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Hydroxyanigorufone

CAS# 56252-02-9

Hydroxyanigorufone

Catalog No. BCN7184----Order now to get a substantial discount!

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Quality Control of Hydroxyanigorufone

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Chemical structure

Hydroxyanigorufone

3D structure

Chemical Properties of Hydroxyanigorufone

Cas No. 56252-02-9 SDF Download SDF
PubChem ID 11471752 Appearance Powder
Formula C19H12O3 M.Wt 288.30
Type of Compound Phenols Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 2-hydroxy-9-(4-hydroxyphenyl)phenalen-1-one
SMILES C1=CC2=C3C(=C1)C=C(C(=O)C3=C(C=C2)C4=CC=C(C=C4)O)O
Standard InChIKey HTELDEYOMOTOBI-UHFFFAOYSA-N
Standard InChI InChI=1S/C19H12O3/c20-14-7-4-11(5-8-14)15-9-6-12-2-1-3-13-10-16(21)19(22)18(15)17(12)13/h1-10,20-21H
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Hydroxyanigorufone

The fruits of Musa itinerans Cheesm.

Biological Activity of Hydroxyanigorufone

DescriptionHydroxyanigorufone is a natural product from Musa itinerans Cheesm.
In vitro

Diarylheptanoids and phenylphenalenones from Musa itinerans fruits.[Pubmed: 24766994 ]

Phytochemistry. 2014 Jul;103:171-177.


METHODS AND RESULTS:
Two diarylheptanoids, musaitinerins A and B, one heterodimeric phenylphenalenone musaitinerone and four known phenylphenalenones, identified as 4-hydroxy-2-methoxy-9-phenyl-1H-phenalen-1-one, musanolone E, Hydroxyanigorufone and irenolone were isolated from the fruits of Musa itinerans Cheesm. Their structures were elucidated using spectroscopic analyses. The antimicrobial activity of these compounds was evaluated against Escherichia coli, Staphylococcus aureus and Candida albicans; the cytotoxic activity of these compounds was also evaluated against human erythromyeloblastoid leukemia (K562) and human alveolar carcinoma epithelial (A549) cell lines, respectively.
CONCLUSIONS:
Musaitinerone and musanolone E exhibited weak effects against the A549 cell line, as compared with adriamycin. However, these two compounds did not exhibit any growth inhibition against K562 cells, S. aureus, E. coli or C. albicans. The other compounds were inactive against all of the tested cell lines and microorganisms, even at concentrations as high as 50 μM.

Protocol of Hydroxyanigorufone

Structure Identification
J Agric Food Chem. 2002 Oct 23;50(22):6330-4.

Constituents of Musa x paradisiaca cultivar with the potential to induce the phase II enzyme, quinone reductase.[Pubmed: 12381112]

A new bicyclic diarylheptanoid, rel-(3S,4aR,10bR)-8-hydroxy-3-(4-hydroxyphenyl)-9-methoxy-4a,5,6,10b-tetrahydro-3H-naphtho[2,1-b]pyran (1), as well as four known compounds, 1,2-dihydro-1,2,3-trihydroxy-9-(4-methoxyphenyl)phenalene (2), Hydroxyanigorufone (3), 2-(4-hydroxyphenyl)naphthalic anhydride (4), and 1,7-bis(4-hydroxyphenyl)hepta-4(E),6(E)-dien-3-one (5), were isolated from an ethyl acetate-soluble fraction of the methanol extract of the fruits of Musa x paradisiaca cultivar, using a bioassay based on the induction of quinone reductase (QR) in cultured Hepa1c1c7 mouse hepatoma cells to monitor chromatographic fractionation.
METHODS AND RESULTS:
The structure and relative stereochemistry of compound 1 were elucidated unambiguously by one- and two-dimensional NMR experiments ((1)H NMR, (13)C NMR, DEPT, COSY, HMQC, HMBC, and NOESY) and single-crystal X-ray diffraction analysis. Isolates 1-5 were evaluated for their potential cancer chemopreventive properties utilizing an in vitro assay to determine quinone reductase induction and a mouse mammary organ culture assay.

