Journal ArticleDOI
Tsavoenones A-C: unprecedented polyketides with a 1,7-dioxadispiro[4.0.4.4]tetradecane core from the lichen Parmotrema tsavoense.
Thuc-Huy Duong,Mehdi A. Beniddir,Grégory Genta-Jouve,Thammarat Aree,Marylène Chollet-Krugler,Joël Boustie,Solenn Ferron,Aurélie Sauvager,Huu-Hung Nguyen,Kim-Phi-Phung Nguyen,Warinthorn Chavasiri,Pierre Le Pogam +11 more
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TLDR
New racemic dispiranic polyketides, tsavoenones A (1), B (2) and C (3), having a novel 1,7-dioxadispiro[4.0.4.4]tetradecane scaffold were isolated from the foliose lichen Parmotrema tsavoense and displayed a moderate activity against human myelogenous leukemia K562 cell line.Abstract:
New racemic dispiranic polyketides, tsavoenones A (1), B (2) and C (3), having a novel 1,7-dioxadispiro[4.0.4.4]tetradecane scaffold were isolated from the foliose lichen Parmotrema tsavoense. These compounds were structurally elucidated by extensive NMR analyses, comparison between experimental and theoretical 13C NMR data and X-ray crystallography. A putative biosynthetic scenario for the formation of 1-3 from parmosidone D, a meta-depsidone previously isolated from the same lichen material, was proposed. Tested for its cytotoxicity, 1 displayed a moderate activity against human myelogenous leukemia K562 cell line with an IC50 value of 66 μg mL-1.read more
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A database of high-resolution MS/MS spectra for lichen metabolites.
Damien Olivier-Jimenez,Marylène Chollet-Krugler,David Rondeau,David Rondeau,Mehdi A. Beniddir,Solenn Ferron,Thomas Delhaye,Pierre-Marie Allard,Jean-Luc Wolfender,Harrie J. M. Sipman,Robert Lücking,Joël Boustie,Pierre Le Pogam +12 more
TL;DR: An open access MS/MS library with 250 metabolites, coined LDB for Lichen DataBase, providing a comprehensive coverage of lichen chemodiversity, revealing the detection of eleven unique molecules that would have been missed without LDB implementation to the GNPS.
Journal ArticleDOI
Salazinic Acid-Derived Depsidones and Diphenylethers with α-Glucosidase Inhibitory Activity from the Lichen Parmotrema dilatatum.
Asshaima Paramita Devi,Thuc-Huy Duong,Solenn Ferron,Mehdi A. Beniddir,Minh-Hiep Dinh,Van-Kieu Nguyen,Nguyen-Kim-Tuyen Pham,Dinh Hung Mac,Joël Boustie,Warinthorn Chavasiri,Pierre-Yves Le Pogam +10 more
TL;DR: Newly reported benzylated depsidones 1: and 2: in particular inhibited α-glucosidase with IC50 values of 2.2 and 4.3 µM, respectively, and are thus more potent than the positive control, acarbose.
Journal ArticleDOI
α-Glucosidase Inhibitory Depsidones from the Lichen Parmotrema tsavoense.
Thuc-Huy Duong,Tai-Xuan-Hoa Hang,Pierre Le Pogam,Thanh-Nha Tran,Dinh Hung Mac,Minh-Hiep Dinh,Jirapast Sichaem +6 more
TL;DR: Chemical investigation of the lichen Parmotrema tsavoense led to the isolation of 5 new depsidones, parmosidones F’- J, which were structurally elucidated using spectroscopic methods including HRESIMS and 2D NMR data.
Journal ArticleDOI
A new depsidone from the lichen Usnea ceratina Arch.
TL;DR: Five depsidones were isolated from the lichen Usnea ceratina Arch, including one new compound ceratinalone, along with four known compounds bailesidone, stictic acid, 8'-O-methylstictic Acid and 8-ethylstictIC acid, determined by analysis of their MS and NMR data as well as by comparison with literature values.
Journal ArticleDOI
DP4-Assisted Structure Elucidation of Isodemethylchodatin, a New Norlichexanthone Derivative Meager in H-Atoms, from the Lichen Parmotrema tsavoense.
Thuc-Huy Duong,Mehdi A. Beniddir,Joël Boustie,Kim-Phi-Phung Nguyen,Warinthorn Chavasiri,Guillaume Bernadat,Pierre Le Pogam +6 more
TL;DR: Isodemethylchodatin represents the first chlorinated lic hexanthone/norlichexanthone derivative bearing a methoxy group at C-5, and was determined based on an integrated interpretation of 13C-NMR chemical shifts, MS spectra, and DP4-based computational chemistry.
References
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Journal ArticleDOI
Assigning Stereochemistry to Single Diastereoisomers by GIAO NMR Calculation: The DP4 Probability
TL;DR: A new probability measure, which is termed DP4, complements the probabilities obtained from the previously developed CP3 parameter, which applies to the case of assigning a pair of diastereoisomers when one has both experimental data sets.
Journal ArticleDOI
Lichens—a promising source of bioactive secondary metabolites
Joël Boustie,Martin Grube +1 more
TL;DR: A global approach of the lichen metabolomic features appears to be essential in developing new and viable biotechnological processes which could afford suitable amounts of unique lichen compounds.
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Identification of the Viridicatumtoxin and Griseofulvin Gene Clusters from Penicillium aethiopicum
TL;DR: Discovery of the vrt and gsf clusters provided the basis for genetic and biochemical studies of the pathways and were identified as the chlorinase involved in the biosynthesis of 2, because deletion of gsfI resulted in the accumulation of decholorogriseofulvin 3.
Journal ArticleDOI
Biosynthesis of Rhizocticins, Antifungal Phosphonate Oligopeptides Produced by Bacillus subtilis ATCC6633
Svetlana A. Borisova,Benjamin T. Circello,Jun Kai Zhang,Wilfred A. van der Donk,William W. Metcalf +4 more
TL;DR: The identification and characterization of the rhizocticin biosynthetic gene cluster (rhi) in Bacillus subtilis ATCC6633 is reported and the product of an in vitro enzymatic conversion was characterized.
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Complexity generation in fungal polyketide biosynthesis: A spirocycle-forming P450 in the concise pathway to the antifungal drug griseofulvin
TL;DR: This work systematically characterized each of the biosynthetic enzymes related to the biogenesis of 1, including the characterization of a new polyketide synthase GsfA that synthesizes the benzophenone precursor and a cytochrome P450 GsfF that performs oxidative coupling between the orcinol and the phloroglucinol rings to yield the grisan structure.