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Neochamaejasmine B

CAS# 90411-12-4

Neochamaejasmine B

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Chemical structure

Neochamaejasmine B

3D structure

Chemical Properties of Neochamaejasmine B

Cas No. 90411-12-4 SDF Download SDF
PubChem ID 21636084 Appearance Powder
Formula C30H22O10 M.Wt 542.5
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2S,3S)-3-[(2R,3S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
SMILES C1=CC(=CC=C1C2C(C(=O)C3=C(C=C(C=C3O2)O)O)C4C(OC5=CC(=CC(=C5C4=O)O)O)C6=CC=C(C=C6)O)O
Standard InChIKey RNQBLQALVMHBKH-JQYHKRKISA-N
Standard InChI InChI=1S/C30H22O10/c31-15-5-1-13(2-6-15)29-25(27(37)23-19(35)9-17(33)11-21(23)39-29)26-28(38)24-20(36)10-18(34)12-22(24)40-30(26)14-3-7-16(32)8-4-14/h1-12,25-26,29-36H/t25-,26-,29-,30+/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 Neochamaejasmine B

The roots of Stellera chamaejasme Linn.

Biological Activity of Neochamaejasmine B

DescriptionNeochamaejasmine B displays nematicidal activity against both Bursaphelenchus xylophilus and Bursaphelenchus mucronatus. It can reduce seedling growth and disrupt root development, the IC50 value of 6.9 ug/mL . Neochamaejasmine B has antibacterial activity on Gram-positive bacterium and Gram-negative bacterium.
TargetsAntifection
In vitro

Phytotoxic flavonoids from roots of Stellera chamaejasme L. (Thymelaeaceae).[Pubmed: 25096753 ]

Phytochemistry. 2014 Oct;106:61-8.

Allelopathy, the negative effect on plants of chemicals released to the surroundings by a neighboring plant, is an important factor which contributes to the spread of some weeds in plant communities.
METHODS AND RESULTS:
In this field, Stellera chamaejasme L. (Thymelaeaceae) is one of the most toxic and ecologically-threatening weeds in some of the grasslands of north and west China. Bioassay-guided fractionation of root extracts of this plant led to the isolation of eight flavonoids 1-8, whose structures were elucidated by spectroscopic analysis. All compounds obtained, except 7-methoxylneochaejasmin A (4) and (+)-epiafzelechin (5), showed strong phytotoxic activity against Arabidopsis thaliana seedlings. Seedling growth was reduced by neochamaejasmin B (Neochamaejasmine B,1), mesoneochamaejasmin A (2), chamaejasmenin C (3), genkwanol A (6), daphnodorin B (7) and dihydrodaphnodorin B (8) with IC50 values of 6.9, 12.1, 43.2, 74.8, 7.1 and 27.3μg/mL, respectively, and all of these compounds disrupted root development.
CONCLUSIONS:
Endogenous auxin levels at the root tips of the A. thaliana DR5::GUS transgenic line were largely reduced by compounds 1, 2 and 6-8, and were increased by compound 4. Moreover, the inhibition rate of A. thaliana auxin transport mutants pin2 and aux1-7 by compounds 1-8 were all lower than the wild type (Col-0).

Nematicidal Activities of Isoneochamaejasmin A and Neochamaejasmin B from the Roots of Stellera chamaejasme L.against Bursaphelenchus xylophilus and Bursaphelenchus mucronatus[Reference: WebLink]

Natural Product Research & Development, 2014 , 26 (5) :639-44.

Two biflavonoids were isolated from ethanol extract from the roots of Stellera chamaejasme L.,and their chemical structures were identified as isoneochamaejasmin A and neochamaejasmin B(Neochamaejasmine B) by nuclear magnetic resonance spectral data.
METHODS AND RESULTS:
The nematicidal activities of the two compounds were tested by bioassay methods with second-stage juveniles(J2s)of Bursaphelenchus xylophilus and Bursaphelenchus mucronatus. The results showed these two biflavonoids exhibited significantly nematicidal activities against both B. xylophilus and B. mucronatus. Neochamaejasmin B (Neochamaejasmine B)displayed better nematicidal activity than isoneochamaejasmin A against two species nematodes under the same conditions.

Protocol of Neochamaejasmine B

Structure Identification
Journal of Northwest A & F University, 2008 , 36 (5) :179-184.

Further study on relationship between structure and antibacterial activity of neochamaejasmine B[Reference: WebLink]

It further studied the relationship between structure and antibacterial activity of Neochamaejasmine B.
METHODS AND RESULTS:
Four compounds,7″-methoxy Neochamaejasmine B(A2-1),7,7″-dimethoxy Neochamaejasmine B(E3),7,7″,4

Neochamaejasmine B Dilution Calculator

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Preparing Stock Solutions of Neochamaejasmine B

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.8433 mL 9.2166 mL 18.4332 mL 36.8664 mL 46.0829 mL
5 mM 0.3687 mL 1.8433 mL 3.6866 mL 7.3733 mL 9.2166 mL
10 mM 0.1843 mL 0.9217 mL 1.8433 mL 3.6866 mL 4.6083 mL
50 mM 0.0369 mL 0.1843 mL 0.3687 mL 0.7373 mL 0.9217 mL
100 mM 0.0184 mL 0.0922 mL 0.1843 mL 0.3687 mL 0.4608 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 Neochamaejasmine B

Phytotoxic flavonoids from roots of Stellera chamaejasme L. (Thymelaeaceae).[Pubmed:25096753]

Phytochemistry. 2014 Oct;106:61-68.

Allelopathy, the negative effect on plants of chemicals released to the surroundings by a neighboring plant, is an important factor which contributes to the spread of some weeds in plant communities. In this field, Stellera chamaejasme L. (Thymelaeaceae) is one of the most toxic and ecologically-threatening weeds in some of the grasslands of north and west China. Bioassay-guided fractionation of root extracts of this plant led to the isolation of eight flavonoids 1-8, whose structures were elucidated by spectroscopic analysis. All compounds obtained, except 7-methoxylneochaejasmin A (4) and (+)-epiafzelechin (5), showed strong phytotoxic activity against Arabidopsis thaliana seedlings. Seedling growth was reduced by neochamaejasmin B (1), mesoneochamaejasmin A (2), chamaejasmenin C (3), genkwanol A (6), daphnodorin B (7) and dihydrodaphnodorin B (8) with IC50 values of 6.9, 12.1, 43.2, 74.8, 7.1 and 27.3mug/mL, respectively, and all of these compounds disrupted root development. Endogenous auxin levels at the root tips of the A. thaliana DR5::GUS transgenic line were largely reduced by compounds 1, 2 and 6-8, and were increased by compound 4. Moreover, the inhibition rate of A. thaliana auxin transport mutants pin2 and aux1-7 by compounds 1-8 were all lower than the wild type (Col-0). The influence of these compounds on endogenous auxin distribution is thus proposed as a critical factor for the phytotoxic effect. Compounds 1, 2, 4 and 8 were found in soils associated with S. chamaejasme, and these flavonoids also showed phytotoxicity to Clinelymus nutans L., an associated weed of S. chamaejasme. These results indicated that some phytotoxic compounds from roots of S. chamaejasme may be involved in the potential allelopathic behavior of this widespread weed.

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