Hydroxyanigorufone Dilution Calculator

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Hydroxyanigorufone Molarity Calculator

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Preparing Stock Solutions of Hydroxyanigorufone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.4686 mL 17.343 mL 34.6861 mL 69.3722 mL 86.7152 mL
5 mM 0.6937 mL 3.4686 mL 6.9372 mL 13.8744 mL 17.343 mL
10 mM 0.3469 mL 1.7343 mL 3.4686 mL 6.9372 mL 8.6715 mL
50 mM 0.0694 mL 0.3469 mL 0.6937 mL 1.3874 mL 1.7343 mL
100 mM 0.0347 mL 0.1734 mL 0.3469 mL 0.6937 mL 0.8672 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Hydroxyanigorufone

Concise Synthesis of Natural Phenylphenalenone Phytoalexins and a Regioisomer.[Pubmed:29281282]

J Nat Prod. 2018 Jan 26;81(1):98-105.

Concise total syntheses of the natural phytoalexins 2-hydroxy-8-(4-hydroxyphenyl)phenalen-1-one (1), 2-hydroxy-8-(3,4-dihydroxyphenyl)phenalen-1-one (2), and Hydroxyanigorufone (4), together with regioisomer 3 are accomplished in 11 or 12 steps. The synthetic strategy features a Friedel-Crafts acylation to construct the 1H-phenalen-1-one tricyclic core followed by a Suzuki cross-coupling to obtain the target compounds.

Phyllosticta musarum Infection-Induced Defences Suppress Anthracnose Disease Caused by Colletotrichum musae in Banana Fruits cv 'Embul'.[Pubmed:25288931]

Plant Pathol J. 2013 Mar;29(1):77-86.

Anthracnose development by Colletotrichum musae was observed to be significantly less in the fruits of the banana cultivar 'Embul' (Mysore, AAB) infected with Phyllosticta musarum than in fruits without such infections. Anthracnose disease originates from quiescent C. musae infections in the immature fruit. P. musarum incites minute, scattered spots, referred to as freckles, in the superficial tissues of immature banana peel which do not expand during maturation or ripening. P. musarum does not appear to have a direct suppressive effect on C. musae as conidia of C. musae germinate on both freckled and non-freckled fruit forming quiescent infections. Our investigations have shown that P. musarum infection induced several defence responses in fruit including the accumulation of five phytoalexins, upregulation of chitinase and beta-1,3-glucanase, phenylalanine ammonia lyase (PAL) activity and cell wall lignification. (1)H and (13)C NMR spectral data of one purified phytoalexin compared closely with 4'-Hydroxyanigorufone. Some of the P. musarum-induced defences that retained during ripening, restrict C. musae development at the ripe stage. This paper examines the potential of P. musarum-induced defences, in the control of anthracnose, the most destructive postharvest disease in banana.

Radical scavenging capacity of 2,4-dihydroxy-9-phenyl-1H-phenalen-1-one: a functional group exclusion approach.[Pubmed:23834597]

Org Lett. 2013 Jul 19;15(14):3542-5.

2,4-Dihydroxy-9-phenyl-1H-phenalen-1-one (4-Hydroxyanigorufone, 1), a compound isolated from Anigozanthos flavidus and Monochoria elata, displayed a high radical scavenging capacity in the ORAC assay. A systematic approach was adopted in order to explore the effect of each functional group. H-Atom transfer from the phenolic hydroxyl, a captodative effect from the hydroxy ketone, and the presumed involvement of the phenyl ring in the termination step of the radical reaction were disclosed as relevant features of this type of antioxidant.

Constituents of Musa x paradisiaca cultivar with the potential to induce the phase II enzyme, quinone reductase.[Pubmed:12381112]

J Agric Food Chem. 2002 Oct 23;50(22):6330-4.

A new bicyclic diarylheptanoid, rel-(3S,4aR,10bR)-8-hydroxy-3-(4-hydroxyphenyl)-9-methoxy-4a,5,6,10b-tetrahydro-3 H-naphtho[2,1-b]pyran (1), as well as four known compounds, 1,2-dihydro-1,2,3-trihydroxy-9-(4-methoxyphenyl)phenalene (2), Hydroxyanigorufone (3), 2-(4-hydroxyphenyl)naphthalic anhydride (4), and 1,7-bis(4-hydroxyphenyl)hepta-4(E),6(E)-dien-3-one (5), were isolated from an ethyl acetate-soluble fraction of the methanol extract of the fruits of Musa x paradisiaca cultivar, using a bioassay based on the induction of quinone reductase (QR) in cultured Hepa1c1c7 mouse hepatoma cells to monitor chromatographic fractionation. The structure and relative stereochemistry of compound 1 were elucidated unambiguously by one- and two-dimensional NMR experiments ((1)H NMR, (13)C NMR, DEPT, COSY, HMQC, HMBC, and NOESY) and single-crystal X-ray diffraction analysis. Isolates 1-5 were evaluated for their potential cancer chemopreventive properties utilizing an in vitro assay to determine quinone reductase induction and a mouse mammary organ culture assay.

