Solid-Phase Synthesis of Polyfunctionalized Natural Products:  Application to Usnic Acid, a Bioactive Lichen Compound

Tomasi, Sophie; Picard, Sylvie; Lainé, Céline; Babonneau, Vincent; Goujeon, Anne; Boustié, Joël; Uriac, Philippe

doi:10.1021/cc050122t

Cited by 27 publications

(14 citation statements)

References 18 publications

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“…Listeria monocytogenes (Tomasi et al 2006). Some anthraquinone derivatives have also shown weak activity on Bacillus subtilis (Ivanova et al 2000) but a more specific lichen compound, protolichesterinic acid exhibit a very interesting antibacterial activity against Helicobacter pylori (Ingolfsdottir et al 1997b).…”

Section: Usnic Acidmentioning

confidence: 99%

Bioactive lichen metabolites: alpine habitats as an untapped source

2010

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International audienceLichens are fungal and algal/cyanobacterial symbioses resulting in the production of specific metabolites. Some of these are forming an available biomass for phytochemical investigations, including the assessment of biological activities of the isolated compounds. The alpine or polar region are characterised by highly stressful environmental conditions for many organisms, but lichens are among the dominating organisms in these habitats. In the performant mutual protective system, lichen fungi often accumulate high amounts of metabolites with specific physicochemical properties (UV absorbents, hydrophobicity) which help the lichens to survive. Unique secondary metabolites and polysaccharides have been isolated and tested from these organisms. Even though this has been tested until now only with a low number of compounds so far, interesting activities have been recorded. We review here some of the antimicrobial, anti-inflammatory, antiproliferative and antioxidant activities properties described. Solutions with axenic biotechnological cultivation of each symbiotic partner and particularly the mycobiont to obtain the lichen secondary metabolites are challenging to overcome the limitations for the supply of these rare compounds. Additionally, these lichens appear to harbour a diversity of culturable microorganisms from which active compounds have also been isolated recently

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Section: Usnic Acidmentioning

confidence: 99%

Bioactive lichen metabolites: alpine habitats as an untapped source

2010

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“…Uriac and co-workers 71 have published the solidphase synthesis of a small set based on a natural lichen dibenzofurane derivative, usnic acid 335a-335f (Scheme 51). The authors took advantage of the antibacterial activity of usnic acid amino derivatives and they functionalized this dibenzofuran with polyamines in order to improve the antibacterial activity and to overcome their poor hydrosolubility.…”

Section: Polyaminesmentioning

confidence: 99%

Highlights in the solid-phase organic synthesis of natural products and analogues

Eifler‐Lima¹,

Graebin²,

Uchôa³

et al. 2010

J. Braz. Chem. Soc.

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Neste trabalho nós apresentamos uma revisão sobre a síntese em fase sólida de metabólitos secundários, tais como alcalóides, poliaminas, esteróides, terpenos e flavonóides, descritos na literatura a partir de 2000. Um número considerável de rotas sintéticas elegantes e desafiadoras, usando suportes sólidos, será discutido.In this manuscript, we disclose solid-phase organic syntheses (SPOS) of small-molecules of some secondary metabolites, such as alkaloids, polyamines, steroids, terpenes, and flavonoids, described in the literature since 2000. A number of elegant, efficient and challenging syntheses on solid support will be presented.

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“…The compounds were prepared from commercial (+)-usnic acid that was condensed with appropriate amine derivatives, chosen because they present interesting features, such as an easy supply of diversity, inferring solubility or affinity for nucleic acids, A potential increase of activity in various fields and specifically as antimalarial agents is also expected when they are conjugated to drugs. [18] (compounds 2-8 ).…”

Section: Introductionmentioning

confidence: 99%

“…[18] Of the three hydroxyl groups, the enolic hydroxyl at position 3 has the strongest acidic character due to the inductive effect of the keto group, whereas the hydroxyl group at positions 8 and 10 are less acidic. [19] …”

Section: Introductionmentioning

confidence: 99%

Synthesis of a Potent Antimalarial Agent through Natural Products Conjugation

et al. 2013

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Three natural products have been assembled to obtain a new antimalarial hit. (+)-Usnic acid was used as scaffold to design and synthesize new products, that were tested on asexual development for P. falciparum and P. berghei. Among them, the ester of (+)-usnic acid-4-aminobutyric acid 14 with dihydroartemisinin shows considerable in vivo antimalarial activity against P. berghei in mice, similar to the synthetic drug artesunate. Compound 14 behaves as a delivery system for dihydroartemisinin and combine the effects of the endoperoxide with the redox properties of the phenolic portions of (+)-usnic acid.

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Solid-Phase Synthesis of Polyfunctionalized Natural Products: Application to Usnic Acid, a Bioactive Lichen Compound

Cited by 27 publications

References 18 publications

Bioactive lichen metabolites: alpine habitats as an untapped source

Bioactive lichen metabolites: alpine habitats as an untapped source

Highlights in the solid-phase organic synthesis of natural products and analogues

Synthesis of a Potent Antimalarial Agent through Natural Products Conjugation

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