Recent studies on the chemical constituents of Trigonostemon plants

Xu, Jin‐Biao; Yue, Jian‐Min

doi:10.1039/c4qo00161c

Cited by 33 publications

(10 citation statements)

References 72 publications

(147 reference statements)

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“…The extracts were prepared from leaves (47%), bark or twigs (48%), whole plants (3%), and fruits (2%) and subjected to polyamide filtration prior to LC-MS 2 analyses and biological evaluations. This botanical family was chosen for its large structural diversity, characterized by unique diterpenoids of various skeletons endowed with a wide range of biological activities. − …”

Section: Results and Discussionmentioning

confidence: 99%

Bioactive Natural Products Prioritization Using Massive Multi-informational Molecular Networks

et al. 2017

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Natural products represent an inexhaustible source of novel therapeutic agents. Their complex and constrained three-dimensional structures endow these molecules with exceptional biological properties, thereby giving them a major role in drug discovery programs. However, the search for new bioactive metabolites is hampered by the chemical complexity of the biological matrices in which they are found. The purification of single constituents from such matrices requires such a significant amount of work that it should be ideally performed only on molecules of high potential value (i.e., chemical novelty and biological activity). Recent bioinformatics approaches based on mass spectrometry metabolite profiling methods are beginning to address the complex task of compound identification within complex mixtures. However, in parallel to these developments, methods providing information on the bioactivity potential of natural products prior to their isolation are still lacking and are of key interest to target the isolation of valuable natural products only. In the present investigation, we propose an integrated analysis strategy for bioactive natural products prioritization. Our approach uses massive molecular networks embedding various informational layers (bioactivity and taxonomical data) to highlight potentially bioactive scaffolds within the chemical diversity of crude extracts collections. We exemplify this workflow by targeting the isolation of predicted active and nonactive metabolites from two botanical sources (Bocquillonia nervosa and Neoguillauminia cleopatra) against two biological targets (Wnt signaling pathway and chikungunya virus replication). Eventually, the detection and isolation processes of a daphnane diterpene orthoester and four 12-deoxyphorbols inhibiting the Wnt signaling pathway and exhibiting potent antiviral activities against the CHIKV virus are detailed. Combined with efficient metabolite annotation tools, this bioactive natural products prioritization pipeline proves to be efficient. Implementation of this approach in drug discovery programs based on natural extract screening should speed up and rationalize the isolation of bioactive natural products.

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Section: Results and Discussionmentioning

confidence: 99%

Bioactive Natural Products Prioritization Using Massive Multi-informational Molecular Networks

et al. 2017

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“…The extracts were prepared from leaves (47%), bark or twigs (48%), whole plants (3%), or fruits (2%). The Euphorbiaceae family was chosen for its large structural diversity, characterized by unique classes of structurally diverse diterpenoids endowed with a wide range of biological activities, such as antiviral activity against human immunodeficiency virus or modulation of P-glycoprotein and protein kinase C. − …”

Section: Resultsmentioning

confidence: 99%

Antiviral Compounds from Codiaeum peltatum Targeted by a Multi-informative Molecular Networks Approach

et al. 2019

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From a set of 292 Euphorbiaceae extracts, the use of a molecular networking (MN)-based prioritization approach highlighted three clusters (MN1−3) depicting ions from the bark extract of Codiaeum peltatum. Based on their putative antiviral potential and structural novelty, the MS-guided purification of compounds present in MN1 and MN2 afforded two new daphnane-type diterpenoid orthoesters (DDO), codiapeltines A (1) and B (2), the new actephilols B (3) and C (4), and four known 1,4-dioxane-fused phenanthrene dimers (5−8). The structures of the new compounds were elucidated by NMR spectroscopic data analysis, and the absolute configurations of compounds 1 and 2 were deduced by comparison of experimental and calculated ECD spectra. Codiapeltine B (2) is the first daphnane bearing a 9,11,13-orthoester moiety, establishing a new major structural class of DDO. Compounds 1−8 and four recently reported monoterpenyl quinolones (9− 12) detected in MN3 were investigated for their selective activities against chikungunya virus replication and their antipolymerase activities against the NS5 proteins of dengue and zika viruses. Compounds 3−8 exhibited strong inhibitory activities on both dengue and zika NS5 in primary assays, but extensive biological analyses indicated that only actephilol B (3) displayed a specific interaction with the NS5 targets.

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“…Spirooxindoles are intriguing synthetic targets in organic and medicinal chemistry owing to their wide spectrum of biological and pharmacological activities [1] . In particular, 3,4’‐pyranyl spirooxindoles with multiple stereocenters have been proven to be a privileged skeleton in a variety of natural products and pharmaceutical molecules that possess important biological activities, such as p38α inhibitor, [2b] antibacterial agent [2c] and trigolutes A–D [2a,d] (Figure 1). Accordingly, considerable efforts have been devoted to exploit highly efficient methods for the construction of diverse 3,4’‐pyranyl spirooxindole scaffolds, [3] especially in an asymmetric manner [4–6] .…”

Section: Introductionmentioning

confidence: 99%

Organocatalytic Remote Asymmetric Inverse‐Electron‐Demand Oxa‐Diels‐Alder Reaction of Allyl Ketones with Isatin‐Derived Unsaturated Keto Esters

Lin

Hou

et al. 2020

Adv Synth Catal

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A remote cascade asymmetric inverse-electron-demand oxa-Diels-Alder reaction of allyl ketones with isatin-derived β,γ-unsaturated α-keto esters has been developed in the presence of a chiral bifunctional squaramide catalyst. Taking advantage of the secondary amide activating group, a series of enantioenriched 3,4'-pyranyl spirooxindole derivatives bearing three contiguous chiral centers were attained in high yields (84 to > 99%) with excellent enantioselectivities (96-99% ee). Moreover, the gram-scale synthesis and the construction of 1-benzazepine scaffold by the product were also demonstrated.

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Recent studies on the chemical constituents of Trigonostemon plants

Cited by 33 publications

References 72 publications

Bioactive Natural Products Prioritization Using Massive Multi-informational Molecular Networks

Bioactive Natural Products Prioritization Using Massive Multi-informational Molecular Networks

Antiviral Compounds from Codiaeum peltatum Targeted by a Multi-informative Molecular Networks Approach

Organocatalytic Remote Asymmetric Inverse‐Electron‐Demand Oxa‐Diels‐Alder Reaction of Allyl Ketones with Isatin‐Derived Unsaturated Keto Esters

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