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.2021 Apr 29;11(5):281.
doi: 10.3390/metabo11050281.

Feature-Based Molecular Network-Guided Dereplication of Natural Bioactive Products from Leaves ofStryphnodendron pulcherrimum (Willd.) Hochr

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Feature-Based Molecular Network-Guided Dereplication of Natural Bioactive Products from Leaves ofStryphnodendron pulcherrimum (Willd.) Hochr

Paulo Gomes et al. Metabolites..

Abstract

Stryphnodendron pulcherrimum is a species known to have a high content of tannins. Accordingly, its preparations are used in southern Pará, Brazil, for their anti-inflammatory and antimicrobial activities, but so far, its chemical profile composition remains essentially unknown. We herein describe the compounds present in a hydro-acetonic extract fromS. pulcherrimum leaves as revealed by dereplication via ultra-high performance liquid chromatography coupled to high-resolution mass spectrometry. The data were combined with spectral organization, spectral matching through the Global Natural Products Social platform, in silico annotation and taxonomical ponderation. Several types of phenolic compounds were identified such as gallic acids, flavan-3-ols and flavone-like compounds. From these, 5 have been recently reported by our group, whereas 44 are reported here for the first time in this tree species, and 41 (out of 49) for this genus. The results highlight the possible role ofStryphnodendron pulcherrimum as a renewable source for natural bioactive products with potential pharmaceutical applications.

Keywords: Stryphnodendron; UHPLC-MS/MS; dereplication; molecular network.

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Conflict of interest statement

We declare no current or potential conflict of interest related to this article.

Figures

Figure 1
Figure 1
Molecular network from UHPLC-MS/MS data in the negative ion mode forS. pulcherrimum leaf extract. Numbers inside the nodes correspond to them/z accurate masses (Da) for the [M–H]− for each precursor ion. Node size is proportional to the intensity of the ion peaks in the total ion chromatogram. Node colors represent the three different groups: gallic acid derivatives (G1, blue), flavan-3-ol derivatives (G2, orange) and flavone derivatives (G3, green). Rhomboid shapes correspond to a match against an experimental MS2; square shapes are identifications from in silico spectra matching.
Figure 2
Figure 2
(A) UHPLC-MS/MS total ion chromatograms in the negative ion mode for the leaf extract ofStryphnodendron pulcherrimum. Zoom sections of the chromatograms for (B) 0 to 10 min, (C) 10 to 14 min and (D) 14 to 22 min. Dashed lines represent the position (retention time) of each dereplicated compound.
Figure 3
Figure 3
MS/MS for representative [M–H]− molecular ions from each group. Group 1 (A), [3,4,5-trihydroxy-6-(3,4,5-trihydroxybenzoyl)oxyoxan-2-yl]methyl-3,4,5-trihydroxybenzoate (9), gallic acid derivatives; Group 2 (B), 3-O-galloyl-(epi)gallocatechin-(epi)gallocatechin (22), flavan-3-ol derivatives; and Group 3 (C), myricetin-3-galactoside (20), flavone derivatives.
Figure 4
Figure 4
Gallic acid derivatives in the largest cluster of the network. Numbers inside the nodes correspond to the accurate mass for each precursor. Node size is proportional to the intensity of the ions in the total ion chromatogram. Node colors represent structural groups: gallic acid derivatives (G1, blue), flavan-3-ol derivatives (G2, orange) and flavone derivatives (G3, green). Rhomboid shapes correspond to a match against an experimental MS2; square shapes are identifications from in silico spectra matching.
Figure 5
Figure 5
Illustrative compounds assigned as flavan-3-ol derivatives (Group 2). Numbers inside the nodes correspond to the accurate mass for each precursor. Node size is proportional to the intensity of the ion peaks in the total ion chromatograms. Node colors represent the three different groups: gallic acid derivatives (G1, blue), flavan-3-ol derivatives (G2, orange) and flavone derivatives (G3, green). Rhomboid shapes correspond to a match against an experimental MS2; square shapes are identifications from in silico spectra matching.
Figure 6
Figure 6
Compounds assigned mainly as flavone derivatives in the cluster belonging to Group 3. Numbers inside the nodes correspond to the accurate mass for each precursor. Node size is proportional to the intensity of the ions in the total ion chromatogram. Node colors represent the three different groups: gallic acid derivatives (G1, blue), flavan-3-ol derivatives (G2, orange) and flavone derivatives (G3, green). Rhomboid shapes correspond to a match against an experimental MS2; square shapes are identifications from in silico spectra matching.
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