantified and the in vitro culture system yielding the highest concentration relative to the wild plant was identified.

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Section: Resultssupporting

confidence: 83%

NMR-based metabolomic analysis of wild, greenhouse, and in vitro regenerated shoots of Cymbopogon schoenanthus subsp. proximus with GC–MS assessment of proximadiol

Abdelsalam

Mahran

Chowdhury

et al. 2017

Physiol Mol Biol Plants

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“…Compound Germanicol 10Lupeol 11Germanicol-3-acetate 133-O-Tigloyl-lupeol ( viously identified from the leaves and stems of A. sericifera [3], whereas virbutinol (21), trigonelline (22), conduritol F (23), and allantoin (26) were found in this plant for the first time. Representative 1 H NMR spectra of the leaf, stem, and fruit methanolic extracts are depicted in ▶ Fig.…”

Section: Metabolites From Methanolic Extractsmentioning

confidence: 85%

“…Flavonoid luteolin-7-glucoside (24) was also significantly increased in the leaves. The metabolic composition of fruits differed vastly from that of the stems and leaves, standing out for high concentrations of viburtinol (21), trigonelline (22), conduritol F (23), serotonin (25), choline (28), succinate (43), or fumarate (30).…”

Section: Metabolites From Methanolic Extractsmentioning

confidence: 99%

Identification of Bioactive Compounds in Polar and Nonpolar Extracts of Araujia sericifera

Palomino‐Schätzlein

Montaño

Escrig

et al. 2017

PMIO

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Araujia sericifera is a native perennial, climbing laticiferous shrub from South America that is currently naturalized in many other countries. Previous data describe promising properties for A. sericifera, but no systematic study of its bioactive compounds and possible medicinal applications has been conducted to date. In the present study, aerial parts of A. sericifera (leaves, stems, and fruits) were explored by combining GC-MS and NMR spectroscopy analysis for both nonpolar (hexane) and polar (methanol) extracts. The hexanic extracts contained high amounts of pentacyclic triterpenes including two new metabolites, 3-tigloyl germanicol (18) and 3-tigloyl lupeol (19). The methanolic extracts revealed the presence of luteolin-7-glucoside (24), trigonelline (22), and conduritol F (23) as the main constituents. A multivariate study of a meaningful number of extracts allowed us to determine the distribution of compounds inside the plant. A cytotoxic evaluation in vitro showed that both leaf and fruit hexanic extracts presented a moderate activity against human breast carcinoma cell lines (MDA-MB-453 and MCF-7) and human colon carcinoma cell line (HCT-116) by the MTS [3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium] assay.

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“…Osmolytes, such as betaine, proline, taurine, β-alanine, hypotaurine, and trigonelline, help maintain cell volume by making the osmolarity between extracellular and intracellular environments similar so that water does not rush out of the cells, imploding them. 25 Nitrogenous pollutants and organic material are far more common in freshwater than sea water, so nitrogenous storage compounds, such as the polyamine, putrescine, which is derived from ornithine, and its catabolite, aminobutanal, are most abundant. 22 These coupled metabolites can readily form the amino acid glutamate, depending on the energy use of the Krebs cycle intermediate alpha-ketoglutarate.…”

Section: Methodsmentioning

confidence: 99%

Assessment of Metabolism of the Eastern Oyster and Eastern Elliptio Using NMR Spectroscopy

Lee¹

2016

J. Braz. Chem. Soc.

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Metabolites are known to characterize the functional responses of a cell. Therefore, a quantitative measurement of metabolite profiles can provide insight into the underlying effect of genetic or environmental actions on cell metabolism. It follows then that the study of the metabolite profiles of bivalve mollusks, such as oysters, can be particularly worthwhile in assessing changes in physiology, pharmacology and toxicology that result from their adaptation to changing environments. We have determined the metabolic profiles of three different organ groups in freshwater mussel and oysters by using 1 H (proton) and 13 C (carbon) NMR (nuclear magnetic resonance) spectroscopy following the infusion of 13 C glucose or 13 C glycine, respectively. The result shows infused glucose formed glycogen by glycogen synthesis, alanine by glycolysis, and glutamate and aspartate through the Krebs cycle and glycine formed serine by the glycine cleavage system in oysters. Decrease in adenosine triphosphate (ATP), glucogen, putrescine and ornithine were observed in the fasting state freshwater mussel. Our result opens the possibility that organ specific metabolic fingerprints can be established to interpret functional adaptations to environmental and nutritional challenges using NMR spectroscopy.

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Quantitative analysis of trigonelline in some Annona species by proton NMR spectroscopy

Cited by 19 publications

References 15 publications

NMR-based metabolomic analysis of wild, greenhouse, and in vitro regenerated shoots of Cymbopogon schoenanthus subsp. proximus with GC–MS assessment of proximadiol

NMR-based metabolomic analysis of wild, greenhouse, and in vitro regenerated shoots of Cymbopogon schoenanthus subsp. proximus with GC–MS assessment of proximadiol

Identification of Bioactive Compounds in Polar and Nonpolar Extracts of Araujia sericifera

Assessment of Metabolism of the Eastern Oyster and Eastern Elliptio Using NMR Spectroscopy

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