Using Ultrahigh‐Resolution Mass Spectrometry to Unravel the Chemical Space of Complex Natural Product Mixtures

Müller, Constanze; Harir, Mourad; Hertkorn, Norbert; Kanawati, Basem; Tziotis, Dimitrios; Schmitt‐Kopplin, Philippe

doi:10.1002/9781118876015.ch15

Cited by 1 publication

(1 citation statement)

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“…This procedure was repeated for all of the 49 NPs of the set, and the chemical space described by the data set (49 NPs × 128 descriptors) was explored using PCA. The PCA is classified as an unsupervised method; indeed, it does not need any prior information about the labelling of the objects and it is usually applied to perform an unbiased data analysis in terms of pattern recognition [34]. The score and loading plots obtained with this unsupervised method are represented in ▶ Fig.…”

Section: Resultsmentioning

confidence: 99%

Passive Intestinal Absorption of Representative Plant Secondary Metabolites: A Physicochemical Study

et al. 2017

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Natural products are generally ingested as part of traditional herbal decoctions or in the current diet. However, in natural product research, the bioavailability of secondary metabolites is often poorly investigated. In this work, a systematic study was carried out in order to highlight the physicochemical parameters that mainly influence the passive intestinal absorption of natural products. For this, a representative set of natural products including alkaloids, coumarins, flavonoid aglycones and glycosides, and carboxylic acids was selected and their physicochemical properties were predicted using relevant Volsurf+ descriptors. The chemical space obtained with this unbiased method was then correlated with experimental passive intestinal permeability data, which highlighted the main influence of lipophilicity, global hydrophilicity, size, and the ionisation state on passive intestinal absorption of natural products. Since the pH range encountered in the intestine is wide, the influence of the ionisation was investigated deeper experimentally. The ionisation state of weakly ionisable natural products, such as flavonoid aglycones, alkaloids, and carboxylic acids, was found to prevent the passive intestinal absorption of such natural products completely. In addition, the impact of solubility issues on passive permeability results was evaluated in cases of poorly water-soluble natural products, such as flavonoid aglycones and coumarins. The biomimetic fasted state simulated fluid-version 2 was found to improve the apparent solubility of such poorly soluble natural products without influencing their permeability behaviours. The use of such a solubilising buffer was found to be well adapted to the hexadecane membrane-parallel artificial membrane permeability assay and can circumvent the solubility issues encountered with poorly soluble natural products in such an assay.

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Section: Resultsmentioning

confidence: 99%