Diarylheptanoids and phenylphenalenones from Musa itinerans fruits.[Pubmed:24766994]

Phytochemistry. 2014 Jul;103:171-177.

Two diarylheptanoids, musaitinerins A and B, one heterodimeric phenylphenalenone musaitinerone and four known phenylphenalenones, identified as 4-hydroxy-2-methoxy-9-phenyl-1H-phenalen-1-one, musanolone E, Hydroxyanigorufone and irenolone were isolated from the fruits of Musa itinerans Cheesm. Their structures were elucidated using spectroscopic analyses. The antimicrobial activity of these compounds was evaluated against Escherichia coli, Staphylococcus aureus and Candida albicans; the cytotoxic activity of these compounds was also evaluated against human erythromyeloblastoid leukemia (K562) and human alveolar carcinoma epithelial (A549) cell lines, respectively. Musaitinerone and musanolone E exhibited weak effects against the A549 cell line, as compared with adriamycin. However, these two compounds did not exhibit any growth inhibition against K562 cells, S. aureus, E. coli or C. albicans. The other compounds were inactive against all of the tested cell lines and microorganisms, even at concentrations as high as 50 muM.

Dimeric phenylphenalenones from Musa acuminata and various Haemodoraceae species. Crystal structure of anigorootin.[Pubmed:11985853]

Phytochemistry. 2002 May;60(1):61-6.

Three fused octacyclic phenylphenalenone dimers were isolated from Musa acuminata: Anigorootin, which was first isolated from Anigozanthos flavidus and hitherto represented the only compound of that type, the new 4'-hydroxy-anigorootin, and 4',4"-di-hydroxy-anigorootin, which is a revised structure. The crystal structure of anigorootin was determined by X-ray crystallography. 3,3'-Bis-Hydroxyanigorufone, a dimer of the conventional type known from Anigozanthos preissii, was also found in Musa acuminata. Phytochemical analysis of several Haemodoraceae species revealed the occurrence of anigorootin, 3,3'-bis-Hydroxyanigorufone, and the novel metabolite 3,3'-bis-anigorufone. The occurrence of the same compounds in Musaceae and Haemodoraceae indicates the close chemotaxonomic relationship of both plant families.

The biosynthetic origin of oxygen functions in phenylphenalenones of Anigozanthos preissii inferred from NMR- and HRMS-based isotopologue analysis.[Pubmed:21047660]

Phytochemistry. 2011 Jan;72(1):49-58.

The biosynthetic origin of 9-phenylphenalenones and the sequence according to which their oxygen functionalities are introduced were studied using nuclear magnetic resonance (NMR) spectroscopy and high-resolution electrospray ionization mass spectrometry (HRESIMS). (13)C-labelled precursors were administered to root cultures of Anigozanthos preissii, which were simultaneously incubated in an atmosphere of (18)O(2). Two major phenylphenalenones, anigorufone and Hydroxyanigorufone, were isolated and analyzed by spectroscopic methods. Incorporation of (13)C-labelled precursors from the culture medium and (18)O from the atmosphere was detected. O-Methylation with (13)C-diazomethane was used to attach (13)C-labels to each hydroxyl and thereby dramatically enhance the sensitivity with which NMR spectroscopy can detect (18)O by means of isotope-induced shifts of (13)C signals. The isotopologue patterns inferred from NMR and HRESIMS analyses indicated that the hydroxyl group at C-2 of 9-phenylphenalenones had been introduced on the stage of a linear diarylheptanoid. The oxygen atoms of the carbonyl and lateral aryl ring originated from the hydroxyl group of the 4-coumaroyl moiety, which was incorporated as a unit.

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