Regiolone

CAS# 137494-04-3

Regiolone

2D Structure

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3D structure

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Regiolone

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Chemical Properties of Regiolone

Cas No. 137494-04-3 SDF Download SDF
PubChem ID 44576009 Appearance Powder
Formula C10H10O3 M.Wt 178.18
Type of Compound Phenols Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (4R)-4,8-dihydroxy-3,4-dihydro-2H-naphthalen-1-one
SMILES C1CC(=O)C2=C(C1O)C=CC=C2O
Standard InChIKey ZXYYTDCENDYKBR-SSDOTTSWSA-N
Standard InChI InChI=1S/C10H10O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-3,7,11-12H,4-5H2/t7-/m1/s1
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 Regiolone

The leaves of Juglans regia.

Biological Activity of Regiolone

Description1. Regiolone can induce apoptosis in MCF-7 cells through the caspase-3 independent pathway. 2. Regiolone demonstrates phytotoxicity.
TargetsCaspase

Regiolone Dilution Calculator

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Preparing Stock Solutions of Regiolone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.6123 mL 28.0615 mL 56.123 mL 112.246 mL 140.3076 mL
5 mM 1.1225 mL 5.6123 mL 11.2246 mL 22.4492 mL 28.0615 mL
10 mM 0.5612 mL 2.8062 mL 5.6123 mL 11.2246 mL 14.0308 mL
50 mM 0.1122 mL 0.5612 mL 1.1225 mL 2.2449 mL 2.8062 mL
100 mM 0.0561 mL 0.2806 mL 0.5612 mL 1.1225 mL 1.4031 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 Regiolone

Botrytone, a new naphthalenone pentaketide produced by Botrytis fabae, the causal agent of chocolate spot disease on Vicia faba.[Pubmed:21780794]

J Agric Food Chem. 2011 Sep 14;59(17):9201-6.

A strain of Botrytis fabae isolated from faba bean (Vicia faba L.) plants displaying clear chocolate spot disease symptoms produced phytotoxic metabolites in vitro. The phytotoxins isolated from the culture filtrate organic extract were characterized by spectroscopic and optical methods. A new naphthalenone pentaketide, named botrytone, was isolated and characterized as (4R)-3,4-dihydro-4,5,8-trihydroxy-1(2H)-naphthalenone together with other well-known closely related naphthalenones such as Regiolone and cis- and trans-3,4-dihydro-2,4,8-trihydroxynaphthalen-1(2H)-ones. When tested on leaves of the host plant, with the cis- and trans-3,4-dihydro-2,4,8-trihydroxynaphthalen-1(2H)-ones assayed in mixture, Regiolone demonstrated the highest level of phytotoxicity together with cis- and trans-3,4-dihydro-2,4,8-trihydroxynaphthalen-1(2H)-ones. Botrytone showed moderate phytotoxic activity at 1 mg/mL and was still phytotoxic at 0.5 mg/mL.

Anti-proliferative and apoptotic activities of constituents of chloroform extract of Juglans regia leaves.[Pubmed:24467376]

Cell Prolif. 2014 Apr;47(2):172-9.

OBJECTIVES: To evaluate anti-proliferative as well as apoptotic activities of compounds identified in chloroform extract of Juglans regia leaves, on human breast and oral cancer cell lines (MCF-7 and BHY). MATERIALS AND METHODS: Column chromatography, MTT assay, flowcytometry and western blotting have all been used in the study. RESULTS: Bioassay-guided fractionation of chloroform extract of J. regia afforded isolation of 5-hydroxy-3,7,4'-trimethoxyflavone [1], lupeol [2], daucosterol [3], 4-hydroxy-alpha-tetralone [4], beta-sitosterol [5], 5,7- dihydroxy-3,4'-dimethoxyflavone [6] and Regiolone [7]. Structures of the compounds were established on the basis of spectroscopic analyses [Nuclear magnetic resonance (NMR) and mass]. All compounds inhibited proliferation of MCF-7 (human breast adenocarcinoma) and BHY (human oral squamous carcinoma) cells in a concentration-dependent manner. Compounds 6 and 7 had potent cytotoxic effects on both MCF-7 and BHY cells (IC50 21-51 mum), yet were not toxic to normal cells. MCF-7 growth inhibition was attributed to apoptosis; population of apoptotic cells increased from 1.12% in controls to 5.64 and 8.1% after 48-h treatment with compounds 6 and 7, indicating their potential at inducing early and late apoptosis. The caspase cascade was not activated, as indicated by only insignificant cleavage of caspase-3. CONCLUSIONS: Our results suggest that compounds 6 and 7 can induce apoptosis in MCF-7 cells through the caspase-3 independent pathway.

Aspergchromones A and B, two new polyketides from the marine sponge-associated fungus Aspergillus sp. SCSIO XWS03F03.[Pubmed:28276769]

J Asian Nat Prod Res. 2017 Jul;19(7):684-690.

Two new polyketides, aspergchromones A (1) and B (2), together with five known compounds, secalonic acid D (3), noreugenin (4), (3S)-5-hydroxymellein (5), (4S)-6-hydroxyisosclerone (6), and (-)-Regiolone (7), were isolated from the ethyl acetate extract of marine sponge-derived fungus Aspergillus sp. SCSIO XWS03F03. Their structures were elucidated by means of spectroscopic techniques (1D and 2D NMR, MS, UV, and IR). The absolute configurations of the new compounds were established by ECD calculations. Compound 3 showed moderate antimicrobial activity.

Enantioselective Separation of 4,8-DHT and Phytotoxicity of the Enantiomers on Various Plant Species.[Pubmed:27110760]

Molecules. 2016 Apr 22;21(4):528.

As a candidate for bioherbicide, 4,8-dihydroxy-1-tetralone (4,8-DHT) was isolated from Caryospora callicarpa epicarp and its two enantiomers, S-(+)-isosclerone and R-(-)-Regiolone, were separated by chiral high-performance liquid chromatography (HPLC) on a Chiralcel OD column with chiral stationary phase (CSP)-coated cellulose-tris(3,5-dimethylphenylcarbamate). Then, the phytotoxicity of 4,8-DHT and its enantiomers toward the seeds germination and seedling growth of the five tested plant species, including lettuce (Latuca sativa), radish (Raphanus sativus), cucumber (Cucumis sativus), onion (Allium cepa), and wheat (Triticum aestivum), were investigated and the results indicated a hormesis at low concentration of 4,8-DHT and its enantiomers, but a retardant effect at high concentration. Between the two enantiomers of 4,8-DHT, the S-(+)-isosclerone was more toxic to seeds germination and seedling growth of the five tested plant species than the R-(-)-Regiolone, and also the phytotoxicity of S-(+)-isosclerone varied with different plants. For example, S-(+)-isosclerone was the most active to seedling growth of lettuce, indicating that S-(+)-isosclerone had specific effects on different organisms. Thus, all of the chirality and concentration of 4,8-DHT, as well as the affected plant species, need to be taken into consideration in the development and utilization of 4,8-DHT.

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