Isolation of Secoiridoid Artifacts from Lonicera japonica

Tomassini, Lamberto; Cometa, Maria Francesca; Serafini, Mauro; Nicoletti, Marcello

doi:10.1021/np50125a020

Cited by 47 publications

(25 citation statements)

References 4 publications

(13 reference statements)

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“…Since overnight exposure of the cantleyoside or secologanin to SiGel and chloroform/methanol results in formation of the acetals, compounds 2 and 7 are proposed to be artifacts. [13] …”

Section: Resultsmentioning

confidence: 99%

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Monoterpenoid glucoindole alkaloids and iridoids from Pterocephalus pinardii

Gülcemal

Masullo

Alankuş-Çalışkan

et al. 2010

Magnetic Reson in Chemistry

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A new secondary metabolite, pterocephaline, along with the known cantleyoside, 7alpha-morroniside, 3beta,5alpha-tetrahydrodesoxycordifoline lactam, 5S-5-carboxyvincoside, sweroside, and loganin have been isolated from the aerial parts of P. pinardii (Dipsacaceae). Moreover, cantleyoside-methyl-hemiacetal and cantleyoside-dimethyl-acetal were obtained as seco-iridoid artifacts. The structures were elucidated by extensive spectroscopic methods including 1D-((1)H, (13)C and TOCSY) and 2D-NMR (DQF-COSY, HSQC and HMBC). Monoterpenoid glucoindole alkaloids were encountered for the first time in Dipsacaceae family.

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“…Since overnight exposure of the cantleyoside or secologanin to SiGel and chloroform/methanol results in formation of the acetals, compounds 2 and 7 are proposed to be artifacts. [13] …”

Section: Resultsmentioning

confidence: 99%

“…Their structures were elucidated by extensive spectroscopic methods including 1D-( 1 H, 13 C and TOCSY) and 2D-NMR (DQF-COSY, HSQC and HMBC) experiments as well as ESIMS analysis (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Monoterpenoid glucoindole alkaloids and iridoids from Pterocephalus pinardii

Gülcemal

Masullo

Alankuş-Çalışkan

et al. 2010

Magnetic Reson in Chemistry

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“…1) and loganic acid (d 7.09). In the case of secologanin, H-3 is changeable, especially at higher pH values because the aldehyde proton can form the dimethylacetal, and this results in the effect on the chemical shift of H-3 of secologanin (Kim et al, 2004;Tomassini et al, 1995). So, the signal at d 7.49 might be due to the artifact of secologanin.…”

Section: Visual Inspection Of 1 H-nmr Spectra and Assignments Of Chclmentioning

confidence: 99%

Metabolic Discrimination ofCatharanthus roseusLeaves Infected by Phytoplasma Using 1H-NMR Spectroscopy and Multivariate Data Analysis

et al. 2004

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A comprehensive metabolomic profiling of Catharanthus roseus L. G. Don infected by 10 types of phytoplasmas was carried out using one-dimensional and two-dimensional NMR spectroscopy followed by principal component analysis (PCA), an unsupervised clustering method requiring no knowledge of the data set and used to reduce the dimensionality of multivariate data while preserving most of the variance within it. With a combination of these techniques, we were able to identify those metabolites that were present in different levels in phytoplasma-infected C. roseus leaves than in healthy ones. The infection by phytoplasma in C. roseus leaves causes an increase of metabolites related to the biosynthetic pathways of phenylpropanoids or terpenoid indole alkaloids: chlorogenic acid, loganic acid, secologanin, and vindoline. Furthermore, higher abundance of Glc, Glu, polyphenols, succinic acid, and Suc were detected in the phytoplasma-infected leaves. The PCA of the 1 H-NMR signals of healthy and phytoplasma-infected C. roseus leaves shows that these metabolites are major discriminating factors to characterize the phytoplasma-infected C. roseus leaves from healthy ones. Based on the NMR and PCA analysis, it might be suggested that the biosynthetic pathway of terpenoid indole alkaloids, together with that of phenylpropanoids, is stimulated by the infection of phytoplasma.

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“…The plant has been reported to possess properties of detoxicating, dispelling noxious heat from blood and arresting dysentery [2,3], and it can significantly increase blood neutrophil activity and promote the neutrophil phagocytosis [4]. The constituents of this plant have been previously investigated and shown to contain iridoid glucosides [5] and polyphenolic compounds [6].…”

Section: Introductionmentioning

confidence: 99%

Determination of Phenolic Acids and Flavones in Lonicera japonica Thumb. by Capillary Electrophoresis with Electrochemical Detection

Peng

Liu

2005

Electroanalysis

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Capillary electrophoresis with electrochemical detection (CE-ED) was employed to analyze active ingredients of Lonicera japonica Thumb., an important crude herb frequently used in Chinese medicines. Hyperoside, chlorogenic acid, luteolin and caffeic acid are the major important active ingredients. Operating in a wall-jet configuration, a 300 mm diameter carbon-disk electrode was used as the working electrode, which exhibits a good response at þ 0.90 V (vs. saturated calomel electrode) for four analytes. Under the optimum conditions, the analytes were baseline separated within 20 min in a 50 mmol L À1 borax buffer (pH 8.7). Notably, excellent linearity was obtained over two orders of magnitude with detection limits (S/N ¼ 3) ranging from 0.1 to 0.5 mg L À1 for all the analytes. This method was successfully used in the analysis of Lonicera japonica Thumb. with relative simple extraction procedures, and the assay results were satisfactory.

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Isolation of Secoiridoid Artifacts from Lonicera japonica

Cited by 47 publications

References 4 publications

Monoterpenoid glucoindole alkaloids and iridoids from Pterocephalus pinardii

Monoterpenoid glucoindole alkaloids and iridoids from Pterocephalus pinardii

Metabolic Discrimination ofCatharanthus roseusLeaves Infected by Phytoplasma Using 1H-NMR Spectroscopy and Multivariate Data Analysis

Determination of Phenolic Acids and Flavones in Lonicera japonica Thumb. by Capillary Electrophoresis with Electrochemical Detection

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