Synthesis of 4-methoxy-1H-phenalen-1-one: a subunit related to natural phenalenone-type compounds

Nanclares, Juliana; Gil, José; Rojano, Benjamín; Lopez-Saez, Jérôme; Schneider, Bernd; Otálvaro, Felipe

doi:10.1016/j.tetlet.2008.04.095

Cited by 15 publications

(11 citation statements)

References 25 publications

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“…1 Chemists have also synthesized many phenalenone derivatives bearing signicant biological activity. [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] Phenalenone derivatives have been reported both from higher plants and microbial sources, 18 and possess signicant biological and chemical importance. Despite their importance, this class of natural polyketides did not receive due attention, therefore, to explore these compounds further, we have focused on phenalenone derivatives, especially of fungal origin.…”

Section: Introductionmentioning

confidence: 99%

Fungal phenalenones: chemistry, biology, biosynthesis and phylogeny

et al. 2014

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Covering up to the end of August 2013. Phenalenones are members of a unique class of natural polyketides exhibiting diverse biological potential. This is a comprehensive review of 72 phenalenones with diverse structural features originating from fungal sources. Their bioactive potential and structure elucidation are discussed along with a review of their biosynthetic pathways and the taxonomical relationship between the fungi producing these natural products.

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Section: Introductionmentioning

confidence: 99%

Fungal phenalenones: chemistry, biology, biosynthesis and phylogeny

et al. 2014

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“…The commercial use of phenylphenalenone scaffolds would only be practical without the need of isolating them from natural sources, as they are normally biosynthesized in extremely low amounts in plants. Efforts to synthesize these compounds have been made [ 47 , 51 , 52 , 53 , 54 , 55 , 56 , 57 ], but the high concentration of phenylphenalenones found in methanolic extracts of S. timida seeds raises the possibility of using this species as an alternative source of phenylphenalenones scaffolds.…”

Section: Discussionmentioning

confidence: 99%

Phytotoxicity of Schiekia timida Seed Extracts, a Mixture of Phenylphenalenones

et al. 2021

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Phenylphenalenones, metabolites found in Schiekia timida (Haemodoraceae), are a class of specialized metabolites with many biological activities, being phytoalexins in banana plants. In the constant search to solve the problem of glyphosate and to avoid resistance to commercial herbicides, this work aimed to investigate the phytotoxic effect of the methanolic extract of S. timida seeds. The chemical composition of the seed extract was directly investigated by NMR and UPLC-QToF MS and the pre- and post-emergence phytotoxic effect on a eudicotyledonous model (Lactuca sativa) and a monocotyledonous model (Allium cepa) was evaluated through germination and seedling growth tests. Three concentrations of the extract (0.25, 0.50, and 1.00 mg/mL) were prepared, and four replicates for each of them were analyzed. Three major phenylphenalenones were identified by NMR spectroscopy: 4-hydroxy-anigorufone, methoxyanigorufone, and anigorufone, two of those reported for the first time in S. timida. The presence of seven other phenylphenalenones was suggested by the LC-MS analyses. The phenylphenalenone mixture did not affect the germination rate, but impaired radicle and hypocotyl growth on both models. The effect in the monocotyledonous model was statistically similar to glyphosate in the lowest concentration (0.25 mg/mL). Therefore, although more research on this topic is required to probe this first report, this investigation suggests for the first time that phenylphenalenone compounds may be post-emergence herbicides.

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“…Compound 345 was cyclized employing FC reaction conditions and gave 4-methoxy-1 H -phenalen-1-one (4-methoxyperinaphthenone) 343 as the sole product in 48% yield ( Scheme 71 ). 340 …”

Section: Applications Of Friedel–crafts In Total Synthesis Of Natural...mentioning

confidence: 99%