Uncommon Chlorinated Xanthone and Other Antibacterial Compounds from the Lichen Cladonia incrassata

Dieu, Amandine; Millot, Marion; Champavier, Yves; Mambu, Lengo; Chaleix, Vincent; Sol, Vincent; Gloaguen, Vincent

doi:10.1055/s-0034-1382827

Cited by 18 publications

(12 citation statements)

References 25 publications

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“…Concerning SAR analysis, the obtained results were consistent with data previously reported for some natural [1,28,29] and synthetic xanthones [19], the halogenated derivatives being in general the most promising antimicrobial agents ( Figure 6). For antifungal activity, the presence of only two hydroxyl groups (3) at C-3 and C-4 seems to be important, since compound 4, with an additional hydroxyl group at C-6, was not as potent as 3; on the other hand, the presence of activating groups (CH 3 ) at C-1 (3) is more favorable than the presence of deactivating groups (COOCH 3 ) at the same position (13).…”

Section: E Floccosum(chenchen)supporting

confidence: 90%

Synthesis of a Small Library of Nature-Inspired Xanthones and Study of Their Antimicrobial Activity

et al. 2020

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A series of thirteen xanthones 3–15 was prepared based on substitutional (appendage) diversity reactions. The series was structurally characterized based on their spectral data and HRMS, and the structures of xanthone derivatives 1, 7, and 8 were determined by single-crystal X-ray diffraction. This series, along with an in-house series of aminated xanthones 16–33, was tested for in-vitro antimicrobial activity against seven bacterial (including two multidrug-resistant) strains and five fungal strains. 1-(Dibromomethyl)-3,4-dimethoxy-9H-xanthen-9-one (7) and 1-(dibromomethyl)-3,4,6-trimethoxy-9H-xanthen-9-one (8) exhibited antibacterial activity against all tested strains. In addition, 3,4-dihydroxy-1-methyl-9H-xanthen-9-one (3) revealed a potent inhibitory effect on the growth of dermatophyte clinical strains (T. rubrum FF5, M. canis FF1 and E. floccosum FF9), with a MIC of 16 µg/mL for all the tested strains. Compounds 3 and 26 showed a potent inhibitory effect on two C. albicans virulence factors: germ tube and biofilm formation.

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Section: E Floccosum(chenchen)supporting

confidence: 90%

Synthesis of a Small Library of Nature-Inspired Xanthones and Study of Their Antimicrobial Activity

et al. 2020

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“…Fortuneanoside G (32) was found to be the most active against this enzyme. 109 Among dioxotetrahydrodibenzofurans, eight derivatives have been isolated from seeds of Iradaceae and named belamcandones (33). 115 None of them have been evaluated for their potential biological activities.…”

Section: Plantsmentioning

confidence: 99%

Dibenzofurans and derivatives from lichens and ascomycetes

2016

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Covering: up to 2016.When looking for dibenzofuran in the biochemical databases, most papers and reviews deal with pollutants and polychlorinated dibenzofurans like dioxins. But dibenzofurans are also biosynthetized by a wide diversity of organisms in nature. Even if dibenzofurans from natural sources represent a small class of secondary metabolites, compared to flavonoids, xanthones or terpenoids, they are often endowed with interesting biological properties which have been recently described. This review provides an update on papers describing dibenzofurans from lichens, ascomycetes and cultured mycobionts. Other sources, such as basidiomycetes, myxomycetes or plants produce sporadically interesting dibenzofurans in terms of structures and activities.

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“…Over the preceding decade, more than one hundred of xanthones of lichen sources were identified [ 4 ], but only a limited number have been investigated for their bioactivities [ 5 ]. Particularly, chlorinated lichen xanthones have been found attractive for their antibacterial and antifungal activities, such is the case of thiophanic and thiophaninic acids with potent fungicidal effects [ 6 ], and of cladoxanthone A with antibacterial effects towards Staphylococcus minimoides [ 7 ] ( Figure 1 ). Other interesting chlorinated xanthones have been recently isolated from marine organisms.…”

Section: Introductionmentioning

confidence: 99%

Lichen Xanthones as Models for New Antifungal Agents

et al. 2018

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Due to the emergence of multidrug-resistant pathogenic microorganisms, the search for new antimicrobial compounds plays an important role in current medicinal chemistry research. Inspired by lichen antimicrobial xanthones, a series of novel chlorinated xanthones was prepared using five chlorination methods (Methods A–E) to obtain different patterns of substitution in the xanthone scaffold. All the synthesized compounds were evaluated for their antimicrobial activity. Among them, 3-chloro-4,6-dimethoxy-1-methyl-9H-xanthen-9-one 15 showed promising antibacterial activity against E. faecalis (ATCC 29212 and 29213) and S. aureus ATCC 29213. 2,7-Dichloro-3,4,6-trimethoxy-1-methyl-9H-xanthen-9-one 18 revealed a potent fungistatic and fungicidal activity against dermatophytes clinical strains (T. rubrum, M. canis, and E. floccosum (MIC = 4–8 µg/mL)). Moreover, when evaluated for its synergistic effect for T. rubrum, compound 18 exhibited synergy with fluconazole (ΣFIC = 0.289). These results disclosed new hit xanthones for both antibacterial and antifungal activity.

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Uncommon Chlorinated Xanthone and Other Antibacterial Compounds from the Lichen Cladonia incrassata

Cited by 18 publications

References 25 publications

Synthesis of a Small Library of Nature-Inspired Xanthones and Study of Their Antimicrobial Activity

Synthesis of a Small Library of Nature-Inspired Xanthones and Study of Their Antimicrobial Activity

Dibenzofurans and derivatives from lichens and ascomycetes

Lichen Xanthones as Models for New Antifungal Agents

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