Isolation and Insecticidal/Anthelmintic Activity of Xanthonol, a Novel Bis-xanthone, from a Non-sporulating Fungal species

Ondeyka, John G.; Dombrowski, Anne W.; Polishook, Jon P.; Felcetto, T.; Shoop, Wesley L.; Guan, Ziqiang; Singh, Sheo B.

doi:10.1038/ja.2006.40

Cited by 25 publications

(32 citation statements)

References 10 publications

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“…Xanthonol is an anthelmintic, as revealed by tests upon the larvae of Lucilia sericata, Aedes aegypti, and Haemonchus contortus. 174 5 Xanthone dimers from lichens…”

Section: Xanthonolmentioning

confidence: 99%

Xanthone dimers: a compound family which is both common and privileged

2015

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Covering: up to 2014. Xanthone dimers are a widespread, structurally-diverse family of natural products frequently found in plants, fungi and lichens. They feature an intriguing variety of linkages between the component xanthones (benzannulated chromanones). These synthetically elusive secondary metabolites are of great interest due to their broad array of bioactivities, which has led to the xanthones being designated as 'privileged structures'. We seek herein to give an overview of all reliably-described xanthone dimers, their structures, occurrence, and the bioactivities established to date. The possible biosynthetic pathways leading to members of this family are also discussed in light of our current knowledge.

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“…Xanthonol is an anthelmintic, as revealed by tests upon the larvae of Lucilia sericata, Aedes aegypti, and Haemonchus contortus. 174 5 Xanthone dimers from lichens…”

Section: Xanthonolmentioning

confidence: 99%

Xanthone dimers: a compound family which is both common and privileged

2015

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“…[28] Symmetrical or asymmetrical coupling of identical or slightly different monomeric units is very common and often increases the bioactivity and toxicity. Some examples of these highly toxic mycotoxins include secalonic acids, [29,30] eumetrins, [31,32] xanthonols, [33] rugulotrosins, [34] hirtusneanoside, [35] phomoxanthone, [36,37] and dicerandrols. [38] Herein, we report the discovery of several new aromatic, hydrogenated, and structurally unique ring-extended xanthones from different endophytic fungi.…”

Section: Introductionmentioning

confidence: 99%

“…Xanthones and partially hydrogenated di-or tetrahydroxanthones are widespread classes of natural products [2] with considerable bioactivity [3][4][5][6][7][8][9][10][11] that occur in fungi, [9,[12][13][14] plants, [15][16][17][18] ferns, [19] and lichens. [20,21] Due to their pronounced toxicity, they are classified as mycotoxins.…”

Section: Introductionmentioning

confidence: 99%

Xanthones and Oxepino[2, 3‐b]chromones from Three Endophytic Fungi

Krohn

Kouam

Kuigoua

et al. 2009

Chemistry A European J

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Three new metabolites, microsphaeropsones A-C (1-3) with a unique oxepino[2,3-b]chromen-6-one (ring-enlarged xanthone) skeleton, were isolated from the endophytic fungus Microsphaeropsis species, co-occurring with their putative biogenetic anthraquinoide precursors citreorosein (4) and emodin (5). From another Microsphaeropsis species, large amounts of fusidienol A (8 a), smaller amounts of emodin (5), the known aromatic xanthones 9 a and 9 b, the new 3,4-dihydrofusidienol A (8 b), and the new aromatic xanthone 9 c were isolated. The endophyte Seimatosporium species produced a new aromatic xanthone, seimatoxanthone A (10), and 3,4-dihydroglobosuxanthone A (12), closely related to alpha-diversolonic ester (13) from Microdiplodia sp.. The structures were determined mainly by extensive 1D and 2D NMR experiments and supported by X-ray single-crystal analysis of 1 and the oxidation product 7. The absolute configurations of the microsphaeropsones A-C (1-3) were established by comparison of the electronic and vibrational circular dichroism (ECD and VCD) spectra of 1 with time-dependent DFT (TDDFT) and DFT calculations by using either the solid-state structures or DFT-optimized geometries as inputs. Preliminary studies indicated that 1, 2, and enone 7 showed antibacterial, fungicidal, and algicidal properties.

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“…Their distribution in the plant kingdom is relatively limited. Some xanthones have also been isolated from mushrooms (Ondeyka et al 2006) and lichens (Rezanka et al 2003). Guttiferae) and the Gentianaceae (Mandal et al 1992;Vieira and Kijjoa 2005).…”

Section: Xanthonesmentioning

confidence: 99%