Anigorufone - CAS 56252-32-5
Catalog number: 56252-32-5
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C19H12O2
Molecular Weight:
272.297
COA:
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Chemical Family:
Phenols
Description:
Anigorufone is a natural phenolic compound found in several plants.
Purity:
>95%
Appearance:
Orange powder
Synonyms:
2-Hydroxy-9-phenyl-1H-phenalen-1-one
MSDS:
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Quality Standard:
Enterprise Standard
Quantity:
Milligrams-Grams
Density:
1.3±0.1 g/cm3
1.Fungus-elicited metabolites from plants as an enriched source for new leishmanicidal agents: antifungal phenyl-phenalenone phytoalexins from the banana plant (Musa acuminata) target mitochondria of Leishmania donovani promastigotes.
Luque-Ortega JR;Martínez S;Saugar JM;Izquierdo LR;Abad T;Luis JG;Piñero J;Valladares B;Rivas L Antimicrob Agents Chemother. 2004 May;48(5):1534-40.
Two antifungal phenyl-phenalenone phytoalexins isolated from the banana plant (Musa acuminata) elicited with the fungus Fusarium oxysporum, together with a methoxy derivative of one of them and two epoxide precursors of their chemical synthesis, were tested for leishmanicidal activity on Leishmania donovani promastigotes and L. infantum amastigotes. Drugs inhibited proliferation of both forms of the parasite with a 50% lethal concentration range between 10.3 and 68.7 micro g/ml. Their lethal mechanism was found linked to the respiratory chain by a systematic approach, including electron microscopy, measurement of the oxygen consumption rate on digitonin-permeabilized promastigotes, and enzymatic assays on a mitochondrial enriched fraction. Whereas the whole set of compounds inhibited the activity of fumarate reductase in the mitochondrial fraction (50% effective concentration [EC(50)] between 33.3 and 78.8 micro g/ml) and on purified enzyme (EC(50) = 53.3 to 115 micro g/ml), inhibition for succinate dehydrogenase was only observed for the two phytoalexins with the highest leishmanicidal activity: anigorufone and its natural analogue 2-methoxy-9-phenyl-phenalen-1-one (EC(50) = 33.5 and 59.
2.Phenalenone-type phytoalexins mediate resistance of banana plants (Musa spp.) to the burrowing nematode Radopholus similis.
Hölscher D;Dhakshinamoorthy S;Alexandrov T;Becker M;Bretschneider T;Buerkert A;Crecelius AC;De Waele D;Elsen A;Heckel DG;Heklau H;Hertweck C;Kai M;Knop K;Krafft C;Maddula RK;Matthäus C;Popp J;Schneider B;Schubert US;Sikora RA;Svatoš A;Swennen RL Proc Natl Acad Sci U S A. 2014 Jan 7;111(1):105-10. doi: 10.1073/pnas.1314168110. Epub 2013 Dec 9.
The global yield of bananas-one of the most important food crops-is severely hampered by parasites, such as nematodes, which cause yield losses up to 75%. Plant-nematode interactions of two banana cultivars differing in susceptibility to Radopholus similis were investigated by combining the conventional and spatially resolved analytical techniques (1)H NMR spectroscopy, matrix-free UV-laser desorption/ionization mass spectrometric imaging, and Raman microspectroscopy. This innovative combination of analytical techniques was applied to isolate, identify, and locate the banana-specific type of phytoalexins, phenylphenalenones, in the R. similis-caused lesions of the plants. The striking antinematode activity of the phenylphenalenone anigorufone, its ingestion by the nematode, and its subsequent localization in lipid droplets within the nematode is reported. The importance of varying local concentrations of these specialized metabolites in infected plant tissues, their involvement in the plant's defense system, and derived strategies for improving banana resistance are highlighted.
3.The intramolecular Diels-Alder reaction of diarylheptanoids--quantum chemical calculation of structural features favoring the formation of phenylphenalenones.
Monakhova Y;Schneider B Molecules. 2014 Apr 23;19(4):5231-42. doi: 10.3390/molecules19045231.
Diarylheptanoids have been reported as biosynthetic precursors of phenylphenalenones in plants. Quantum chemical calculations of molecular geometry and orbitals were used to elaborate which structural features are required to determine if diarylheptanoids can undergo an intramolecular Diel-Alder reaction to form phenylphenalenones. The computational data showed that an ortho-quinone- or a hydoxyketone-bearing ring A, containing the dienophile moiety, and a heptadiene chain with conjugated cisoid double bonds at C-4/C-6 and a saturated segment consisting of two sp3-carbon atoms, are required. Only four diarylheptanoids out of eighteen studied compounds proved to be suitable candidates. Among them are two 3,5-dideoxy compounds and two other compounds oxygenated only at C-3, suggesting that lachnanthocarpone, a representative of the 6-oxygenated phenylphenalenones, and anigorufone, a representative of the 6-deoxy phenylphenalenones, are not connected via a precursor-product relationship ("late reduction at C-6") but formed through partially separate pathways.
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Chemical Structure

CAS 56252-32-5 Anigorufone

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