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Molecules
2019 Dec 30;251:. doi: 10.3390/molecules25010153.
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Integrated Analytical Tools for Accessing Acridones and Unrelated Phenylacrylamides from Swinglea glutinosa.
Calheiros de Carvalho A
,
De Camillis Rodrigues L
,
Ribeiro AI
,
Fernandes da Silva MFDG
,
Soman de Medeiros L
,
Moura Veiga TA
.
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In natural product studies, the purification of metabolites is an important challenge. To accelerate this step, alternatives such as integrated analytical tools should be employed. Based on this, the chemical study of Swinglea glutinosa (Rutaceae) was performed using two rapid dereplication strategies: Target Analysis (Bruker Daltonics®, Bremen, Germany) MS data analysis combined with MS/MS data obtained from the GNPS platform. Through UHPLC-HRMS data, the first approach allowed, from crude fractions, a quick and visual identification of compounds already reported in the Swinglea genus. Aside from this, by grouping compounds according to their fragmentation patterns, the second approach enabled the detection of eight molecular families, which presented matches for acridonic alkaloids, phenylacrylamides, and flavonoids. Unrelated compounds for S. glutinosa have been isolated and characterized by NMR experiments, Lansamide I, Lansiumamide B, Lansiumamide C, and N-(2-phenylethyl)cinnamamide.
Figure 1. (A) Base peak chromatogram (BPC) of S. glutinosa hexane stem fractions. (B) BPC of S. glutinosa hexane leaf fraction. The chromatogram is overlaid with the extracted-ion chromatogram from detected compounds. The colored peaks represent compounds listed in the “in-house” database, some of them identified in Table 1 and Figure 2. The peaks numbered in red correspond to the isolated amides in this work, not yet reported for the genus.
Figure 2. Identified compounds from Swinglea glutinosa through UHPLC-HRMS (compounds 1–22, using Target Analysis; compounds 23–29 using GNPS). The compounds indicated in red correspond to the phenylacrylamide class; the compounds in blue belong to the acridonic alkaloid class and in black are compounds belonging to the flavonoid class.
Figure 3. Molecular families for S. glutinosa extracts. Nodes outlined in blue represent isolated and identified compounds in this work. The nodes outlined in pink represent dereplicated compounds, which had the chemical structure suggested by the GNPS platform. Compounds indicated from non-prominent nodes suggest substances compatible with metabolites already described for S. glutinosa. Structures highlighted in the red frame indicate compounds not related to the Swinglea genus and that were identified by our “in-house” database. Different portions visualized at nodes are not quantitatively representative.
Figure 4. (A) Part of molecular family I, corresponding to amide detection, with highlighted cosine values. (B) MS/MS spectrum acquired (black) vs. registered spectrum on the GNPS platform (green), for the ion m/z 307.186. The pseudomolecular ion was not detected in both cases.
Arato Ferreira,
Acridone Alkaloids from Swinglea glutinosa (Rutaceae) and Their Effects on Photosynthesis.
2016, Pubmed,
Echinobase
Arato Ferreira,
Acridone Alkaloids from Swinglea glutinosa (Rutaceae) and Their Effects on Photosynthesis.
2016,
Pubmed
,
Echinobase
Ito,
Chemical constituents of Glycosmis citrifolia (Willd.) Lindl. Structures of four new acridones and three new quinolone alkaloids.
2000,
Pubmed
Klitgaard,
Aggressive dereplication using UHPLC-DAD-QTOF: screening extracts for up to 3000 fungal secondary metabolites.
2014,
Pubmed
Kuete,
Cytotoxicity of a naturally occurring furoquinoline alkaloid and four acridone alkaloids towards multi-factorial drug-resistant cancer cells.
2015,
Pubmed
Matsui,
Lansiumamide B and SB-204900 isolated from Clausena lansium inhibit histamine and TNF-α release from RBL-2H3 cells.
2013,
Pubmed
Wang,
Sharing and community curation of mass spectrometry data with Global Natural Products Social Molecular Networking.
2016,
Pubmed
Weniger,
Bioactive acridone alkaloids from Swinglea glutinosa.
2001,
Pubmed
Winnikoff,
Quantitative molecular networking to profile marine cyanobacterial metabolomes.
2014,
Pubmed
Wu,
Acridone alkaloids from the root bark of Severinia buxifolia in Hainan.
2000,
Pubmed
Yamazaki,
Induction of adiponectin by natural and synthetic phenolamides in mouse and human preadipocytes and its enhancement by docosahexaenoic acid.
2008,
Pubmed